Declaring ‘To-Do List Bankruptcy’

Sometimes you gotta burn it all down and start fresh

“Fire”, by Vladimir Pustovit

Last week I had to take drastic measures in my organizational life.

I declared “to-do bankruptcy”.

I took my mammoth to-do list — a huge teetering pile of undone tasks — and burned it to the ground.

Why? Because it had grown Too Damn Big. For the last year I’d been using a simple app that lets me write all my tasks in one big text file. I’d organize my tasks into categories — like “household”, “Wired column”, “story ideas”, etc. Then I’d put a bunch of sub-tasks in each bucket.

Over the last few months, though, I’d been adding tasks at a faster rate than I was doing them. That meant my list kept on metastasizing, embiggening every week. By the time 2022 rolled around, my list was scores and scores of items long. I had to scroll down a couple of feet on my app to view it all. My “household” section had 30+ items; each reseach projects had dozens each; there was a “Misc” section that stretched to the horizon and fell off the flat earth.

When I looked at it, my head swam. I felt depressed. I knew there was no way I’d accomplish all that.

This, as it happens, is a well-known phenomenon in the world of productivity.

It’s called “The List of Shame”.

Why tasks spiral into a “List of Shame”

I learned that evocative phrase last year while reporting a story for Wired on the eternal horror of to-do lists.

It turns out that the entrepreneurs who build and run to-do apps have noticed that their users often get themselves into the same pickle I did. They tend to put way too many things on their lists.

We do this for a perfectly understandable reason: We’re trying to get those tasks out of our heads so we won’t be haunted by them any more. It feels awesome! Each task we set down in an app (or on paper) temporarily clears our head: Whew, I’m getting organized!

The problem is, putting things on our lists feels like such a relief that we begin overloading those lists. Every last thing that comes across our desk spawns a new to-do. We want to feel that momentary burst of…