(2026-07-14) The Man Who Tried 200 To-do Apps Has Some Advice About AI

The man who tried 200 to-do apps has some advice about AI. Over the coming weeks, I'll be talking with people who can help us map which AI tools and strategies might help us keep your advantage at work — for now, at least. And there's no better person to join me first than David Pierce.

More recently he has launched Version History, a show about the defining products from tech's past, from the hoverboard to Vine, and what they can teach us about its future.

He estimates that he has personally installed, used, and abandoned some 200 to-do apps

You're infamous for a perpetual quest to find the best notes app. After all your years of tinkering, what has actually survived, and how solid does your current setup feel?

there are a handful of apps that all have every feature that I want minus one. Then they keep adding things that are like the thing that I want, so I go back to try that app. I realize it still doesn't have the actual feature that's very important to me

I'm switching between Todoist and Reminders at all times, for a variety of reasons, and then I'm bouncing between four or five notes apps depending on which particular pain point I'm willing to put up with at a given time

I switched from an app called NotePlan, which I really like. Obsidian has become this very popular app by building an app on top of a set of Markdown files. I think that idea is very important: that fundamentally, the thing at the base of it should be a bunch of things that I own

I discovered that actually, the problem was I would make these really beautiful to-do lists and never look at them. Just never. I'd be like, "Well, that's weird — I don't do anything on my to-do list. Maybe I'll get a new to-do list." So the biggest change for me has been figuring out what I need to be successful.

NotePlan takes that idea and spins a bunch of really interesting task-related stuff on top of it. Obsidian is very good for writing notes; NotePlan is much more geared toward being a daily notes and tasks app, and it does it very well. So I used it for a long time.

Newton: And when you say you're in Craft, you are also in Reminders. Does that mean you're also in Todoist as well?

Todoist and Reminders are two apps with opposite strengths for me. My running theory of all this stuff is that capture is the most important thing by a mile, and none of the rest of it matters. I think AI is actually increasing that fact

Reminders I really like because it has unparalleled Siri integration; it's the cleanest way I've ever found to get something out of my head and into a system, so I always end up coming back to it, because it's so fast. Todoist is a vastly better app for managing projects and to-dos, but most of the time, what I actually need is just a list of all my tasks. I don't need it any more complicated than that. Reminders, because it does a good job percolating around other apps too, is mostly the one I've gravitated to.

When you interviewed your colleagues at The Verge about their productivity systems, the lesson you took away was that simplicity and a single source of truth beat the perfect system. Why are those two elements so essential?

Having a single source of truth solves two problems at once, and we don't think enough about either of these problems. It's knowing where to put it, and then it's knowing where it is. I think that is the whole thing

So the idea of saying, "This is the place I put things," is the single most important thing you can do. Then the reverse of that is: I know where it is now. You don't have to build some elaborate system that will reveal it to you at the right time

I've become a big believer in mess in those spaces. I used to think I didn't want to see any tasks that I didn't need to worry about right now; I only wanted to have the most important things in front of me every minute. Then I started talking to authors and very productive people working on lots of creative projects. What they discovered is that actually seeing things over and over again is really important.

That I'm forced to wade through my to-do list every day makes me more likely to accomplish the things on it, because it plants them back in my brain. It helps create connections (associative) between things. You should be confronted by all of your stuff as often as possible.

We've seen a lot of productivity fads over the past 15 years: Inbox Zero, Getting Things Done, second brains. Now I think we're in some sort of Claude Code, Obsidian and OpenClaw moment. What do you think AI has genuinely changed about the way that normal people work in the last year?

I've heard from a lot of people that one of the things they like to do is say, "Show me all the stuff in Slack and my email and my to-do list that I missed yesterday. Just show me some high-priority stuff." They're getting mixed results

But there are so many tools out there now that are like, "We are going to perfectly prioritize your time for you, we're going to base it around your energy levels — all you do is plug in the API keys for five apps you use and we'll take care of everything for you." There is just absolutely no evidence in my life, or anyone else's that I talk to, that any of that stuff works at all.

Then there's Craft — which is the white whale of my productivity applications, because it is the one that is closest to doing everything correctly. It's almost a really great calendar app, it's almost a really great notes app, and it's almost a really great tasks app. Every time they make a tiny bit of progress in one of those directions, I throw my entire life back into it, run into the edges again, and leave.

I remember a few years ago when the Notion community really took off.

The Notion Reddit became completely overrun with people showing off these gorgeous, incredibly beautifully designed bespoke dashboards that accomplished nothing

there's a lot of basic day-to-day life-task stuff that is very helpful to offload to AI. It's the same as the Claude Cowork level of things to do: "I need to find a plumber." Just a real thing that happens all the time. I can go onto Nextdoor and Yelp and cross-reference all these different platforms to find a plumber. Or I can just go to Claude or Gemini or ChatGPT and say, "Can you find me a plumber that generally has pretty good reviews?" And they do a good job

But people are telling these stories about the agents they have managing their finances — don't do that! Just don't do that. If you're offloading your work priorities to AI and trusting that it will do a good job, it is going to fail you over and over and over again. It just will.

I've been using AI for podcast prep.

I also host this podcast called Version History. The show is part litigation of interesting products over time, and it is partly just straightforwardly a history show. So it has to be deeply researched; it has to be full of interesting reporting. I spend an enormous amount of time researching those shows. On the one hand, it's very fun, and I set it up as a show because I like doing that work. But I've also found myself wondering: is there a beginning of this process that I could offload? Yes, absolutely.
But every time I've done that, I think the show is worse.

Newton: There's a great Andrej Karpathy quote [it turned out to be a quote-tweet] that's just: "You can't outsource your understanding." There's a lot that you can hand over to AI, but the more you hand over, the less you are going to understand. And that really matters when you're hosting a podcast.

I also don't think I have an intellectual problem with, "Hey, can you recommend the 10 most-cited things about XYZ? If I were to start researching Nest, where do you think I should start?" I don't think that is outsourcing your understanding. But it falls down such a slippery slope into "I've actually done none of the work, and now I have an outline for a show that I've never read

Let me see how far I can get having AI clean up my email.
It was the most fascinating experience, because it turns out there's a bunch of stuff in your inbox that is obviously not useful. Lands' End sends me an email every eight minutes, and I don't need those. Claude very quickly was like, "David, you don't need these," and it was able to cut out a lot of the stuff in my email very quickly. That's the kind of Cowork-y busywork that I think is incredibly useful.

The minute it turned to my primary inbox, it started getting almost everything wrong.

Because what it does is it looks at something and thinks, "Well, this person seems to think that what they're emailing you about is very important, so it's probably very important." And it just made me think of SEO — you can game your way to the top of the search

I think the history of spreadsheets is really instructive in the history of AI.

So I extrapolate that out: can you do a reasonable job of telling me the facts, in order, about the history of Nest? Absolutely. Probably very well, and increasingly well over time. Can you actually point out the things that matter in this story? No. I just don't see it.

Everybody thought we would never have accountants again. And then what it turns out is Excel is really hard to use, and one of the skills of being an accountant is now proficiency in Excel. I think there's going to be a lot of that with AI.

It's not creative. It's not even thoughtful. It's just administrative. There is a limitless supply of administrative tasks in our lives,

Anyone who tells you that we're all going to stop having to do work because of all this, and we're going to live on universal basic income and just live lives of leisure, is ridiculous.

Think of AI the way you think about your laptop: it is a thing that I can do things with, not a replacement for my brain or my family, and I think you're going to be fine.

I can't let you get out of here without a recommendation. If a listener wants to turn their life over to one new piece of software tomorrow, in the realm of making them more productive, what should they check out?

Pierce: There's an app called MyMind that I really love. They developed it as a really beautiful visual reference guide

you wander through beautiful museums and take pictures of them and upload them, and it does a really interesting job. This, actually, I think is a fascinating and great use of AI: it automatically categorizes everything you put in

And again, when I come back to "you just need to know where everything is": MyMind is a really great place to put stuff. The way I've been using it is as an endless compendium of things that I like. If I read an article that I like, I save it into MyMind. If I watch a movie that I like, it goes into MyMind. If I read a quote in a story that I like, it goes into MyMind. If I take a picture of my kid that I like, it goes into MyMind

There's a very old idea of a commonplace book that people have been using forever, which is essentially this thing: you write down little snippets of things that are important or relevant to you. This is that, but in a way that is sortable and remixable