No Prize for Pessimism

A book!

I’ve been writing these letters for about 12 years now. I started writing them when I was at Box, as a way to both keep myself accountable and to build some common cultural ‘heartbeats’ with the engineering team. I liked the habit and kept it up at Google, and then later at Microsoft. Most of them are private to those companies, but for the past 3 years I’ve been writing these external ones too (two a week! It’s a bit).

Folks have asked me from time to time to put them into a book, so this year, just in time for AI to make books an amusing anachronism, I did!

The book isn’t entirely these letters, they only make up about 1/3 of it. The rest of it is sort of a … love letter to messiness, I guess. I realized, reviewing these letters to look for ones worth including, that most of what I talk about is how counterintuitive innovation feels in the moment - in retrospect, obvious, but in the moment, messy and hard.

And I realized, talking to college students, that there is an inversion these days: the kids are often “doomers” about innovation and new tech. Back in my day (yes, grandpa) we were very excited about things like the PC, and just wanted the skeptical old guys out of our way. Now, I feel like I’m usually more excited, curious and optimistic, about new tech, and I want to play more with it. That inversion bothered me, and so the book is a review of the history of Google Docs with a view towards how what seems obvious now, wasn’t obvious then, and an observation that real innovation requires a tolerance for mess and errors that the current generation sometimes struggles with.

The book is being published under a new imprint from Microsoft, called 8080 Books. I get to be first! Which seems kind of appropriate given the topic. It’s also up on Amazon, and I put up a GPT that can answer questions about it and some of the letters, at www.schillace.com/letters.

Thank you all for reading my letters and encouraging me. It means a lot when someone reaches out to say how a particular letter helped them. It’s a modest effort, and of course, these are all just my personal takes on things, but it’s been great writing them and talking with you all.

And there is more to come…I don’t intend to stop any time soon!