Source Code: Your daily look at what matters in tech.

source-codesource codeauthorDavid PierceNoneWant your finger on the pulse of everything that's happening in tech? Sign up to get David Pierce's daily newsletter.64fd3cbe9f
×

Get access to Protocol

Your information will be used in accordance with our Privacy Policy

I’m already a subscriber
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.

Messy calendar

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

Image: Clockwise

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.

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.

Protocol | China

Livestreaming ecommerce next battleground for China’s nationalists

Vendors for Nike and even Chinese brands were harassed for not donating enough to Henan.

Nationalists were trolling in the comment sections of livestream sessions selling products by Li-Ning, Adidas and other brands.

Collage: Weibo, Bilibili

The No. 1 rule of sales: Don't praise your competitor's product. Rule No. 2: When you are put to a loyalty test by nationalist trolls, forget the first rule.

While China continues to respond to the catastrophic flooding that has killed 99 and displaced 1.4 million people in the central province of Henan, a large group of trolls was busy doing something else: harassing ordinary sportswear sellers on China's livestream ecommerce platforms. Why? Because they determined that the brands being sold had donated too little, or too late, to the people impacted by floods.

Keep Reading Show less
Zeyi Yang
Zeyi Yang is a reporter with Protocol | China. Previously, he worked as a reporting fellow for the digital magazine Rest of World, covering the intersection of technology and culture in China and neighboring countries. He has also contributed to the South China Morning Post, Nikkei Asia, Columbia Journalism Review, among other publications. In his spare time, Zeyi co-founded a Mandarin podcast that tells LGBTQ stories in China. He has been playing Pokemon for 14 years and has a weird favorite pick.

Over the last year, financial institutions have experienced unprecedented demand from their customers for exposure to cryptocurrency, and we've seen an inflow of institutional dollars driving bitcoin and other cryptocurrencies to record prices. Some banks have already launched cryptocurrency programs, but many more are evaluating the market.

That's why we've created the Crypto Maturity Model: an iterative roadmap for cryptocurrency product rollout, enabling financial institutions to evaluate market opportunities while addressing compliance requirements.

Keep Reading Show less
Caitlin Barnett, Chainanalysis
Caitlin’s legal and compliance experience encompasses both cryptocurrency and traditional finance. As Director of Regulation and Compliance at Chainalysis, she helps leading financial institutions strategize and build compliance programs in order to adopt cryptocurrencies and offer new products to their customers. In addition, Caitlin helps facilitate dialogue with regulators and the industry on key policy issues within the cryptocurrency industry.
Power

The video game industry is bracing for its Netflix and Spotify moment

Subscription gaming promises to upend gaming. The jury's out on whether that's a good thing.

It's not clear what might fall through the cracks if most of the biggest game studios transition away from selling individual games and instead embrace a mix of free-to-play and subscription bundling.

Image: Christopher T. Fong/Protocol

Subscription services are coming for the game industry, and the shift could shake up the largest and most lucrative entertainment sector in the world. These services started as small, closed offerings typically available on only a handful of hardware platforms. Now, they're expanding to mobile phones and smart TVs, and promising to radically change the economics of how games are funded, developed and distributed.

Of the biggest companies in gaming today, Amazon, Apple, Electronic Arts, Google, Microsoft, Nintendo, Nvidia, Sony and Ubisoft all operate some form of game subscription. Far and away the most ambitious of them is Microsoft's Xbox Game Pass, featuring more than 100 games for $9.99 a month and including even brand-new titles the day they release. As of January, Game Pass had more than 18 million subscribers, and Microsoft's aggressive investment in a subscription future has become a catalyst for an industrywide reckoning on the likelihood and viability of such a model becoming standard.

Keep Reading Show less
Nick Statt
Nick Statt is Protocol's video game reporter. Prior to joining Protocol, he was news editor at The Verge covering the gaming industry, mobile apps and antitrust out of San Francisco, in addition to managing coverage of Silicon Valley tech giants and startups. He now resides in Rochester, New York, home of the garbage plate and, completely coincidentally, the World Video Game Hall of Fame. He can be reached at nstatt@protocol.com.
Protocol | Policy

Lina Khan wants to hear from you

The new FTC chair is trying to get herself, and the sometimes timid tech-regulating agency she oversees, up to speed while she still can.

Lina Khan is trying to push the FTC to corral tech companies

Photo: Graeme Jennings/AFP via Getty Images

"When you're in D.C., it's very easy to lose connection with the very real issues that people are facing," said Lina Khan, the FTC's new chair.

Khan made her debut as chair before the press on Wednesday, showing up to a media event carrying an old maroon book from the agency's library and calling herself a "huge nerd" on FTC history. She launched into explaining how much she enjoys the open commission meetings she's pioneered since taking over in June. That's especially true of the marathon public comment sessions that have wrapped up each of the two meetings so far.

Keep Reading Show less
Ben Brody

Ben Brody (@ BenBrodyDC) is a senior reporter at Protocol focusing on how Congress, courts and agencies affect the online world we live in. He formerly covered tech policy and lobbying (including antitrust, Section 230 and privacy) at Bloomberg News, where he previously reported on the influence industry, government ethics and the 2016 presidential election. Before that, Ben covered business news at CNNMoney and AdAge, and all manner of stories in and around New York. He still loves appearing on the New York news radio he grew up with.

Protocol | Fintech

Beyond Robinhood: Stock exchange rebates are under scrutiny too

Some critics have compared the way exchanges attract orders from customers to the payment for order flow system that has enriched retail brokers.

The New York Stock Exchange is now owned by the Intercontinental Exchange.

Photo: Aditya Vyas/Unsplash

As questions pile up about how powerful and little-known Wall Street entities rake in profits from stock trading, the exchanges that handle vast portions of everyday trading are being scrutinized for how they make money, too.

One mechanism in particular — exchange rebates, or payments from the exchanges for getting certain trades routed to them — has raised concerns with regulators and members of Congress.

Keep Reading Show less
Tomio Geron

Tomio Geron ( @tomiogeron) is a San Francisco-based reporter covering fintech. He was previously a reporter and editor at The Wall Street Journal, covering venture capital and startups. Before that, he worked as a staff writer at Forbes, covering social media and venture capital, and also edited the Midas List of top tech investors. He has also worked at newspapers covering crime, courts, health and other topics. He can be reached at tgeron@protocol.com or tgeron@protonmail.com.

Latest Stories