Why To-Do Apps Don’t Work (For Me)

Back in June, I wrote about the project management paradox. In that piece, I tried to answer the question,

Why is it that I can manage large, complicated, technical projects at work, but be paralyzed with indecision when it comes to managing my own to-do list outside of work? What’s worse, I can’t even settle on a way to manage that to-do list.

Well, Clive Thompson1 may have the answer. In his recent article in the September issue of WIRED, Thompson asks the question: why don’t to-do apps help us get stuff done? It turns out, there are a lot of good reasons, and even the makers of the apps agree with them. He writes,

The creators of personal to-do apps–or task management software, as it’s sometimes called–generally agree that they haven’t cracked the nut.

The fact that to-do apps makes it easier for us to record what we have to do is part of the problem. We accumulate more stuff because it is easy to accumulate. The fact that there are market forces driving us to feel more productive also help to proliferate tasks. Then, too, we don’t often think of the accumulation of to-do items in a time-context: we only have so much time in our lives to get things done, so we need a better way of figuring out what matters and then actually doing that stuff.

It is a fascinating read, especially for someone (like me) who has tried and failed with so many to-do apps. And some of the conclusions drawn in the article vindicate my recent musings on the lure of paper. Thompson writes,

In this vein, a whole bench of task management philosophers believe that the best interface isn’t digital at all–it’s paper.

For anyone interested in the psychology of task management, to say nothing of the failure of to-do list apps to achieve their goals, this article is for you. I recommend checking it out.

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  1. If you haven’t read Thompson’s book, Coders, it too is a great read. It described the kinds of things I do in my day job more accurately than other things I’ve read about coding.


  1. This reminds me of the email problem IBM had when they started using it as outlined in A World Without Email. When they first installed their email system they looked at all communication and built the system for that plus a bunch of buffer. The system died quickly under 5 or 6 times more communication. The lack of friction made it easier to send messages that didn’t matter.

    Page 70 (or there abouts) if you end up looking the story up.

  2. A very familiar story.
    It looks like no real to-do tool will soon arrive and it would need a lot more intelligence from an app.

    For instance, when you enter a recurring “Mow the lawn” item in a to-do app on a weekly schedule with a timeslot in a calendar, the app will have to check a weather app if the weather will be favourable in the allocated slot. Was the weather that week good enough (not too hot and not too cold) for the grass to grow and that it doesn’t rain that day. It also needs to synchonize with other reminders if the grass needs scarifying, fertilising or chalk. You have to do the one of the to-do’s on short grass, the other on just-cut-grass, and a third on cut-grass when it starts raining within 2 days. And there are a lot more combinations to program.
    So for the time being, I suppose. we’ll have be “stuck” for this to-do with human intelligence.

    After using Things and Bullet Journal I went back to Apple’s “Reminders” on iPad and iPhone (my old version of macOS is not included in the syncing!!), where I only enter recurring to-do’s. Weekly I check the Reminders-app and bring the due to-do items over to a piece of paper. During the week I keep that paper on my desk and update that with other to-do’s that come up or that I think of during the week.

    It’s a pity though having a free to-do app on the mac that you cannot allocate time-slots in the nearby located free calendar-app from there (my other project tool, Agenda, is able to do that, but that’s another app again). Apple could for this purpose put a lot more intelligence in the combination of their applications.

    Maybe they just want to leave some business to other app developers!(??)

    1. Jaap, reading the article, I was intrigued by the notion of time-blocking, which I seem to recall reading about in Cal Newport’s book Deep Work, which relates to your idea of scheduling the mow the lawn task on a calendar when it won’t be raining. In the article, Thompson write,

      Instead of putting tasks on a list, you do “time blocking,” putting every task in your calendar as a chunk of work. That way you can immediately see when you’re biting off more than you can chew… Time blocking forces us to wrestle directly with the angel of death. It’s natural that we then screw around less. Several researchers who study tasks told me they generally agree that time blocking avoids the problems of to-do apps and lists.

      I like this idea because it creates a visual picture of your capacity: what you can take on and what you can’t. And if you push that, you do so at your own risk. But it also raises additional questions:

      • What is the right level of granularity? Half-hour chunks? Ten minutes?
      • How good do you have to be at estimating how long something will take?
      • If something takes more time, what happens to everything else on your calendar?

      I agree that it would be a real innovation if Apple integrated its Reminders app with the Calendar app in a way that let you put tasks in slots, and also, limit what you can put in slots. The apps can then have a view that shows you how busy you are. They could even use AI to tell you when the best times to do certain tasks. Something light that might be worth looking into.

      1. While I personally don’t use a to-do app anymore, this reminded me of Sorted (www.sortedapp.com) and what they’re trying to accomplish. Well worth a look for all the to-do app junkies of the world 🙂


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