(2021-07-28) Thompson Hundreds Of Ways To Get S#!+ Done, and We Still Don't

Clive Thompson: Hundreds of Ways to Get S#!+ Done—and We Still Don’t. Even with a glut of tools claiming to make us all into taskmasters, we almost never master our tasks. (ToDoList, Getting Things Done)

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

Within half a year, IDoneThis was the two creators’ full-time job.

But then those users started clamoring for more

Guzman and Chen updated IDoneThis with a new feature: to-do lists. Which is when things went a little off the rails.

It wasn’t long before the two founders noticed something odd in the (anonymized) data they had on their users: People were lousy at finishing their to-dos

Half of completed to-do items were done within a day of writing them down. These weren’t longer-term, complex tasks.

when people reported their day’s accomplishments (the initial point of IDoneThis, you’ll recall), barely any of them had even appeared on a to-do list

The more Chen and Guzman pondered it, the more useless to-do lists seemed to be. They thought about getting rid of them. If to-do lists weren’t helping people accomplish stuff, what was the point? (Hero's Journey)

But they worried that users would squawk. Which they might have, if they’d hung around—the founders noticed a frustratingly high churn rate.

People loved to write down their tasks. But that didn’t seem to help with completing them. Chen and Guzman became gradually chagrined

I think I know why: It might be impossible.

“There are hundreds of commercially available to-do lists right now,” says my friend Mark Hurst.

when I talk to folks who use these apps, I see a strange inconclusiveness. A scant minority of us check off everything every day. An equally tiny minority simply Cannot Even and are curled in a fetal ball awaiting imminent firing. But most of us? We’re just sort of … meh.

people often have surprisingly deep feelings about their apps. But rarely is a category of software linked to such vistas of despair.

Zeigarnik found a quirk of the human mind: When a task is unfinished, we can’t seem to stop thinking about it. We perseverate

today this is known as the Zeigarnik effect, and psychologists who study task management say it’s part of why so many of us feel perpetually frazzled by the challenge of organizing work and life.

A good to-do tool ought to ease the Zeigarnik effect. In 2011, psychologists E. J. Masicampo and Roy Baumeister showed that this does seem to be the case

And indeed, those who regularly write down their to-dos seem to possess a mind less jittery

One of the most famous productivity systems—David Allen’s Getting Things Done—is ruthlessly focused on rigorous planning and editing of tasks.

The problem is that we too often don’t really plan. Digital apps make it easy to add more tasks to the pile, and it feels good to get tasks out of our Zeigarnicized heads. So we do, frenetically.

“We call it snowballing,” says Amir Salihefendić, who founded the app Todoist

Omer Perchik, the creator of another app—Any.do—calls this problem “the List of Shame.”

The mere act of making a to-do list relieves so much itchy stress that it can, paradoxically, reduce the pressure to actually get stuff done

No matter whose fault it is, we take this stuff personally. American to-do behavior has a deeply puritan streak.

With to-do apps, we are attempting nothing less than to craft a superior version of ourselves. Perhaps it shouldn’t be a surprise that when we fail, the moods run so black. (self-improvement)

Jesse Patel created the app Workflowy because he had ADHD and wanted a tool that worked as his mind required. In the late 2000s he was working as a head of business development, with “five different big-picture opportunity areas and, like, 30 different subprojects in each of those. It was just so overwhelming.” He noticed that each work task tended to spawn tons of subtasks. But most software, he found, wasn’t great at allowing for that Russian-nesting-doll quality. He wanted a “fractal” tool where every to-do could contain more little to-dos inside it.

I heard from people who loved Workflowy; I also heard from people who thought the whole fractal thing was a dead end. Salihefendić’s app Todoist once allowed levels upon levels of subtasks, but he got rid of them after noticing that only a fraction of people used them, and they were mostly just dorking around, organizing their subtasks instead of actually doing work. (wanking)

Pick virtually any postulate about “the best way to get organized” and app designers will have diametrically opposing views. The app Things lets you put a due date on each task; Hurst, the founder of Good Todo, hissingly denounces due dates as a form of productivity self-harm that turns into a screenful of blinking red overdue alerts

For years, I had a very rudimentary to-do system. Using a piece of paper, or maybe a document on my PC

Sometimes my system would work for days or weeks, but eventually it’d balloon into a List of Shame, and I’d guiltily declare bankruptcy.

So I decided to make the app myself

The next day I started using it and found, to my delight, that it worked much as I’d hoped

The thing is, it didn’t improve my productivity

I still use my app, intermittently. But building it made me realize a grim fact about to-do software, which is that even the most bespoke, personalized version couldn’t unfrazzle my mind

a big part of our problem lies deeper than interfaces or list-making. It’s in the nature of time itself, and our relationship to it.

If you ask people to accomplish a loony amount of work this week, they’ll go, No way. Can’t be done. But if you tell them they’ll need to do that same bonkers amount in a single week one year from now? They’ll think, OK, sure, I could do that

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.

“What is this class of software supposed to do?” asks Patel, the creator of Workflowy, rhetorically. “It’s supposed to answer the question ‘What should I do right now in order to accomplish all of my life goals?’ The most scarce resource many of us have is time.”

The only solution, this line of thinking goes, is to use an organizational system that is itself composed of time: a calendar.

Instead of putting tasks on a list, you do “time blocking,” putting every task in your calendar as a chunk of work. (cf time-boxing)

Though, as you might expect by this point, other productivity thinkers are equally vehement that calendars alone won’t save you.

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?’”

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.

a to-do list is, ultimately, nothing more or less than an attempt to persuade yourself.