How to Take an 11 Month Sabbatical

A sequel to the last one, but a bit longer.

On Leaving Slack

After nearly 6 years, I left Slack in August of 2025. It was for a combination of reasons that added up to "it's time".

The biggest reason was that Salesforce (who acquired Slack while I was there) would not grant tenured/high level Slack employees equity refreshers. So, I was on track to make ~30% less in 2025 than I was in, say, 2023. Fully vested, my last refresher was less than my annual bonus (and spread over 4 years!).

I really loved working at Slack, but didn't love feeling forced out by our new corporate overlords. This happened to a lot of good people at Slack.

Time Off

I also knew I wanted to take extended time off. Not just because I'd enjoyed it last time and was financially in a position to do so, but because I think it's healthy to do it if you can. This time wasn't a big life change or moving or long term travel sabbatical, this one was just doing what I wanted for a while.

My usual routine during the week was wake up, go for a run/do my workout, make some lunch, go hang at a cafe and work on Metro or something else in OSS for a couple hours, then usually be busy most evenings with run groups or friends or soccer or dating or whatever else came up!

Things I Wanted to Do

• Running! I ran a new PR in the half marathon this spring: 1:19:05. Being able to prioritize my training was huge, and hitting new PRs in my mid-30s is a lucky space to be. I also ran an indoor mile PR of 4:48 in the middle of that training block at The Armory, which will never not be cool to me after watching the Millrose Games on TV for years.
• Work on Metro. Not full time (though productive weeks maybe got close), but more than the nights and weekends I was spending on it at Slack. I got to go back to subjects I hadn't touched since university, like compilers and algorithms. I also don't remember enjoying them in university, but now I did. In university they're often taught purely on theory, but as an engineer I think I thrive on real-world applications and Metro gave me that. It's come such a long way in that time, and it's a distance I couldn't have covered (in that time) working full time.
• Keep fostering dogs
• Some travel still! I had largely stopped traveling for years when my mom was sick, rarely going far from NY. But I wanted to recapture that habit now.
  • Tokyo, Osaka, Kyoto
  • London, Houston
  • Boston
  • DC
  • Munich, Ljubljana, Zagreb, Split, Mostar, Dubrovnik, Kotor
  • Houston, Austin, Kansas City, Philly
• Revisit hobbies I'd lost, like building LEGOs (unsuccessful) or reading (successful, but also Project Hail Mary is just good easy reading)
• Watch my home country of Curaçao play in its first World Cup

Some Unexpected Things

• While I was in Japan I started feeling mystery pain in my lower left abdomen. It went off and on for months without any real explanation. The running guesses varied from GI to musculoskeletal in nature, before a saint of a doctor had a hunch that there was an occult hernia they couldn't visually see but might find on an ultrasound. Sure enough, I had what's called an inguinal hernia and the pain I was feeling was referred pain from it. Ultimately nothing serious and I was able to delay the surgery repair until after my race, finally getting it done in late March. Had to spend a month on the couch but otherwise smooth sailing and fully recovered now.
• I wasn't able to go home this past December due to uncertainty around the US-Venezuela situation. My home islands are just off the coast of Venezuela, and I was worried about getting stuck there if a prolonged hot war broke out and airspace was closed. There was a near mid-air collision around the time I'd normally go, and that flight is literally the flight I take home when I go (Curaçao -> JFK).
• I learned I think a bit differently than others: I have no internal monologue or mind's eye. I've always known this, but didn't really know the extent or what the names of these things are until last year. They're called anendophasia and aphantasia, respectively.
  • This video is a pretty good description of what it's like!
  • It's helped explain a lot of things I've struggled with in the past.
    • I'm dreadful at debating in person. When I think through something, it kinda disappears into a black box and the conclusion pops out the other side. But if I have to then defend that I'm basically reverse-engineering how I got there, whereas inner monologuers have already had that debate on the way there.
    • I'm also terrible at creating new animations without a spec, but I can refine animations I can see really well. Ya know?
• It's also explained a lot of things I'm good at
  • I can work in loud places, "I can't hear myself think" is literally not a problem I've ever had
  • Thinking in structures and concepts almost certainly jives with programming

Job Hunt

My plan was to take the rest of 2026 off and see if I was bored in January. January came, I wasn't bored yet. March came, I started to itch for what was next. Metro sponsorship had unfortunately (but not surprisingly) not garnered many corporate sponsors. The job hunt took longer than expected, but maybe not surprising in 2026. I interviewed at a few companies, ultimately doing (virtual) on-sites at four of them.

I ultimately accepted an offer at OpenAI, which was honestly nowhere on my radar going into the process. It took a lot of convincing from people I've known for years and respect to give it a shot given a lot of the negative public perception around that time. Something I really enjoyed about Slack was that it was fundamentally not controversial. I mean, shit, the most controversial thing about it was that it was too distracting. That was so refreshing after leaving Uber.

I was pleasantly surprised by how positive of a culture signal I got from the interview loop and people I knew that worked there. Everyone had thoughtful answers to the (not easy) questions I asked, and the company appears to genuinely found a focus the past few months that's made it an exciting time to join. They also, frankly, came and got me. They came up later in my job hunt and sped up the process to catch up, and were by far the most outwardly interested company and backed it up with their excellent recruiting process.

I'll be joining a team of talented people I've known for years, in an office walking distance from me with other talented people I've known for years, and reporting to a manager I worked with for years at Slack. I start July 7th. I still have concerns in the AI space and some figures within it, but I think it's also got a lot of exciting potential. Better to be on the inside and build something good.

Some Pictures

Still fostering dogs!

Still running a lot!

Travel

People

Life, NYC, and the things along the way

World Cup