How To Get Rid Of Your Scariest To-Dos

I have a bad to-do habit. I make big ambitious lists of things I want to do, then let them pile up in my to-do app until I'm so scared that I quit the app and start a new one. But I've found a way out of my to-do debt.

It follows.Screenshot: Northern Lights Films

The Shape of Design author Frank Chimero keeps a sophisticated to-do list. He estimates the difficulty of each item, so he doesn't overload any one day.

He tries to tackle a couple of hard tasks in the morning, then spend the afternoon knocking out easy ones. When he finishes a task, he checks if he correctly predicted its difficulty, so he improves at balancing his workload. And every three months, he zooms out, for what he calls "The Reckoning."

In The Reckoning, Chimero looks at all the to-dos that he keeps putting off — those tasks that get shamefully shuffled from one day's to-do list to the next, over and over. They're usually something he's afraid to do. At the end of the quarter, he has to do one of two things to those tasks: Handle them immediately, or accept that they will never get done. Either way, they have to leave his to-do list.

You could hold your reckoning once a month, or even once a week: however long it takes to experience the consequences of not doing the task. That way, you can actually "reckon" whether you can get away with just not doing the task. Maybe you're never going to repaint the bedroom; maybe you can put your home brewery on the curb. Maybe you really don't have to go to the dentist!

The point is to relieve you of the mental burden of these undone tasks. If you're not getting them done, you're not helping yourself by pretending you'll get them done. And you can always add them back later. So let them go.

Because otherwise, you might become me, holding onto your undone tasks for dear life, your crowded to-do app laying out all your imagined accomplishments like the map at the front of a fantasy novel. Those unrealistic to-do items might be pretty to look at, but they can't help you navigate the real world.

Do them next, or delete them.

The Reckoning is just one part of Chimero's dense list of productivity advice, which you should read twice, then save to read again later. Here's another highlight: "When the day's list is done, do not go back to the master list. The rewards of productivity must not be a bottomless well of work."

A Modest Guide to Productivity [Frank Chimero]


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