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Jeremy Caplan
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  • Gretchen Rubin’s Secrets of Adulthood: Live with Jeremy Caplan
    Get full access to Wonder Tools at wondertools.substack.com/subscribe
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  • What's in My Conference Bag šŸ’¼
    In part one of this post, I shared my conference prep and networking toolkit. But here's the thing: conference value often gets lost the week after. You return exhausted, with a phone full of photos and a head full of ideas that slowly fade. Two things can help. A little hardware — worth its carry-on weight— and a few smart post-event tools. These streamline how I show up — and follow-up.My Conference Gear1. The Digital NotebookreMarkable Paper Pro Move This new digital notebook is like a cross between a Kindle and an iPad. It doesn’t have apps. It doesn’t send notifications. It doesn’t play video or audio. It has a screen designed to feel like you’re writing on paper. It bridges handwritten notes and searchable text.I often prefer to take live session notes on my laptop, with Granola, as noted in part one. But in some sessions, writing by hand feels less distracting. My notes are searchable later and they’re backed up and accessible on the reMarkable phone app and my laptop.I like the new templates and workbooks so I don’t always have to start with a blank page. And having digital notes means I avoid adding to the stack of paper notebooks under my desk. To justify the $450 expense for the well-made Norwegian device you’ll want to use it regularly for several years. For a cheaper reusable option, consider a Rocketbook. The mini is $20 and other— like the Flex Planner— are under $50. Read more about my exploration of paper vs digital notes.2. Backup Buddy šŸŽ™ļøSony ICD-UX570 Digital Recorder ($98) This fits comfortably in my pocket, with a pop-out USB connector for transferring recordings to my laptop. * It comes in handy if you’re in a front-row seat, where laptop typing may feel intrusive. * It beats phone apps that can crash, or a laptop mic that picks up more ambient noise.* The audio quality, while not as good as a pro device, may be decent enough for a podcast sound bite. Post-event transcription* MacWhisper is free for transcribing audio files locally on your laptop.* NotebookLM also provides fast free transcription, for files up to 200mb. * Alice enables high-quality, secure transcription for $3 to $10/hour. * Good Tape, a Danish service created by journalists for journalists, is free for three 30-min transcriptions a month, or ~$15/month billed annually for 20 hours of transcription.* Escriba is free to try for a week, then $10/month for 6 hours of transcription. Like Good Tape, it works in 90+ languages. Developed by Brazilian fact-checking organization Aos Fatos, all revenue is reinvested in the newsroom.* Want more options? Check out a recent post on the best transcription tools.3. The Quiet Saver šŸŽ§Sony WH-1000XM6 Noise-Cancelling Headphones Find moments of quiet and crystal-clear phone calls even in chaotic convention halls. Yes, like the reMarkable, they cost an eye-watering $450. But my last pair (XM3) lasted 7 years— and still work as a backup. That's about $5/month for daily peace of mind. The new AirPods 3 ($250) look to be a cheaper and more easily portable alternative. I may test them soon.4. A Lighter Laptop šŸ’»13-inch MacBook Air After lugging a heavy backpack around for decades, I’m now carrying less. I bought this slender backup so I don’t have to haul my chunky Macbook Pro to and from work. For 95% of what I do, the laptops function equally well. Sponsored MessagešŸŽ„ Effortless Tutorial Video Creation with GuiddeTransform your team’s static training materials into dynamic, engaging video guides with Guidde. Here’s what you’ll love:1ļøāƒ£ Easy to Create: Turn PDFs into impressive video tutorials with a single click.2ļøāƒ£ Easy to Update: Refresh video content to keep your training materials relevant.3ļøāƒ£ Easy to Localize: Generate multilingual guides to ensure global accessibility.Empower your teammates with interactive learning. And the best part? The browser extension is 100% free.II. Post-Conference Processing4. Reflect on what you’ve learnedThe OpenNews After Party Toolkit is a smart guide to conference follow-up. When a pile of work greets you, it’s easy for event takeaways to melt away. That’s why this guide is so useful, with tips to help you: * Reflect during the flight home* Write a one-pager for your boss* Host a brown-bag at work * Make follow-up handouts The guide was prepared by Emma Carew Grovum for SRCCON, a gathering of forward-looking journalists. 5. Create Your Conference Brain 🧠NotebookLM Drop your notes, slides, audio recordings, handouts, photos—into NotebookLM for an AI-powered knowledge base. Query your collection, generate audio summaries for the flight home, or create video overviews for team debriefs. You can now generate custom reports as well, focused on specific topics. The reports include helpful citations, pointing you back to the spot in your notes where something was mentioned. Upload materials daily during the conference to avoid post-event overwhelm. Here’s what I like about NotebookLM.Create a master notebook: A senior journalist at the Online News Association conference told me she uses NotebookLM to create an uber-conference notebook with notes from all the conferences she attends. That way she can query across multiple events. That’s valuable months later when it’s hard to remember which conference had the panel covering some specific topic of interest. It also helps surface recurring themes. Author Steven Johnson, who co-founded NotebookLM, does something similar, relying on a notebook that has the text of all his books and major writings. 6. Process Through Conversation šŸ’¬ChatGPT Advanced Voice Mode Let AI interview you about conference takeaways. Speaking freely helps process ideas you haven't fully formed yet. Ask for a summary of your own insights to capture thoughts while they're fresh. You can also chat with Claude, Gemini or Copilot, asking your AI assistant to interview you about the conference and then summarize your responses. You can use a simple prompt ā€œInterview me about the conference I just attended and help me think through what was most notable and what I can follow-up on.ā€ Or draw on these more detailed prompts.7. Visualize Your Insights šŸ“ŠMyLens Transform your summary notes into visual mind maps and infographics. We often remember things better when we visualize them.Alternatives: ChatGPT’s new image generation engine can create informational graphics as well. Napkin designs detailed infographics (see why I like it), while Gamma works best if you want slides rather than infographics (why Gamma is useful).ps. Here’s a Wonder Tools Interactive Conference Toolkit Guide, made w/ Claude. Get full access to Wonder Tools at wondertools.substack.com/subscribe
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  • My Conference Survival Kit šŸ“±
    I go to conferences just a few times a year. To make the most of the frenzied days, I rely on a suite of tools. Read on below for those worth trying, and then read my follow-up post: What’s in My Conference Bag šŸ’¼ I. The Week Before1. Mine Your Network GoldmineClay | This personal rolodex enhances your contact list with info from LinkedIn and whatever other social platforms you choose (Instagram, Facebook, X). You can use Nexus, its new AI-enhanced search, to surface contacts in your conference city, or people in your network with specific expertise or interests.If you connect Clay to your calendar and email, it shows you a list of past meetings and email threads you’ve exchanged with a given contact for context. At the conference you can also use it to add private notes to a contact. It’s free for up to 1,000 contacts, or $10/month billed annually for unlimited. Pro alternative: Folk is a more advanced CRM (Customer Relationship Management) tool that’s useful if you’re attending conferences for sales, or if you manage a service business that involves a lot of outreach. It’s a pro tool, but surprisingly well designed. There’s a new ChatGPT integration so you can use ordinary language to query all your contacts and sales leads. If I were to run a sales-heavy project, I’d use this.2. Build Your Intelligence HubPerplexity Spaces | Create a dedicated Space for your conference—think of it as a smart folder for all your research queries. * It can be private, shared with colleagues who can contribute, or public. * Use it for queries related to conference sessions you’re attending or leading. * You can also use Spaces to plan for free time between sessions. Customize a Space’s instructions with your preferences to discover restaurants, music, museums, or whatever else interests you near the conference. * Upload files to give the AI assistant further context. Add reference docs from conference organizers, recommendations from friends, or a city guide you like.Learn more: Check my most recent Perplexity guide.. Alternative: you can similarly set up a project in Claude or ChatGPT with relevant documents and queries. Or set up a notebook in NotebookLM.For further prep: Check out this pre-conference Planning Exercise, part of a helpful OpenNews toolkit by Emma Carew Grovum. 3. Create Pop-Up Networking MealsPartiful | Set up open lunches or dinners that conference connections can join spontaneously. Group meals build on hallway small talk for relationship building. Many people eat alone because coordinating is tricky, or they don’t know where to go outside the hotel or conference center.It’s completely free. Create events during the conference, then share the QR code when you meet someone interesting—they can RSVP instantly on their phone. You can use the app to check RSVPs, or to send updates or follow-ups. Or post the RSVP link to an event discussion thread, or include it in an email. Schedule 2-3 meals throughout the conference and cap attendance at 6-8 people for rich conversations.For informal conference get-togethers Partiful is a good alternative to Lu.ma — the RSVP app I like using to send invites for my paid subscriber events online. Both are great, but Partiful integrates texting in a smart way, includes QR codes for RSVPing, and has a more social feel for spur of the moment gatherings.Sponsored MessagešŸŽ„ Guidde | Create how-to guides with AITired of explaining the same thing over and over again to your colleagues?Guidde is an AI-powered tool that helps you explain the most complex tasks in seconds with AI-generated documentation.* Turn boring documentation into stunning visual guides* Save valuable time by creating video documentation 11x faster* Share or embed your guide anywhereJust click capture on the browser extension. The app will automatically generate step-by-step video guides complete with visuals, voiceover and call to action.The best part? The extension is 100% free.II. At the Conference: Capture What Matters4. Never Miss a MomentGranola | This hybrid note-taking app combines your typed notes with AI-enhanced transcription. Record sessions on your phone or laptop while jotting down key thoughts—Granola merges both into session summaries you can query.When my mind wanders during a session, I like being able to review the transcript to catch up. And if I have to step out for a minute or respond to an important message, I still have full notes. No audio or video is stored, just the transcript and summary. I’ve been surprised at how accurate the transcripts tend to be, even when I’m sitting in the middle of a large presentation room. It’s free for 25 meetings or $18/month for unlimited.Case in point: At the Online News Association (ONA) conference I just attended in New Orleans, I created a folder with Granola for all my session notes. Now I can query my whole collection of conference notes for follow-ups.Alternatives* Bloks is a pro option I’ve written about before. It integrates with Salesforce, HubSpot, and other pro platforms, but it’s now $69/month billed annually after a 14-day trial, so it’s only relevant for hard-core business use.* Macwhisper is a great free app that can record and transcribe locally on your laptop, but it doesn’t show you the live transcript or let you mix in your own notes. 5. Connect with PeopleLinkedIn QR Code Scanner | Skip the business card shuffle. To use LinkedIn's free built-in QR scanner, tap the mobile app’s search bar and click the scanner icon on the far right. You can then scan someone else’s LinkedIn QR code or have them scan yours. You’re instantly connected without having to type anything. No need to spend an hour processing a stack of business cards later.Uniqode | If LinkedIn doesn’t suit you for connecting, create a free Uniqode digital business card. Save to your Apple or Google Wallet to easily share contact info without having to hunt through your photos app.Or if you want a simple way to give people you meet a link, a PDF, a group of images, or a vCard with contact info, QR Codes Unlimited lets you quickly create and download a QR code for free with customized colors and designs.6. Digitize EverythingScanner Pro by Readdle | Transform blurry photos of slides or awkward snapshots of handouts into clean, readable documents. The features I like: * Quality scans | New tech improves on previous apps I’ve tried. * Smart cropping | The app auto-detects slide or paper edges. * Conversion | I usually render scans in high-contrast black and white, unless the colors are crucial.* Organization | It’s simple to keep scans in topical folders, e.g. receipts, books, mementos, recipes, ONA25. * Less paper | At conferences I try to scan most handouts now instead of hauling a stack of paper home. It lightens my bag, limits my office paper mess, and shortens processing time back at work.* Cleaner camera roll | I prefer scans in a dedicated app so they don’t clutter up my camera roll. * Access your scans from anywhere | Use Dropbox, Google Drive, or OneDrive for automatic backups and to see or share your scans on any device.This post is continued in Part 2 — What’s in My Conference Bag šŸ’¼. Get full access to Wonder Tools at wondertools.substack.com/subscribe
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  • šŸ“š Meet Your New AI Tutor
    AI assistants are now more than simple answer machines. ChatGPT's new Study Mode, Claude's Learning Mode, and Gemini's Guided Learning represent a significant shift. Instead of just providing answers, these free tools act as adaptive, 24/7 personal tutors. Sponsored MessagešŸŽ„ Guidde | Create how-to guides with AITired of explaining the same thing over and over again to your colleagues?Guidde is an AI-powered tool that helps you explain the most complex tasks in seconds with AI-generated documentation.* Turn boring documentation into stunning visual guides* Save valuable time by creating video documentation 11x faster* Share or embed your guide anywhereJust click capture on the browser extension. The app will automatically generate step-by-step video guides complete with visuals, voiceover and call to action.The best part? The extension is 100% free.New Tools for Studying and LearningChatGPT Study ModeGet Started: Select Study Mode from the plus menu when starting a new chat. [Screenshot]. Start with context. Tell ChatGPT what you want to learn, why, and what you already know. The model excels at adapting to your level and guiding you step by step. My take: I’ve been experimenting with AI learning modes to understand the intricacies of venture capital investing. ChatGPT initially overwhelmed me with info [screenshot], then seemed to notice I was drowning and adjusted its pace. It must have seen my confused frown. šŸ˜µā€šŸ’« Note: You can use ā€œStudy and learnā€ mode on mobile and with ChatGPT in a browser, but you can’t yet access it in the desktop app or within a ChatGPT Project. Below is a quick example of a dialogue in Study Mode šŸ‘‡Gemini Guided LearningGet Started: Visit g.co/gemini/guidedlearning My take: Gemini has been an excellent tutor. It replies concisely to my questions about venture capital. For example, so far it has: * Quizzed me (try a basic example)* Created a helpful infographic* Generated an audio overview, in the style of NotebookLM * Made me a custom Web page* Shared simple digital flashcards The tangible artifacts help me visualize concepts and test my own understanding. The model takes a minute or so to produce infographics and a little longer to create audio overviews. I’m repeatedly returning to these materials to review what still feels fuzzy — arcane details of valuation, cap tables, dilution, and convertible notes. Below is an example of a scientific infographic šŸ‘‡Other Google Learning Tools* Illuminate turns academic papers and research into audio summaries* Learn About responds thoroughly and helpfully to any inquiry* Learning Coach Gem is an assistant you can chat with. * Little Language Lessons offers quick takeaways. * LearnLM is Google’s family of language models for learning, grounded in educational research.Claude Learning ModeGet Started: Select "Learning" from the style menu. This step initially confused me because the other options in that menu are writing styles.My take: Claude's scenario-based questions —like these— push me to think through real-world situations to practice applying what I’m learning. Tips: As you learn, ask Claude to create artifacts—little interactive apps— that help you practice what you're learning. Also request occasional challenges, case studies, or quizzes.Advantage: Unlike ChatGPT, you can use Learning Mode within Claude Projects. That allows you to benefit from personalized learning alongside your uploaded documents and context. So you can upload a slew of files, reports, and research resources and let Claude tutor you on those materials. Learn Mode vs. Answer Mode 🌟Turn on the learning features for any of these AI assistants and you’ll quickly notice the difference. * Learning modes use Socratic questioning — asking rather than telling. * They adapt to your level of understanding. * They nudge you to make your own observations. * They help you test your understanding with informal quizzes. * They guide you step-by-step through complex topics rather than rushing to throw answers at you. In learning mode, these assistants feel like tutors; in standard mode they’re more like interactive encyclopedias.The difference is significant. On previous occasions when I wanted to analyze data, I'd ask for quick insights. In study mode I've learned, among other things, how to use pivot tables more effectively so I can analyze data more thoroughly myself. Rather than getting fish handed to me, I'm learning to fish.Topics to try in learn mode* ā€œHow do tariffs impact supply chains?ā€ or ā€œHow does cryptocurrency work?ā€* ā€œGuide me through the basics of [science/math concept]ā€* ā€œIn what ways might Shakespeare have influenced Montaigne’s essays?ā€* ā€œHow do private equity firms operate? Help me understand the nuances.ā€4 Ways to Learn with AI šŸ“š1. Understand a complex concept or skill šŸ’ŖWhat it's for: Work or school topics you need to grasp thoroughly, or just topics you’re curious aboutMy experience: I'm using AI study modes to review probabilities for dice, tile and card picking for tabletop games like Qwixx, Splendor, Azul, Point Salad, and backgammon. The AI helps me move forward step-by-step, checking my progress and slowing down when I get confused. I like being able to ask dumb questions without embarrassment. 🫢2. Indulge your intellectual curiosity šŸ¤”What it's for: Topics you find fascinating. Learning for its own sake.My experience: After reading HernĆ”n DĆ­az’s Trust recently, I went down a rabbit hole learning about metafiction (stories within stories) and polyphony (stories from multiple vantage points) and discovering new connections between various authors. This pure intellectual exploration feels different from work-focused learning. It's driven by curiosity rather than necessity. I like that I can leap from tangent to tangent whenever I feel like it. I can also stop suddenly and return to a thread days later. The assistant loses no momentum and continues as if we never paused. 3. Deepen your expertiseWhat it's for: Expand your understanding of something you’ve already studied.My experience: I'm using AI learning modes to explore connections between classical composers whose music I’ve spent my life listening to and playing. I’m also sharpening the way I use spreadsheets for data analysis. The AI builds on what I already know, rather than starting from scratch.4. Learn how to learnWhat it's for: Discover how you learn best. Learn about learning and how to sharpen your brain. My experience: I'm experimenting with AI learning approaches to see what works best for me, and getting to know more about learning science. Most valuable so far: Gemini's quizzes and infographics, Claude's short answer questions, and practicing summarizing and expanding on ChatGPT’s explanations. The most useful learning mode features* Short quizzes with instant feedback that force me to apply what I’m learning * Scenarios I have to analyze that force me to make nuanced distinctions* Realistic case studies that require me to summarize new concepts* Asking as many dumb questions as I wantRequesting tangible learning artifacts, like infographics, audio overviews, flashcards, and tables In my own teaching (at CUNY’s Newmark Graduate School of Journalism) I’m planning to incorporate more formative micro-assessments — brief in-class ungraded quizzes using tools like Slido and Socrative to help me check what students understand and to give them more tiny opportunities to practice what we’re learning.🌟 Take my learning quiz to pick the tool best for you! Get full access to Wonder Tools at wondertools.substack.com/subscribe
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  • Weird prompts, better answers 🧠
    AI assistants are surprisingly conservative by default. Push them to be unconventional, and you’ll get dramatically different results. This updated guide shares my favorite techniques for getting fresh, useful responses instead of predictable pablum.[Editor's note: Are you actually reading these episode notes? If so, I'd love to hear from you. Are they useful? Would you prefer they were shorter summaries of the post, rather than full text? Email jeremy at jeremycaplan.com if you have thoughts or feedback]The prompts below push ChatGPT, Claude, or whatever other AI tool you prefer to break its conventional patterns, progressing from bland to provocative. The payoff: your AI assistant becomes a creative crane, helping you reach in new directions. Rather than serving as a generic answer machine, your queries can point you toward unexpected angles and radical insights.5 ways to push AI to be boldAdd weird constraints. Force creative breakthroughs by setting up artificial limitations. Example: ā€œHelp me explain [X] using words a 12-year-old would understand, but make it engaging enough for experts in the field.ā€Channel historical problem-solvers. How might figures who made their mark on the past manage my little strategic query. Example: If Maya Angelou were mediating this team conflict, what questions would she ask that no one else is considering?Insist on strange cross-pollination. Require the borrowing of concepts, frameworks, or terminology from vastly different domains. Example: ā€œAnalyze my [business / creative project] through the lens of marine biology. What patterns or ecosystem principles could apply here?ā€Apply disaster movie logic. Push an AI assistant to consider a workplace problem with the urgency of a crisis scenario to explore unconventional ways to quickly address a slow-moving issue. Example: ā€œThis team project has 48 hours before catastrophic failure. What unconventional resources could we deploy? What rules would we break to succeed?’Embrace absurd analogies. Challenge the AI to reply in terms that may seem silly at first, but may yield unexpected clarity.Example: ā€œTo help me simplify the most confusing aspect of my presentation, explain my fundraising strategy [X] as if it were a board game instruction manual.ā€Give me strange and surprising feedbackWhen I’m in a creative rut, I paste in a section of writing and prompt AI to be bold and unconventional: ā€œOffer 5 surprising, bold suggestions for specific ways to improve the following piece of writing. Along with each suggestion, include a detailed, creative explanation with your rationale.ā€ā€œAct as an unpredictable, brilliant writing coach who offers strange, quirky, creative suggestions. Provide specific, granular input.ā€ā€œDetail novel topic ideas or peculiarly provocative questions I could answer to help me disrupt the conventionality or predictability of the following outline I've begun.ā€ ā€œPoint out blindspots. Spotlight what others with radically different perspectives might find problematic if they were to read this with a critical eye. Offer a list of unconventional suggestions for addressing these issues.ā€10 odd AI prompts to get radically new resultsĀ What are 3 quirky, unusual analogies to explain [your phenomenon of interest]. See my ChatGPT example prompt and result. Propose 5 questions a reader would be surprised to find answered on [your topic X]. See my ChatGPT example.Who are 7 surprising, odd historical figures to cite as examples of [X]. For each individual include a detailed explanation. See my Perplexity example.What rarely discussed, counterintuitive insights on the subject of [X]Ā might startle readers accustomed to bland observations?Ā See my Gemini example.Give me 5 lively, colorful, unusual words to use in a description of [X]?Ā See my Microsoft Copilot example.Provide 3 extreme, surprising examples of [X] or silly, ridiculous instances.Share 5 counterintuitive ways to address situation [X]. See my Grok example Imagine I shocked people with a one sentence answer to the following question: [X]. Give me 10 versions of that one-sentence reply.Ā See my Jan AI example.I have [X challenge] in [Y situation]. Assume I want to surprise people with a wildly creative solution. Describe three solutions that would stun people while addressing the root of the issue.Ā For a syllabus I’m creating on [X], imagine seven radically different people teaching the same course. Provide three bullet points representing each teacher, explaining the surprising and distinct learning outcomes each would aim for in their version of the class.Ā How to get started with provocative prompts Step 1: Pick an AI chat tool to experiment with: ChatGPT, Claude, Gemini or Microsoft Copilot. Step 2: Initiate a new chat by typing in a role for the AI to adopt for the prompt you’re going to give it. For example: ā€œAct as a bold, experienced, expert who provides distinctive, unusual perspectives to push my thinking in creative new directions.ā€Step 3: Adapt one of the unusual AI prompt templates above to fit your context. Step 4: Follow-up. After the initial response, iterate. Steer the dialogue in a direction of interest. Ask for even more radical suggestions. AI assistants excel at generating lots and lots of ideas, out of which it’s easier to find one good one.Step 5. Set up a project (Optional). To create an ongoing space where you get bold, unconventional responses, set up a Claude Project or ChatGPT Project with instructions, and prior examples. Note: both require paid plans. A free alternative: train a bold bot on Poe. Get full access to Wonder Tools at wondertools.substack.com/subscribe
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