HEY! That calendar app won’t help

We all like to start the work week off with a plan. But as Mike Tyson once said: everyone has a plan until they get punched in the face… or in this case, until Monday rolls around and the demands for our time start piling up.

It’s a new year and, not surprisingly, people are thinking more about how they want to spend their time. Right on cue, several calendar-related items popped up in my newsfeed:

• January 2nd: HEY Calendar was launched by 37signals
• January 8th: Maggie Appleton raises the idea of speculative events
• January 17th: Cron is re-launched as Notion Calendar

But in all the chatter kicked up by these posts, something was missing: everyone was talking about the calendar interface and not the underlying scheduling problem itself.

At their core, HEY and Notion are both Yet Another Calendar App (YACA)…just two more in a long line. And most are excellent in their own right (see: Fantastical or Vimcal), though some fade away, never to be seen again.

Ultimately a YACA is just an interface to the same old platforms, streamlining the classic calendar interface and adding some UX sugar on top of it. The best ones also offer a variant on the Calendly-style scheduling experience; Vimcal and Notion, for example, are quite good for external attendees. 

HEY Calendar does even less than the average YACA  — despite some big claims:

HEY is everything wrong with YACAs

No doubt, it has some  interesting concepts. And Microsoft and Google have absolutely gotten complacent. But as its own calendar platform, HEY is nowhere close to being able to displace them in the workplace, and complaints are stacking up (see comments) for that very reason.

And yet, HEY Calendar was met with great fanfare, as most slick new YACAs (see: Notion Calendar) are. HEY’s buzz was partly due to outrage marketing, but also because people connected Maggie Appleton’s idea of speculative events — the notion that calendar events don’t have to fit the binary of “always free” or “always busy — with HEY’s “maybe events” concept and got excited.

And it is exciting to envision something that visually manifests the fluidity of our time and our ever-changing priorities. It promises a more nuanced approach to managing our complex and multi-dimensional schedules. Particularly (and almost exclusively) in the context of our busy and time-crunched workplace, this is one of the most critical issues that makes scheduling hard: because our calendars don’t know what matters to us, and what’s truly important or not, they can’t make the tradeoffs we all make daily to keep our calendars chugging along.

But I’m here to tell you: the problem is not going to get solved via a calendar app that puts the emphasis on how you see your schedule. A solution to our face-punching chaotic weeks has to put the emphasis on the entire network that interconnects your schedule with the hundreds or thousands of people with whom you work. It’s the only way to defray, deflect, and optimize the perpetual incoming demands for your time. 

We won’t solve it simply by making calendars prettier or faster, or by adding features that work inside a walled garden but not within the constraints of our workplaces and lives. The solution is to make our scheduling platforms smarter, and it has to be delivered in a way that is ultimately compatible with the Big Two (MSFT and Google) and with the real social and professional implications of where we spend our time, what we can say no — or “maybe” — to, as well as the aspirations that we have to focus our time on what matters most.

Smarter scheduling is the way

Calendly figured this out before most: they didn’t build a calendar app, they built a scheduling solution that addressed a critical infrastructure gap in calendar platforms — external visibility of your availability. It’s no surprise that they have found more success than pretty much all the YACAs combined! 

And while most YACAs support Microsoft/Google (not HEY) and some have external scheduling support (not HEY), very few do anything to facilitate the overall schedule as it relates to your coworkers. 

I’m not the first one to highlight this. Six years ago, as he was preparing Dropbox to enter the public markets, Drew Houston shared this note in their S-1 filing:

“… over time, machine intelligence will allow Dropbox to better understand both you and your team. Imagine getting to work in the morning to find your calendar reorganized so you have a three-hour block of time to actually focus. Imagine starting your day and seeing the perfect to-do list – one based on a deep understanding of your priorities and your team’s priorities.”

Note that nothing in this vision mentioned the calendar app itself. Drew understood that to truly have an impact, the scheduling platform  itself must evolve. Fortunately, with the advance of ML and AI, there are a number of solutions that are focused on optimizing the work schedule, the two most well-known ones being Reclaim (my startup) and Clockwise (a competitor that I respect greatly). 

This new breed of scheduling solutions focuses on optimizing the total schedule, and on making it smarter — or at least a lot less dumb. 

It does things like reschedule lower-priority stuff when higher-priority items emerge. It keeps your schedule flexible, but not so flexible that your workweek suffers. It keeps the entire network of competing demands for your time — internal and external to your company — in mind. And importantly: it’s actually compatible with the calendar systems our workplaces, for better or worse, have no intention of sunsetting. 

What’s needed here isn’t another YACA; what’s needed is what Drew predicted: a smart assistant working 24×7 to optimize your schedule, considering your unique needs, constraints, and aspirations. It’s the only way your face-punching Mondays are going to get better.

Special thanks to Matthew Porter, Yaniv Bernstein, Dion Almaer, Ben Galbraith, Tom Uebel, John Zeratsky, Lenny Rachitsky, and Elle Morrill for reviewing drafts of this post and providing fantastic feedback.