My friend and colleague writes an excellent newsletter, Write at the Edge, with helpful writing tips and best practices. She’s a professor, journalist, and author who has written for The New York Times, The Washington Post, and other outlets. She recently published an important debut book, Slip: Life in the Middle of Eating Disorder Recovery.

Mallary recently interviewed me about writing tools. She wrote up a summary of our conversation, highlighting the tools I talked about. I’m turning the rest of this post over to her summary.

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Mallary Tenore Tarpley: What tools are out there, and how might I and other authors use them to organize our materials and make our processes more efficient? I decided to reach out to Jeremy Caplan for answers. We met in 2010 through our work at The Poynter Institute, and we’ve stayed in touch ever since.

On Substack Live we chatted about a variety of tools that writers and authors can use to make their workflows more organized and efficient. I don't believe writers should ever use AI to do their writing for them, but AI tools can help with related tasks, including research, timeline creation, notetaking during interviews, and more. Watch the full recording here, and get a breakdown of the tools below.

Pick, stick and dig

During the Substack Live, Caplan recommended that writers “pick, stick, and dig.” In other words, pick one or two tools, stick with them, and then dig into them to better understand how they can help you. The number of tools can feel overwhelming at first, which is why Caplan recommends starting small rather than trying everything at once.

Swiss Army Knife tools

He noted four “Swiss Army Knife tools” that are great starting points for beginners: ChatGPT, Claude, Gemini, and NotebookLM (now called Gemini Notebook). These tools, and others, are continuously improving. “A lot of people base their impressions of AI tools based on something they did a couple of years ago,” Caplan said. “And we are at a world of difference at this point.”

With that in mind, Caplan recommended checking out the following tools, not to write for us, but to help improve our processes:

ChatGPT, Claude, and Gemini

For brainstorming and challenging ideas:

These tools are sometimes criticized for their sycophancy; they tend to be flattering and can reinforce a user’s biases. But when prompted, they can also point out areas for improvement.

“If you choose to use AI to challenge yourself, to identify your blind spots, to identify assumptions you’ve made that are baked into a piece of writing that you’re working on, or an argument you’re making, or an outline you’ve set up — if you do that, AI will often, in my experience, point you to things you haven’t thought about enough or that you haven’t noticed or you haven’t realized,” Caplan said. “In some cases, if we’re not using AI to challenge our work or to expand the way we’re thinking about something, we’re missing an opportunity and letting ourselves off the hook in terms of not aspiring to improve our work as much as we could.”

He suggested asking these tools questions along the lines of: Which parts of this piece might lose readers’ attention? Which parts lack a stat, fact, or evidence? Are there any parts where I need to provide more information to support my arguments? What questions would a reader be asking that I haven’t yet answered?

The tool will provide answers and will suggest other ways it can help (including writing or rewriting passages). The key for authors, of course, is making sure we use the tools in ways that let us preserve our own writing and voices. As I’ve written before: “When people use ChatGPT to do their writing for them, it can start to sound like everyone’s singing in the same choir. There’s harmony, but there’s no memorable originality.”

For deep research

These three tools can generate thorough research reports for authors and journalists working on big projects. “As opposed to a simple … Google search that just returns a quick summary and a list of results, a deep research report can be 10, 20, even 40 or 50 pages in length,” Caplan said. “So these are really exhaustive reports.” (For more, see the Wonder Tools post on deep research.)

Caplan suggests that writers be specific about the parameters they’re looking for, with regard to time periods, the kinds of sources you’re looking for (e.g. peer-reviewed articles), and the formats you’re looking for (bullets, quotes, data sets, etc.) Occasionally, the reports may include hallucinated links or sources, so double-check the information.

For organizing information from different sources

Caplan said writers can put various documents (Google Docs, photos, PDFs, etc.) into ChatGPT, Claude, and Gemini, and ask them to surface relevant information. “You can basically say, ‘I have these five documents with my notes from these past five years. Find me the ones about XYZ that are concise and clear,’” he said.

It’s worth trying out, especially if your approach to organizing materials isn’t working as well as you’d like. “I think the way people collect and organize their digital materials is a very personal thing,” Caplan said. “If your system is working for you, that’s great; you don’t need to do anything that’s different … But if you’re like most other people I encounter, you may have leaks in your system.”

For discovering new tools and learning how to use them

I recently used ChatGPT to inquire about digital tools for creating timelines. It introduced me to several options, including Aeon Timeline, Miro, and TimelineJS, built by Northwestern University’s Knight Lab. I then asked ChatGPT to explain how they worked and which seemed best suited to my needs. I was impressed by the results (but I’m probably still going to stick with my butcher paper approach)!

(Here’s a Wonder Tools post about the best timeline tools)

For copy editing

ChatGPT, Claude, and Gemini can offer copy editing help, which may be particularly helpful for independent writers who aren’t working alongside a full-time editor.

“AI can give you all these suggestions, and if you don’t find them useful you can just say, ‘No thanks, give me something else, give me a different suggestion, give me a different weakness I can address,’” Caplan said. “In my experience, almost always one of them or several of them are worth addressing.”

I personally wouldn't advise writers to put their work into AI when writing for another publication that isn't their own, as some publishers have rules and restrictions around this. And some writers choose to avoid AI for copy editing altogether, even when writing for their own publications.

For more, be sure to watch the end of the Substack Live video for more details about privacy, copyright, and ethical concerns related to sharing your copy with these tools (a huge topic that deserves its own series of Substack Lives). Caplan mentioned Jan and Msty as part of this discussion, as well as Pangram, which helps determine whether text may have been generated by AI.

Related recent Wonder Tools posts: Gemini, Explained | Claude Turns Ideas Into Apps | Private AI

NotebookLM (Now called Gemini Notebook)

After hearing Caplan talk about this tool, I came away thinking it could be a really helpful resource for writers, speakers, and educators. NotebookLM lets you upload a variety of materials: PDFs, Google Docs, articles, interview transcripts, notes, websites, book excerpts, etc. and helps you work across your research collection. It can generate infographics, slides, data tables, and more based on the information you give it (a great perk for authors giving talks related to their books).

Each notebook you create is divided into three “panels.” The first panel is for uploading your source materials. “You can put 50 different sources into one notebook,” Caplan said, “and you can have 100 different notebooks if you’re working on different projects.”

The second panel is for the query. You can prompt it, for instance, to review all of your materials and generate key points. “Unlike other AI tools — ChatGPT, Claude, etc. — it’s not going to look into the web unless you direct it to do that,” Caplan said. “It’s just going to look at what you have in the notebook. It’s called ‘grounded’; it’s grounded in the materials.”

The third panel is for generating content related to your materials. Again, you wouldn’t use this to generate writing, but you could use it to create infographics, slides, flashcards, video and audio overviews, and more.

Related Wonder Tools post: NotebookLM: The Complete Guide

Perplexity

This is a search tool that provides concise summaries of complex topics.

“What Google did historically was throw these 100 links at you and say, ‘figure it out,’” Caplan said. “What Perplexity says is, ‘Here’s what we’ve found so far — here’s some background information, here are some citations that you might want to check out, here are some citations on a different specific question you were also looking into.’ It just makes the process of gathering and verifying that information a lot more efficient.”

Related Wonder Tools post: Perplexity Update: How I Use AI for Search

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Consensus and Elicit

These tools are especially helpful for finding academic citations for deeply reported books or research projects.

Consensus describes itself as an “AI academic search engine for peer-reviewed literature.” It allows you to search millions of professional and academic journals, and it summarizes the results. Elicit works similarly and can conduct literature reviews and organize findings across papers.

Letterly and Wispr Flow

These are voice AI tools that allow you to dictate information, then have it transcribed and summarized. “You can just talk your way through the blank page and get your ideas out,” Caplan said. “These are your own ideas, and AI is helping to transcribe and summarize those for you.” (I can see this being especially helpful for writers like me who tend to email myself notes that all too easily get lost!)

Granola and Model Context Protocol

Simply put, Granola is an AI-powered notepad for meetings. It’s similar to Apple Notes but has the added benefit of being able to transcribe and enhance notes.

Caplan talked about this tool at length in our Substack Live and has written about it too. As he noted in a recent post about Granola: “Most AI note-takers give me only the AI’s version of what happened. Granola shows my own notes alongside the live transcript. I can refer back to either. Knowing I’ll have a thorough record frees me to focus on listening. I can be more present when I don’t have to worry about jotting down each detail.”

He went on to say: “I upgraded to the paid plan ($14/month) so I can give other AI assistants access to my meeting history through the Model Context Protocol. MCP provides a simple way to link Granola to AI tools like Claude and ChatGPT. … I can ask Claude to cross-reference what I’ve talked about in my presentations with what I’ve published. Claude can also help me generate dashboards, spreadsheets, handouts, and reports from material I’ve presented.”

Related Wonder Tools posts: Granola AI | Connect your Tools to AI

Mem, Capacities, and Tana

Mem is a note-taking tool comparable to a digital notebook that remembers details and surfaces them when they’re relevant. Capacities and Tana occupy a similar space and can help writers organize and connect large collections of notes.

“Each of these tools has their own little quirks and slight differences in style, so it becomes a matter of personal preference,” Caplan said.

Scrivener

Authors have long used Scrivener, a great tool for organizing book-length projects. It allows you to see the entire structure of your book all at once and rearrange sections visually.

“A lot of us are visual thinkers, and we like to see things mapped out. John McPhee, one of my writing teachers way back when, used to have snippets of his stories on his office wall and he would say, ‘This would work really well here,’ sometimes with index cards,” Caplan said. “And Scrivener basically gives you a digital version of that. It gives you multiple different visual ways to organize your material, so I think that can be really helpful for people, and it’s fairly easy to use.” He added that Scrivener wasn’t “made for the AI era,” so it doesn’t have AI features baked into it (which may be part of its appeal for some authors).

I love that Caplan mentioned McPhee, who I returned to at the very end of our conversation. I wondered out loud what McPhee, a Pulitzer-winning author and New Yorker staff writer, would think about all these tools we’d been discussing. We talked about how he has been incredibly prolific in his writing career but is also known for having worked slowly.

As McPhee himself once noted: “People say to me, ‘Oh, you’re so prolific’ … God, it doesn’t feel like it — nothing like it. But, you know, you put an ounce in a bucket each day, you get a quart.”

That seems like a good motto to follow, both for writing itself and for the gradual adoption of new digital tools.

What’s a writing tool of particular value to you? Leave a comment 👇

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So I was delighted to meet A.J. at a recent Substack event. Afterwards we spent an hour talking live on Substack about two dozen of the odd and creative tools he uses and trading ideas about our experiments. Watch the recording above, including some surprising confessions, and see a summary of the tools and links mentioned below.

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Add surprise to your day

Algorithms narrow what we see and filter outliers. So A.J. seeks out serendipity.

• Wiki Roulette serves up random Wikipedia entries, while Window Swap lets him peer out of windows all over the world.

• Ground News A.J. uses this app to see how outlets across the political spectrum cover the same story. Its Blindspot feature surfaces stories covered mostly by one side. I mentioned a related newsletter, The Flip Side, which picks a daily topic and spotlights commentary from the left and right.

• Seek out surprises A.J. asked Claude for 10 articles he would probably find boring, annoying, or offensive. It surfaced one gem, about ancient Egyptians buried with golden tongues so they could speak in the afterlife.

• Try it yourself Here’s my own anti filter-bubble prompt, and the 5 odd links ChatGPT gave me in my first experiment.

• Serendipitous Reddit For stumbling onto curiosities, I’ll type a keyword into the Reddit search box. During my live chat with A.J. I found r/Whatisit, where people post photos of unidentifiable objects. The crowd figures out what they are. And r/MadeMeSmile, which is heartwarming. Try the free Random Reddit Stumbler Chrome extension to discover new Reddit communities. Caveat: You might waste time procrasti-surfing in rabbit holes.

• A.J.’s NYTimes archive trick Search the Times all the way back to 1851 for a word of your choice, then read early mentions. Searching for “dogs” led A.J. to a disturbing 1896 editorial titled “All Dogs Deserve Death” (screenshot), which argued that dogs spread disease. “It was proof that clickbait is not a totally new phenomenon,” he says. A.J.’s caveat: the archive surfaces ugly history. Searching “cocaine” turned up overtly racist reporting. Accessing the archive requires a subscription.

• Read A.J.’s take on injecting randomness into your life

Play with words

• Parseword The creator of Wordle, Josh Wardle, made this tricky new word game. A.J. describes it as an on-ramp to British cryptic crosswords, which blend wordplay with anagrams and obscure puns. “They’re infuriating,” he says, “but at the same time, very addictive.” I find this one fun but hard.

• Raddle Try this word ladder with a twist. The clues are are out of order. A.J. says he enjoys it because you can finish in two minutes. I appreciate the hints so I don’t get stuck.

• OneLook “An amazing search engine for words,” A.J. says. Type a word and get its history, related terms, definitions from numerous dictionaries, or quotes, phrases, and lyrics that use it. Or use wildcards to find words that start or end with a group of letters. OneLook scans 17 million entries in 805 dictionaries to answer queries. They also designed an amusing new word game called Cadgy.

• Anagram sites. The Word Finder and other multi-word anagram tools like Anagram Solver handle phrases, not just single words. Scrabble Solver helps you find words with your tiles.

• Droodles This playful format for minimalist drawings centers on absurd captions, as in these examples. Play by guessing the captions, or make up your own.

Wake up your senses

• The Sommelier Wine Aroma Kit by Aromaster A.J. bought is a training kit for aspiring oenophiles. It has 88 tiny bottles of individual scents, including Rose and Lemon. Horse sweat, the set’s last bottle, isn’t something you want in a wine. The kit is $400 on Amazon, but you can make a simpler one for $30. A.J. tries to identify scents for three minutes each morning to strengthen his nose for food. Smell is our least trained sense, he says.

• Use your own spice rack When my daughters were little, we’d play a guessing game, taking turns holding a spice bottle beneath our noses with our eyes closed. It entertained us in the kitchen and cost nothing.

• Vision-distorting glasses A.J. ordered 10 pairs that alter how you see. One simulates a bee’s vision. Another tries to represent macular degeneration. Some are prisms that flip the world upside down. He started this exploration after hearing that yellow-tinted glasses brighten your mood. The tint did little for him. But it made a point, he says. “What we see is a very narrow spectrum of reality.”

Watch movies better

• Audio description Most streaming apps have an accessibility feature that lets you hear a narrator describe what’s happening on screen. It’s designed for blind and low-vision viewers. A.J. isn’t vision impaired, but uses it anyway. “It’s educational,” he says. “I learn a lot from the voiceover that I didn’t know before.” Watching an Agatha Christie film, he discovered what a cloche is. And a trilby. The narration also alerted him to a novel detail: the O in the Focus Features logo is deliberately out of focus. A.J. says he admires the concise writing required to fit every word between the dialogue.

• Closed captions A simpler feature we both use. A.J. turns them on for song titles and for accents. “You’re watching Derry Girls and you have no idea what people are saying.” I started relying on captions for The Wire.

• Playback speed A.J. watches films at 1.5x or 2x speed. “I see twice as many movies,” he says. “I admit, I may get 80% as much out of them.” He knows filmmakers hate it.

  • Netflix offers 1.5x, but not while casting or on the ad-supported web player

  • Apple TV and Prime go to 2x

  • Chrome extensions like Video Speed Controller give you finer control

• Slow motion A.J. also watches at 0.5x speed sometimes to study scene design. Dense shows like Veep need to be slowed down, he says, not sped up.

• WhenJumpScare A.J. appreciates psychological horror, but he hates jump scares. This free site tells you exactly when surprises are coming so you can look away. “I love a horror movie,” he says, “and I’m not going to watch it if I’m going to be jumping in my seat the whole time.”

• RunPee (iPhone/Android) This free app (screenshot) tells you the ideal minute to run to the bathroom during a long movie, and sums up what you missed. A.J. used it for Christopher Nolan’s nearly three-hour Odyssey.

Stretch your brain

reMarkable tablet We both own one. I use mine to sync, back up, and organize my handwritten notes. A.J. never connects his to the internet. Every morning he spends ten minutes brainstorming with it by hand.

Sometimes he flips open a magazine for an improvised prompt. He saw a snowman picture recently and started riffing: “What if it’s a snow woman? What if the pipe is a vape? What if the coal eyes are solar panels?”

“99% of these ideas are terrible,” he says. But he doesn’t mind. “If you believe the brain is a muscle, and I do believe there’s something to that metaphor, then this is like going to the gym for me.”

Add color to your space

I shared with A.J. three of the most colorful objects in my office. I have no affiliation with any of these companies. I’m just sharing what’s on my desk.

CMY Cubes A small glass cube reflects light next to my laptop. Each face has a different color. Look through it at an angle and the light refracts into new colors. Designed in Australia, the smallest cubes cost about $23. No batteries, no app. I found mine at the Toy Fair, the annual trade show at NYC’s Javits Center where thousands of toymakers show new wares.

Merge Cube A foam cube that supplements augmented reality apps. When you use a compatible app, each of the cube’s faces renders a distinct three dimensional image on your computer or phone screen. I confess, though, that sometimes I just use it as a stress ball.

T2 double-walled glass tea flask Some teas smell as good as they taste, and some have a lovely tint. I can see, smell, and savor tea with this clear flask I got as a gift. I do wonder, though, if it’ll shatter if I accidentally knock it off my desk someday.

Think with games

Brainspin I use dozens of games in my teaching, including those in my Pinterest creativity card game collection. Brainspin is the simplest. It’s a deck of two-dimensional pictograms I use as a brainstorming warm-up in the classes I teach. $25 for a set of two decks, designed by , who is now on Substack.

Bonus links for more of A.J.’s quirky takes on life

• Read A.J.’s newsletter, Experimental Living for more on his adventures.

• Watch his five TED talks for more on his unique life experiments

• Listen to his Puzzler podcast

• Check out his books, which are consistently quirky and funny

I’m looking forward to the book A.J.’s working on next, about misinformation. He’s fact-checking his own life. “How do I know the world is round?” he asks. “How do I know my wife loves me?”

What experiment are you trying these days? Leave a comment 👇

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Thanks to , , , and many others for tuning into my live conversation!

I can ask Claude to add to my calendar, query my meeting notes, update me on my email, or find a passage I highlighted in my digital notebook.

Claude Connectors and ChatGPT plugins connect to hundreds of services. These include Superhuman Mail for email, Google Calendar, Granola for meeting notes, and Readwise for my online highlights.

Read on for how and why to link your favorite tools to your AI assistant, and examples of connections and queries I’ve found useful so far.

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Why Connecting Tools to Claude and ChatGPT Is So Useful

Claude and ChatGPT know the context for my work because I’ve set up Projects for my primary work areas. Each has detailed instructions and reference documents. And the AI has a memory of the work I do, my style, my preferences, and my objectives. So I can ask my AI assistant to:

• Plan: Add four prep sessions to open morning slots on my calendar next week for the classes I’m teaching this fall. Include in each event description relevant excerpts from my meeting summary and reference the recent planning notes I dictated.

• Research: Gather recent links I’ve saved to Raindrop, my bookmarking tool, that might be relevant to my team’s research. Then create a new reminder with those links and a summary of my recent related notes.

These multiple-part commands require context. They won’t work in Google Calendar, Raindrop, or Granola directly. That’s why it’s so helpful to have Claude or ChatGPT as the command center.

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I often finish a good nonfiction book with a handful of useful ideas. Then I gradually forget the details. Can you relate?

Shortform gives me a practical way to revisit the books I want to remember. Its guides are written and edited by people, not robots. The guides include clear book overviews as well as deeper analysis, which I appreciate because I want to get beyond the surface. I also like that the guides include examples and quotes. And they often mention connections to related books, which is useful for ideas on what else to read.

On the Shortform app I recently read the guide to The Meaning of Your Life, by Arthur Brooks, which led me to Vivek Murthy’s book, Together, about the loneliness epidemic.

I use Shortform both to refresh my memory on books I’ve already read, and to explore potential new titles before I decide what to read next. Try it to find guides for business books, education, psychology, biography, and more.

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MCP is the New USB 🔗

These connectors have a technical name: MCP, or Model Context Protocol. But just as you don’t need to think about USB details when you plug in a printer, or http specifications when you use the Web, you can use MCP without understanding its technical details. All you need to know is that MCP is a way of linking software tools, sites, and apps to AI platforms like Claude and ChatGPT.

Remember the world prior to USB? Printers, hard drives, cameras, and external monitors had their own special cords to connect to your computer. I just cleaned out dozens of them from a drawer in my Manhattan apartment. Now they’re obsolete because USB ports are everywhere. MCP is a similar unifying standard for linking tools to AI.

5 Ways I’m Using Tools Connected to Claude

Manage Email 📧

I rely on Superhuman Mail to read, organize, and respond to email. It’s fast, easy to use, reliable, and integrates with my calendar. I use it with three distinct email addresses. Because I have to act on important messages, I’ve linked it to Claude.

Get started: The connection guide walks you through linking your email to Claude or ChatGPT. You can then ask your AI assistant to:

• “Help me turn a bunch of starred emails into an afternoon plan.”

• “List important messages I’ve sent this month that the recipient hasn’t yet opened.”

• “Draft concise responses to routine customer questions for my review.”

Some of these tactics will also work with Gmail and Outlook connectors.

Example query: “Look at my five most recent starred emails, suggest an action list for this afternoon based on my priority list, then put an hour on my Google Calendar to act on them.”

Do More with Meeting Notes 🗒️

I use Granola as my notepad during meetings. It transcribes conversations, then creates a summary based on the transcript and my own notes. (See my guide). I can already ask questions about my meetings in Granola without needing a separate AI tool.

But the advantage of linking Granola with Claude (or ChatGPT) is that Claude has access to insights in my notes, email, and Google Drive, so it can integrate the info it pulls from Granola within the context of a broader analysis.

Get started: The Granola MCP guide explains how to link it to your AI. Unlike many other paid services, Granola actually lets free users query meeting notes (for the past 30 days) using your AI tool of choice.

Example query: “Give me a summary of the research questions I said I’d follow up on in my meeting with Pat. Next to each task include a bulleted list of the background details I already collected in my research spreadsheet.”

Edit Images and Videos 🌆

Photoshop and Premiere are powerful but complicated. Now you can edit an image or video without even opening a separate app. Set up the plugin, then tell your AI assistant to use it in your prompt. The AI assistants are often clever enough to figure out which tool to use even if you don’t explicitly mention it.

Get started: Install the Adobe app in ChatGPT. Or add it to Claude, using this guide. Your AI assistant will now have access to the capabilities of Photoshop, Premiere, Firefly, Express, Acrobat, and other Adobe apps. You don’t even need an Adobe account to get started, though it might be helpful to get a free one if you want to organize, improve, and act on your creations later. (Canva’s MCP is also useful).

Example query: “Help me change the text in this graphic.” Or “Reformat this horizontal video clip for YouTube Shorts or Instagram Reels.” Or “Add background blur to this headshot, fix the lighting, and crop it for a portrait.”

As a test, I changed the first line in an illustration from “Bold” to “Kind.” Notice that the first attempt wasn’t perfect. The period after “Kind” was missing. But a quick edit request fixed that. The Photoshop edit preserved the font, style, spacing, and angle.

The benefit: Instead of hunting through Photoshop menus trying to figure out how to do this, I just asked ChatGPT to use Photoshop to make a change. In the long run, being able to use natural language to accomplish tasks like this may shift how we spend our time away from technical menu-hopping toward more creative work. We’ll spend more time thinking about what to do and why, rather than how to technically get it done.

Find Highlights 📚

I use Readwise to collect the passages I highlight when reading online or on my Kindle. It also hosts passages I save when listening to podcasts with the Snipd app.

Get started: The Readwise MCP lets you make use of the highlights you’ve made while working on other projects with an AI assistant.

Example query: “Show me a bunch of my Readwise highlights that include descriptions of desserts, especially from European novels, then gather a list of related recipes I can make with my daughters before our trip.”

Research Legal Cases 🔎

Court Listener from the Free Law Project is a handy way of gathering info about court cases. You can ask for records related to Elon Musk’s recent testimony without paying for a legal research service. Thanks to for the tip.

Get started: Use the Court Listener MCP guide for free with Claude or ChatGPT. First set up a free Court Listener account.

Example query: “Review the news article at XYZ link, find the case that’s being discussed, and give me additional details about the case and any other related recent cases.”

Other Useful MCP Tools 🛠️

• Rize is my favorite tool for time-tracking. I linked it to Claude so I can learn from how I’m spending my time and assess that alongside info from my meetings, email and calendar. The Rize MCP page includes use-cases and helped me get started. Rize requires a paid subscription.

• I use Raindrop to save links I’ll need later. I checked the Raindrop MCP page to set it up and learn about the kinds of queries I can run from Claude. When I’m doing research in a project, for instance, I can ask it to pull in relevant links I’ve saved. Or I can even ask Claude to put the links from a spreadsheet I’m working on into my Raindrop bookmark collection with appropriate tags.

• Sublime is another tool I use to save quotes, images and useful pages online. Unlike Raindrop and other well-designed clipping tools like MyMind, which are fully private, Sublime lets me see related material other people have saved. Now I can ask Claude to pull in relevant material from .

• Substack has a new MCP, available to select publishers as of now. It lets Claude coach me on my analytics. I recently asked for an analysis of send times to figure out how they impact open and click rates. Substack’s help page notes that the MCP has “read-only access to publication data such as dashboard metrics, traffic data, and publication settings. It cannot publish posts, send Notes, or modify your account.”

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How to Link Tools to Your AI Assistant

• Decide what kind of connector will be useful to you.

  • Email: Gmail, Outlook, Superhuman, and other email services now let you analyze and respond to your messages.

  • Files: Analyze or act on files in your Google Drive, Dropbox, Box, Slack, Notion, or anywhere else you keep your documents and files.

  • Planning: Add events to your Google or Outlook calendar, or organize projects with tools like Airtable, Monday, ClickUp, Asana, and Linear.

  • Fun: Create Spotify playlists based on your work vibe or search StubHub or SeatGeek for tickets your family or friends might enjoy.

• Pick from your AI tool’s curated list. Claude and ChatGPT each have a bunch of services pre-configured to work. Perplexity now does too. Popular ones include Google Drive, Gmail, Google Calendar, Canva, Figma, and Notion.

• Paste in the address of a custom connector. For tools that are not on the default list, you put in an MCP address, which is like a special website to connect an external service to your AI tool. Find more to try in a directory.

Step by Step

1. Click connect on the service you want.

2. Log in to that service in the window that opens.

3. Approve permissions your AI assistant asks for, so it can access the external tool. Limit permissions to view only if you want your AI to see info from a linked service but not change anything. You can update permissions later in your AI tool’s settings.

Getting started with MCP connections doesn’t require any programming or technical wizardry. If you can add an app to your phone, you can do this. (Note: Google’s Gemini doesn’t yet enable easy MCP connections).

Be Careful About Linking Private Data

Think twice before connecting services that host sensitive info. I haven’t linked my bank accounts to my AI tools, for example. If you do that and someone gets access to your AI account, they’ll be able to find out a lot about your finances.

• It can happen when a thief uses a “prompt injection” to manipulate an AI tool into releasing sensitive info.

• Or it can happen if your phone is lost or stolen. New York, London, Paris, and other major cities see thousands of phones stolen each year (Zipdo 2026 report).

• Data can also leak from AI systems. It’s rare, but there have been cases like this one.

Be Cautious About Letting AI Tools Act on Your Behalf

I’m not yet letting AI tools send emails for me. Or submit forms or applications. If Claude or ChatGPT generates something odd because of a glitch, or because I rushed a query, I want to be the one noticing the error.

When you start connecting AI tools to external services, you have the option to give your AI assistant power to do things on your behalf. That can be useful for research, summarizing meeting notes, or cleaning up messy computer folders.

But you or your AI assistant could make a costly mistake with important info. In a rare but alarming case, Cursor, an AI tool, deleted PocketOS’s company database and its backup (Guardian article). A related 2025 case involved Replit (Fortune article).

Other Ways Connected AI Can Go Wrong

• Travel booking blunder. You ask it to cancel a reservation, and it cancels your entire itinerary. Or you ask it to book a flight on 7/1/27 and it books a nonrefundable ticket on 1/7/27, assuming you were using the European date system and meant January 7, not July 1.

• Disappearing Files. You ask it to get rid of duplicate files. It deletes an entire folder with a similar name.

• Calendar Chaos: You ask it to “find a time for everyone” and it reschedules an existing meeting in the wrong time zone, because you were traveling when you wrote the request.

I haven’t encountered any of these errors. But these services are still new, so you may encounter occasional bugs or blunders.

From Answer Machine to Headquarters

I initially thought of AI tools as answer machines. Ask for info, get back useful text. Then I thought of AI assistants as question machines, provoking me to think about things I hadn’t considered. Now I think of them as my online headquarters.

Claude serves as a dashboard where I can act on my email, notes, documents, calendar, designs, saved links, and meeting transcripts. It’s like having a new partner to support me and help make work a little more efficient and creative.

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p.s. To see these connections in action, watch a recording of my live workshop. You’ll find it on the perks page for paid subscribers.

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This is a guest post from , following up on his Digital Investigator’s Toolkit. Craig and Alexios Mantzarlis run Indicator, which publishes digital investigative guides and tools. They also have a free newsletter.

Yutori Scouts

Use it to: get an agent-curated summary of new info about a topic you care about, delivered on your schedule.

Think of Scouts as an AI-infused version of Google Alerts.

Specify a topic to keep an eye on, like the latest research in your field, new films, or news about your favorite sports team. Then, on a schedule you choose, AI agents scour the web and send back a collection of links with a summary of what they found. I get a nightly email at 7 p.m. ET with new OSINT tools, techniques, and writing.

It doesn’t surface something great every single day, but that’s OK. Set it up once, tweak as needed, and then it just runs. It’s simple, free, and a nice complement to other monitoring tools, like Google Alerts.

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Search by Image

Use it to: check where an image really came from, and whether it’s been published before, across several search engines at once.

Reverse image search is one of the easiest, most powerful digital investigative techniques. You can easily find out where an image (or visually similar ones) have appeared online. It’s often the first step in verifying whether an image is authentic. A reverse image works for products, logos, and more. It also works for videos, which you convert into images by snapping a few screenshots.

If everyone knew how to conduct reverse image searches, we’d have fewer misleading images and videos circulating unchecked. It’s a powerful way to uncover the context and history of an image. It’s useful for research, but also for online shopping.

The concept is simple. In an ordinary web search, you type words and get back links (or, increasingly, an AI summary). With reverse image search, you give a search engine a picture and ask it to find matching or visually similar images. If you’ve used Google Lens, you’ve done a reverse image search.

The Search by Image extension makes it easier to search for the same image across the four leading reverse search engines: Google Lens, Bing, TinEye, and Yandex. You can select additional specialized search options in the settings.

Once installed, there are two ways to search an image.

1. Click the extension

• Click the red camera icon in the Chrome extension bar.

• It opens a menu where you can choose to search across the default engines or just pick one to start (screenshot).

• After you select the search engine, a button pops up to invite you to select an image to search (screenshot).

• Click on the image and the results open in a new tab(s).

OR 2. Right click

• My preferred method is to simply right-click on an image I want to search. This opens up a menu for “Search by Image.”

• Choose to search all default engines or select a specific one. Results open in a new tab.

There are lots of customization options. For example, you can add one-click searches of stock-image sites like Shutterstock or other specialized sources.

SearchWhisperer

Use it to: find what you’re looking for through powerful, operator-based searches without having to memorize technical terms.

One of the true superpowers of the internet is knowing how to use advanced search operators.

Operators are specialized commands that help ensure a search engine understands what you’re looking for and returns relevant results. Operators are even more important now that search engines like Google and Bing are shifting to deliver AI-generated summaries instead of lists of relevant links. You increasingly need to force a search engine to show you the results you’re looking for. Operators are the way.

View a list of Google operators and descriptions of what they do.

Two of my favorite operators are:

• site: restrict results to a single domain.

• filetype: return results that fit a specific document type.

They’re particularly powerful when you use them together. For example, if I want to search the U.S. Department of Commerce’s website for PDF documents that contain the words “confidential” and “spacex,” I could enter this into Google:

An advanced query that uses operators is often called a “dork.” Most people never learn operators and don’t know how to craft a dork. That’s a missed opportunity. If there’s one research skill worth investing in, this is it.

That’s why I recommend dork generators to anyone who wants to improve their search and research skills. There are many options, but I suggest Search Whisperer from , a trainer who also builds tools for journalists and researchers and writes .

• Start with a general search query like you’d enter into Google (screenshot).

• SearchWhisperer starts by analyzing your query 👇

It suggests refinements:

But the real magic is with the menu options at the top (screenshot).

Click on one and it will generate dorks that can help you home in on specific documents, sources, keywords, and other elements. Let’s test with “Hotfix.” It gives several options:

• I picked “The Document Hunter” and it suggested searches that focus on PDFs (screenshot).

• I clicked the button for “Find PDF Documents about US government and spacex” and it opened a new tab with this Google search (screenshot).

• I also chose “Find recent research content where ‘US government and spacex’ appears near ‘research’” under one of the Full Repair categories. It generated a pretty advanced Google dork (screenshot).

To get the most out of it: don’t just read the results. Look closely at the dorks built by the tool. Notice how they’re constructed. That’ll make it easier to earn to use operators and start writing your own.

Final tip: combine reverse image search with Gemini’s AI-image detection tool I recommended in my previous post.

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Wonder Tools subscribers can claim 20% off an Indicator Membership. It’s a great way to build your digital investigative skills. Get access to our investigative and research guides, original reporting, a monthly workshop, plus all recordings. You’ll also get increased access to OSINT Navigator so you can find the right investigative tool for whatever you’re researching.

How can I use AI to challenge me to think more, not less? Read on for five tactics I’m leaning on to avoid cognitive surrender when my brain’s overheating.

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1. Challenge Me, Don’t Praise Me 😯

• The Tactic: Use AI as an intellectual sparring partner.

• The Infographic: A visual summary of this approach.

• Explore alternative perspectives. Ask an AI assistant: How might someone from X or Y professional background think about this? What tough questions would they ask?

• The Benefit: Identify potential blind spots and weak assumptions before finalizing a presentation or making an important decision.

• Try This: Present a plan, idea, draft, or decision to an AI assistant with instructions to challenge your thinking in multiple ways. Identify risks you haven't considered and add nuance to your analysis.

Prompt Template

"I'm planning to [decision/plan] because [reasoning] and with a goal of [objective]. Play devil's advocate. Give me multiple perspectives on this. Be bold and surprising in your reply, and address these questions:

• What are the strongest arguments against this approach?

• What alternatives should I consider?

• What risks might I be overlooking?

• What questions should I be asking myself?

• What challenges should I expect to face?

• What could I do to learn more before I move forward?

• Who else could I talk to about this?

• What could I do to increase the chances of success?

Pro Tip: Ask your AI assistant to role-play. It can respond as a coach, a teacher, a family member, a competitor, or an audience member. Varied viewpoints can be useful. Or ask it to act like a person you admire, living or dead, real or fictional. You can even ask it to simulate a council of advisors, each with a distinct perspective. has written about using that tactic for feedback on material in his book.

Microsoft’s Copilot AI now has a new free “Team of Advisors” experimental feature to give you multiple perspectives from an animated expert panel. Here’s an example of what a panel suggested in reply to my open-ended query (though you won’t hear the animated voices). And here’s the transcript.

Limitation: Unless you provide detailed context, you may get bland responses.

To Keep it Private: Use a free offline AI tool like Jan, which I wrote about recently.

Example: During a dialogue with ChatGPT about a new morning routine I was adopting, I realized I had left several things out of my planning. In addition to posing questions that helped me think more carefully about my goals and my timing, it produced a PDF plan with tables.

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2. Think Out Loud 🤔

The Tactic: I like talking out loud to clarify my ideas. It’s my way of free writing. I use voice AI tools to turn my stream of consciousness into organized text. I call it bionic dictation. The AI assistant records and transcribes what I say. It then goes a step beyond dictation by transforming my words into an outline or summary. That helps me add structure to my meandering thoughts. (My guide to voice AI).

The Infographic: A visual summary of this approach.

Step 1. Pick an AI dictation app.

Apple Notes and Google Keep work well for free mobile dictation. They won’t summarize your text or transform your words into an outline, as Letterly can.

Letterly is the reliable mobile app I prefer. It’s a standalone app, or you can use it within your iPhone keyboard to dictate texts, email, or notes. I make lots of typos when thumb typing, so I often use my voice instead in any app. It’s more accurate than the iPhone’s built-in dictation. It now also works on my laptop.

Wispr Flow is what I often use on my computer. It lets me hold a function key to dictate into any app. It’s several times faster than typing and works in 100+ languages. It’s free for 2,000 weekly words, or $12/month for unlimited use.

Lispr is a good new free alternative to Wispr. It can instantly translate your spoken words into any of 99 languages. I tested it by dictating various messages and translating an email reply into Portuguese, which worked well.

MacWhisper is another excellent free option. It can record your system audio for online meetings, or even transcribe uploaded audio files. I paid $73 for a one-time upgrade to use the best AI models, but the free version has almost all of the same features.

Step 2. Create a new note. Hit record. Talk. The app won’t judge you or care whether you speak quickly or slowly. It doesn’t care whether you’re saying something brilliant or sputtering nonsense. When you finish it will summarize your rambling. It doesn’t care how long you pause, or whether you contradict yourself or digress. It just patiently transcribes and then sums up your words.

4 ways I use voice AI

• Brainstorm out loud. I start with a question and list as many related thoughts as I can.

• Journal at day’s end. I reflect on whatever happened that day, what I realized, what open questions I need to address, and any nice moments I want to remember.

• Talk through a draft. I narrate a lesson plan I’m figuring out, or a newsletter draft I’m working on to get to a stage where I can edit it.

• Capture what’s fresh. After an important meeting, or a presentation, or after I finish a book, I use a voice AI app to save my impressions.

I’m not asking the voice AI to write something for me. Or to think for me.

I’m using it like a digital bucket. It takes my blah-blah-blah blathering, with my ums and ahs and digressions, and helps me organize my thoughts.

Pro Tip: Record with AirPods while walking, screen off. The lack of a visual editing screen frees me up to just talk. The editing part of my brain interferes less when I’m talking than when I’m typing.

Limitation: Voice AI won’t sharpen weak thinking. Read and edit your own words and refine them before sending anything important.

Example: I sometimes start my day at work by talking through my priorities for a few minutes with a voice AI tool.

3. Do Deep Research Before a Big Decision 🔎

The Tactic: Before making an important decision or beginning a new phase of a project, I run multiple deep research queries. Within 5 to 25 minutes I have a citation-rich report that would in the past have taken days to prepare. After reading I can follow-up on the most promising citations and links.

The Infographic: A visual summary of this approach.

The Tools: ChatGPT, Gemini, Perplexity, Copilot, and Claude all have similar deep research modes.

How it Works: Dictate or type in an extensive research query. The AI assistant will then analyze your query and search through dozens of sites, or sometimes hundreds. It will synthesize its findings in a report with citations, so you can go to the original sources. I usually export the analysis into a Google Doc for easier reading or printing.

Try This: Toggle on the deep research setting in your AI of choice. Then write a query that includes:

• What you’re researching and why you care.

• Any relevant supplemental documents. You can attach relevant PDFs or other materials you’ve already gathered.

• What format you want. Maybe you’d like tables, or a timeline, or a beginner’s step-by-step guide, adapted for your specific context.

• What level of understanding you’re aiming for, or what you already know. Are you a scientist looking for updates on a field related to yours, or a novice trying to make sense of something brand new?

• Which sources to prioritize, if you have preferences or favorites. Maybe you want only peer-reviewed research, or info from particular publications or specific countries or government agencies.

• What questions the report needs to address, and what it should avoid. If you’re not interested in historical background or scientific explanations, say so. If you don’t want it to assume prior knowledge, say that.

Vague queries produce generic reports. Detailed direction is what makes deep research worth the wait.

Pro Tip: Tell the AI assistant to ask you questions to clarify your objectives before it begins the research. That gives you an extra chance to refine your query.

Edit the Research Plan: ChatGPT, Gemini, and Copilot let you review and edit their research plans before beginning. When editing, narrow or broaden the scope based on what you care about most.

Limitation: A report is only as good as its sources. For sparse topics, AI may lean on publishers with flimsy fact-checking. Specifying preferred sources can help. Afterwards, check the source list. Spot-check the citations, which don’t guarantee accuracy.

Each Model’s Strengths: Perplexity races to return results in three minutes. It’s concise and clear. Gemini is also fast, and exports neatly into a Google Doc. ChatGPT produces exhaustive reports and helpful tables. It can sometimes take 20 to 30 minutes. Claude is similarly thorough. It researched 574 sites in 17 minutes for one report.

Examples: Copilot took 10 minutes to prepare this brief summary report about why some nations excel at the World Cup. Gemini’s analysis on the same query was much more detailed.

4. Learn Something New 🧠

Design Your Own Curriculum: Ask your AI assistant to guide you through whatever you’re curious about. Unlike textbooks or generic explanatory sites (e.g. Wikipedia) designed for anyone and everyone, an AI assistant can tutor you in ways you prefer. ChatGPT has Study and Learn mode. Gemini has Guided Learning. These prioritize helping you learn, not giving you answers.

Ask for diagrams, analogies, examples, or case studies that relate to topics or places or people that interest you. Get a detailed overview of key concepts in archeology, or a beginner’s guide to soccer’s offside rule. Specify your prior understanding. Ask follow-up questions. (My guide to AI for learning).

Space your learning over days or weeks. AI assistants excel at creating structured learning plans tailored to your schedule and interests. And they’re better now than they used to be at keeping track of what you’ve already learned.

The Infographic: A visual summary of this approach.

Summarize Your Learning Preferences

• Include context about what you want to learn, why, and how. Specify sources you prefer. Explain what you already know.

• Note whether you learn best by reading, listening, watching, or trying something yourself.

• Mention if you like quizzes, drills, or exercises you can do while commuting or during breaks at work. Ask for learning games.

• Ask for specific book or article recommendations using web search or deep research. Hallucinations are less common now, but ask for verification links and check them yourself.

• If you need a human learning partner, ask for guidance on finding one. Or ask for sample language you can adapt when reaching out to someone.

• Connect your calendar to ChatGPT or Claude to have the AI schedule learning time for you. Making the plan concrete increases the likelihood you’ll follow through.

Pro Tip: Request a learning plan you can print out. Get suggestions for useful experts to follow and strategies for avoiding learning pitfalls. Ask for help setting learning targets, measuring progress, choosing resources, and motivating yourself.

Short Prompt Template: Make a [timeframe] learning plan for me so I can learn more about [skill/topic] because [reasons for learning]. I’d like to spend [hours/week]. As a [beginner/professional/other skill level], I prefer to learn in [learning style]. I have the following [learning goals]. Include milestones, resources, and practice ideas.

Detailed Prompt Template

5. Make a Learning Dashboard 💻

You can ask an AI assistant to help you make an app to track reading or eating goals, fitness metrics, your Wordle streaks, or your book writing progress.

Try This: Describe an idea you have for a learning tracker. Experiment with Claude Artifacts or Gemini's Canvas. Or try Lovable or Bolt, specialized AI tools that make it easy for anyone to create a site or app. Glaze is another option for making a mini app that lives on your computer.

• Resources: Here’s my Glaze guide, and tips on making artifacts.

• Here’s a prompt template.

• Bonus: I like these examples of how journalist David Bauer uses AI.

How are you using AI lately? Leave a comment 👇

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ChatGPT, Gemini, and Claude aren’t your only AI options. To use AI privately for free, you can download local AI tools that run on your computer, not online. You can use them without a subscription, avoiding the risk of having sensitive info ingested into a large language model. The newest versions of private AI tools like Jan run on my 2021 Mac laptop, cost nothing, and are easy to use. They’re a good alternative to costlier AI platforms.

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🔰 How to get started

1. Download and install the free Jan. Other good free alternatives to consider include Msty, AnythingLLM, or LM Studio.

2. Open Jan and pick an open-source large language model. The model you use impacts the AI’s response style. You can switch anytime. I use the Jan-v1 model.

3. Close other processor-intensive apps on your computer, like video editing tools. That reduces the likelihood your computer will slow down.

4. Try your first query. Here are a few quick mini prompts to start with:

   1. “Summarize the pros and cons of using AI for [specific task].”

   2. “Turn my rough notes below into a short summary and bullet points.”

   3. “Turn this angry email draft to my service provider into a constructive message more likely to generate a helpful response.”

5. Adjust the app’s appearance settings, including font size and shortcuts.

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🕵🏻 5 reasons to use private AI

• Save money: Avoid subscription fees by running AI models on your own computer. Generate unlimited responses without monthly charges.

• Keep your data private. Using private AI on your computer ensures no data is sent to or stored on big tech firms’ servers. No conversations leave your device. You can even run these tools offline.

  • For sensitive legal, medical, financial or personal issues, ask questions without worrying about your data ending up in a large language model’s training data.

• Work offline: Having full offline access is handy whether you’re traveling without WiFi, working in a remote area, or hesitant to trust a random public network.

• Experiment with hundreds of open source models. Choose an open source large language model that suits you. Each is trained differently. Some are stronger at certain languages, others specialize in coding. New ones emerge regularly. Switch as often as you’d like. By contrast, ChatGPT, Claude, Copilot and Gemini limit you to the platform’s own models.

  • Tip: Use LM Arena to compare two models’ responses side by side.

• Reduce your environmental impact: If you run hundreds of daily prompts, a local AI app may mean less use of Internet infrastructure and remote data servers.

💫 Jan is a good, free, private AI tool

• Platforms: Mac, PC, Linux.

What I like about it

• Fast and easy to set up and use. Jan takes a minute to download and install. Using Jan is as easy as using ChatGPT, Claude, or any other chatbot, though you do have to make an initial decision about which model to use.

• Assistants. Create customized AI helpers for various purposes. One for translating Chinese, another for coding. Task it to “Act as a software engineering mentor focused on Python and JavaScript. Provide detailed explanations with code examples. Use markdown formatting for code blocks.”

• Projects. Organize queries into distinct folders for easy access to subjects of interest without searching through hundreds of threads.

• Integrations. Link Jan to Canva, Todoist, Linear, or other tools using MCP (Model Context Protocol) connections.

• Documentation and resources. Lots of useful documentation including a handbook and blog.

What’s Next: Jan AI is developing mobile versions for iOS and Android and adding integrations to link Jan to other services.

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A lot of summary apps have 5-minute, AI-generated book overviews. Shortform’s human writers and editors produce much fuller guides to nonfiction titles.

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🩺 A Jan case study

Becki Lee, a Senior Technical Writer, uses Jan to explore health questions she wants to keep private.

“I have a chronic illness I’m struggling to get diagnosed,” she emailed me. “So I created an assistant to help interpret test results and brainstorm possible explanations for my symptoms.

Obviously, it’s super important to take this with a grain of salt (a chatbot is absolutely no substitute for a doctor). However, this helps bubble up conditions I can research further on my own, and it also generates questions I can ask my actual doctor.”

Other free AI options for Mac, PC or Linux

Msty

The free version of this well-designed app has multiple unique features. Unlike Jan, which is completely free, Msty also has paid advanced features.

Its best free features include:

• A built-in prompt library with hundreds of options.

• Special focus and zen modes that strip away side menus.

• Create multiple personas, which are assistants with distinct personalities. Each can adopt a different style or approach in answering your queries.

• Knowledge Stacks let you import document collections for analysis. These can include PDFs, Word documents, PowerPoints, spreadsheets, lists of YouTube links, or even an Obsidian vault.

• Advanced features, like multi-step automations, require a paid subscription. I’ve only used the free version. It’s easy to use, powerful, and well-designed. I chose the Gemma 3 model from Google.

AnythingLLM

Like Jan, this is a straightforward open-source AI app that’s a good option for novice AI users.

How it’s different from Jan

• You can upload files for AnythingLLM to summarize

• Enable it to make simple charts

• Turn on Web search, which requires a free API key from Google.

• There’s also a new beta Android version.

Caveat: It’s not quite as nicely designed as Jan, and isn’t updated as often.

LM Studio

This more developer-friendly option is less simple for beginners.

What’s notable: Florent Daudens, an AI expert and educator who used to oversee daily editorial coverage at CBC/Radio-Canada, relies on LM Studio for private AI use.

I asked him why and he said, “It’s practical, with a user/developer-friendly interface, quick updates when new models drop, a server option, and helpful model compatibility info.”

In a LinkedIn post, Florent shared an example of using LM Studio on his laptop. He used Google’s Gemma 3 model to analyze plane photos for extracting registration numbers as an investigative journalist might, without sending data to external servers.

I wrote a related post on private AI mobile apps.

Limitations of private AI tools

• Feature limits. Many special features on other AI platforms won’t work on these private AI platforms. ChatGPT’s new Plug-ins for Canva or Figma, for instance, won’t work with private AI. You may not be able to export results directly to Google Sheets or Slack, as you can with other AI tools.

• No interactives or advanced visuals. You can’t create infographics and visual illustrations like ChatGPT’s. No coding and hosting interactive applications, as you can with Claude or Gemini. No advanced searches with detailed citations like those from Perplexity.

• Quality variation. Some open-source models have limited or older training data, so results for certain queries may be worse. For ordinary queries and text summarization, this quality difference may not be noticeable.

• Slower speed. Depending on your query, you might wait longer with some open-source models than with ChatGPT, Copilot, or other private AI platforms. Speed hasn’t been a big concern for me so far.

• Can’t handle as much text at once. A smaller “context window” means that private AI tools may not be able to analyze text blocks as large as those ChatGPT or Claude can handle. Some small language models may resort to skimming longer text. They may also be more likely to hallucinate details if asked for summaries of long, complex documents.

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Bonus resources 🧑‍🎓

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Craig: We’re all trying to make sense of a chaotic information environment awash in synthetic fakes, sophisticated scams, undisclosed ads, and unverified claims. It’s difficult to figure out what’s real, where it came from, and whether you can trust it.

I’m a journalist who’s spent more than 15 years investigating digital deception and teaching people how to spot it. Roughly a year ago I left a job at ProPublica to launch Indicator, an independent outlet that covers online deception and equips people with digital investigative tools and skills.

We all need to get sharper at finding and interrogating information, so here are four free tools I’d put in any curious person’s toolkit, and why each one earns its place.

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1. The Wayback Machine browser extension: Save a page and view its history

Use it to: publicly archive a page, and see at a glance how often it’s been archived before, and how a page or site has changed over time (screenshot).

The Internet Archive’s Wayback Machine is the biggest collection of webpage snapshots anywhere. But most people never use its best features. The free browser extension works with Chrome, Firefox, Edge, and Safari. It’s the best way to get the most out of the Wayback Machine.

First, you can save the page you’re on in the Internet Archive without having to copy the URL, navigate to archive.org, paste it in, and wait for it to capture. Just click the icon to open the extension, press “Save page now,” and the extension saves it to the archive.

The extension also offers a quick way to view historical versions of a page. Click “Oldest” and a new tab opens with the first capture of the page; or select “Newest” to see the most recent. The calendar icon will take you to the Wayback Machine’s full record of captures for the page.

The extension has a lot of customization options in Settings. Two of my favorites are in the Context menu (screenshot).

• “Wayback Machine Count” shows how many times the current page has already been archived (screenshot).

• If you find yourself on a dead site, “404 Not Found” instantly tells you if an archived version of the page is available.

Last thing: Go to archive.org and sign up for a free account. Then click the login icon on the extension (the arrow in the bottom right) and sign in. The pages you save with the extension will now be stored in your private archive on the site.

Wonder Tools subscribers can claim 20% off an Indicator Membership. It’s a great way to build your digital investigative skills. Get access to our investigative and research guides, original reporting, a monthly workshop, plus all recordings and increased access to OSINT Navigator (see below) to find the right tool for the job.

2. Ubikron: Preserve pages privately

Use it to: keep a private, timestamped trail of what you saw and when, organize screenshots by project, and make notes.

Web capture and archiving work on two levels.

• The Wayback Machine is for public capture: saving a page so it’s part of a (mostly) permanent archive that anyone can find and link to.

• Ubikron is for private capture. When you’re deep in research, you move fast: opening pages, following links, chasing breadcrumbs from one tab to the next. It can be hard to retrace your steps later if you weren’t recording where you went.

Ubikron is a continuous capture tool that you add as a Chrome extension. It automatically captures webpages as they load in your browser and stores them in folders in the cloud. You can stay in the flow of researching, confident it’s recording what you see.

To turn it on, click the extension icon in Chrome and flip on the “Navigation Recording” toggle:

You can also enable a hovering widget that allows you to quickly turn on and off recording (screenshot).

One important caveat: Ubikron grabs the top of the page as it first loads and does not automatically scroll down. So it doesn’t capture the full page as you navigate. But you can click the “Save MHTML/PDF” button to take a snapshot of exactly what’s in front of you.

You can also make a note as you capture a specific page or image within a page (screenshot).

To review your captures, click the red Ubikron icon in the center of the widget (or the extension icon). It opens a new tab where you can look over what you’ve saved. It also has a side panel (screenshot) where you can write notes and drag in screenshots.

Everything gets saved into a project folder you create. It’s also easy to switch between folders as you browse.

In the free version, your captures are stored on Ubikron’s servers. If you’re privacy-conscious, the paid version lets you run it on a server you control.

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3. Use Gemini to check if an image might be AI

Use it to: check a suspicious image, video, or audio file for an invisible watermark.

Synthetic images and videos are everywhere. If you suspect you’re looking at an AI-generated pic (or video), a reverse image search is a great first step. You should also run it through Gemini, Google’s chatbot. Upload a photo or a video screengrab and ask: “Is this AI?”

Important caveat: this doesn’t work on all synthetic media. It’s only useful if the content was created using Google or OpenAI’s generative tools.

I generally don’t recommend that people use synthetic media detection tools because of the risk of false positives/negatives. Here’s why this case is different. Google created watermarking technology called SynthID. It embeds invisible imprints into images, video, and audio made with Google AI models like Gemini and Nano Banana. OpenAI recently announced it will use SynthID for its images, too. The difference with SynthID is that it’s an invisible signal that’s embedded into the content at the point of creation. This increases, but doesn’t guarantee, the potential for detection.

As a test, I generated an image in Gemini, renamed the file, and removed the visible Gemini logo/watermark. Here’s the result (screenshot).

As of this writing, SynthID can only be detected in visual or audio content generated with Google’s tools, and for images generated by OpenAI tools. There are sites claiming they can remove SynthID watermarking, so don’t assume that the lack of SynthID means an image is authentic.

Warnings aside, it’s worth a shot. Gemini may also be able to detect if a file contains metadata that could assist with verification. (Metadata is information that’s embedded in the file itself.)

4. OSINT Navigator: Find investigative tools

Use it to: find the digital tools available for an investigative task.

My final recommendation is OSINT Navigator (OSINT = open-source intelligence), which we built with journalist and programmer Tom Vaillant. It’s free, and it’s the easiest way to discover useful OSINT tools.

Start by typing what you’re trying to do: “How do I find the owner of a website?”, “How do I investigate a social media profile?”, or “How do I trace a crypto wallet?” Navigator scans a dataset of more than 11,000 OSINT tools listed by 19 online toolkits.

Bellingcat, the nonprofit investigative outlet, maintains one such free toolkit; they and others let us check their lists every week and track what’s been added or removed. The result is, as far as we know, the largest database of OSINT tools. Ask Navigator a question and it returns tools recommended for your task.

You get 10 free searches a day if you sign up with your email.

I ran a query for “How do I track a ship’s location?” and it showed me an AI-generated summary (screenshot) that suggested five tools. Below that is more detail on those tools (screenshot).

If you’re starting an investigation and wondering what’s out there to help, it’s a good first stop. Over time, it can introduce you to the wider landscape of what’s available and who recommends it.

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I like remembering the good ol’ days of Internet 1.0. Some of my defunct early favorites:

• Sixdegrees was my first taste of a social network way back in 1997. I loved finding friends. The web felt like magic.

• Friendster, launched before Facebook, was fun. It peaked at 115 million users and a $53 million valuation. Domain guru Mike Carson recently bought the URL for $30k to revive it as a network for people you know in real life.

• Plastic.com was an early social news aggregator I relied on before Digg and Reddit. It was founded by , one of my favorite non-fiction writer/entrepreneurs, who went on to co-found NotebookLM.

• Google Reader was the most valuable early RSS reader. Before it was killed, I depended on it to read cool online writing and random blogs by my friends.

• Epinions, founded in 1999, was the most useful review site online, before the days of bot-generated, spammy reviews.

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In honor of that old Internet, I’m sharing a short piece below by Lizzy Spano of mymind, a private place online to save everything you care about.

(I wrote about the app here. It’s like a digital garden for saving your ideas and inspiration and keeping them organized and searchable).

Lizzy runs the excellent Mind Palace Substack on creativity, philosophy, and a bit of everything in between. Here’s her essay: 👇

Lizzy: On the old internet, you were in charge. You said “show me this” and then dug your own rabbit holes.

The new internet just says “you’ll probably like this” over and over to keep the feedback loop open.

The new internet steers your attention. Algorithms and AI-driven feeds reward continuity. Their survival depends on keeping you hooked. Every click, pause or reaction you give becomes a signal. That signal is used to keep you engaged and your attention moving in one predetermined direction.

Remember when you discovered new singles on MySpace and purchased each one with excitement, then became obsessed with the entire album for months?

Remember when you joined that weird niche chatroom and got in an argument for two hours with the handle @real_avril_lavigne8 who ended up being your best online friend for two years?

Remember when you were planning a trip and found a random site for a tiny local lodge or bed & breakfast instead of Airbnb recommending a room to you?

The beauty of the old internet was the manual process. It was HARD to find good stuff. That was the fun of it. You had to consciously dig and seek out what interested you, which further deepened your connection to it.

The things you found were random, scattered. They required you to pull them together and make sense of them in your own way. Using the internet was more of a creative act back then. You carved out this little corner of it that felt like yours only.

Now, ironically, we have the “For You” tab. A feed of garbage endlessly optimized to keep you scrolling. It doesn’t care about the quality or depth of what it’s showing you. It’s like spoon-feeding a child sugar cubes. We keep eating it and even start craving it. What was never really “for us” consumes our minds and our time to where we don’t really know what IS for us anymore. Four hours later we look up from our phones and have already forgotten everything we scrolled by, wondering why we feel like sh-t.

mymind (the product I work on) feels like the closest thing to the old internet I’m getting right now, which was our whole idea building it. I don’t see it as a replacement for the current internet, but more as a retreat.

It’s a private place online where you can escape and rest your mind for a little while. A version of the internet in which you control your attention. No feeds wasting your time, no ads convincing you to buy something you don’t need, no notifications distracting you. No algorithms putting you in a perpetual loop of the same tired aesthetics and ideas. In mymind you follow your own curiosity and build a space that’s entirely yours. I think of it as my private digital garden.

I’m not trying to avoid the internet entirely. It still offers so much. I’m just trying to change how I behave online so I’m not constantly responding and reacting. The passivity of that makes me feel like my life isn’t even my own. Like every thought I have, thing I purchase, opinion I form, place I go, emotion I have is actually manipulated by an algorithm to serve some other purpose.

I still use social media, and it still sometimes gives me little gems that open up my curiosity and lead me somewhere new. But now I try to be more conscious about finding sources and content that’s meaningful. Which is hard. Which is a lot more like using the old internet. You can see how I’m doing that in practice in this essay (I call it “bloomscrolling”).

When I do find those gems that actually feel like they’re FOR ME, I put them in mymind. I’m slowly building a treasure trove of things I care about in a beautiful, peaceful place away from the algorithms, where I can explore them deeper later or find connections between them. The way we did in the 90s and early 2000s, when it all felt so much purer.

The internet is still a magical place (Substack right now is proof of that) but more than ever, it requires intentionality and digging to benefit from it, instead of it benefiting from you.

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Google’s Pinpoint is now open to everyone. It’s a surprisingly powerful free tool for making sense of giant piles of digital stuff. (Before June 3, it was restricted to journalists and academics). Read on to learn more about creative ways to use Pinpoint; its new AI features and their limitations; and how Pinpoint differs from NotebookLM.

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How Pinpoint Works

Pinpoint lets you store and analyze hundreds of thousands of files so you can find tiny needles in gigantic digital haystacks.

• Pinpoint can transcribe hundreds of hours of audio and video.

• It also makes your handwritten text, scans, and PDFs searchable, like my enormous collection of scanned handwritten notes and whiteboards.

• Once Pinpoint processes your files you can search, summarize, and organize your collections.

• Pinpoint makes it easy to query, label, and extract data from hundreds or thousands of documents. It’s simple to use. No complex menus or commands.

Getting Started

• Start by uploading PDFs, emails, audio and video files, handwritten notes, or other file types.

• Each collection can have up to 200,000 files. You can have an unlimited number of collections, which function like folders.

• Journalists and academics can request “Pinpoint for Professionals,” which provides 100GB of storage. Others start with 1GB.

• Audio and video files can be up to 2 hours long and 8GB. The limits are much more generous than what other AI tools, like NotebookLM, offer.

• Pro tip: Create separate Pinpoint accounts for each of your Google accounts. That gives you more storage. It’s also how I keep personal projects separate from work. You can always download files you’ve previously uploaded. And request additional storage if you reach your limit.

Pinpoint Features to Try

• Scour through audio recordings to locate key moments. Pinpoint transcribes in more than 100 languages. Upload and transcribe your recorded presentations to review how you frame a particular topic. Or how water pollution is described in local council meetings.

• Explore text within images and handwritten notes. I’ve scrutinized my old handwritten notes for ideas and checked whiteboard photos for explanations I can improve.

• Share a document collection. Invite individual collaborators or publish a collection for public exploration. Giving readers access to source material can be a valuable form of transparency in journalism.

• Analyze an email or document archive. Assess a public email trove or document collection, like files from the Enron trial, for connections between politicians and companies, or financial impropriety.

• Focus your research on particular people, organizations, locations, or date ranges. Pinpoint automatically lists a collection’s most frequently-mentioned entities. Click on an entity to jump to exactly where it’s mentioned.

• Export important Gmail folders with Google Takeout in .mbox format. Takeout lets you export and back up anything Google hosts. You can then upload your email collection to Pinpoint to find patterns, or locate references to specific people, places, or organizations.

Pinpoint in Newsrooms

News organizations have relied on Pinpoint for award-winning investigations involving thousands of documents, including:

• Blind Spot by the Boston Globe (Pulitzer)

• Poisoned by the Tampa Bay Times (Pulitzer)

• Secret Sauce: Expired from North Carolina’s Blue Ridge Public Radio (BPR) (Edward R. Murrow Award).

  • Z. Waite’s detailed case study explains how and why BPR used Pinpoint. Waite also notes four good, free, alternative tools: DocumentCloud, Datashare, OpenRefine, and Datasette.

Public Collections

• Pinpoint’s “Explore” section lets you examine document collections from more than 200 news organizations, ranging from The New York Times and The Washington Post to The Hindu and Süddeutsche Zeitung. Test out the searching and filtering features before uploading anything.

• Notable document sets include JFK assassination records, Mueller Court filings, and 80 years of U.S. foreign agent registrations (86,018 documents) uploaded by the Center for Public Integrity.

New AI Capabilities

Pinpoint has a bunch of new AI features in beta available in more than 80 countries. In my testing, not all of the AI capabilities work reliably yet, but you can request early access. Pinpoint’s AI features are designed to help you analyze your files, not generate original content as you might with Gemini or NotebookLM.

1. Explain words or phrases in any file. Highlight any text and ask Pinpoint to put it in context. I like the short, useful explanations based on what else is in a document.

2. Google words or phrases inside your text to learn more from Google. In my tests, this beta feature consistently yields error messages.

3. Summarize Collections. I like how Pinpoint gives me an AI-generated overview of every file I upload. It can also summarize an entire collection.

   

4. Extract data into spreadsheets. Pull info from up to 100 documents at once and deliver it as a sheet, with links back to the source text for each data point. That’s handy for tracking mentions or doing comparative research. Try this feature for analyzing public government contracts or other information in PDF form that would be easier to work with in a spreadsheet.

5. Automatically label hundreds of your files in a collection. Let’s say you have a public email dataset. You may want to evaluate just those written by a particular person, or just those discussing a particular stock. Instruct Pinpoint and it will label your collection for you. Limitation: Pinpoint can label 1,000 files at a time. In my tests, the interface only let me select 100 files. If you’re working with tens of thousands of files, labeling may be tedious.

6. Transcribe audio quickly. Pinpoint now claims to give you high-quality transcribed text 20x faster than it used to. I couldn’t verify that specific metric, but it’s generally fast. Each file is helpfully time-coded. Click on any section of text to hear the corresponding audio. Limitation: unlike Wispr Flow and Letterly, which I use for my personal dictation, Pinpoint sometimes mangles names, and doesn’t learn from its errors.

   

7. Compare any two or three files. See what changed in multiple versions of a document, or how three different people addressed the same subject.

8. Query your collection with ordinary language. Results are often fast, useful, and linked back to the original document. Expect occasional errors, though. One search I tried, for example, returned a document mentioning someone with a similar but different name from the one I was searching for.

9. Create a timeline. If you’re looking at how something developed over time, you can pick up to 100 files and generate a timeline. You can optionally specify a topic for the timeline. This might be useful if your dataset has dated transactions, for example, or multiple reports you want to put in order.

Pinpoint vs NotebookLM

• What’s similar: Both NotebookLM and Pinpoint are free Google services that allow you to efficiently summarize and search though large documents.

• What’s different: NotebookLM synthesizes and generates (slides, infographics, video and audio podcasts, and reports). Pinpoint, on the other hand, focuses on finding patterns and organizing a wider array of file types in much larger collections of email, multimedia, and scanned images.

  • NotebookLM allows 50 files per notebook for free users. (See my guide). Pinpoint lets you upload 200,000 files into each collection.

• Combine the two: If you have a large collection of documents, consider gathering, storing, organizing, and transcribing in Pinpoint. Then move the most important files into NotebookLM for further analysis and to generate artifacts like reports, slides, infographics, flashcards, audio, and video.

Privacy

• Your documents are private. Nothing you upload is public unless you publish a collection. Read Google’s Pinpoint privacy details.

• Your files are not used to train AI models. Google explicitly notes that documents you upload won’t be used to train Large Language Models. Read Google’s statement.

• The bottom line: I trust Pinpoint for non-sensitive document work. But because uploads are processed on Google’s servers, Pinpoint may not be a fit for everything or everyone. Here are additional privacy details.

Limitations

• No mobile app. You can view docs on a phone browser, but not all features work.

• No NotebookLM integration yet. You can’t easily move files from one service to the other.

• Storage caps. On a 1GB account, you may hit storage limits with large files.

• AI features aren’t error free. No AI implementation is.

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AI is leading to a boom in email slop. I get hundreds of marketing messages every week. Many seem AI authored.

I’m not alone in getting swamped. The average worker now gets 117 emails a day, according to Microsoft's Work Trend Index Report. Only 24% require an action, per SaneBox’s report.

I still use Superhuman for my primary email. It lets me act on messages quickly. It has helpful calendar functionality so I can schedule meetings without having to switch apps. But it doesn’t yet have a universal inbox for my three distinct addresses. I have to check each separately, trudging through each box’s digital slime.

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Two inbox cleaning tips

1. If newsletters are clogging up your inbox, read them in an app like Meco or Readwise Reader. These dedicated readers keep your newsletters organized separately from personal and professional messages you have to respond to. We listen to podcasts and watch videos in separate apps, so why not newsletters?

2. Try a tool like Yorba for quickly and permanently unsubscribing from spam and irrelevant mailing lists. (Paid subscribers to Wonder Tools get a free year-long subscription to Yorba as a perk).

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I’ve begun assessing a slew of other new email tools to cope with the sludge. I’m not ready to write about them yet. But if you’re curious about new services to explore, here are a few I’m testing, along with the benefit each promises:

• Cora: Screen your email and get two daily briefs. It’s made by Every.to, a media and software company I like. I pay to subscribe.

• Clean Email: Organize your mailbox with smart folders and filters. Dump junk more efficiently. Especially useful if you’re running out of inbox space.

• Shortwave: Prompt an agent to organize, schedule, write and search your inbox. I mentioned it in my piece on email efficiency.

• Talanoa: Sort your email by sender, not by chronological order

• Extra: Organize your inbox in auto-organized categories like travel, news, and receipts. Founded by Pinterest’s former Chief Product Officer, it’s invite only for now, with a waiting list.

• Filo: Pull tasks out of your inbox with an AI email agent.

Other AI email assistants, like Fyxer and Stamp, focus more on corporate use. Some focus on privacy, like Fastmail. Or like Missive, they’re made for teams.

The biggest tech firms are also rethinking email: Google is adding AI capabilities to Gmail, as are Microsoft with Outlook and Apple with Mail.

I’m exploring a bunch of these new tools and tactics this summer. Which email tactic/tool are you finding most useful? Leave a comment 👇

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For more on cleaning out unwanted mail, I’m handing off to Jared Newman, who writes the helpful Advisorator newsletter.

Jared Newman: Cutting down on those unwanted emails is easier than you might think. Whether it’s marketing junk, social media updates, or even (gulp) a no-longer-desired newsletter, here are some quick ways to get yourself off those mailing lists:

1. Search for “unsubscribe”

Under U.S. law, every company that sends you email also has to let you unsubscribe. That usually means they’ll include a little “unsubscribe” link at the bottom of the newsletter.

Searching your inbox for the word “unsubscribe” will therefore turn up a list of every company that’s sending you bulk mail. (You can also try searching for other terms like “opt out” or “manage your preferences.”) Click on the sender’s message, scroll to the bottom, and click the unsubscribe link to opt out.

Using Gmail, Yahoo Mail, or Apple’s Mail app? In Gmail and Apple Mail, you may see an “Unsubscribe” button at the top of the message, no scrolling required. With Yahoo Mail, click the “…” button while viewing a message, then click “Unsubscribe.”

2. Use your email app’s subscription manager

Gmail, Yahoo Mail, Outlook.com, and Proton Mail all have features that round up your bulk mail and let you unsubscribe with one click:

In Gmail: Click the “Manage subscriptions” button in the left sidebar menu, or head to https://mail.google.com/mail/u/0/#sub on Gmail’s desktop site. You’ll see a list of all bulk senders, arranged by how often they email you, plus a link to unsubscribe from each one.

In Yahoo Mail: Look under the “Views” tab in the left sidebar, then click the “Subscriptions” button. You’ll see a list of bulk mailers and options to unsubscribe from each, plus a separate “Unsubscribed” tab where you can opt back in later.

In Proton Mail: Look under the “Views” tab in the left sidebar, then click “Newsletters.” You’ll see a list of senders and how often they email you, plus an option to unsubscribe or move their messages to a folder. There’s also an “Unsubscribed” tab for opting back in.

On Outlook.com: Head to Settings > Mail > Subscriptions. Look under “Your current subscriptions” and select Unsubscribe for the messages you don’t want.

Heads-up: These lists can include things like travel booking sources and order confirmations. Before you unsubscribe, look at the sender’s messages to make sure you won’t miss anything important.

3. Sort email into categories

Some email apps can automatically sort messages into categories, ensuring that only the most important messages reach your inbox. Gmail and Apple’s Mail app, for instance, can sweep up marketing emails into a “Promotions” tab, while Yahoo Mail does the same with its “Offers” tab. Sorting your emails this way makes it easier to skim over and delete those that aren’t as important.

You may have these categories set up already. If not, see the documentation for Gmail, Yahoo Mail, and Apple Mail.

4. Use email aliases

The next time you sign up for a new app, service, or newsletter, consider using an email alias or masked email address instead of your actual address.

Some Gmail users, for instance, have signed up for my newsletter with the address theirname+advisorator@gmail.com instead of just theirname@gmail.com. (Gmail ignores the + and anything after it, so the messages will still get to you). That way they’ll know who to blame if I ever start sending out spam, and they can set up filtering rules to sort my messages into a folder.

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JC: For more of Jared’s tips, check out his useful Advisorator newsletter.

I love new gadgets and gizmos, and I’m constantly trying new sites and apps. So I was intrigued by the title of ’s upcoming book, Saying No to New.

Eric’s an editor at the New York Times, where he helps journalists make the most of new tools. He’s also a lifelong early adopter. He told me he used to wait in line for new iPhones. But his upcoming book is about thinking twice about new stuff.

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In our Substack Live conversation, we talked about old gadgets we still love and new gadgets we never use. Eric shared advice on how to tell the difference between things that might genuinely improve your life, and gizmos that will end up at the back of a closet. We even did a little show and tell with various odd gadgets in our offices.

📺 Watch the full conversation above, or read highlights below.

1. The Vanishing Gap Between Wanting and Getting

When Eric and I were growing up, if you wanted to buy something cool you saw on TV, you’d have to drive to a store. You or your parents would have to spend cash. If you ordered something by mail, you’d wait weeks for delivery.

Today, you can tap on a phone and the thing that caught your eye appears at your door the next day. You can even buy now, pay later, so you don’t need cash. Coming next? AI agents that shop for you proactively. They anticipate what you want so you don’t have to make any decision at all.

Eric calls this the collapse of the “new thing gap.” The time, distance, and cost between seeing something new and acquiring it has shrunk. That gap used to protect us from buying on impulse.

• One-click ordering eliminated distance.

• Free shipping removed the physical effort of the pickup errand.

• Deferred payments eliminated financial friction. You don’t even need the money.

Eric suggests we reintroduce friction by pausing long enough to ask whether the new thing will actually matter a month from now.

2. Show and Tell: Our Gadget Graveyards 🎪

Eric and I compared old odd gadgets in our offices.

From my desk:

• Multiple VR headsets. I have at least three, including one with the plastic still on it. You slot your phone in, close it up, and get an immersive view. Remember when the New York Times announced in 2015 it would ship a million Google Cardboard VR headsets? Eric confirmed that the headset now lives in the Times’s in-house museum.

• Lumo posture band. This posture sensor had a belt that wrapped around my waist and buzzed when I slouched. It was a cool, if weird, concept, but the buzzing was distracting, I still slouch, and the product was discontinued. It’s lived in my drawer for years.

• PLAUD AI recorder next to my brother’s old tape recorder. The old one has a red record button, a play button, and a stop button. You know exactly what to do with it. The Plaud is sleeker but less intuitive.

• Sand timer. This one is both decorative and useful. It’s silent, easy to use for timing, and never needs to be charged. I use it to stay focused during hard tasks.

From Eric’s desk:

• A USB coffee mug warmer. Cracked. Unused. Eric’s take: once you introduce a USB cord into the coffee experience, it loses its magic.

• NeeDoh stress balls. A kid craze. Eric’s children wanted them, squeezed them for a day, and abandoned them. He wrote about the NeeDoh fad here. I have multiple stress balls, and I use them often. Consumer Reports warns they can create a sticky mess or worse.

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3. New Things Worth Saying Yes To ✅

Eric’s book isn’t about rejecting everything new. It’s about choosing things thoughtfully so the genuinely useful things don’t get crowded out. Some of the new tools we like:

• Seek app. Free. Point your phone at any plant or animal in nature and learn what it is. I discovered it during the pandemic and still use it regularly.

• Merlin app. Free. Record birdsong and the app identifies the species. Eric and I are both fans.

• Granola. AI meeting summaries. It’s now part of my workflow. Here’s why. It’s infrastructure for me, not novelty. Free for basic transcriptions and summaries. I pay $14/month for additional features, like storing meeting notes for months and querying them with Claude.

What these tools have in common: they solve a real problem, they’ve lasted, and we’ve stuck with them.

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4. Our Brains Chase Seductive Novelty 🧠

Eric’s new book is grounded in neuroscience. When we encounter something new, we get a dopamine hit. That neurological response evolved to help our ancestors survive. New food sources, new paths, new shelter: those discoveries were rewarding.

But sometimes novelty seduces us without offering anything meaningful. In one study Eric described, rats repeatedly crossed an electrified grid just to explore an unfamiliar area. They chose pain plus novelty over a known food source. Humans do something similar. We covet a new phone partly for its camera, but partly just because it’s new. Then we do it all over again. Even if we can’t afford it. That’s one reason why so many Americans are in debt.

I recently read Dopamine Nation, a surprisingly engrossing book by Dr. Anna Lembke, about how our brains are so readily seduced by pleasure.

What results is an unfortunate cycle. We get something new, enjoy it briefly, and soon we’re scanning for the next new thing. My college advisor, Daniel Kahneman, studied and wrote about this “hedonic treadmill” effect.

His research showed that we overestimate how much a new purchase will improve how we feel. And novelty tends to wear off quickly. He called it “hedonic adaptation.”

That doesn’t mean we should avoid all new things. But it does mean we should think carefully about whether there’s something genuinely meaningful behind the new shine.

5. Experiences Outlast Products 🎒

Research shows that trips, cooking classes, concerts, and other new experiences tend to give us more lasting delight than new products do.

That’s partly because experiences tend to be social. You go with someone. Or you meet people there. You talk about it afterwards. Trips have a beginning, middle, and end. You have a story you can retell. A new pan doesn’t generate much conversation after the first week. Its novelty fades fast.

Kahneman, who was one of the best teachers and advisors I’ve ever had, introduced me to the related “comforts vs. pleasure” theory. It was originally described by Tibor Scitovsky in The Joyless Economy: The Psychology of Human Satisfaction. It changed the way I think about spending money.

Comforts are things we buy and then quickly adapt to. A nicer couch. A bigger TV. They feel great at first, then they fade into the background.

Pleasures, on the other hand, are transient experiences: a delicious dinner with friends, a live concert, surprise flowers, or a summer walk with someone you love in a new city.

These kinds of experiences are brief, but they retain their emotional charge when you reflect back on them. Kahneman’s argument, supported by numerous studies, was that pleasures enhance happiness more durably than comforts, because we don’t adapt to them. The research findings’ bottom line: if you want more happiness, splurge on special experiences with loved ones rather than expensive things.

Eric’s suggestion: if you’re drawn to something new, try turning the purchase into a social experience. Waiting in line with a friend for trendy cookies transforms a dopamine-seeking buying excursion into an experience and a fun shared memory.

recently made a compelling video on the same theme: how to spend money so it actually makes you happier. His take aligns with Eric’s and Kahneman’s. Spend on experiences, not things.

6. Ask These Questions 🔍

Eric suggests a few questions to ask before you acquire something new:

• Will I still use this in a month? Will this serve an ongoing purpose, or will it get stuck in the background? (I’ll use this one the next time I’m tempted by a kitchen gadget or iPhone app).

• Is it intuitive to use? Eric points to modern car dashboards as a cautionary tale: touchscreens that look futuristic can end up being more confusing than the knobs and buttons they replaced.

• Is it likely to distract you? A sand timer, a paper book, a physical photograph: these do one thing well without pinging you. A single-purpose app on your phone, on the other hand, puts you one swipe away from email, Instagram, and other Internet rabbit holes.

7. Good Enough is Sometimes Enough 👍

Eric’s coffee maker still works. His wife wants him to upgrade. He resists, not out of stubbornness, but because it does exactly what he needs. He programs it at night. He wakes up to fresh coffee. No learning curve.

His suggestion: before replacing something, ask whether what you already have is still good enough. Something better always exists, but if the upgrade is just about novelty, it might not be worth the effort, expense, or space.

I have more than 600 apps on my phone. I use only a small fraction regularly. But I’ve realized that going back and manually deleting everything I’m not using is a waste of time. In the digital domain, unlike the physical one, unused things don’t take up much space. Going back and deleting emails or apps one by one feels like more of a waste than letting them sit idly in the graveyard.

8. Paper Books and Quiet Treasures 📖

About two-thirds of Americans still read books on paper despite the convenience of ebooks. Part of what’s appealing about them is sensory: the way pages turn, the way a book feels in your hands, the smell of the paper.

But there’s another advantage. A paper book doesn’t send notifications. It offers no tempting apps. The same goes for vinyl records, Polaroid photos, sand timers, and handwritten journals. Each of these enables you to deeply focus on what you’re doing.

My grandfather taught me to use a Minolta camera when I was little. The quality of its pictures doesn’t match that of an iPhone. But old objects like the Minolta have intrinsic value beyond their function. A hand-me-down camera is a reminder of love.

I have more than 50,000 photos on my phone. That abundance, paradoxically, devalues each individual image. When film was limited and developing took days, every picture felt more precious. Anticipating which pictures might turn out was part of the thrill of photography. I don’t want to return to that era. But the photos my wife and I have printed and framed mean more to me than many of the ones sitting in my phone’s camera roll.

9. Choices Are Contagious 😷

The last chapter in Eric’s book is about invisible influence. If your friends are constantly upgrading their homes, devices, or apps, you might feel the pull to keep pace. It’s tempting to follow the cultural lead of those around us.

The reverse is also true. Choosing to stick to what you have quietly signals to other people that it’s okay to keep the old thing, to skip the trend.

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Read more 📚

• Saying No to New Available for pre-order. Out September 15 from Balance.

• Eric Athas on Substack Behind-the-scenes updates, pre-order bonuses, and a decision-making tool tied to the book’s ideas.

• Dopamine Nation by Dr. Anna Lembke. The neuroscience of novelty-seeking. Eric and I both referenced it.

• The Joyless Economy by Tibor Scitovsky. A psychology classic about what impacts happiness and how comforts differ from pleasures.

What’s a new thing you say no to? Leave a comment 👇

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Thank you , , , and many others for tuning into my live video with and thanks to you, reader, for making it all the way down here to the end of this post.

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How Glaze is Different: Unlike other vibe coding tools, like Lovable, Bolt, Gemini Canvas, Google’s AI Studio, or Claude Artifacts, Glaze creates software that runs locally on your computer, not on the web. That means:

• Your apps works offline

• Your data stays on your machine

• Apps you make benefit from your computer’s file system, keyboard shortcuts, menu bar integration, and background processes. They’re more like real software than the browser apps other vibe coding tools generate.

Platform and Pricing: It’s Mac only for now. It’s free to use with limits, or $20/month for additional credits. Join the waitlist at glaze.app to get an invite.

The Team: Glaze comes from the startup that makes Raycast, my favorite launcher app. (Why it’s so useful.)

The First Apps I Made with Glaze

I began by making tiny apps. Four steps: plan, create, refine, and publish.

1. Box Breath One-minute meditation breaks. Built in 12 minutes.

2. A links app for storing URLs I use often, so I can copy them to my clipboard quickly. Built in 10 minutes.

3. QuotePop, which can turn any text or quote into an image file. I use the images for presentations and social sharing. I can customize the image dimensions, style, and gradient background. Built in an hour.

Here’s an example of QuotePop in action:

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Free Public Glaze Apps I Like

• macHealth Identify battery, memory, or other issues impacting your laptop. Quickly find out why your Mac is slow (screenshot). (I also use separate software, CleanMyMac, to diagnose issues, but it takes longer and isn’t free.)

• Pinfont Preview text across all your fonts to pick one you like (screenshot)

• Focus Soundboard Play sounds together to help you focus (screenshot)

• Silly Sounds Press keys to make playful noises. Useful for nothing in particular. 🤪 (screenshot)

• Word Connections An offline version of the NY Times game (screenshot)

• PDF and Image Merger Combine multiple PDFs and images (screenshot)

How to Get Started

1. Join the waitlist at glaze.app. When you’re invited, download & install Glaze.

2. Explore the Glaze “store,” a collection of free apps people have built.

3. Download and try a few to see what’s possible.

4. Open Glaze’s planning mode. Explain in detail what kind of app or game you want.

5. As Glaze prepares your app, it may ask about your feature or design preferences. Answer those questions.

6. Once you’re happy with Glaze’s plan, which it will summarize for you, tell it to build. Then test the app and ask for improvements.

7. Keep your app private or publish it to a group or the public store.

Pro Tips

• Customize Glaze’s Instructions. Summarize your preferences in Glaze’s settings (screenshot). That way your apps will have your preferred design elements or features.

• Include options for your apps. Instruct Glaze to give anyone using your app choices. In my QuotePop app, for example, you can pick your image dimensions, background color, and font.

• Plan first. The clearer you are about what you want before Glaze starts building, the fewer credits you’ll burn on rework. Put Glaze in planning mode to start. Or, if you already pay for another AI tool like Claude or ChatGPT, plan there and give Glaze a summary. That saves your Glaze credits for building.

• Iterate to improve. Once Glaze builds the first version of your app, give it a list of fixes to improve the app’s design or make it easier to use.

Limitations

• Mac only for now. No specific timeline for Windows and Linux.

• Credits for complex apps may be costly. More intricate iterations use more credits. If you’re using Glaze for free, you may run out of credits and have to pay for more. If you’re making multiple complex apps, expect to pay $20/month for a subscription, at least while you’re building and refining.

• Local only, not mobile. If you use multiple computers, you’ll have to install and use Glaze separately on each. You won’t be able to use your apps on your phone or tablet, as you can with web apps.

Alternatives

Lovable lets you create sites and apps with no code. Start with a text prompt, attach a screenshot of something you like, or build on the template gallery | Pricing | Example: Color Drenching, an exploration of the interior design trend.

Bolt also lets you make a web app or landing page with AI prompts. You can use your brand guidelines to match company designs. | Pricing | Example: I mocked up a landing page design for Amazing Animal Tales.

Claude Artifacts works well for quick interactives like flashcards, quizzes, calculators, mini-games, and simple visualizations. Unlike Glaze, Claude Artifacts and the other alternatives noted here don’t create local software that lives on your computer. Examples: my flashcard maker and a 60-second breathing app. Free. For more, see my full guide to Claude Artifacts.

Gemini Canvas is easy to use for building apps, games, dashboards, or interactive infographics inside Gemini. Feed in a document to have Canvas design an app around it. Make a quiz game from your vocabulary list, or a dashboard from your metrics file. Free. Example: my simple alt-text generator (which I used for this post) works for five images at a time. | My guide to Gemini |

Google has several other good free options. Each has useful templates to help get you started. AI Studio (video) is its most powerful, though the interface can be intimidating for beginners. Stitch lets you vibe code mobile app designs. And you can guide Opal (video) to design Web apps by linking together various skills and steps (screenshot).

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I love Vanderkam’s books about how to make the most of time.

It’s never about stuffing more into our days. It’s not about productivity. It’s about savoring and being creatively thoughtful about what we choose to do.

Her books 168 Hours and Tranquility by Tuesday changed how I think about my own weeks. For example, her argument for “effortful before effortless,” nudged me to spend more of my discretionary time on my hobbies.

Her latest book, Big Time, new this week, makes the case for time abundance: we have more time than we think, and there are surprising ways we can savor it.

In our live conversation May 7, we talked about why weeks matter more than days, how to make work more satisfying with small changes, and why your weekday evenings may hold more free time than you realize.

📺 Watch the full conversation above, and read highlights below.

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My Favorite Ideas from Our Conversation 💡

1. Your Life Is a Circus. Be the Ringmaster. 🎪

When people say “my life is a circus,” they mean chaos. Laura says that’s a slander against circuses. A real circus is a super-organized performance. Nobody gets shot out of a cannon at the wrong time.

She thinks of life as a well-orchestrated three-ring circus: career, relationships, and self. You’re the ringmaster. Each ring may have a bigger or smaller act at any given moment. A good circus is managed for delight. You want to run a show you’d actually want to watch.

The circus also needs a safety net. Complex lives require backup plans so that complexity doesn’t descend into chaos.

2. Think in Weeks, Not Days ⏳

There are 168 hours in a week. That number matters more than 24.

If you work 40 hours and sleep 56, you still have 72 hours for other things. That’s not all free time. But we have much more discretionary time than we often realize. Laura says the time-crunch feeling often results from looking narrowly at today. Zoom out to the week and you’ll often see more room.

3. Track Your Time Simply 📊

Laura tracks her time on a basic Excel spreadsheet. Half-hour blocks. Monday through Sunday. She checks in three times a day and jots down what she did since the last check-in.

She doesn’t make pie charts. She uses plain language: “Email.” “Cooking.” “Reading.” “Driving.” Whatever you’d casually tell a friend if they asked what you were doing right now.

At the end of each week, there’s room to reflect. What were the highlights? What did you enjoy most? What was most memorable this week? What was frustrating? She then archives the log and opens a new one.

Laura has been doing this long enough that she can now pull up an old log from the same week in a prior year. She recently compared this past April with April 2020. She now has a kind of personal time capsule. (My wife and daughters use Gretchen Rubin’s 5-Year One-Sentence Journal for a related time capsule).

Tip: You can use Laura’s simple, free time-tracking spreadsheet. If spreadsheets feel like too much work, try Toggl. I use Rize, which automatically categorizes my time so I don’t have to remember to log.

4. Enjoy Work More with 3 Small Experiments 🔧

Laura tested three tactics with hundreds of people over three weeks. Each tactic helped people feel more satisfied with their work to a statistically significant degree. The approaches don’t require that you change your job. They also don’t depend on you having a ton of autonomy. So they’re designed to work for all sorts of roles.

• Spend one more hour per week on the work you like best. Every job has tasks you prefer. Even a short conversation with a manager can shift the balance toward more of those. (This reminds me of “job crafting,” a tactic I once wrote about for Time Magazine).

• Spend 15 more minutes per week at work with someone you like. Friends at work are people you’d willingly spend time with outside the office. Social time at work matters more than we may realize.

• Take two intentional breaks per day. Everyone takes breaks. Most are unplanned. When you decide in advance how you’ll spend a break, you can choose something rejuvenating rather than defaulting to scrolling or other screen time.

One participant in Laura’s study told her: “I thought about leaving my job. I may still do that. But now I see ways to make work better whether I quit or not.”

5. Reclaim Your Golden Hours ✨

Golden hours are what Laura calls the stretch of weekday time after work and before bed. For most people, that’s roughly 6 p.m. to 11 p.m. Five hours.

Laura’s challenge: set one golden hour intention each day. Thirty minutes of something you chose and genuinely enjoy. Not work. Not housework.

It might be: reading. A puzzle. A walk. A board game. Playing music. Even watching a movie with a loved one, if you chose that.

The point is awareness, and intention. Once you claim 30 minutes of chosen leisure, you’re less likely to tell yourself the story that you have no free time.

Laura also noted that Golden Hours is the title of her next book. Given that this book just came out, I’m impressed that she’s already ready for the next one.

6. Try Effortful Fun Before Effortless Fun 🎯

This was the most memorable and useful tactic I learned from Laura’s previous book. It pops up again in this one. Here’s the idea: when your schedule allows for a bit of leisure time, start with at least a few minutes of something that takes effort, before you default to screens or other mindless activity. Read three pages of a book before opening Instagram. Start drawing or playing an instrument (my choice) before picking up your phone.

One of two things will happen. You may get absorbed in the book and keep going. Or you might switch to Instagram anyway, but at least you’ve enjoyed a few minutes of something you care about first.

Laura likes taking on big, year-long projects, like listening to all of Bach or Beethoven, or reading all of Jane Austen or Shakespeare, all of which she’s done in years past. Those all require just 10 pages a day or listening to one piece. If you sprinkle your days with effortful moments, you’ll get deep into projects you care about over the course of a year. If not, you’ll have a year’s worth of scrolling or other mindless diversion that may not add up to something memorable.

Laura’s insight: effortful fun is especially enjoyable and valuable once you clear the initial hurdle of getting started. But when you start with effortless fun, it’s easy to get sucked in and hard to switch to something effortful with more friction.

7. Go Outside After Dinner 🌿

Laura’s family uses the acronym TOAD: Time Outside After Dinner. Once daylight extends past dinner, go outside. Walk. Play. Just be out there. It breaks the default drift toward screens during the post-dinner hours.

8. Practice Active Patience 🌱

Some things just take time. Laura talked about how her books reveal themselves slowly as she writes them. She may start with a detailed outline, but the nuances within each chapter emerge gradually.

A piece of music becomes part of you only after many hours of practice. I’ve spent years on some of my favorite violin pieces; I often find new wrinkles, like dynamics or articulation marks I hadn’t paid much attention to, even after I’ve spent hundreds of hours looking at the music.

After 11 years of tracking, Laura knows exactly what fits in 168 hours. Her weekly priority lists are short and realistic. If something is on the list, she’ll do it. If not, she’ll push it to a future week.

That precision eliminates guilt. She doesn’t assign herself things she won’t actually do. And she doesn’t feel bad about things she deliberately chose not to do this week. If you occasionally feel guilty about not doing enough, as I do, check out I Didn’t Do The Thing Today: Letting Go of Productivity Guilt, by . It’s a brilliant take.

9. Leave Room to Say Yes 🚪

Most productivity advice is about saying no. Laura flips that. Almost all new opportunities, relationships, and breakthroughs come from saying yes to something you’re not entirely sure about.

The reason to clear your schedule isn’t just to have less going on. It’s to create the mental space to say yes when something unexpected appears. If you feel completely swamped, you might not even consider new possibilities. Managing mental load isn’t just about getting things done. It’s about staying open to what could come next, and allowing for serendipity. It’s about being open to what Laura calls little bets, giving time to something new that might end up being terrific.

Tip: In his book, Flourish, Daniel Coyle describes this approach as opening yellow doors. They’re yellow (like a yellow traffic light) because they aren’t a clear GO. You’re not sure where they’ll lead. You may instinctively resist them in favor of more obvious green doors. Coyle points out, as Laura does, that these yellow doors can lead you to surprising places you wouldn’t otherwise go.

10. This is Probably Not Your Last Day 🐾

“Live every day as if it’s your last” sounds inspiring. But it’s not practical for consistently making real decisions about how we spend our time.

If everything was about living for the moment, you wouldn’t save money, learn a new language, or practice cello. Planning would seem futile or foolish.

Laura prefers a different frame: ”Someday we will die. But on all the other days, we will not.” She attributes it to a Snoopy cartoon.

Most days are not the last day we’ll be alive. It’s worth investing in things that pay off later. Build skills. Start the long project.

The Social Security Administration publishes actuarial tables if you want reassurance about your own life expectancy. For most ages, your odds of making it to next year are excellent. That’s true whether you’re in your forties, like Laura, or 92. Interesting fact: Only when you’re 105 do your odds of dying within a year start to exceed 50%, according to those tables.

11. Make Fewer Decisions. Rely on Presets 🍝

Laura’s family has a routine meal schedule. Pasta on Mondays. Fajitas on Tuesdays. Breakfast for dinner on Thursdays. (They love bacon). Weekends are for trying something new.

That approach extends beyond food. Sticking to formulas frees up mental energy for things where decisions are crucial. You’re not being boring. You’re being strategic about where your decision-making efforts go.

Jeff Bezos and other visionary leaders talk about separating reversible small decisions from impactful ones that can’t be reversed. If you don’t like one lunch, you’ve got another one coming. If you fire someone or leave a partnership, you may not get an easy redo.

Laura’s Simple Toolkit 🧰

Laura doesn’t focus much on tech. Here are a few tools she relies on.

• Microsoft Excel for time tracking. Basic spreadsheets, half-hour blocks, simple categories.

• iPhone Notes App works well for scanning. Open a note, press the paperclip icon, then scan a permission slip, agreement doc, or some other form straight to PDF. You don’t need a separate scanner.

• Toggl for time tracking if you prefer an app over a spreadsheet. The free version works well. It works on your computer or laptop, and integrates with many other apps. I use and recommend a different app called Rize.

• Two laptops. She started using two screens by accident when an old laptop couldn’t run Zoom. Now she writes on one and references notes on the other.

• A digital recorder for her brief daily podcast called Before Breakfast. She batches episodes ahead of time and sends audio files to her production team.

On AI ✍️

Laura loves both writing and puzzling. She says using AI for writing would be like paying a robot to do a puzzle for her.

She has used it for brainstorming and research. She once asked for a list of productivity newsletters. About half the results were ones she already knew. Half of the rest turned out not to exist. But some of the results were useful discoveries.

She’s open to the idea of feeding time logs into AI for pattern recognition. Her take: it’s a bit like a tarot reading. If you agree with the AI’s categorization or summarization, you’ll think the results are great. If you don’t like the AI’s assessment, you’ll assume it malfunctioned.

For my own takes on AI, check out my AI-related posts.

Laura’s Resources 🎁

• Free time-tracking spreadsheet: lauravanderkam.com/manage-your-time

• Before Breakfast Laura’s daily micro podcast with short weekday tips. I’ve listened to it for years. I love that each episode is just a few minutes long (though I tend to skip over the lengthy opening ads). She’s been publishing episodes daily since early 2019.

• Best of Both Worlds Laura cohosts this podcast with Dr. Sarah Hart-Unger, focusing on real-world issues that arise when balancing work and family. (Laura has five kids, aged six to 18, so she speaks from experience).

• Big Time Her excellent new book on time abundance.

• Tranquility by Tuesday and 168 Hours Two of Laura’s best prior books, both worth reading, both full of specific, practical, non-intuitive ideas that I’ve found useful.

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Thank you to my brother , , and many others for tuning into my live video chat with . And thanks for reading all the way down to this note. Leave a comment with your own thought on time. I’d love your input. 👆

Most people treat AI like a question-answering machine: Ask a question, get an answer. What is chili crisp, and why is Gen Z so obsessed with it? What’s the best starting guess for Wordle? What’s the best time of day to post on LinkedIn? (My own real queries from today.)

There’s nothing wrong with using AI to get answers to your questions. But there’s another mode of interacting with AI that many people never consider — one I find much more useful for my creative process.

Here’s what I do instead: I flip the script and let the AI ask the questions. Instead of prompting AI, I get the AI to prompt me.

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You may have heard Jeremy call this technique the “reverse interview,” and he’s previously written about it as a tool for reflection. You might use reverse interviewing, say, to conduct a soul-searching interview about what you want from your career.

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I take that same role reversal and apply it to the writing process. I call it the “Socratic interview.” It’s the foundational technique I teach for using AI as a thinking partner instead of a content generator. It’s also what inspired the name of my company, Socratic AI, and my upcoming masterclass with Narratively Academy. (See below for details, including an exclusive discount for Wonder Tools readers.)

The Socratic interview works for any writing task — a first-person narrative, a Substack post, a pitch deck, a talk for SXSW, even a speech for my best friend’s wedding. I use two versions of the technique: one to help me figure out what to say, and one to figure out how to say it.

Socratic Interviewing Level 1: Excavating raw material

How to use AI to help you surface memories, examples, and stories

I sometimes meet people who use an even more basic version: the adversarial interview. “Play devil’s advocate. Pressure-test my assumptions. Poke holes in my argument and reveal gaps in my logic.” Maybe call that the starting level.

What I find much more helpful is using the Socratic interview as a tool to access my own creativity.

As a writer, I’ve always had plenty of ideas, insights, and stories. I know they’re in there somewhere. But staring down the blank page is hard. What’s much easier is answering when someone asks me a direct question.

So I use Socratic interviewing to draw out the ideas, memories, stories, and examples I have in my head but haven’t gotten down in writing. For me, it solves the blank page problem — without ever using AI to generate prose.

Let’s say I need to write a groomsman speech for my best friend’s wedding. If I were to use ChatGPT as a ghostwriter the way most people do, it would output something lazy and trite. Look what happens when I ask it to generate a draft.

“That’s not luck, that’s character”? Pure slop.

Socratic interviewing is a different process altogether. Here, I give Claude a bunch of messy context about the writing task and ask it to help me remember the adventures and funny moments I’ve had with Tim over the years.

Generating answers is AI’s default mode, but it also excels at asking evocative questions to jog your memory and get your creative juices flowing. You just need to flip it into that Socratic mode.

I can ask for questions in a batch or, if I want it to feel less like a writing assignment and more like a conversation, take them one at a time. Either way, instead of sweating over a blank page, I’m now in a playful conversation about funny memories from my formative years.

Once I’ve answered these questions, the task ahead of me changes. I’m no longer struggling to compose some perfect sentence to encompass the totality of our friendship. All I have to do is look at my own stories and start choosing and shaping my favorite moments.

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I open Shortform for books I haven’t had time to read, books I finished years ago, and books I’m not sure are worth my time.

Take What the Most Successful People Do Before Breakfast by Laura Vanderkam (screenshot above). The Shortform guide surfaces the essential ideas fast. It’s particularly useful for nonfiction books, biographies, self-help, and other genres where you’re reading for tangible takeaways.

I appreciate that smart humans write Shortform’s guides. In an era when AI-generated summaries are everywhere, there’s a difference. These feel like notes from thoughtful readers.

Shortform now covers podcasts and long articles too, not just books. If your reading list grows faster than you can get through it, Shortform is one of the more practical tools I’ve found for making progress on it.

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Socratic Interviewing Level 2: Defining your purpose and strategy

How to use AI to clarify your writing goals

Just as important as figuring out what you want to say is figuring out how you want to say it.

Like all art, writing is about making a thousand tiny decisions. It’s hard to get those decisions right if you don’t even know you’re making them. If the only directive I have in mind as I’m typing is “I need to make this good,” that doesn’t help me figure out how much explanation is sufficient, which words match the register I’m aiming for, and which details will evoke the experience I’m trying to evoke in the reader.

The solution is to define my strategy before I start writing. The best way I know to write something good is to clarify what I’m trying to accomplish, keeping a sort of design brief in mind (or in a separate doc) as I write. If I’ve clearly defined what experience I’m trying to evoke and what elements of craft I want to deploy to get there, I can make those decisions more intentionally.

“Here’s what I’m going for here. I want these opening pages to be super suspenseful. I want the reader to immediately root for the protagonist, and the scene to be fast-paced and easy to visualize, nothing vague or abstract.”

The thing is, I don’t figure this stuff out by staring harder at the draft itself. So before I start writing, I have AI interview me about that too. The questions it asks force me to clarify my purpose and strategy for the piece before I even start drafting.

I might use a prompt like this:

I’m writing a short satire piece for The New Yorker Shouts & Murmurs. Before I draft, ask me a series of questions about my goals for the piece: who my reader is, what kind of experience I want to create for the reader, and what craft choices I plan to use to achieve the desired effect.

Fleshing out my writing goals through Socratic questioning has a dual benefit.

• First, it clarifies my own thinking, so I’m writing with purpose instead of brain-dumping whatever’s in my head.

• Second, it gives the AI a clear set of criteria. So when I ask it for feedback — “How’s this paragraph?” “Is this section working?” — Claude already knows what I’m trying to achieve. It can assess how my writing succeeds against those specific standards, rather than an abstract ideal of what good writing looks like.

Instead of generic notes like “This is a little casual” or “consider tightening,” I get feedback against my own criteria: “You said you wanted this to be visual, but you’re doing a lot of explaining.”

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My 6-Week Course for Writers Who Actually Want to Finish

Socratic interviewing is just one piece of how I use AI in my writing process (and never to generate writing). If you’re interested in learning how to use AI not just as a thinking partner, but as an accountability coach to keep you on track with your writing, I’m teaching a six-week class that covers the whole system.

The class is called The Socratic AI Intensive, taught in partnership with Narratively Academy, and it starts May 18. It’s built around how to use AI as a taskmaster, project manager, and accountability coach to help you set a goal, stay on task, and actually finish what you start. All without ever letting AI generate a single word.

The accountability coaching is just one piece of the Socratic AI system. The class also covers a set of advanced principles I’ve never seen taught anywhere else — the signature techniques of Socratic AI I’ve developed over three years of working with AI in my own writing process as a thinking partner instead of a content generator. Here’s a taste of what we cover:

1. Getting non-sycophantic feedback. As I’ve said ad nauseam, I don’t use AI to generate prose. Nor do I allow AI to rewrite my prose when it inevitably tries to jump in and “smooth and refine” my drafts. But I do use AI as a thoughtful first reader to get an external perspective on how my writing is coming across.

   I ask for high-level feedback on how to make a piece better. What’s repetitive, what’s vague, what’s unclear, where it gets boring, where it needs to get more concrete. Then I do the rewrite myself, based on feedback. The AI’s feedback is even more specific and useful if you’ve already gone through the Level 2 process I described above: defining for the AI what you’re trying to achieve and how.

2. Name what you suspect the problem is. When asking for feedback, it also helps to let the AI know where to focus its attention. If you simply say, “How’s this section working?” the AI will do its best to be helpful. But it’s better to flag your specific concern:

   • “Is this paragraph sappy/melodramatic?”

   • “Does this headline sound defensive?”

   • “Is it clear why she didn’t just walk back in and apologize, or do I need to spell out her motivation?”

   Tell the AI what to focus on for a better, more targeted answer.

3. Socratic revision. As William Zinsser said, “Writing is rewriting.” Writing never comes out quite right the first time. What makes good writing good is revising and rewriting early drafts until they get good. To flip AI into an iterative, Socratic mode, I use one magic phrase: “iterate and improve.” My favorite Socratic prompt: “Don’t rewrite this for me. Ask me questions to lead me to my own creative insights, and give me ideas so I can iterate and improve.” The AI gives you feedback. You’re always the one writing.

4. Make every conversation Socratic. AI’s default mode is to spit out answers. But AI is more helpful when it has relevant context. The problem is the context you don’t realize you’re leaving out. So even when you’re not doing a Socratic interview, you can still flip the script. In practice, I try to make all my AI conversations Socratic. Here’s a single sentence you can paste at the end of any prompt: “Before we proceed, ask me a question or two to make sure you understand what I want.” One sentence, and Claude stops guessing what you need. It asks. It’s the easiest way to break out of the vending-machine pattern.

In the class, I teach all of these techniques in detail over six weeks and show you how to use them for your own writing. We’ll cover project planning, daily accountability, Socratic interviewing, iterative revision with feedback, and advanced workflows for working with AI on your actual files and projects.

The structure: Five weekly live sessions of two hours each, a system for using AI as an accountability coach, and a private community for support between sessions. You bring your writing project: a novel, a book proposal, a screenplay, a collection of essays, whatever you’ve been wanting to finish. You set an ambitious but achievable goal. By the end of six weeks, you’re done.

Here’s what you get:

• A set of tools and techniques for how to use AI to set milestones, break your project into daily tasks, and keep you on track

• A cohort of fellow writers doing the work alongside you

• Weekly live sessions with me

• A Slack channel for questions, technical help, and shared progress

This is the class where you actually finish your draft. By the end of six weeks, the project you committed to is done.

It’s $795, and Wonder Tools readers get $100 off with code WONDERTOOLS. Sign up at socraticai.co/intensive.

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Jay: I’d also love to invite you to follow my own writing on Substack, where I share tips and techniques for how to use AI as a thinking partner instead of a content generator.

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Jay Dixit is the founder of Socratic AI, where he teaches writers, educators, and knowledge workers how to use AI as a thinking partner instead of a content generator. He was previously Head of Community for Writers at OpenAI and has taught writing at Yale. His journalism has appeared in The New York Times, Rolling Stone, and Psychology Today.

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I spoke on a panel about how journalism training evolves when AI does entry-level work. Here’s a visual summary of my 5 ideas.

I attended 15 other sessions. Five ideas stuck with me, each about how journalism can be more human, more sustainable, and more inventive, even as the industry contracts.

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Live Journalism Resonates » Watch the Session

Madrid-based Diario Vivo puts journalists and ordinary people on stage to tell personal stories. Nothing is recorded. It’s pure human storytelling.

Audiences don’t know what stories they’ll hear when they arrive at a show. Founder Vanessa Rousselot says the format is designed to make people laugh and cry and to restore trust between journalists and the public. Diario Vivo began in 2017 with 100 people in the audience. Now they sell out 1,000-seat venues. More than 25,000 people have seen their shows thus far, in various cities.

Correctiv, a German nonprofit newsroom, turns its investigations into theater performed by professional actors. Editor in chief Jean Peters says Correctiv is building a network of 50+ theaters across Europe to distribute journalistic productions. Correctiv’s publisher, David Schraven, estimated that each two-hour theater performance is “equivalent to 3.6 million seconds spent on TikTok, but with a much bigger impact.”

These projects follow in the tradition of Pop-Up Magazine, which launched in California in 2009 and hosted sold-out shows for tens of thousands of people around North America until closing in 2023 after the pandemic devastated their business. Diario Vivo, Correctiv and others are now reviving the live journalism movement.

Resource: Journalism, media, and technology trends & predictions for 2026

Nonprofit Newsrooms Can Thrive » Watch the Session

Five non-profit news leaders shared strategies that are actually working.

• The 19th‘s founder and CEO Emily Ramshaw raised a $30 million endowment in six months. She started out by sending 100 cold messages per week to wealthy people. She targeted non-traditional news philanthropists like women’s rights donors. Now she’s aiming to raise a total of $100 to $200 million to put the organization on strong footing for the long run. She joked that her $75 Instagram verification and $1,000 LinkedIn Pro accounts were her most valuable investments for donor cultivation.

• ProPublica has 90,000 individual donors, ensuring that they’re not relying on any one rich person’s whims. They’re on eleven different platforms and have partnered with hundreds of publishers, from the NYTimes to NPR. They’re now developing a Local Reporting Network.

  

• The Center for Investigative Reporting merged with Mother Jones to expand from documentary film and audio to a broader digital media portfolio. CEO Monika Bauerlein said the newsroom hit 50 million video views in the first three months of 2026. Her advice to nonprofit leaders: “Get over your attachment to how you used to do things.”

• Memphis-based MLK50 has a tagline of “Justice Through Journalism.” They pursue stories with a direct financial impact on the lives of locals, like businesses profiting from the poor. They belong to two organizations that support hundreds of independent newsrooms: the Institute for Nonprofit News and the Local Independent Online News publishers.

Resource: The Institute for Nonprofit News Resource Hub

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AI That Actually Helps Reporters » Watch the Session

The Lenfest Institute’s two-year fellowship program has embedded AI engineers across the country. More than 50 projects are now in development across 11 metro newsrooms.

Kevin Hoffman, an AI Engineer at The Philadelphia Inquirer, said he was surprised how quickly some projects have taken flight. With AI assistance, development that would once have taken a year can now be done in a few months.

• The Philadelphia Inquirer has been publishing for more than 190 years, but their archives have always been tricky to navigate. So they launched Dewey to make it easy for staffers to find anything. They also built Scout, a local media aggregator that helped reporters cut down the 15 hours a week they spent gathering info for local newsletters. Rather than just scraping what they needed, they sought permission from local publishers.

• The Seattle Times built an AI tool that transcribes city council meetings and automatically notifies beat reporters when their topics come up. They also developed an AI prospecting tool for their sales team. One salesperson used the tool to find a new advertiser, then pitched and closed a deal the same day.

Resource: The Lenfest Institute’s Communities of Practice & News Solutions

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One Journalist. Five Videos a Week. » Watch the Session

Dave Jorgensen, who built the Washington Post’s TikTok account into one of the most-followed in the industry, left last year to launch Local News International, a video startup. Jorgensen researches, scripts, shoots, and edits five videos a week. Each takes a full day, including extensive research and fact-checking.

He and a team of former Washington Post collaborators hit 330,000 YouTube subscribers within 10 months. His most-viewed video: a 30-second clip about negotiations over Egyptian rockets, with 45 million views.

Revenue comes from YouTube ads, brand partnerships, and video strategy consulting. Jorgensen has a knack for explaining the news with a light touch. “Humor is a really powerful tool,” Jorgensen said, “because it’s getting people important information... they might never have clicked on or engaged with.”

Resource: Watch the 8 panels focused on creator journalism

Hype Literacy for Journalists » Watch the Session

A group of international researchers focusing on “hype studies” challenged popular narratives around AI. They analyzed 231 AI benchmarks and 138 model releases in 2025. They found that most AI benchmarks aren’t independent measures. They're company self-tests. 63% of benchmarks were used by only a single model, and 41% by only one company. The researchers questioned whether journalists should accept AI companies’ metrics at face value, rather than developing independent assessments.

Because hype centers around claims about the future, it’s hard to critique. You can’t fact-check far-off predictions, but you can identify inflated claims and point out hidden assumptions. The toolkit helps detail how hype shapes public perception, and how journalists can step out of the hype cycle.

Resource: The free Hype Literacy Toolkit for Journalists.

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Bonus Resources

• Reuters Institute’s on festival highlights: What We Learned in Perugia

• A searchable NotebookLM collection of 167 conference panels

• Festival highlights, from AI to press freedom from the Incubator for Media Education and Development

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1. Visualize Your Career Options

Try: Google’s Career Dreamer

What it is: A free tool for exploring jobs adjacent to yours. See a map of professional fields related to your interests.

How to use it: Start by typing in a current or previous role. Or name a job that interests you. Use up to five words. You can also name a specific organization or industry, if you have one in mind.

Career Dreamer asks what work activities interest you, then maps related career paths. Pick one at a time to explore.

You can then browse actual job openings. Refine the search based on location, company size, or other factors you care about.

Example: I’m not job hunting, but I tested out the service by typing in “journalist, writer and educator” as roles and then “journalism and education” as my industries of interest. 📺 Watch my short video demo below👇

Why it’s useful: I like that Career Dreamer suggests a range of relevant fields, then summarizes what a typical day in those jobs might be like. It also suggests skills you’ll develop, and other jobs that might follow on your career path.

Next step: After exploring potential paths and looking at available jobs, use Gemini for further career planning. Read my guide to Gemini

Here’s how: Use Career Dreamer’s copy and paste feature to grab your career interests and skills to your clipboard. You can then jump to Gemini (screenshot below) to paste that material as a summary prompt into a chat about your career plans.

2. Figure Out What You Actually Want from Work

Try: Gemini Gem — Career Guide

What it is: Gemini Gems are customized AI assistants. They are AI models tailored to be helpful in a specific context. One of the template Gems that Google created is a career guide. You can copy the Career Guide gem to make your own editable version, then adapt it for your own professional interests.

How to use it: Start by conducting a thorough “soul-searching” reverse interview with Gemini. Rather than Gemini answering your questions, task it to ask you the questions. Tell it to nudge you to dig deeper into your own preferences, attitudes, objectives and needs. Then have it summarize what you’ve said. You’ll get better at understanding and articulating your own career perspectives.

Try this career self-interview prompt: Give this prompt to Gemini or another AI tool of your choice to conduct a reverse interview. As Gemini — or another AI assistant— interviews you, you’ll develop a richer understanding of your own job preferences.

Next steps: Use your Gemini Gem AI assistant to clarify your strengths and career objectives, and for help developing your search strategy.

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What I'm reading on Shortform this week

Shortform has helped me get inside more books. I use it for books I haven’t had time to read. I also open it to rediscover ideas from books I finished years ago but have already started to forget. It’s like having a smart friend sum up a book so you really understand what it’s about, beyond the surface.

One to check out on Shortform: Make it Stick, an excellent book I’m re-reading (screenshot above) about how to teach so your students remember. Instead of having to re-read the full book for 10 hours, I can remind myself of the key insights in a half hour. When I’m deciding between books on a new subject, Shortform helps me make a quick decision by previewing the books’ key ideas.

Shortform also now has podcast and article guides. Those help give you the gist of a long interview or a sprawling article.

If your reading list sometimes overwhelms you, as it does for me, it’s worth a try.

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3. Research Potential Employers

Try: ChatGPT Deep Research

How Deep Research is different: Unlike typical AI chat queries, which yield responses of less than a page, Deep Research enables AI models to autonomously develop exhaustive reports. Some are 30 to 40 pages. The Deep Research agent searches the Web and examines hundreds of research sites. It returns a complete report, of the kind a researcher might spend days compiling. You also get citations and links to verify the info and explore more on your own.

See 9 ways to use Deep Research.

You can use these personalized reports to learn more about industries of interest. Or you can narrow your scope and investigate specific aspects of companies that intrigue you.

How to use it: Toggle on “Deep Research” in ChatGPT. Type a detailed query. Describe your specific interests, skills, and the kinds of organizations you're curious about. Request a comprehensive table of relevant companies with detailed information about culture, growth trajectories, or whatever else.

Example: Here’s a journalism industry query for Deep Research you can adapt.

Benefits: Learn valuable context about companies you may apply to, and discover new organizations you didn’t know about. Use this research to tailor your applications and to prepare for interviews by understanding industry trends.

Pricing note: You get several free Deep Research queries a month on ChatGPT’s free plan, or more on a paid plan. Gemini offers a good free Deep Research alternative, as does Claude. Perplexity also offers free Deep Research reports. They are faster, but not as thorough.

Alternative tools: Exa’s Websets is a powerful, pricey, pro AI search tool that organizes results into a detailed table. It can draw on datasets like these, helping you identify companies you might want to target, based on your own criteria.

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4. Keep Your Search On Track

Try: ChatGPT Projects

What it’s for: Set up a dedicated AI folder for your career search. Provide instructions about what kind of help you’d like. Attach relevant files like your resume, interest list, or research reports.

Once you’ve provided that context, you’ll never again have to re-prompt ChatGPT about what you’re looking for, or how you want to be helped.

How to use it: Try having it guide you in building a realistic timeline for preparing applications, sending follow-ups, and reaching out for informational interviews. Ask it to assist you in designing a structured daily job search agenda. If you’re applying to many different positions, with lots of tasks to juggle, it can help to organize your plans.

Advanced tactic: You can upload examples of your past outreach or other writings as project resources. That will enable the AI assistant to help you draft new emails in your own style, whether you’re letting people know you’re open to new opportunities or reaching out to new contacts. You can even connect the project to Google Sheets or Excel to keep your tracking list updated.

Organize your career search tasks: ChatGPT’s “Scheduled Tasks” feature can help by sending you custom reminders. That could include an automated daily reminder of specific tasks to complete to maintain momentum. You can even ask it to periodically send encouraging messages.

Free alternative: ChatGPT’s Projects require a paid plan, $20/month. For a free alternative, you can create a limited number of free Claude Projects, or create a Gemini Gem with similar functionality.

5. Sharpen Your Applications

Try: Claude Projects

What it does: Gives you personalized AI assistance to help polish any materials you’re creating. Give it specific instructions and upload background documents to ensure that it understands your preferences, strengths, and style.

I have Claude Projects set up to assist with many of the things I work on, from new classes I’m developing to volunteering projects. Here’s why I find Claude Projects so useful.

How to use it: Upload past cover letters, resumes, lists of accomplishments, awards, vision statements, or anything else you’ve created.

In your project instructions, tell the AI to respect your authentic voice while providing you constructive criticism.

• Ask for feedback on writing you’re submitting. Specify what will be most useful for you. For instance, ask for grammar, spelling, and syntax suggestions, or warnings about exaggerations, cliches, or jargon.

• Ask what additional information you should consider including based on a particular job description.

• Warning: submitting purely AI-composed material can weaken your application. Your text may sound artificial and lack soul. That’s why I’m recommending using AI for critical feedback, not to replace your writing.

Alternatives

• ChatGPT’s Projects & Custom GPTs have similar functionality. You can add resource files and instructions to adjust how the AI assistants support you.

• Perplexity Spaces also allow you to organize prompt threads and add custom documents and instructions.

• Gemini Gems noted above, offer a free alternative. I prefer the quality of Claude’s responses and some of its features, like a custom editing style I’ve trained it to use. Google also just launched Gemini Notebooks, which I’ll soon test.

6. Rehearse Interviews Out Loud

Try: ChatGPT Advanced Voice Mode

How to use it: Brainstorm interview questions specific to your target role, industry, and even the particular company you're applying to. Then practice answering these questions using voice mode for a realistic simulation.

Read 7 ways to use Advanced Voice Mode

Ask for detailed feedback as you rehearse your answers. Prompt your voice assistant to highlight strong points and suggest areas for improvement. Ask it to be as specific as possible and to help you practice strengthening your responses.

Ask it to help you prepare for whatever interview context you expect to encounter, from technical questions and case studies to fact-based questions or casual, open-ended lunch conversations.

Pricing: Full access to ChatGPT’s Advanced Voice Mode requires a paid plan, but free users can access a daily preview of advanced voice mode powered by a model slightly less advanced than the top paid models.

Alternatives

• Microsoft Copilot Voice is free. Choose from eight voices. You can even adjust the voice speed. I like Wave, with his British-sounding accent, at 1.25 speed.

• Gemini Live from Google is also an excellent voice AI assistant. Like ChatGPT Advanced Voice Mode, it can even use computer vision to comment on something you show it. Initiate a conversation while pointing your phone camera at a company’s leadership org chart, for example, or public balance sheet, or a list of questions you’ve handwritten.

Bonus tip: If your job search involves speaking or understanding multiple languages, you can use these voice models to practice speaking or listening in any number of tongues. It’s a great way to practice live language skills.

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7. Negotiate Your Salary

Try: Deep Research (from Perplexity, Gemini, or ChatGPT)

How to use it: Research average salaries for similar positions in your industry, accounting for variables like location, company size, and experience level. Ask for a salary table you can reference when negotiating. You can also research relevant benefits, company culture, and other factors.

Compare Deep Research salary reports

I’m not job hunting, but I generated these reports as examples, so you can compare them side by side:

• Perplexity Report + original Perplexity thread

• ChatGPT Report

• Gemini Report

Practice negotiating: Use the aforementioned voice AI tools to role-play negotiations or to prepare for difficult benefits conversations. Practice responding to everything from a dream offer to one below your market value.

Two Bonus Ideas

• Put together a video reel. Try Google Vids or Captions to create a little video about what makes you distinct.

• Make a great deck. Gamma, Beautiful.ai, Pitch, Canva, and the new Chronicle are helpful for turning talking points into polished slide presentations. You can even create surprisingly strong slides about your qualifications with NotebookLM and the brand new Claude Design.

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Catch up on Part 1 👇

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12pm: Midday Break

Healthy Minds 🧠

This free app helps me with mindfulness. The 5-10 minute audio lessons work well as walking meditations. I sometimes also use Headspace or Calm for meditation or focus music.

Libby 📚

I rely on Libby for free library audiobooks. I listen when walking to lunch or commuting. Here are tools I rely on for finding great books.

Lunch

• Resy and OpenTable 🍱 for quick reservations nearby

• The Infatuation for opinionated local restaurant recommendations

• Too Good To Go for trying heavily discounted (66% off) dishes from local restaurants, bakeries, and juice bars. The fixed-price mystery bags reduce restaurant waste. Sometimes you get a delicious bargain, but the quality varies. I’ve occasionally gotten a weird bread or a bland pastry.

• MealPal When I don’t bring my own lunch, I like MealPal, a lunch subscription service. Local restaurants offer one dish a day as part of the subscription, which costs about $6/day. I like the variety: you can choose which restaurant to try on any given day. It’s available so far in 12 cities.

1-3pm: Preparing to Teach

After lunch, I continue developing teaching plans or work on other school-related projects for my job as Director of Teaching and Learning at CUNY’s Newmark Graduate School of Journalism. (More of my thinking in a recent Columbia Journalism Review interview).

Craft 📄

My go-to for creating visually engaging digital handouts. It’s easy to use and works wonderfully on mobile or desktop. See my post on why Craft is so useful.

Wispr Flow, Text Blaze and Raycast

• I often use Wispr Flow to type with my voice. It works in any app. I just hold the function key and talk.

• When I do type with my hands I use Text Blaze keyboard shortcuts to add snippets into my email and documents. It works for email addresses and signatures, search prompts, and phrases I type a lot.

• Raycast also works well for these shortcuts. Why I rely on Raycast.

Notes by Hand 📝

I like writing notes away from my laptop periodically to get my eyes off the screen and to change my brain mode. I alternate between:

• I use a Rocketbook reusable notebook for lists and reminders.

• A giant whiteboard helps me draw connections and play around with ideas away from the glowing distractions of my screens.

• My reMarkable Paper Pro tablet hosts notes I will return to repeatedly. What works for me, paper vs. digital

Keynote for Slides

This Mac presentation software works reliably offline or on for in-person and remote classes and workshops I lead. Keynote is now part of Apple’s new Creator Studio, a package of software that includes video and image editing tools.

I haven’t found the Keynote AI features useful so far, but the basic software is excellent for designing and delivering compelling slides.

Pricing: Keynote is free with any Mac. I wouldn’t recommend the subscription upgrade, at $129/year or $30/year for students and educators, unless you’re a heavy user of Final Cut Pro, Logic Pro, or the other pro software tools.

iA Presenter

I vary slide apps to keep things interesting. I sometimes write a lesson outline and paste that text into iA Presenter, which turns it into clean, typographically sharp slides. Like Keynote, it works offline. For more on why this app is so useful, watch the demo video or read my post.

Kahoot, Padlet, and Slido 🤔

I rely on this trio of teaching tools to power activities that promote active learning in classes or workshops — rather than passive listening. Here are more of my favorite apps for teaching.

Time Out for Screen Breaks⏳

I set this app to remind me to give my eyes a screen break every 15 minutes. It pulses over the screen to nudge me to stretch or look out the window. The Raycast Focus Mode also helps, blocking email and distractions during short, focused, deep work sprints.

3-5pm: Meetings 👥

I try to schedule meetings for the late afternoon to conclude the day with collaboration, after starting with more creative work.

Granola for Summaries🤖

Granola weaves my own notes into its summary, sends no bot into my Zooms, and lets me search across meetings for tasks, patterns, or insights. My full post about it👇 describes 10 of the features, along with tips, limitations, and alternatives.

Camo for Webcam Customization

Camo lets me modify my camera to zoom in, adjust lighting, or add overlays during video calls. It also lets me use my phone or other external cameras. Prezi Video and Airtime enable lower-thirds, annotations, and overlay visuals I occasionally use for presentations.

Sony UX570 Voice Recorder for Interviews

My reliable backup for recording audio. I like that it doesn't require an open laptop or running phone. I often transcribe the audio files with MacWhisper.

6pm: After work

Snipd for listening to podcasts on my commute

This smart podcast app lets me preview podcasts and save highlights to my notes. I triple-tap my AirPods to save my favorite moments to Readwise, a service that acts as a repository for highlights from my online reading, Kindle books, and other apps I use.

A recent favorite: The history of Trader Joe’s episode of the excellent Acquired podcast, which features multi-hour deep dives into remarkable companies.

Sony Noise Cancelling Headphones

I splurged on the $460 WH-100XM6 headphones to block noise on the exhaustingly loud New York City subway. I had my previous pair (WH-1000XM3) for seven years, so hopefully this investment will prove equally durable. I use them for commuting and focus music.

Nex for Games and Exercise Breaks

I love playing the sports and workout games on this family video game system. They’re all active games played with your body, not your thumbs. I play solo or with my wife & daughters. It’s like a next-generation Nintendo Wii, which we also still play (especially the balance board games).

To get away from screens, we also play these family tabletop games.

11pm: Bedtime 🌙

Glocusent Rechargeable Reading Light

This tiny $13 light clips onto any book. The battery lasts for months.

Yogasleep Dohm White Noise Machine

This $50 gadget masks random night sounds, making it easier to sleep.

Peakeep “Invisible” Alarm Clock

I turn off the display on this $13 bedside clock so it doesn’t glow at night. I tap the top to see the time if I need to. Its morning alarm lets me keep my tempting phone out of the bedroom.

That’s my noon to night kit. What tools carry you through your day?

What’s One Tool You Recommend? Leave a Comment👇

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Bottom line: Granola has transcribed and summarized nearly 1,000 of my meetings since I began using it in September 2024. It helps me keep track of what I’ve learned and what I’ve promised to do.

What it does: It’s a software download, not a bot, so it’s not visible in meetings. It just runs on my computer or phone. I connected my Google Calendar. Now it auto-detects my meetings and opens automatically. I can use it to record in-person meetings, or anything online: Zoom, Google Meet, or even Substack Live.

How it’s different: Unlike other bots that spit out a generic summary, Granola gives me a typing window for my own note-taking. That means I can include my own thoughts and highlight what I find most important. Afterwards, I can search for patterns across my meetings, projects and presentations.

Pricing: Granola’s free plan includes unlimited meeting summaries and access to 30 days of meeting history. I pay $14/month for a full archive and AI integrations.

Cheat-Sheet: Here’s a PDF summary of this post for easy reference.

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👇10 ways Granola stands out

1. Write your own notes while AI fills in details

Most AI note-takers give me only the AI’s version of what happened. Granola shows my own notes alongside the live transcript. I can refer back to either.

Knowing I’ll have a thorough record frees me to focus on listening. I can be more present when I don’t have to worry about jotting down each detail.

I type my own most important observations, priorities, and reactions during a meeting. The AI assistant fills in other details. That ensures I’m not reliant on a generic synopsis. My own emphasis and perspective help shape the summary.

• Smart design: After a meeting, the summary weaves in my own points in black, distinct from the gray AI summary notes. I can easily distinguish my own material. I can later revisit my own notes or the AI-assisted summary.

• Zoom in for detail: I like being able to click on any summary line to see a more detailed view of that section of the transcript.

2. Catch up mid-meeting

This is the feature that surprised me the most. During a meeting, I can ask Granola to summarize what’s been said, or to catch me up on what I missed.

This saved me recently. I was in a live session. My mind wandered. I didn’t hear what a couple of people said. I asked Granola for a concise recap of the last few minutes. It caught me up while continuing to transcribe. I like that I can also scan back manually through the live transcription while a meeting progresses.

3. Take private notes without a bot joining your call 🔒

Granola captures only text. It transcribes in real time but doesn’t store audio or video files. Some people don’t want to be recorded video-wise, or they don’t want their voice recorded. Granola works well for that, because it stores only text.

That’s a deliberate design choice. As CEO Chris Pedregal told me when I interviewed him for Fast Company, the value is in useful notes, not in retaining audio.

The tradeoff: you can’t go back and listen to verify a quote, or hear the emotion in someone’s voice. If that matters for your work, pick an alternative below.

Open a typical AI note-taker and you’ll see a bot listed as a meeting participant and a robotic rectangle in your video window. Some people find these bots intrusive.

Granola doesn’t join your meeting. It runs on your computer (or phone). Nobody else in the meeting needs to know it’s there, though I recommend getting people’s consent.

Your data is protected. Granola is SOC 2 Type 2 compliant, which basically means an independent auditor has checked that the company has safeguards to protect sensitive info. And you can delete parts of a transcript.

4. Take it to conferences, workshops, or doctor visits

Granola is useful beyond work meetings. Here are some ways I’ve used it:

• Learn from conferences and workshops. Capture notes from panels and talks. Later, search across all the sessions. “Which speakers mentioned AI regulation?” or “What books did speakers recommend?” You get a searchable archive of an entire event.

• Catch up with online courses and webinars. I use Granola when I’m hosting or watching a Substack Live. If I have to step away, I can catch up. Or I can search across a series. “Remind me which tactics we covered.”

• Capture medical or personal appointments. Ask for permission to use Granola for therapy sessions, vet visits, or doctor appointments. When you later forget what the expert said about dosage or next steps, ask Granola.

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There are more great books than any of us will ever finish. I made peace with that, though I still wish I could read more. So I found a tool that helps.

Shortform has helped me get inside more books. I use it for books I haven’t had time to read, and to rediscover ideas from books I finished years ago but have already started to forget.

What sets it apart is that it’s powered by human writers and editors, not AI summaries. You get substantive analysis, useful examples, and quotes from the book. You also get recommendations for related titles and a one-page overview. It’s like having a smart friend sum it up for you.

A few to check out on Shortform: a guide to What the Most Successful People Do Before Breakfast, by Laura Vanderkam (I’m a big fan) and Better than Before by Gretchen Rubin (also an author I admire). Shortform also has podcast and article guides to get the gist of long interviews or sprawling posts.

If your reading list ever creates anxiety for you, as it does for me, it’s worth a look.

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5. Search across meetings by person or company 🔍

Granola organizes meetings by people and organizations. I can select someone’s name and search across all of our conversations. Or I can search through discussions I’ve had with people at Dorot, where I volunteer.

This is useful for questions like: What did we agree to last month? What themes keep coming up? What did I promise that I haven’t followed up on?

You can also create folders for specific projects or events. If I’m attending or teaching workshops, I can search across all of those sessions. I can use natural language rather than hunting for keywords.

Tip: If you’re a writer or give presentations, ask Granola to compile key points or ideas you’ve shared in past meetings or presentations. It’s helpful for exploring and building on your own material. Instead of using AI to think for you, use it to help you organize and make more of your own ideas.

6. Record in-person meetings w/ a phone or laptop 📱

I’ve been to public events where I wanted to remember what was discussed. The iPhone app is great. Same account, no separate setup.

Granola uses a device’s built-in mic. I’ve been surprised that works well even when I’m not sitting near the person presenting. I can even transcribe and summarize outgoing phone calls, with permission, if I initiate the call from the Granola app.

Other recorders I’ve tried occasionally crash when I get a call or open other apps. Granola has been consistently reliable, even for long meetings.

Available on: Mac, Windows, and iOS. There’s no Android app yet, though I expect that will launch later this year.

7. Analyze meetings with “recipes”

Recipes are prompt templates built specifically for your meetings. Instead of recreating the same query every time, you save it once and reuse it. To use these, open up an individual Granola meeting note, or query a folder or your whole library of notes. (Screenshot)

A few I recommend:

• List recent to-dos. Scans recent meetings for tasks mentioned. I recently caught a missing follow-up this way. Someone asked me for a logo. I forgot to put it on my to-do list. The recipe surfaced it.

• Prep next meeting. Reminds me about prior conversations I’ve had with someone I’m meeting, including any relevant follow-up questions.

• Coach me. Analyzes my comments and suggests what I might do differently.

• YouTube description. I created this for workshops I lead. Some of them end up on my YouTube channel. Granola has the full text, so the recipe helps me generate a description.

Browse the public library of recipes and grab ones that interest you. There are special recipes for sales, marketing, customer interviews, and other common business use-cases.

I wish there were more recipes designed for writers, teachers, creatives, and other non-business use-cases. Fortunately, it’s easy to create your own recipes. It’s as simple as writing a prompt.

8. Give Claude or ChatGPT access to your Granola notes

I upgraded to the paid plan so I can give other AI assistants access to my meeting history through the Model Context Protocol. MCP provides a simple way to link Granola to AI tools like Claude and ChatGPT.

Why this is so useful: I can ask Claude to cross-reference what I’ve talked about in my presentations with what I’ve published. Claude can also help me generate dashboards, spreadsheets, handouts, and reports from material I’ve presented. All of that is possible because Claude has access to my newsletter archive, via a tool called Mizal, and my presentation transcripts, via Granola.

9. Share meeting notes others can explore

You can share a link to a Granola summary with anyone. The person on the other end doesn’t have to log in or have a Granola account. They can read the summary and even search the transcript. They won’t see your private queries, and you won’t see theirs. You can also share an entire folder with a colleague or team, or even a workspace with lots of folders.

Example: Here’s a Granola summary of my most recent Wonder Tools Live workshop. For context, this is one of the live monthly sessions I host for paid subscribers. I show how I’m using tools, new ways to use AI, and tips on working productively and creatively.

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10. Start free with unlimited meetings

• Students at accredited universities in the US, UK, and Canada get Granola free for a year.

• Startups with fewer than 30 employees who have raised pre-seed or seed funding also get a free year.

• The paid plan is $14 a month. That’s worth it for me for unlimited access to past meeting summaries, being able to query my notes from other AI tools like Claude, and access to the strongest AI models for analysis.

• The free plan limits you to 30 days of meetings. That’s not an issue unless you often reference old summaries or need to access your notes from other AI tools.

Try Granola free for a month with this link.

How to make the most of Granola

• Create “personal hashtags.” In any note-taking tool I use, I find simple shorthand helpful, like triple asterisks (***) for key points and &&& for memorable quotes. Pick symbols easy to type during a live meeting. Search for your symbols later to find what you flagged.

• Ask permission first. Even though Granola doesn’t record audio, let people know you’re using an AI note-taker if it’s not a public event. I usually say something like: “Is it okay if I use an AI note-taker to sum up the meeting? I’m happy to share the summary with you.” Turn on Automatic Consent Messaging to send a chat message when meetings start letting people know you’re using Granola.

• Split long events into separate sessions. If you’re at a three-hour workshop with distinct segments, stop and restart Granola between sections. You’ll get more detailed summaries for each section instead of one sprawling summary.

• Choose your AI model. On the paid plan, you can select an advanced AI model. I like Claude’s Sonnet 4.6 Thinking. You can switch to a Gemini or ChatGPT model.

Limitations

No tool does everything. Here are some of Granola’s limits so far:

• No audio or video playback. You can’t go back and listen to what someone said for the emotion in their voice.

• No file uploads yet. You can’t drag in an old interview recording or audio file for transcription. So far the focus is on live meetings.

• Chats can get messy. Granola doesn’t have a place to store answers you get when you query your meetings. You have to copy & paste into a separate notes tool. And it’s not optimized for taking notes without audio.

• Limited free archive. On the free plan, you only get access to 30 days of meeting archives.

• No Android app yet. Available on Mac, Windows, and iPhone. I expect the Android app to launch later in 2026.

Alternatives to Granola

Granola is best for people who take their own notes during meetings and want AI to fill in the rest. If you’re on Android, Otter is a popular alternative until Granola’s Android version is available. If you want to upload recordings, or if you need video or audio saved, consider these alternatives instead:

• Fathom is a good option if you want video and audio recordings tied to a time-coded summary. Click on part of the summary to jump to that part of the recording. Start with the free version. It’s useful for sessions where you want to go back and watch specific moments. I sometimes use Fathom alongside Granola for this reason.

• MacWhisper is useful for transcribing audio files you’ve recorded elsewhere. It can run locally on your Mac, so nothing leaves your device. You can buy it as a one-time purchase for $74. The free version also works well.

• Supernormal just launched version 2.0, which I’m testing. So far I like the new desktop app. It no longer sends bots to meetings; like Granola, it runs on your device. Unlike Granola, it can also act as an AI agent, creating materials for you. In my testing, its agent generated helpful post-meeting summary slides. Here’s how Supernormal compares its tool to Granola.

• For more options: Wonder Tools contributor Ulrike Langer, who writes the great News Machines newsletter about how news orgs are using AI, recently wrote a guide to transcription tools with additional alternatives.

• 🦄 Unicorn: Back when I started using Granola, it was a small startup. Now it’s valued at $1.5 billion dollars, with a $125 recent investment round.

How to get started 🚀

1. Try it for one meeting. Download Granola on Mac or Windows, or grab the iPhone app. Connect your calendar and join a meeting. Take a few notes. See how Granola combines them afterwards with the transcript into a summary.

2. Try an in-person meeting. Bring your iPhone to a coffee meeting or a live event and open the Granola app. See how the mobile transcription feels.

3. Chat with your first summary. After your meeting, try asking:

   • “What were the three main takeaways?”

   • “What deadlines or follow-ups should I remember?”

   • “Summarize this meeting in 3 sentences for a colleague.”

Try Granola free for a month →

What note taker do you use and why? Leave a comment 👇

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Takeaways from Our Conversation 🛠️

• Teach your AI assistant to offer personalized editing suggestions. I’ve trained a Claude Project to learn from my past writing and editing. It catches typos like double commas, cliches, redundant language, weak verbs, and sloppy copy. Instead of having it make changes, I ask it for a punch list of suggestions.

• Talk before you type. I turn on my AI dictation app, Letterly, and just start talking. The AI-enabled transcription and summary I get helps me make sense of ideas rolling around in my mind. Then the next part of the writing process becomes more about shaping and editing those ideas, rather than staring down a blank screen.

• Ask AI to interview you. After a conference or a day of meetings, get your AI assistant to ask you follow-up questions. That conversation forces you to articulate ideas you haven’t fully formed.

• Teach your AI assistant to be a critic, not a ghostwriter. Ask it to challenge your structure, suggest sections to cut and to explain why, and to point out your blind spots. Your friend might be too polite to tell you a section of your piece you’ve worked on for hours is redundant or dull. Your AI assistant will, if you train it to.

• Let’s read books collectively. We’re reading 10 AI books in 2026 through the Wonder Tools Book Group. (For WT paid subscribers). We started with AI Snake Oil, whose co-author was a surprise guest at our first gathering. Reading together allows us to benefit from dialogue. And we can learn more deeply from books than we can from a random diet of posts and videos.

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Tips Jason shared during our conversation

• Work from a calendar, not a to-do list. Sometimes what’s most valuable is a workflow, not a specific tool. Like timeboxing. Jason predicts how long a task will take, blocks time in his calendar (iCal), then learns from the difference between his estimate and how long the task actually took. His timeboxing Medium post about the process went viral.

• Build a grumpy editor. Jason created a J. Jonah Jameson–style editor persona in Gemini. If you’re not familiar with the Spider-Man character, he’s a cantankerous, chain-smoking newspaper editor who tears apart a writer’s drafts. Jason says he takes about half of the suggestions.

• Choose your tools based on who built them. Jason uses Grammarly and Gemini, but refuses to use Meta AI or Grok. If he doesn’t trust those building a platform, he opts out.

• Learn the analog way before you go digital. Jason suggests students draw by hand first, not on an iPad. If you draw a bad line with a dip pen, you can’t hit undo. You learn through that process.

• Use AI to brainstorm, but know when to stop. Cartoonist of Cartooning in the Age of AI used an AI assistant to riff on cartoon premises from messy notes. Jason said she was intrigued by the results, until the bot offered to draw the cartoon for her. 👇

Tools & Apps We Discussed 👇

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🌤️ 7:00 am Wake up and prepare for the day

⏰ Peakeep “Invisible” Alarm Clock

This $14 bedside clock wakes me up. I set its brightness at zero to keep the bedroom dark at night. I tap the top to check the time if I need to. I bought the clock when I decided to store my phone in another room so it doesn’t suck me in before bed.

⭕️ Oura Ring

For the past five years I’ve worn an Oura ring to keep track of my exercise, sleep, and heart rate volatility. I like that, unlike an Apple or Google Watch, it has no distracting screen or notifications.

I ran a two-week experiment pairing the Oura with a Stelo glucose biosensor to see how my diet impacts my sleep, fitness, and energy levels. I can export my data and query it with AI assistants. Or I use Oura’s own AI chat to ask things like “How is my evening snacking affecting the quality of my sleep?”

In the morning I check my sleep quality and resilience scores to calibrate my expectations for the day. Having an objective measure of how well I’ve slept helps me decide whether to push my meager exercise regimen a bit or take it easy. It also helps motivate me on dreary days, and signals when I’m getting sick before I notice.

(Read my original Oura 2020 post. Note: I’ve bought my own Oura rings — no affiliation).

🧠 Brain Games and 🎶 Music

A breakfast ritual: playing the NYTimes’ Spelling Bee, Wordle, and Connections with my wife and daughters while listening to our favorite classical music host, Jeff Spurgeon, on WQXR. We talk about the music and what’s ahead at school or work, avoiding stressful headlines.

Quick tip: We listen on our old Google Home Mini kitchen smart speaker. A quick voice command pulls up just about any radio station in the world. (I saw the newer Google Nest Mini on sale this week for $19).

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That’s why I’ve been relying on Shortform for the past several years to help catch up with books I’m curious about but haven’t had time to read. I also use Shortform to remember key points from books I read years ago. I like the biography section, where I’ve learned about the lives of Malala, Bono, and Leonardo da Vinci.

While a lot of summary apps I’ve tried have 5-min, AI-generated, surface-level book overviews, Shortform’s writers and editors produce in-depth coverage of nonfiction titles.

I also like the business section, which has detailed guides for classic titles and new books I’m curious about like Two Awesome Hours by Josh Davis. In addition to an expert-written overview of key points, with examples, excerpts, and references to related books, you get a one-page summary and contrasting ideas from other authors. Now Shortform has podcast and article guides as well. Wonder Tools readers get a discount. Try it free to explore.

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🚶🏼8:00 Walk My Daughter to School 🏫

No tools or tech.

🚊 8:25 Commute

I use Snipd to listen to podcasts on the way to work. Here’s my full take. I also rely on Readwise Reader to catch up on articles I’ve saved. It works offline on the subway. Here’s why it’s worth trying. I use Superhuman to check work email.

📆 8:50 Plan the Day

When I get to work, I map out what's ahead with a mix of paper and apps.

📅 Google Calendar I check GCal for meetings. I‘ve tried other calendars, including Vimcal, Akiflow, Fantastical, and Notion Calendar. They each have useful features, but I tend to return to the free GCal out of habit. It’s reliable, simple, and lets me easily see shared calendars.

✅ Apple Reminders I keep three priority tasks at the top of my list. I add to that tier only when I’ve completed one. I have a menu of other tasks and reminders in a “Soon” list. I adopted that tactic from ’s great book, Four Thousand Weeks.

📄 Remarkable Paper Pro Move I use this paper tablet — or a notebook — to timebox my day. I map the hours based on priorities, energy level, and scheduled meetings. Having a detailed plan helps me avoid decision fatigue later. When I inevitably lose focus, the plan pulls me back on track.

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✍️ 9:00 Writing

I start creative work early, when my focus is freshest.

Letterly I dictate my thoughts into this app. That helps me get ideas flowing, and I get a bulleted summary or outline to build on. When I want an AI assistant to challenge my ideas, I use ChatGPT’s Advanced Voice Mode or Gemini Live.

Letterly and other apps like it (AudioPen) are great for what I call bionic dictation— using AI to structure raw speech into a clean outline or summary.

Free alternatives: You can use Apple Notes for dictation on iOS or Mac, or a variety of Google apps if you’re on Android or a Chromebook.

Google Docs / iA Writer I like both of these reliable blank canvases with minimal friction. (Read my take on what’s new in GDocs and why I like iA Writer). I’m also exploring new writing apps like Versey, a minimalist editor with thoughtful AI features.

Raycast Without switching apps, I type [control-space] to open a floating Raycast window. I can then quickly add something to my reminder list or calendar, check a thesaurus, calculate something, or do other tasks. That helps maintain my writing flow. (Why Raycast is a hidden gem).

Headspace Focus music without lyrics helps me block out noise around my Times Square office.

📨 10:00 Email Sprint

Superhuman I use keyboard shortcuts to move quickly through 80 morning messages. To help me keep track of replies I’m waiting for, Superhuman lets me attach automated reminders to resurface messages weeks later. Boomerang is a good alternative for follow-ups if you use Outlook or Gmail.

Flow Dictating messages saves my hands from typing fatigue. It’s remarkably accurate and plugs text directly into whatever app I’m using.

⏸️ 10:55 Break

Wakeout This app features short video loops of real people doing stretching and cardio moves. I can imitate their movements for one-minute exercises. These body breaks improve my focus.

🔬 11:00 Research

• Perplexity provides thorough, citation-backed search results powered by AI models that understand my detailed queries. The summary saves me from digging through hundreds of raw links. (My Perplexity update).

• Claude Projects & NotebookLM These AI tools help me find common themes, key ideas, and examples in prior materials I’ve created, so I can build on my own past work. (More on Claude Projects & my guide to NotebookLM).

That's a glimpse into my morning toolkit. In a follow-up I’ll share tools I use from late morning through bedtime. 🛌

What tools are YOU using today?

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