Sabbatical!

tl;dr – last Friday was my last day at Calm. It’s been a truly remarkable three-and-a-bit years. I’ve learned so much and I’m grateful to the founders Alex and Michael, President Alex, CEO David, my peers and the team I’ve been privileged to work with. Next up, I’m taking a sabbatical to work on a few projects, and I’ll start thinking about my next role in June or July.

Sometimes when I’m writing something, I feel trapped by the narrative structure. At this moment, tapping on this keyboard, I find myself trapped in the “I left my job, but I’m really, really proud of the folks I worked with” retrospective. Because, well, last Friday was my last day at Calm, and I am really, really proud of the folks I worked with over the past three-and-a-bit years. So anyway, I’m just going to embrace the narrative structure here and see where it takes me.

I joined Calm in January, 2020. A few weeks before, I’d pulled together Your first 90 days as CTO based on my notes, but I had no idea what was really coming my way. Two months later, the pandemic hit, followed a few months later by our first child. Did things slow down then? Certainly not.

Calm had an extraordinarily good 2020, we launched our B2B business, kicked off landmark partnerships with Kaiser Permanente and American Express, a viral sleep story from Harry Styles, and enough subscriber growth to briefly threaten site stability. The next year was good, too. We embraced machine learning to allow us to grow our content catalog without making users feel like we’d grown it (with the best meditation or sleep story for each person, always right where they expect it), which allowed us to significantly accelerate how our content team launched new content. As one must anticipate from this kind of post, I’m going to say the other years were also good, but it’s true: they were good! We acquired Ripple Health Group to support an expansion into healthcare, scaled our B2B business significantly, and remained the #1 DTC mindfulness app on the AppStore.

There’s so much other stuff I don’t even know how to fit it into the “I left but I’m proud” narrative! We successfully executed an incremental migration to TypeScript, and a wholesale migration to AWS Aurora, while speeding up product velocity rather than slowing it down. Calm got a new CEO, David, who’s fantastic. I weathered some medical challenges and managed to come out the other side whole. Staff Engineer was released! Even now, I’m leaving out a bunch.

I’ve also learned a tremendous amount. It was a chance to get back into Product engineering after my six year detour into Infrastructure, and a return to working on a consumer-facing product with millions of deeply passionate, highly engaged users. It was also my first chance to be the functional engineering leader at a scaled company, which was quite different than being the functional engineering leader during Digg’s last year.

Most importantly, I am deeply grateful to the people I’ve gotten to work with: David Ko, Alex Tew, Michael Acton Smith, Alex Will, Dun Wang, Mads Johnsen, Anastasios, Anne, Scott, Mike, Brenda, Ellen, the many Chrisses, Nate, Maya, Melissa, and many, many others. This was a great group, and I’m excited to work with y’all again soon.

My decision to leave Calm is the happy confluence of a few different events. First, our acquisition of Rally Health Group brought on an experienced engineering leader who was more than able to take on my responsibilities leading engineering and data science at Calm. Second, our son is almost three years old, and spending time with him is uniquely wonderful right now, and that’s not something I want to take for granted. I’m excited to have some focus time with our son and with myself before sticking my head back up in a few months to decide what to do next. Admittedly, sometimes opportunities show up that are hard not to consider, so it’s not impossible that I am working again sooner than expected, but that’s not how I’ve written the plan.

No need to worry if you’re afraid I’ll get bored. In addition to family time, I have a few projects I’ll be focused on over the next few months:

• Writing my next book. I don’t have any specific details to share quite yet, but if you look at my most recent posts you’ll get a sense of what the subject matter is about. It should be available digitally by the end of the year, and in print early next year
• I have a couple of software projects that I’m excited to spend some time on. Nothing too sophisticated, just enjoying the motions of personally building something from scratch
• Doing more running. Building from 3-4 mile maintenance runs back up to a weekly ~10 mile run, and also getting in a weekly speed session

My current plan is to take on another engineering leadership role after my sabbatical, and I hope to start chatting with folks about opportunities in June. Until then, I’ll be focused on some active rest!