Calendars are some of the most used apps in our smartphones. They are an indispensible utility with a wide spectrum of usage patterns. Some use it casually, but for many it dictate their lives - if it isn’t on a calendar, it isn’t happening (I suspect this behaviour is correlated with age).

Despite this, the calendar remains fairly undeveloped. The calendar today is not a far cry from the one that was preloaded with the original iPhone in 2007. Managing your life through today’s calendars is still full of friction - and from personal experience can become the sole reason why events don’t take place. For some, it is so cumbersome that it requires a full time assistant. This is an expensive problem.

I believe this is for a few reasons, centered around two fundamental design flaws.

First, the calendar is an inherently social app that we are all forced to play in single player mode. We plan events with colleagues, friends and family, but the social mechanics of event planning feels like a bad turn based game. The lack of real time back and forth, the consistent context switching between our communication apps and calendars is a massive point of frustration.

Second, the primary calendar abstraction as a ledger of time is woefully incomplete. Events have way more nuance - whether it’s the decisions leading up to acceptance, the last minute flurry of activity close to events, or sharing meeting notes with attendees. All these activities require context switching that could be unnecessary. Working through a calendar today is like doing all your accounting directly on the ledger - it works, but it can drive you crazy.

Just fixing these two would be enough - but the calendar is also highly underleveraged.

Calendars are a utility, but can also be a network and platform. They contain long term intentions through events - meetings, social gatherings, even vacations - which is central to to reservation centric businesses and service providers. A calendar can become a central distribution point for these businesses.

This is best illustrated by some use cases. For example - airlines can automatically send me flight deals when they see I’ve booked off certain dates for vacation. I can automatically book service providers without explicit contact by adding an event to my calendar and getting real time feedback on availability. Restaurants can even “bid” for future time in a shared calendar with my friends, sending us offers on deals on days where we are all free (this has clear privacy and security issues, but just an illustration).

As mobile enters it’s second decade - I’m looking forward to seeing how calendar apps might evolve to help address some of these problems. I think there is a lot of potential here.