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Nobody likes digital calendars. But they're hard to improve, and even harder to change entirely.

Image: Clockwise
Messy calendar
People

Everybody hates digital calendars, so everybody’s trying to build a better one

Too many people feel like they're always late, always behind, and never have time to do real work. A bunch of startups are betting that better calendars are a key part of the future of work.

Digital calendars are a mess. They're a crucial part of modern life, especially as remote work becomes more prominent. They help employees make sense of their day and bosses make sense of the work that's getting done. But too often, the work that's getting done is just … dealing with calendars. Employees fill all their half-hour boxes with tasks, meetings and personal commitments, only to have bosses, clients and co-workers steal that time, one unexpected invite at a time. Once-focused days turn into a haphazard series of too-long meetings and too-short breaks, with little time to get actual work done.

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Most people feel this, even if they can't put their finger on the actual problem. Superhuman CEO Rahul Vohra said that in all the time he's been building and selling an email app, the single most-requested feature had to do with fixing the calendar. "They don't have specific ideas," Vohra said. "They just tend to say, 'please make it better.'" Making it better requires a lot of change, both in how calendars work and how people use them.

Improvement is long overdue, too. Consider the digital calendar, virtually every one roughly the same: a blank grid in day, week or month view, for a user to fill with their hopes and dreams and deadlines. In Matt Martin's original pitch deck for Clockwise, a calendar management startup, he included a picture of an ancient calendar chiseled onto a stone tablet, with the same basic form and structure as Google Calendar circa 2020. "We've translated this thing for literally thousands of years," Martin said, which proves both that the idea is really old and that the format seems to work.

Tim Campos, the CEO of Woven, said that it's not that the grid calendar is somehow immutably perfect, it's that nobody has ever really tried to improve it. "Calendar technology in general has been a feature of a bigger product," he said. It's an add-on to Outlook or Gmail, and certainly not a reason people pick one over the other. It's a hard market to crack, particularly for startups, because your calendar only works if others can see and interact with it. So calendars live in suites of work tools and mostly get ignored. Until recently.

Scheduling problems

So far, it looks like the reinvention of the calendar will happen in two phases. First, users will get access to a new set of tools, integrated with Google and Outlook calendars but opening up lots of new features. If that takes off, the next step will be to turn calendars into a tool worthy of a standalone service (and maybe a wholesale redesign). What Slack is to email, Zoom to the desk phone, Airtable to your Excel sheet, all these companies hope to be to your Outlook calendar. Time is money, all these calendar companies will argue to investors and customers, and we'll save you both.

We're only in the beginning of the first phase, though, and still attacking the first problem worth solving: scheduling. (Actually, the first phase is combining work and personal calendars, but that's mostly solved. Call that phase zero.) Vohra told me that almost a third of emails sent through Superhuman are about scheduling in some way, and plenty of studies have shown that people spend many hours a week simply trying to find time to meet.

One solution? Simply speed up the process. After a recent update, Superhuman scans emails for dates, like "next Friday," and with a few keyboard shortcuts lets users send an invitation to that effect. Scheduling is really an email problem, Vohra figured, so it should be an email solution, too. Vimcal, a new app often referred to as "Superhuman for calendars," is a similarly big bet on speed, and CEO John Li said what most people want is a lightning-fast way to create meetings.

Superhuman event creation Superhuman makes calendaring really fast — and does it from your inbox.Image: Superhuman

Tools like Calendly exist entirely to make scheduling easier, turning a long chain of emails into a simple point-and-click exercise. These apps test certain unwritten rules about calendars, though. How many people should be allowed to put time on your calendar? And is it rude to send someone your Calendly link, as if to say, "Look how few slots I have open, good luck fitting into my enormously important life?" (Some say yes, but the growth of Calendly and others says otherwise.) Patrick Lightbody, co-founder of calendar service ReclaimAI, said he found a middle ground: When he's trying to schedule a meeting with someone, he writes, "We're usually pretty flexible, so if you want to name a few days or times, I'm happy to make one of those work, or if it's easier, click this link." Most people click the link. It's much faster.

ReclaimAI also takes scheduling a step further into the next phase of calendar reinvention: optimizing your schedule. Lightbody, for instance, has several different kinds of things on his calendar. There are a few immovable events, time slots that can't change no matter what. But most things are more flexible: They just need to happen that day, or that week, or sometime soon. So when Lightbody sends his scheduling link, it shows every slot he could possibly make happen. "It's totally flipped around," he said. "This is your most deferential self." When I picked a time on his calendar, for instance, I grabbed a half-hour slot originally reserved for Lightbody to spend with his 3-year-old son. But ReclaimAI's software just automatically pulled that forward 30 minutes, so he was wrapping up some kid time when I called.

Calendar GIF Clockwise and other apps will actually shift your schedule around to make you more productive.GIF: Clockwise

ReclaimAI has the same long-term goal as that of Clockwise, Woven and others: to turn calendars from a block of hours into a more malleable, relentlessly optimizing thing. Programmers who need 15 hours of deep work each week shouldn't have to schedule it in advance, these companies think; their calendar should make sure they have space for it. One-on-one meetings that need to happen once a week but not necessarily at a set time should shift to accommodate everyone's schedule. Martin said Clockwise has 16 different categories of calendar entries, including everything from doctor's appointments (personal, immovable) to general "catch up on email" holds (important, but easy to move around), each with its own unique characteristics. There are more categories to come. Over time, the more a calendar actually understands what's on it, the better it can take care of a user's time.

This kind of thinking has a second benefit: It turns corporate calendars into a powerful analytics tool. If you want to know what your company values, look at how people spend their time. Or, just as often, how their time gets wasted. Everyone's had a boss who liked to blow up their subordinates' calendar with last-minute meetings and deadlines. Lightbody said his goal is to at least confront those bosses with the productivity-destroying nature of those interruptions, and to help teams identify and then make time for the things that are actually important. Martin agrees: "Ultimately, for every private and public company, there should be a slide powered by Clockwise that says, 'Is the utilization of our time actually tracking our top-level priorities?'"

How to calendar

There's a psychological question hidden in all this: What's the best way for people to spend their time? Is there even a right answer? The power of uninterrupted, flow-inducing deep work is well known — multiple people told me Cal Newport's "Deep Work" is a seminal text in the time-management space — but corporate realities mean there will always be meetings and deadlines. Some subscribe to Paul Graham's idea of a Maker's Schedule and a Manager's Schedule, and try to find ways to accommodate both. Others bring up Steven Sinofsky's "Reaching Peak Meeting Efficiency," which proposes a framework for thinking about work, meetings and time management. Everybody has a pet theory about the best way to work.

Above all, calendar developers say they just want to help people be more deliberate. It's simple, really: Studies have shown that things that get scheduled tend to get done. "Put an event on the calendar — not a recurring event because that's easy to ignore, but an actual event on your calendar — and I guarantee you're more likely to do it," Campos said. There, too, Campos said, adaptability is important. "Life happens! You get stuck in traffic, or somebody goes into the hospital. Things change, and if I have to go back in and update thousands of things on the calendar, that's just not going to happen."

The idea of building your calendar by essentially stating your intentions and trusting software to schedule them for you will take time for software to get right and likely much longer for users to trust. Developers are also still working on solving the network-effect problem: Unless a tool has access to everyone's calendars, it can't reschedule everything. So developers are starting small. They're automatically adding travel time or automatically blocking off time for personal commitments or deep work.

But the calendar dreams get big fast. What if calendar events could be living documents, where you store notes and tasks, essentially turning your corporate calendar into the center of your workflow? What if calendars could sync with project-management software or to-do lists, and automatically tell everyone what to do and when? What if your calendar understood your energy levels and could optimize your schedule for your mood and capabilities?

Right now, calendars are based on old, outdated technology. They're like SMS. All these companies are vying to be the WhatsApp or WeChat of the space, to build a new standard that does more and works better. Your calendar is your time, and your time is everything. So maybe a calendar should be much more than a grid.

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