The last time I took a sabbatical was in 2015, a few months before I joined Automattic. Back when I wasn’t yet a husband, a father, or even an employee. I was a self-employed entrepreneur in a transformative season, trying to shake things up and figure out what I really wanted to do with my life and creative energy.

Fast forward to today: nearly a decade into my time at Automattic, I’ve taken my second sabbatical. Once again, I find myself in a season of transformation. I didn’t go into it with a strict checklist, just a few intentions: rest, reconnect, and make space for creativity. But more than anything, I was looking for a real reset. Not the kind that comes from a long weekend or even a vacation, but the kind that only happens when you step fully outside your usual rhythm and take a hard look at how you’re spending your time, energy, and attention.

One of the first things I committed to was a practice called Rituals 66: a daily rhythm of five actions: move, read, meditate, journal, hydrate. Nothing groundbreaking on its own, but together, they became a quiet anchor for my days. They gave structure without pressure. Over time, I felt my baseline shift. I had more energy. More clarity. I was sleeping better. And I started thinking more intentionally about how I wanted to shape my time instead of just letting it slip by.

Creatively, I finally had the space to focus on a project that’s been close to my heart for a while: finishing my album. Without the usual day-to-day demands, I was able to dive deep, refine the sound, and wrap the creative phase. The record is slated for release later this year or early next; seeing it come together has been one of the most fulfilling parts of this time away.

I also made time for rest. I wish that meant more sleep, but my 2-year-old still doesn’t consistently sleep through the night. The rest I did get came from a break in the pressure to always be on. I had space to be in my own head, which led to a wave of creative experimentation: new visual art and design, exploring AI tools, learning piano, rebuilding my site, and rethinking how I want to share my work more consistently. Not everything I tried landed, but the process opened creative doors I might not have walked through otherwise.

Outside of the creative stuff, I just lived life. There was plenty of family time, especially with the kids home from school and between summer camps. A few brunch and dinner dates with my wife. I even started tending to our tiny deck garden, which turned out to be a surprisingly calming ritual. We’ve got basil, two kinds of mint, dill, tomatoes, and jalapeño peppers coming in nicely now. The fresh basil is perfect on pizza and pasta, and I’ve been using the mint in teas and lemonades—soooo good. I also chipped away at a few home maintenance projects while I was at it. And along the way, we got some big news: our family is still growing. We’re expecting a baby girl this winter. I’m still a bit in shock, but I’m also really excited.

And of course, I couldn’t return to work without a trip to my second home: New York. The city has changed a lot over the years. So much of what I remember has been replaced, but wandering through my old neighborhoods in Brooklyn and Manhattan still sparks ideas like nowhere else.

Now that I’m back, things feel different but in a good way. I’m managing my calendar with more intention; planning instead of reacting. Projects feel less chaotic, and communication already feels smoother because I’m coming in with more focus and clarity. The daily habits I started have stuck. They’re not perfect, but they’ve become part of the rhythm.

Most importantly, I’m not trying to go back to “how things were.” This time away reminded me that productivity isn’t always the goal; presence is. Creativity, balance, execution, all of it flows better when you’re grounded. I’m excited to carry that energy into my work and see how it shapes what’s next, both at Automattic and beyond.

Here’s a mashup of various images from my sabbatical. No particular order, just glimpses of the moments that made it meaningful.