Today is my first day post-sabbatical, getting back in the swing of things with Automattic. W.org, all the things. What a unique experience! I found the lead up to the sabbatical and planning process to be infinitely valuable, the sabbatical itself to be interesting experentially, and I’m curious to see what the post-sabbatical effects are. I have that nervous excitement like it’s the first day of school, which I haven’t felt in years. What should I wear? Who will sit with me at lunch?

I could now give a much better talk about the value of sabbaticals, having finally done one myself vs observing the hundreds that have taken place at Automattic. Like having a kid, it’s something you can understand intellectually but the direct experience is profound in ways that are hard to articulate.

There’s so much to catch up on and it’s kind of delightful to check in on progress of things after a few months rather than day-to-day like I normally do. If I had one bit of advice it would be to not get a big surgery (I had a sinus one) or plan for other major health things during a sabbatical, that should be on a different track if you can help it.

At the beginning I allowed myself two goals around sailing and chess. Sailing I decided to postpone to take advantage of a peak opportunity in July, but chess has been a fun incorporation into my daily habits and also incredibly humbling playing with folks who have been at it longer. The thing I didn’t plan for that became actually really important to me was getting back to the saxophone, not even trying to perform but the ritual and zen of long tones and practice is incredibly grounding in a way I didn’t know I was missing.

A few bullet point highlights:

• Rowed to Alcatraz.
• Got Covid the 4th time.
• Went to Super Bowl.
• Spent time at my alma mata University of Houston.
• Toured the modern cathedrals of datacenters.
• Did a ton of health scans, blood tests, doctor meetings.
• Got my DEXA body fat down to 17.9%.
• Skied Big Sky and Yellowstone Club.
• Went to friend’s 40ths and 50ths.
• Got a major sinus surgery.
• Hosted an epic eclipse party from a plane with 100+ flash talks.
• Studied Qigong and yoga.
• Spent time in Houston, San Francisco, Big Sky, Austin, Orlando, Tokyo, Taipei, Amsterdam, Paris, and Mallorca.
• Cleaned up a ton of personal projects.
• Read a ton.
• Swam in the ocean.
• Played saxophone at 40k feet.
• Equine therapy.
• A lot of progress on renovation projects in Houston and San Francisco.
• Hiked many places, walking in general more than normal.
• Tweaked my back. :/
• Couple of podcasts and interviews, a few meetings.
• Binged Three Body Problem.
• Did a lot of solo time and introspection.

Also, there was actually a lot of Automattic stuff happening most notably the acquisition of Beeper! I wasn’t able to unplug as much as I hoped, but I did definitely reverse my normal priorities. One thing I really missed was that I had very high hopes to see a lot of people, but a lot of stuff came up so outside of the events it was probably smaller social circle than I normally have.

It does make me think about apophatic theology or how Nassim Taleb talks about via negativa. Whatever you’ve been doing, it’s nice to try the opposite for a while, just to see what happens.