No one on their death bed wishes they'd taken a few more meetings. Instead, studies find people consistently say things like: I wish I'd spent more time with my friends and family; I wish I'd focused more on my health; I wish I'd picked up more hobbies. That's what life's all about, after all. So, question: Why don't we ever put any of that stuff on our calendar?
That's precisely what the folks behind Timeful want you to do. Their app (iPhone, free) is a calendar designed to handle it all. You don't just put in the things you need to do---meeting on Thursday; submit expenses; take out the trash---but also the things you want to do, like going running more often or brushing up on your Spanish. Then, the app algorithmically generates a schedule to help you find time for it all. The more you use it, the smarter that schedule gets.
Even in the crowded categories of calendars and to-do lists, Timeful stands out. Not many iPhone calendar apps were built by renowned behavioral psychologists and machine learning experts, nor have many attracted investor attention to the tune of $7 million.
It was born as a research project at Stanford, where Jacob Bank, a computer science PhD candidate, and his advisor, AI expert Yoav Shoham, started exploring how machine learning could be applied to time management. To help with their research, they brought on Dan Ariely, the influential behavior psychologist and author of the book Predictably Irrational. It didn't take long for the group to realize that there was an opportunity to bring time management more in step with the times. "It suddenly occurred to me that my calendar and my grandfather's calendar are essentially the same," Shoham recalls.
Like all of Timeful's founders, Shoham sees time as our most valuable resource--far more valuable, even, than money. And yet he says the tools we have for managing money are far more sophisticated than the ones we have for managing time. In part, that's because time poses a tricky problem. Simply put, it's tough to figure out the best way to plan your day. On top of that, people are lazy, and prone to distraction. "We have a hard computational problem compounded by human mistakes," Shoham says.
To address that lazy human bit, Timeful is designed around a simple fact: When you schedule something, you're far more likely to get it done. Things you put in the app don't just live in some list. Everything shows up on the calendar. Meetings and appointments get slotted at the times they take place, as you'd expect. But at the start of the day, the app also blocks off time for your to-dos and habits, rendering them as diagonally-slatted rectangles on your calendar which you can accept, dismiss, or move around as you desire.
In each case, Timeful takes note of how you respond and adjusts its "intention rank," as the company calls its scheduling algorithm. This is the special sauce that elevates Timeful from dumb calendar to something like an assistant. As Bank sees it, the more nebulous lifestyle events we'd never think to put on our calendar are a perfect subject for some machine learning smarts. "Habits have the really nice property that they repeat over time with very natural patterns," he says. "So if you put in, 'run three times a week,' we can quickly learn what times you like to run and when you're most likely to do it."
The other machine learning challenge involved with Timeful is the problem of input. Where many other to-do apps try to make the input process as frictionless as possible, Timeful often needs to ask a few follow-up questions to schedule tasks properly, like how long you expect them to take, and if there's a deadline for completion. As with all calendars and to-do apps, Timeful's only as useful as the stuff you put on it, and here that interaction's a fairly heavy one. For many, it could simply be too much work for the reward. Plus, isn't it a little weird to block off sixty minutes to play with your kid three times a week?
Bank admits that it takes longer to put things into Timeful than some other apps, and the company's computer scientists are actively trying to come up with new ways to offload the burden algorithmically. In future versions, Bank hopes to be able to automatically pull in data from other apps and services. A forthcoming web version could also make input easier (an Android version is on the way too). But as Bank sees it, there may be an upside to having a bit of friction here. By going through the trouble of putting something in the app, you're showing that you truly want to get it done, and that could help keep Timeful from becoming a "list of shame" like other to-do apps. (And as far as the kid thing goes, it might feel weird, but if scheduling family time on your calendar results in more family time, then it's kinda hard to knock, no?)
Perhaps the bigger question is how much day-to-day optimization people can really swallow. Having been conditioned to see the calendar as a source of responsibilities and obligations, opening up one's preferred scheduling application and seeing a long white column stretching down for the day can be the source of an almost embarrassing degree of relief. Thank God, now I can finally get something done! With Timeful, that feeling becomes extinct. Every new dawn brings a whole bunch of new stuff to do.
Bank and Shoham are acutely aware of this thorny problem. "Sometimes there's a tension between what's best for a user and what the user wants to accept, and we need to be really delicate about that," Bank says. In the app, you can fine-tune just how aggressive you want it to be in its planning, and a significant part of the design process was making sure the app's suggestions felt like suggestions, not demands. Still, we might crave that structure more than we think. After some early user tests, the company actually cranked up the pushiness of Timeful's default setting; the overwhelming response from beta testers was "give me more!"
The vision is for Timeful to become something akin to a polite assistant. Shoham likens it to Google Now for your schedule--a source of informed suggestions about what to do next. Whether you take those suggestions or leave them is entirely up to you. "This is not your paternalistic dad telling you, 'thou shall do this!'" he says. "It's not your guilt-abusing mom. Well, maybe there's a little bit of that."