Thank you Alex Hallatt, John Ward, Lynette, Des Kennedy, Doreen Schmid, and many others for tuning into my live video with Jeremy Caplan! Join me for my next live video in the app.
When I first sat down to chat with Jeremy Caplan about artificial intelligence and digital productivity tools, I genuinely did not think we would end up talking about him playing the violin. I certainly did not expect the conversation to pivot into a deep, philosophical appreciation for the irreplaceable magic of humans sitting in a room together, simply enjoying a live performance.
But tha’s the funny thing about talking to someone who spends their life evaluating machines. You inevitably end up talking about what it means to be human.
The frictionless technological utopia we were promised feels increasingly like a relentless, exhausting deluge. Every week brings a new platform to master, a new algorithm to appease, and a new artificial intelligence threatening to automate us into oblivion. It’s like drinking from a fire hose while someone yells at you to “pivot to video!”
This is exactly why I was so incredibly relieved to sit down with Jeremy on this episode of Draw Me Anything.
Jeremy is a rare beacon of sanity in the digital miasma. He is the Director of Teaching and Learning at CUNY’s Newmark Graduate School of Journalism. He is a former journalist for Time Magazine. Before that, he was a classical violinist. But more importantly for my own daily survival, he is the creator of the massively popular Wonder Tools newsletter on Substack. Jeremy spends his days wading into the chaotic, deeply overwhelming waters of the internet. He tests, breaks, and reviews new apps, software, and digital features so the rest of us don’t have to waste our precious human hours doing it.
Distilling the Chaos
We kicked off the stream talking about the exhaustion of trying to keep up with tech news. It is not just about discovering new tools anymore. It is about tracking the constant, aggressive updates to existing tools. ChatGPT has a new voice feature. Gemini just launched a massive update. Claude is now doing something entirely new with your phone. And you can’t opt out of it.. It never stops.
Jeremy explained that his superpower for distilling this madness down to accessible, bite-sized pieces actually came from his time writing for Time for Kids. When you have to explain complex global news to an eight-year-old in exactly one hundred words, you learn to cut the jargon immediately. You learn to anticipate a human reader’s questions and preemptively answer them.
He also cited the legendary tech writer Walt Mossberg as a major mentor and influence. Mossberg succeeded wildly at The Wall Street Journal because he approached technology not as a deeply entrenched engineer, but as an ordinary guy just trying to figure out how a tool could actually be useful in his daily life.
“I find writing to be extraordinarily difficult. I read The Elements of Style. I read Anne Lamott’s Bird by Bird. I read David Sedaris constantly to study comedic pacing and essay structure. But actually getting the words out of my head and onto the page feels like passing a kidney stone…”
That is exactly what Jeremy does with Wonder Tools. He doesn’t just list fifty new AI tools that launched on Product Hunt this week. He gives you three specific, highly actionable ways to use one feature of NotebookLM to make your Tuesday slightly less miserable. He gives you templates. He shows you what a forty-page deep research report from Gemini actually looks like, so you do not have to spend twenty minutes generating one just to see if it is useful.
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Evergreen Processes over Disposable News
One of the most fascinating things about Jeremy’s approach is his focus on evergreen content. We’re constantly blasted with disposable news. A tech CEO gets fired, a new app launches and dies in a week, a company changes its name. Jeremy actively avoids the daily churn. He wants to create resources that a reader can save and return to three weeks later, knowing the information will still be fundamentally useful.
This really resonated with me. I told him about a post I wrote on Medium over a decade ago. People constantly ask me how I manage to juggle cartooning, stand-up comedy, writing, and running a business without completely losing my mind. The answer is timeboxing. I work strictly from a calendar, not a to-do list. I estimate how long a task will take, block it out in my iCal, and adjust the time block later if it took longer or shorter than expected.
I wrote a simple, straightforward piece explaining this exact process. I thought it was old news. Cal Newport had written about it years prior. But the piece went incredibly viral, and I made two thousand dollars from the Medium partner programme purely off that one specific workflow explanation. Sometimes the most valuable tools are not shiny new apps. Sometimes, they are just fundamentally sound ways of organising a chaotic human brain.
The Ethical Calculus of AI
We eventually had to talk about the elephant in the room. Artificial intelligence…
I frequently get accused of being either a doomer or a total Luddite, but the truth is, I am an early adopter. I was one of the very first cartoonists in my circle to embrace Wacom tablets, Cintiqs, and the iPad Pro. I actively test out tablets for companies like Xencelabs. I do not shy away from folding digital tools into my workflow when they help automate the absolute drudgery of administrative freelance life.
However, the rapid acceleration of generative AI requires a lot of mental arithmetic. I told Jeremy about my personal ethical boundaries. I use Grammarly for proofreading. I am currently experimenting with Gemini for deep research. But I absolutely refuse to use Meta AI or Elon Musk’s Grok because I fundamentally distrust the ethics of the people building them. I opt out of the platforms where I find the creators ethically compromised.
Putting these streams together, wrangling brilliant guests, manually untangling the spaghetti bowl of a brain to pull out the best insights, and writing these recaps requires a heady cocktail of intense caffeine and sheer willpower. If you value this little digital monastery, please consider upgrading to a paid subscription for just $1 a week. It pays for my time, repays the time and labour of writing these up, and keeps Morris supplied with the unnecessarily expensive dog food he demands…
