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It’s 2016 Why Can’t Anyone Make a Decent Freaking To-Do App

Technology has given us one-tap access to taxis, laundromats, all of history’s collected information, and sex. Yet it can’t give us a decent to-do list.

It’s not for lack of trying. There’s an entire corner of the Internet dedicated to making people more productive. It’s full of 5 Simple Ways and 31 Genius Tips and One Weird Trick. Hundreds of apps run the gamut from beautiful list-makers to an electronic nag that literally curses at you until you get your shit done. It’s remarkably fulfilling to spend so much time organizing and planning instead of actually getting stuff done. Trust me, I do it all the time. I’m not alone, either.

The startup iDoneThis once found that 41 percent of the tasks that users placed in its system were never completed. Maybe they should’ve called it iAin’tDoingThis, because it’s axiomatic that the longer your list, the less you accomplish.

Making and keeping a to-do list is almost as hard as completing the tasks on it. What’s most frustrating is it feels like we should have solved that by now. As work becomes increasingly gig-based, distributed, and complex, people increasingly need time- and task-management tools. For those people, there’s Wunderlist and Todoist and Any.do and Asana and Toodledo and Omnifocus and Things and Trello and Clear and Checkvist and Due and TeuxDeux—and those are just the apps on my phone. Tens of millions of people use them, and they’ve attracted hundreds of millions in funding.

Most of the myriad to-do list apps are fine. Some of them are very good. But none of them has ever solved my problem—your problem—of having too much to do, too little time to do it, and a brain incapable of remembering and prioritizing it all. Which explains why the old ways remain so popular.

“A lot of tech people I know are going back to paper,” organization and time-management guru David Allen tells me. “Because a paper planner … there’s still no better tool than a paper planner.”

Wait a sec. You’re telling me Silicon Valley, with all of its brains; the Internet, with all of its data; and my phone, with all of its power, can’t find a way of making sure I pay the bills, buy some milk, and finish my presentation?

Allen laughs at my question. He knows a few things about to-do lists. He wrote Getting Things Done, which spawned an entire industry of go-getting thing-doers. He’s been trying to make us all more productive since the days of the Franklin Planner. He’s got some crazy ideas about the day when AI-powered holographic reminders will tell you to do your taxes. Until then, we’re stuck with lists. So I ask another question:

How do we make better lists?

You’re Everywhere to Me

The first thing a to-do list needs is to-dos. If your list is incomplete or, worse, outdated, you simply aren’t going to do check it. This makes it imperative that developers make it really, really easy to create lists and add things to it. But technology isn’t especially good at this. “If you have to turn on your phone,” Allen says, “click here, click that little icon, go to there… Come on!” He sounds exasperated just thinking about it. “Input and output is too hard.” That’s one reason pen and paper remain so popular. Jotting things down is faster, easier, and better for cognition. A to-do list must be fast and flexible enough to keep up with your thoughts.

Remember the Milk cracked this in part about a decade ago. The app featured a concept called “Smart Add” that let you, say, type “Pay rent on last day of month” and have it land on the right list, the right date, whatever. Equally important, you could add tasks from anywhere: tweet them, email them, Skype them, even IM them. The app integrated into Gmail before doing so was cool and with Siri before Apple deigned to let it. It was everywhere you needed it, when you needed it, and faster than writing things down because you could pretty much use whatever box you happened to be typing into.

Such ubiquity is common now. And Siri and Cortana and Android Widgets are closing the gap even further. Until someone creates a telepathic smartphone interface, the problem of immediacy is pretty much solved. Great job, everybody! There’s just one problem. It’s still not enough to ditch the pen and pad once and for all.

Having made it easy to jot down a thought almost as soon as it enters your head, developers are moving on to making you check things off. Michael Ciarlo, creator of a new app called Doo, thinks the best way to do this is to make you establish eye contact with the task in front of you. In Doo, each task gets its own card. The easiest way to move on to the next card is to complete it or “snoozing” it, which is another way of saying, “Yeah, I’m not doing that now. Next…” There’s just enough guilt involved in hitting snooze that I often just complete the task. That’s the point. “Having an awareness of what you need to get done helps motivate people,” Ciarlo says.

Other apps use push notifications as the default hey-remember-me gesture for keeping you on task. These reminders will grow more powerful as your devices learn more about you. An app can use the time and your location to remind you of tasks not just at the right time, but in the right place. Wearables have access to vital signs and other data that could optimize your productivity. All of these things mean the to-do list is giving way to the task cloud that follows you everywhere, jolting you with a lightning bolt when you need to do something.

Google’s already well down this road with its productivity tools, which by design do not include a dedicated to-do list app. Instead, Google brings tasks to you. “Rather than building a standalone task-management place, we should give you light interactions in the places you already visit,” says Jacob Bank, who joined Google after the company bought his task-management app Timeful. In Google’s world, your tasks live in and interact with your email, your calendar, your phone.

Google is still honing that. But Bank’s real goal is to make that list for you. That, by the way, might explain why he went to Google: Millions of people email in Gmail, work in Drive, chat in Hangouts, take notes in Keep. Bank thinks Google can get smarter about mining that data to figure out what you actually need to do with it. It’s already doing this to some extent with Inbox, sorting your email by priority rather than time. “The 10-year vision,” Bank says, “is GPS for your life.” You give it the basics: I want to exercise more. I have a big project. I’m renovating the kitchen. “And it tells you the turn by turn.” Timeful’s big innovation was to automatically program your calendar, filling empty time with productive suggestions. With Google’s data in hand, he could go even further.

Robot Taskmasters

Amir Salihefendic, the founder and CEO of Todoist, has a similar vision to Google’s. As part of a recent redesign, his team looked into building a machine learning algorithm that could determine how you live and seamlessly integrate your to-do list. It would even recommend the best day to accomplish a given task. “If you look at our data,” he says, “almost all days look very similar” for most users. “We can predict stuff.”

Building a predictive to-do list is easy, he says, if you have perfect data. But getting access to that kind of data—everything from the date to your precise location to what you had for lunch—is hard to gather, and hard to parse. So most of the work in creating and following a to-do list remains on you. For now, the ability to quickly add items and receive a helpful push notification is as good as it gets.

But remember David Allen and his wild idea about AI holograms? He’s serious about it. “At some point,” he says, “you’ll walk into the room with a chip in your arm, and it knows that you’ve showed up. You’ll have a hologram show up in front of you, because it’s Friday afternoon at 3:00.” The AI will know all about you, and help you figure out what needs to be done and how best to do it. And he says all the tech needed to build such a system is available now. “It just costs you about $6 billion to make it for yourself.”

Allen built a voice-based productivity tool in 1995 called Actioneer, which was incredibly powerful and incredibly ahead of its time. More recently, he’s been working with Intentional Software, founded by Charles Simonyi, the mastermind behind Word and Excel, to build the one tool everyone needs to get everything done. They’re still at it. “We spent two years looking at whether there really was a next generation of productivity software that was ready to be developed,” he says. “And it’s not yet. It’s not yet.”

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