Introducing "season 2" of my newsletter. First topic: reconciling "perfect", "good", and "done" during a pandemic.

Some thoughts about a long-standing cliche about product leadership.

Years ago, during one of my first big presentations to execs, my director interrupted my presentation multiple times, and eventually just…

For whatever reason, while I've not hesitated to write tech/business think pieces or IT tutorials on my personal blog all these years, I've…

22 February 2011 was my first day on the Typekit team. 23 February 2018 will be my last one. After (roughly) seven years, I'm…

From time to time my wife and I will get emails from our friend Andy, just to catch up. He sent one this week,…

Some rules for blogging: Write only about things in which you have a personal stake. In applying the above rule, always ask yourself: are…

Hello friends. Quite a lot has happened since my last letter. I first moved to Chicago a little over fifteen years ago, to start…

Good evening. First of all, this newsletter has a title now: "Monday Letters". The actual reason is super, super boring: these are letters from…

Marco Arment and Andy Baio and Jason Snell and Gina Trapani have all written about returning to “middle-form” blogging—blogging that's longer than a tweet…

First, some inside baseball. This letter is just over 1900 words. It's actually two subjects in one, and though I considered splitting this into…

It feels important to me to try to send this first letter to no one in particular*, before I've put out my link and…