Hooked on To-Do Lists

Hundreds of Ways to Get S#!+ Done—and We Still Don’t

As someone who has tried quite a few apps over the year to try and organise myself better, and is currently getting by with just Reminders and Calendar, this article from Wired goes into the psychology behind these apps and why people have so much trouble with them.

Back in 2010, Walter Chen and Rodrigo Guzman had a weird idea: a website where you write down the stuff you accomplished that day, and which then emails you a summary. It would be a productivity tool that worked by a neat psychological hack, impressing yourself with your daily wins. “Often you discover that you’ve done more than you gave yourself credit for,” Chen says. “And this kind of motivates you—inspires you!”

Chen was a disenchanted lawyer; Guzman, a witty and talkative hacker. They built the tool in less than a week and launched it as IDoneThis. Soon they built an app by the same name and acquired 6,000 users. Within half a year, IDoneThis was the two creators’ full-time job.

But then those users started clamoring for more. People didn’t want merely to track the stuff they’d already done. They wanted to help plan for what they were going to do—from projects at work to the blizzard of tasks in their personal lives. Guzman and Chen updated IDoneThis with a new feature: to-do lists.

Which is when things went a little off the rails.

The results of their analysis of what their app’s users were doing sounds an awful lot like my experience with Wunderlist and OmniFocus, and to a lesser degree with Todoist.

Most common office tasks have well-settled software “solutions.” If I asked you to write a document, you’d probably use Word or Google Docs. To make a presentation, you’d pull up PowerPoint or Keynote or Google Slides.

Not so for to-dos. There is no Way That Everyone Does It. It’s a crazy Pokémon deck of options: Trello, Todoist, Gmail’s tasks, Microsoft To Do, Remember the Milk, Things, OmniFocus, Any.do,
Evernote’s Tasks, and Clear, to name just a few. And that doesn’t even count the whackload of us using one big ol’ Notepad file on our computers, or even plain old paper.

Unfortunately, as the article uncovers, these apps mainly help you see and organise your tasks — they don’t help you decide what tasks to put in there and why they need to be done.

Part of the reason why I ended up solely using Reminders and Calendar was that I’d realised I was spending a lot of time fretting over my to-do lists instead of actually doing stuff. So now I have a few recurring daily habit tasks, subscription renewal / expiry dates, and various ad-hoc reminders for things I need to do today or in the next few days. Meanwhile, my Calendar has subscriptions to various organisational schedules for reference, plus any appointments that I need to keep.

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

Paper forces you to repetitively rewrite tasks, as when, say, you transfer all last week’s undone to-dos to this week’s list, or when you erase and rewrite calendar events. That’s what I do when the productivity software I wrote for myself fails me. “Making that choice over and over again,” Carroll tells me, “is the first opportunity where you’re like, ‘Why am I doing this?’” The inconvenience can be clarifying. Making a list on a sheet of paper is an unusually rich metaphor for life: It takes effort, and the space fills up more quickly than you expect.

The usefulness of paper here cuts to the real heart of what makes to-do management such a grim problem. Apps, lists, and calendars can help us put our priorities in order, sure. But only we can figure out what those goals are. And setting limits on what we hope to do is philosophically painful. Every to-do list is a midlife crisis of unfulfilled promise. Winnowing away things you’ll never do in a weekly review is crucial, yet we dread it for what it says about the boundaries of existence. Our fragile psyches find it easier to build up a list of shame, freak out, and flee.

This is what makes to-do software unique. The majority of tools we use in our jobs are about communicating with someone else. All that messaging, all those Google docs, all that email—it’s about talking to other people, documenting things for them, trying to persuade them. But a to-do list is, ultimately, nothing more or less than an attempt to persuade yourself.

I’ve not yet been tempted to go down the paper route, but I suspect that doing so would probably be good for me in the long run, since a lot of the reminders I put in linking to online sources are at best putting off things I could probably get done there and then, or at least put them on a wish-list if they’re potential purchases.