Calendars seem like real green space for product innovation.

The business opportunity seems large

Calendars are a logical extension of a fairly basic investment hypothesis - “Every piece of the Google Suite or MS Office Suite is a potential billion-dollar+ startup”. I remember the shock at seeing advancing (paper!) graphing at the Churhill War rooms in London and realizing just how many jobs used to exist to perform the basic functions of a spreadsheet. Startups like Notion, Coda, and Quip all have attempted to replace docs and spreadsheets. Startups like Superhuman and Hey are trying to replace Gmail and Outlook. If any of these extend further, it’s usually more into project management. I’m not sure what I’m missing to understand why there isn’t a bigger rush into calendering.

It is a critical aggregation layer for a number of important activities. If you own the calendar, you are a necessary platform for a variety of other huge businesses like video-conferencing.

The pain is apparent

Managers always miss lunch and are double-booked, skipping 1-on-1s weekly.

People feel guilty blocking time to “think” or turning down meetings. Culture initiatives like “No Meeting Friday” are fairly difficult to enforce or maintain over long periods of time.

And it’s not just meetings, it is meeting rooms! At bigger companies, you are lucky if you only lose about a half hour a day waiting for rooms to open or booking the right room size for your audience.

Calendaring is difficult

Calendaring just seems wrong today. It is imperative and manual. It’s low-level code. It’s the equivalent of a manual transmission. Calendaring should be declarative and automatic. It should conform to the mental model of the people who want to meet, rather than worry about the operational model of their calendars. I don’t need to know what gear to use to get from Point A to Point B.

Calendaring problems are like linear optimizations - “I am optimizing for X with the following constraints”. This is not an area where we need to be weary of algorthimic approaches; it is very hard to hit global optimimums when everyone is focused on just their meeting.

Calendars are not innovating

Most calendaring seems to be done on Outlook, Google Calendar, and Apple Calendar.

None of these three companies seem to be investing deeply into productivity features, instead any updates seem to be about interoperability.

For example, the data is all there but nothing effectively considers intentions and state. I recently did my annual review at work and my first pass to remember what I did was look at all the meetings I was in. It is powerful to review what I actually did with my time, and could be more powerful if I was able to declare my intentions of how I wanted to spend my time.

When I was at LinkedIn, Jeff Weiner suggested doing this frequently and to go so far as to schedule family time onto your calendar. Because you can’t manage what you don’t measure, and what is next on your calendar often rules your life (for office workers). This idea seems intense for some, breaking work/life balance - but has increasingly made sense to me in a world where work and life frequently disrespect each others’ boundaries.