July 5, 2026

The Self-Cleaning To-Do List

One of the things I really like about my system for managing to-dos is that it’s a “self-cleaning” process.

Here’s what I mean by that...

Rather than stating in advance to myself how high or low priority a given task is, I just throw it in on the pile, and my true priorities will be revealed over time.

For example...

Last Saturday morning, I thought, “It’s going to rain all week... I should really clean the gutters tomorrow,” so I added “Clean the gutters” to my list for Sunday.

When Sunday rolled around, I felt like doing a bunch of other stuff besides cleaning the gutters, so I did the other stuff and snoozed the gutters todo til Monday.

Then Monday rolled around and again, I chose to do other stuff besides cleaning the gutters and snoozed the todo til Tuesday.

On Tuesday, it started pouring, so I deleted the todo.

Is this a moral failure on my part?

No, it’s a revealed preference.

Is this a failure of the system?

No, it’s a core strength.

Why?

Because it revealed to me that I hate cleaning the gutters so much that even when I know they are clogged and it’s going to pour for a week, I’m still not going to do it.

Which led to a new todo:

”Find a gutter cleaning service”

Here’s the thing...

I see my to-do list more as instrumentation than storage.

Snoozing a to-do is not a failure.

It’s data.

It tells me what I like doing and what I don’t like doing in practice, not in theory.

Over time, this data helps me to say NO more often to things I don’t like doing, so I can say YES more often to things I do like doing.

That’s the self-cleaning part.

Yours,

—J

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