Why There’s No Perfect To-do Manager


This article published last week at Wired is rather alarmingly titled “Why Can’t Anyone Make a Decent Freaking To-do App?” It looks at how the majority of the consumer public is not getting value from the litany of task management software options available out there, and contends that many people are returning to paper to help them:

Most of the myriad to-do list apps are fine. Some of them are very good. But none of them has ever solved my problem—your problem—of having too much to do, too little time to do it, and a brain incapable of remembering and prioritizing it all. Which explains why the old ways remain so popular.

I’m not sure there I agree that there are “no freaking decent to-do apps,” but I take the writer’s point. It does seem surprising that, at this late date, we still don’t have a clear winner in a software category that seeks to fulfill such a basic, universal human need.

For myself, I continue to be a daily user of Todoist, which has become invaluable to me. It brilliantly fulfills my basic requirements of task management software: it allows me to capture tasks easily and assign them to specific days. Every morning I look at what I have slated for that day; tasks that I didn’t complete the previous day I simply roll forward. It’s not rocket science but for me it’s very effective.

That may sound pretty standard, but even among Todoist users, I imagine you’d be hard pressed to find a dozen of us who use the software exactly the same way. For instance, I supplement Todoist with Apple’s Reminders app and Siri, so that I have a place to stash long-term and recurring tasks that I don’t want to see every day in Todoist, and so that I can enter tasks quickly with Siri (allowing me to add new tasks to Todoist via Siri would be a huge boon).

The finer details of how I use these various tools together are not really the point. What matters is that task management is highly idiosyncratic. Everybody wants a system that works in a very specific way, that matches their own particular cadence for interacting with such a system, that complements other tools, etc.

That’s why I’m a little skeptical of the Wired article’s assertion that artificial intelligence will fix this problem. It even features comments from Todoist’s own founder Amir Salihefendic, who believes that machine learning will help task management break through to a new level of relevance and usefulness, and that by and large our patterns for using this software are predictable enough that software will eventually be able to parse and anticipate them reliably.

I’m actually optimistic that this will be the case eventually, but I’m less sure that adding A.I. will result in an immediate breakthrough. Even with a system that can automatically parse our tasks, we’ll still each want to use that intelligence in very different ways. In some respects, the challenge of creating to-do apps is more about creating a framework that is compatible with a large user base’s countless individual definitions of “task management,” than about creating a single, unilateral method. Artificial intelligence will clearly be a powerful tool, but even when we have it in our toolbox, we’ll have to design systems that match real user needs.