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. It would be a productivity tool that worked by a neat psychological hack, impressing yourself with your daily wins. “Often you discover that you’ve done more than you gave yourself credit for,” Chen says. “And this kind of motivates you—inspires you!”
Chen was a disenchanted lawyer; Guzman, a witty and talkative hacker. They built the tool in less than a week and launched it as IDoneThis. Soon they built an app by the same name and acquired 6,000 users. Within half a year, IDoneThis was the two creators’ full-time job.
But then those users started clamoring for more. People didn’t want merely to track the stuff they’d already done. They wanted to help plan for what they were going to do—from projects at work to the blizzard of tasks in their personal lives. 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. Chen and Guzman could see an accumulation of sprawling, ambitious lists of tasks that users utterly failed to accomplish. In 2014, fully 41 percent of to-do items on IDoneThis were never … done.
Sound familiar? The tasks you so diligently enter into your fancy app or productivity method linger for days or weeks or months (or even longer—one colleague recently told me his to-do app has undone tasks from 2019). They stare back, unchecked, with baleful expressions, disappointed at how very un-crossed-off they are.
Another thing that might feel familiar: The things that IDoneThis users actually did accomplish, they did very quickly. Half of completed to-do items were done within a day of writing them down. These weren’t longer-term, complex tasks. Ten percent were done within a minute. It was almost like people were writing them down just so they had something to check off. A nice psychological boost, to be sure, but it somewhat defeated the purpose of a to-do list.
More subtly, there was a big disjoint between the tasks people planned to do—i.e., wrote down on lists—and the tasks they actually did. Chen and Guzman found that 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 majority were tasks that users had just, well, remembered. Or maybe it was something that just popped into their head, or something a colleague had emailed them about.
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? But they worried that users would squawk.
Which they might have, if they’d hung around—the founders noticed a frustratingly high churn rate. A minority would mind-meld with IDoneThis, but most would, in time, drift away on a seemingly endless hunt for the best way to manage their to-dos. “It involved a lot of, not dilettantes, but people who wanted to try something new or were interested in a different system,” Chen says.
People loved to write down their tasks. But that didn’t seem to help with completing them. Chen and Guzman became gradually chagrined. After five years of working on IDoneThis, they sold the company to a private equity firm. “We felt like we’d exhausted what we knew to do,” Guzman says. IDoneThis isn’t gone; you can still use it today. But its creators couldn’t shake the feeling that building the perfect system to effectively manage tasks was itself a task they couldn’t accomplish.
I think I know why: It might be impossible.
Most common office tasks have well-settled software “solutions.” If I asked you to write a document, you’d probably use Word or Google Docs. To make a presentation, you’d pull up PowerPoint or Keynote or Google Slides.
Not so for to-dos. There is no Way That Everyone Does It. It’s a crazy Pokémon deck of options: Trello, Todoist, Gmail’s tasks, Microsoft To Do, Remember the Milk, Things, OmniFocus, Any.do,
Evernote’s Tasks, and Clear, to name just a few. And that doesn’t even count the whackload of us using one big ol’ Notepad file on our computers, or even plain old paper.
“There are hundreds of commercially available to-do lists right now,” says my friend Mark Hurst. Fifteen years ago he created one of the first productivity apps, Good Todo. Today it has a relatively small user base, but in general, productivity apps are big business; Americans downloaded them 7.1 billion times last year.
Chen and Guzman’s experience with trying to make one turns out to be common. The creators of personal to-do apps—or task management software, as it’s sometimes called—generally agree that they haven’t cracked the nut. Every one of these apps attempts to handle the same kind of basic actions: Give people a way to write down tasks, like “Get milk” or “Finish the sales memo,” and offer tools to sort and prioritize those tasks. Ideally, that improves your productivity, which broadly is how many things you can actually get done in a given amount of time. It seems easy enough.
But 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. We bounce from app to app, never quite finding a home. “I’ll try that one. I’ll try that one. I’ll try that one. Maybe this will do the magic!” as Randy Shulman, editor and publisher of Metro Weekly, Washington, DC’s LGBTQ paper, tells me. Sure, we’re getting work done! But we always feel slightly out of control, haunted by the to-dos at work and home that we just aren’t nailing.
The question is, why? Not just why it’s so hard to make a to-do app that works, but why people often feel so distraught by their hunt for the perfect organizational system. I’ve written about software for years, and I can tell you that people often have surprisingly deep feelings about their apps. But rarely is a category of software linked to such vistas of despair.
In the 1920s, the German psychologist Kurt Lewin was dining in a restaurant and noticed something remarkable. As one version of the story goes, Lewin realized that the waiters were able to meticulously recall specific food orders—until they’d served the food and the customer was gone. After that, they couldn’t remember any of those details at all. Lewin’s student, a Soviet psychologist named Bluma Zeigarnik, became fascinated by this phenomenon. She started working on it in her lab. In a now classic set of experiments, she gave volunteers a series of tasks (assemble a cardboard box, make a figure out of clay, do some arithmetic). Then she’d interrupt them, checking to see what the volunteers actually remembered.
Zeigarnik found a quirk of the human mind: When a task is unfinished, we can’t seem to stop thinking about it. We perseverate. Psychologists still argue about why; possibly it’s a kind of constant refresh to keep whatever’s pending from vanishing from our short-term memory, like putting something by the front door at night so you don’t forget to take it with you the next morning.
Whatever the cause, 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. When we face all that undone stuff—emails to write, calls to return, people to contact, friends to check in on, memos to draft, children to help—it’s like being a waiter serving a hundred tables at once. If you’ve found yourself in bed at 2 am with your brain screaming at you about that thing you didn’t do, that’s a Zeigarnik moment.
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. They triggered the Zeigarnik effect in volunteers by giving them a task and not letting them complete it. It lingered in their minds and interfered with their ability to do other work. Then the psychologists allowed the subjects to write out a plan for how they’d get that outstanding task done, and, presto, it lessened the effect. Speccing out what you’re going to do—getting it outside of your head—seems to help you stop perseverating.
And indeed, those who regularly write down their to-dos seem to possess a mind less jittery. Shamarukh Chowdhury, a PhD student in psychology at Carleton University, has found that people who create to-do lists are less likely to procrastinate than those who don’t. More delightfully yet, a study by Baylor University psychologist Michael Scullin found that people who created a to-do list fell asleep nine minutes faster, on average, than those who didn’t.
The creators of to-do apps all intuit the challenge of the Zeigarnik effect. They say that a key part of their apps is how frictionless they make it for us to input tasks. They’ve all worked to make this an instantaneous process: Open the app on your phone, shout at Siri or Alexa, or even email a new to-do item to your software.
Alas, this often makes things worse. Sure, the Zeigarnik effect is eased if you make a plan: I’ll do this, then do this, then do this, and then I’m done. One of the most famous productivity systems—David Allen’s Getting Things Done—is ruthlessly focused on rigorous planning and editing of tasks. It can take hours, but once you’ve done that hard work, you can plow through the tasks, one after another, with the metronomicity of a Chrysler line robot.
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 in 2007; it currently has 30 million users. “They keep postponing stuff. And then suddenly you have a hundred tasks that you need to do.” Weeks or months later, your Todoist app is a teetering ziggurat of tasks, too painful even to behold. Omer Perchik, the creator of another app—Any.do—calls this problem “the List of Shame.”
And then what do we do? You’ve probably done it: We panic, give up, and quit. We “declare to-do bankruptcy.” We toss the list away in defeat and start fresh.
You can blame Zeigarnik again. 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. “People feel that when they put all their tasks somewhere, they’ve already done most of the work,” Perchik says. But it’s an illusion. The pile of work is still there.
More than a pile! If you feel adrift on a turbulent sea of unmanageable tasks, that might be because there is objectively more expected of us. By one estimate, work hours for those with college degrees went up about 7 percent between 1980 and 2016. Got a graduate degree? For you it went up more than 9 percent. And quite apart from one’s paid toil, there’s been an increase in social work—all the messaging and posts and social media garden-tending that the philosopher and technologist Ian Bogost calls “hyperemployment.”
(We could snap the lens open even wider and have a fuller reckoning with capitalism. Focusing on our individual ability to tread water—with apps and lists—can look like a bleak exercise in blaming the victim, when in reality the only solution is not better apps but non-hideous workloads, debt relief, and a saner landscape of civic care. Frankly, if you took “managing grotesquely useless and bloodsucking for-profit health insurance” off people’s to-do lists, it would remove one remarkably stressful item, as my Canadian upbringing compels me to suggest. But I’m writing this particular article from within the belly of the whale, as it were.)
No matter whose fault it is, we take this stuff personally. American to-do behavior has a deeply puritan streak. Benjamin Franklin was among the first to pioneer to-do lists, creating a checklist of “virtues”—temperance! frugality! moderation!—that he intended to practice every day. That’s what the information scientist Gilly Leshed and computer scientist and cultural theorist Phoebe Sengers, both at Cornell University, found when they talked to people about their to-do lists. “They abide by the norm of ‘We need to be productive citizens of this world,’” Leshed tells me. Doing more is doing good.
To-do lists are, in the American imagination, a curiously moral type of software. Nobody opens Google Docs or PowerPoint thinking “This will make me a better person.” But with to-do apps, that ambition is front and center. “Everyone thinks that, with this system, I’m going to be like the best parent, the best child, the best worker, the most organized, punctual friend,” says Monique Mongeon, a product manager at the book-sales-tracking firm BookNet and a self-admitted serial organizational-app devotee. “When you start using something to organize your life, it’s because you’re hoping to improve it in some way. You’re trying to solve something.”
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.
Programmers often describe software as being “opinionated.” In the guise of helping us try to do things, productivity software recommends we do them in a particular way. A to-do app is offering an opinion about how we ought to organize our lives, which is, when you think about it, a kind of intense opinion for a piece of code to hold, right?
This is part of why we have such strong feelings about any given task-management tool. We either love it or hold it in bitter contempt.
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.
So he taught himself to program and created Workflowy to function just so: When you open a new project, you write items that can spawn endless sub-items, all of which can be dragged around and reorganized. If things look too cluttered, you can collapse everything so you see only your top-level tasks. “It’s a universe for your thoughts,” Patel says.
It’s a big universe—250,000 active users, like the construction site manager who told Patel that he made items for each room, with sub-items for anything the room needed. (“That room has, like, four missing bolts.”) 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.
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.
So the software is opinionated, as are its makers. But they’re also weirdly humble. Most of the app builders I spoke with admitted that, for many who try their tool, it won’t help. Maybe their app doesn’t match the way that customer’s mind works. Maybe the customer is a hot mess. Maybe their workload is unreasonable. Either way, the app creators are surprisingly willing to admit defeat. April Ramm, who does customer support for OmniFocus, will sometimes recommend a rival app to a potential customer.
This stance is … kind of unusual in the world of software, yes? One rarely hears founders candidly admit that their tool probably won’t fulfill its stated goal for many users, much less that it probably isn’t specifically right for you, either.
For years, I had a very rudimentary to-do system. Using a piece of paper, or maybe a document on my PC, I’d list my main areas of work (“WIRED Column,” “Household,” and so on). Then I’d write out all my tasks under each heading. (Under “WIRED Column”: “Call scientist about study.”) Finally, I’d make a plan. I’d number all my subtasks. Typically I’d hopscotch from project to project: My number one task would be the fourth item under “Household,” then number two was the seventh item under “WIRED Column,” and so on. Finally, with my plan laid out, I could power through my list.
Or at least I’d try to. 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.
I often suspected the problem was that my system was visually confusing. I had to scan the page to figure out what my next item was. Wouldn’t it be nice if, instead, I could click a button and my to-dos would arrange themselves in numerical order?
So I decided to make the app myself. I’m a hobbyist programmer, and I figured this spec was simple enough that even my hazy coding skills could pull it off.
One evening a year ago, I sat down and bashed out a prototype. The next day I started using it and found, to my delight, that it worked much as I’d hoped. I now had a numbered list I could sort and unsort quickly. I used it every day for months. Projects came and went; I filed stories and juggled tons of household errands. It felt lovely to have a tool designed for precisely the way my mind worked.
The thing is, it didn’t improve my productivity. It certainly did not increase how much paid work I accomplished. I was still filing the same number of stories, and doing the same life chores, in the same amount of time. I still found myself getting piled up and spiraling into to-do bankruptcy.
Sure, I could visualize my tasks better. But that didn’t move the needle on my efficiency. In fact, one day while working on the very story you’re reading now, I found myself staring at a monstrous List of Shame in my app. I declared bankruptcy, and then I shakily pulled out a single piece of paper and reprioritized, writing down a small handful of things I could actually accomplish.
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. And after dozens of interviews with users and coders, talking to them about my failure—and theirs—I began to realize that 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.
Something about the future defeats our imaginative capacity. “Present self screws over future self,” says Tim Pychyl, a psychologist at Carleton University who studies procrastination. He says that we regard our future self as a stranger, someone onto whose lap we can dump tons of work. On some weird level, we don’t get that it’ll be us doing it.
One of Pychyl’s students recently tried a clever experimental trick to get people to procrastinate less. The student took undergraduates through a guided meditation exercise in which they envisioned themselves at the end of the term—meeting that future self. “Lo and behold,” Pychyl says, those people “developed more empathy for their future self, and that was related to a decrease in procrastination.” They realized that time wasn’t infinite. Future them was no longer a stranger but someone to be protected. To get us off our butts, it seems, we need to grapple with the finite nature of our time on Earth.
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. (“Dost thou love life?” wrote Ben Franklin. “Then do not squander time, for that is the stuff life is made of.”)
I began to suspect that this is the truly deep, arterial source of some of the emotions around to-do lists. The people who make to-do apps agreed with me. “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.”
Ryder Carroll, the creator of the Bullet Journal paper-based method for organizing your work, puts it in even more starkly existential terms. “Each task is an experience waiting to be born,” he tells me. “When you look at your task list that way, it’s like, this will become your future.” (Or if you want the European literary-philosophical take, here’s Umberto Eco: “We like lists because we don’t want to die.”)
No wonder we get so paralyzed! The stakes with PowerPoint really aren’t that high.
Given that life is composed of time, a whole sector of the task-management philosophical magisteria argues that mere lists will always be inherently terrible. Just as Pychyl showed, we overload ourselves with more than we can accomplish and create Lists of Shame because we are terrible at grasping how little time we actually have. 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. That way you can immediately see when you’re biting off more than you can chew. Cal Newport, a computer scientist at Georgetown University and guru of what he calls “deep work,” is probably the staunchest advocate of time blocking. “I think it is pretty undeniable that time blocking, done well, is going to blow the list method out of the water,” Newport tells me. He says it makes you twice as productive as those suckers who rely on lists. Time blocking forces us to wrestle directly with the angel of death. It’s natural that we then screw around less.
Several researchers who study tasks told me they generally agreed that time blocking avoids the problems of to-do apps and lists. One to-do app, Reclaim, actually has an AI that estimates how long each task will take and finds a slot in your calendar. (The secret point is to show you there isn’t much room in there.) “We’ll not only tell you when tasks are overdue, we’ll tell you that tasks are going to be overdue,” says Patrick Lightbody, Reclaim’s cofounder.
Though, as you might expect by this point, other productivity thinkers are equally vehement that calendars alone won’t save you. You also have to develop a Jedi-like ability to say no to your own craving to do more, more, more. Salihefendić says the people who are “really into” Todoist—and most productive—are fanatical about completing more tasks than they add.
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?’” The inconvenience can be clarifying. Making a list on a sheet of paper is an unusually rich metaphor for life: It takes effort, and the space fills up more quickly than you expect.
The usefulness of paper here cuts to the real heart of what makes to-do management such a grim problem. 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. Winnowing away things you’ll never do in a weekly review is crucial, yet we dread it for what it says about the boundaries of existence. Our fragile psyches find it easier to build up a list of shame, freak out, and flee.
This is what makes to-do software unique. The majority of tools we use in our jobs are about communicating with someone else. All that messaging, all those Google docs, all that email—it’s about talking to other people, documenting things for them, trying to persuade them. But a to-do list is, ultimately, nothing more or less than an attempt to persuade yourself.
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