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 addingtasks at a faster rate than I was doingthem. 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 waytoo 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 relief again and again.

But pretty soon our app is so crammed that it’s like a closet where you can barely jam the door shut. We no longer want to open it, because we’re terrified of the tentacled mess that’ll spill out. The irony is rich; we initially began using a to-do list to feel the thrill of organization, but now it only delivers the darkest sense of failure. We know we’ll never get allthat stuff done.

So we stop even opening our to-do app. We regard it with primal dread. I think it’s because to-dos are inherently existential; they remind us of how finite is our time on earth. As I wrote in my Wired piece …

This is the black-metal nature of task management: Every single time you write down a task for yourself, you are deciding how to spend a few crucial moments of the most nonrenewable resource you possess: your life. Every to-do list is, ultimately, about death.

The list has now become a “List of Shame”. That’s the coinage of Omer Perchik, the creator of the app Any.do. When I called him up he neatly described the grim cycle …

There’s this paradox! You need to write down everything — because you’re stressed with all the things that you need to do in the back of your mind. So you put them down on a list.

But then you stare at these lists of tasks that you need to do — and it’s very frustrating, because it’s like staring at all the decisions that you need to make, that you’re afraid of doing.

So this list becomes the List of Shame — of all the things you haven’t done, right.

That’s the paradox of task management.

Burning my to-do list to the ground

So. What do you when things get out of control like that?

Personally, made two decisions.

The first: I declared to-do bankruptcy. I took my entire List of Shame and torched it to the ground. (Metaphorically. More specifically I hit “delete”, but that doesn’t sound as heroic.) Then I started a new one.

Now, if you declare task bankruptcy, you might be tempted to look at your old List of Shame just to see if there’s anything you should transfer to your new list. But some people regard that as a bad idea. The point, they argue, is to start entirely fresh, untriggered by one’s previous stumbling to-do fail-itude. When the digital marketer Rick Galán declared to-do bankruptcy a while ago, he never looked back, as this story by Becky Kane of the Doist blog describes …

“Honestly, I haven’t missed anything important. The important stuff comes back or it’s already in my head anyway. When I think about them, I put them back on my list.”

All those other things he put on his lists? He doesn’t miss them. “I was never going to come back to them anyway.”

I wasn’t quite that brave. While I was building my new list, I took a quick peek at my old List of Shame.

But the cool thing was, now that I’d declared bankruptcy, it was oddly easier to regard those old tasks with a cold eye. I was no longer attached to them. I could see just how unfeasible so many were. Some were just little rando weird things I should never have written down in the first place. Others were such massive hairballs they weren’t really accomplishable “tasks” in the first place. They were more like “goals” or projects on their own — “figure out an idea for my next book!” — or i.e. projects that ought to have been broken into a dozen sub-tasks.

Either way, I was bloodless. I cut those tasks outta my life surgically.

One interesting question is: How can you tell when you’ve truly gone too far, and you need to declare bankruptcy? Versus when you should just pare things down a bit, and soldier on?

It’s not easy, but in Becky Kane’s blog post (which I mentioned above), she distilled some interesting heuristics in this graphic …

That’s a pretty good way to decide, and I’m going to rely on it the next time I’m staring into the void. (You should go read her whole post on to-do bankruptcy, it’s great!)

So my first big decision was to declare bankruptcy.

But my second big decision was …

Harness the “novelty effect” — by arbitrarily picking an entirely new to-do app

I decided to switch to an entirely new to-do system.

This time, I picked Todoist.com. It’s one of a pretty huge field of online to-do apps available today.

I didn’t pick it Todoist for any particular reason. The truth is, I find most to-do apps pretty interchangeable for my purposes. I could use any of them.

The point wasn’t to find the perfect new one. But point was merely to pick a new one.

I wanted to harness the “novelty effect”.

The novelty effect is a burst of excitement and freshness that comes with using a new system, merely because it’s new. A novel tool tends to render our work environment newly strange, which gives us a temporary burst of energy. I’ve written about the novelty effect a few times before, including this essay from last fall about how I’ll switch to a different word processor when I’m rewriting an article, because the new environment helps me see my words with fresh, alien eyes.

The same thing happened with my tasks. Because I was now using Todoist, I felt less clotted by my previous task-management failures. As I typed out each new to-do, I could be both more skeptical (do I really need to do this?) and more optimistic (hey, I’m gonna do this!)

Now, to be clear, the novelty effect is something of an illusion. It’s a trick, a technological placebo effect. But it’s a trick I play upon myself with full consent, knowing that it’s a trick. I understand that the burst of new energy won’t last, but if it can help break the ice and get me moving, that’s good enough.

And thus far, dear reader, it has worked! The combination of razing my temple of Shame to the ground and hey-sailor fraternizing with a new app has helped break my torpor. I’m actually getting things done. I’m not peeking through my fingers at my List of Shame and procrastinating.

For now, anyway!

Check back with me in December.