Today the sun finally sets on Sunrise, the calendar app that Microsoft acquired last year. Microsoft announced its plan to merge Sunrise into Outlook, its mobile email client, last October. And now Sunrise, which began life as a more socially adept calendar, will now be a feature inside an email app. And to anyone looking for a next-generation calendar app to serve as its replacement, the awful truth is that there isn’t one.
The state of calendar apps in 2016 is an embarrassment, but it’s a revealing one. The marketplace reflects the insane difficulty of finding customers, and of profiting from them. The smart money is not invested in calendars, and the result is that your calendar hasn’t meaningfully improved since the dawn of the App Store.
Your calendar hasn't meaningfully improved since the dawn of the App Store
That’s not to say that calendar apps don’t work. There’s a calendar app that comes pre-installed on your smartphone, and it works just fine. You can create new events, view your daily schedule, and get a buzz in your pocket when it’s time to leave for your next meeting. With some tinkering, you can synchronize your calendar between your phone and your laptop, and in most cases it will work OK. Want a slightly different look or feature set? There are dozens of options in the App Store. All of it is better than jotting down new appointments on a paper calendar — mostly. For most people. Sort of.
This is the part where you tell me that no, actually, you have a calendar app that works just great. You use Fantastical, or TimePage, or BusyCal, and they keep you on time and do it in style. I'm a Fantastical man myself, having been drawn in by its natural-language processing: type in nearly any combination of who you're meeting with, and when, and where, and Fantastical turns it into a calendar entry. That was the last meaningful calendar innovation I can remember, and it happened in 2011. Nearly all of these apps rely on Apple's iCloud, Google, or Microsoft Exchange to manage calendar data, and they're limited by what those giants will allow.
Think about what your calendar app looked like in 2011 and what it looks like today. Mostly the same, right? Now think about your maps app in 2011 — a godsend, to be sure, but a pale imitation of its 2016 counterpart. Today your maps app will start your trip by telling you when you will arrive. It will nudge you when it’s time to change lanes. If there’s an accident up ahead, it will alert you. And if it finds a better route, it will change up your driving directions on the fly.
Meanwhile, calendar apps brag that they can now support... printing! The future of scheduling has never looked more like the past.
Why is this the case? In May, former Facebook executive Sam Lessin offered an answer. Writing in The Information this May, Lessin described what he called "the non-monetizable product blind spot." "There are plenty of products people want, but they’re not good businesses," wrote Lessin, who is currently building a bot company named Fin. Notes, to-do lists, address books, calendars: the vast majority settle for the good-enough, preinstalled apps on their phone
A glut of free apps makes it a terrible business
If you’re a tiny startup with a brilliant idea for how to improve calendars, you face two intractable problems. The first is that the glut of free calendar apps makes it very difficult for you to charge customers more than a few dollars. Unless you can continuously acquire thousands of new customers, that’s not a sustainable business. The second is that it’s going to cost money for you to acquire customers — your best bet is probably to buy installations with ads on Facebook and the App Store. Very few companies have or are willing to spend this kind of money, and venture capitalists aren’t likely to invest in them.
Sunrise was born in an earlier era, and on the strength of an impressive team and good design sense, raised more than $8 million before Microsoft bought it for an undisclosed sum. It won fans with a variety of smart integrations, including Google Maps for directions and Facebook for parties and birthdays. (In a great touch, Sunrise imported friends’ profile photos to show you who else was going to events.)
At the same time, Sunrise offered never really offered much that iOS Calendar didn’t, beyond a pleasing user interface and some useful integrations. It didn’t advance our notions of how mobile scheduling should work. It just took someone else’s job and did it 20 percent better.
That’s more than enough for Sunrise to deserve to continue its work. And Microsoft Outlook, which became my favorite email client after Mailbox died (for reasons similar to the ones I describe here!), is as good a home as any. As you would imagine, Microsoft promises that the union of Outlook and Sunrise will usher in an era of personal productivity unlike any the world has ever known. "The entire Sunrise team is now working side-by-side with the Outlook team and it’s a thrilling moment for us to work on an app of this scale," the company said.
An excellent email app — but a mediocre calendar
I am not thrilled. Outlook is an excellent email app but a mediocre calendar. Its idea of scheduling innovation under Microsoft is letting you add a link to a Skype call when you create a new event. You have to tab over from your inbox to even see the calendar, making Outlook’s take on Sunrise less convenient than a dedicated app.
On one hand, a calendar belongs inside your email: 70 percent or more of my calendar entries originate from the messages I receive there. On the other, I’ve never seen a calendar that feels native to email. Nearly everyone still uses the same old grid-of-squares metaphor we’ve been using since we bought print calendars for our physical desktops. Grafting a grid of squares onto a list of messages is not the scheduling solution of the future. And while they still nibble around the edges of the problem, the Googles and Microsofts of the world have dozens of strategic priorities more important than this one.
In the future I hope to forward a complete email chain to my calendar and have it parse the time, place, and participants of the meeting we just set up. Better yet, I’d like to click a "schedule this" button in my email and have a bot iron out the details on my behalf, with a couple of taps from me to confirm. (I schedule 90 percent of my meetings at the same coffeeshop; how hard could it be?)
My future calendar should know I prefer to walk to meetings within a mile or so of my office, and time my alerts accordingly. My calendar should be tactical, finding me time for my stated priorities. (Google, to its credit, has begun to work on this.) It should offer analytics on the time I spend on meetings, and with whom, and follow up with me on any action items.
Almost none of this is going to happen. Not any time soon, not in an app you can download to your phone. The gap between the calendar we deserve and the calendar we can get has never been bigger. For players both big and small, building the calendar of the future is simply more trouble than it’s worth.