Advice for a productive sabbatical

About this time last year, I went on sabbatical.

This was my first time taking an extended break from full time work, so I asked for advice from anyone who'd taken time off work for one reason or another.

The advice I got was awesome: a tossed salad of specific, open-ended, weird, wise, and sometimes contradictory ideas. Some of this was specific to my founder-probably-planning-to-found-another-startup situation, but a lot wasn't. Some of it doesn't even need to be specific to sabbaticals.

Here's a somewhat-grouped list, paraphrased as best I captured it at the time, omitting any personal or identifying details.

Thanks to everyone who shared this advice—it did a lot to shape my time and mindset in 2025. In no particular order, Diego Oppenheimer, Marc Chen, Kyle Matthews, Kristen McEldery, Grant Gordon, George Davis, and all three of my brothers: Sam, Christopher, and Matthew.

• Your brain is like a sponge. You’re probably burned out. No matter what, it’s been squished and contorted by the role you’ve been in. Give it time to unsquish and find its normal shape. This will take months.
• This is a chance to explore alternative versions of yourself. Do stuff you wouldn’t do otherwise. What does "radical self-expression" mean to you?
• Spend extended time in settings that are new and unfamiliar.
• Have excellent adventures.
• Don’t feel pressure to relax like everyone else does. Your rhythm will be different. Be ready for being unfocused and not having goals to be stressful in its own way.
• Tune into what brings you joy and fulfillment. Set a morning routine that focuses on the things that are most important to you at a basic human level: fitness, food, spirituality, etc.. If you start the day with an hour of something meaningful on this level, then it was a productive day, no matter what else you did/did not accomplish.
• Reconnect with people more deeply than you could while grinding. Travel to them. Take long walks. Do memorable things together.
• For career development, spend your time in ways that will naturally bring you into contact with good people and ideas: relationships, consulting, etc.
• Cultivate serendipity by making your bar for saying yes very low. The best way to do this is to refuse to commit to any recurring meetings.
• Lean into serendipity. Your best ideas and experiences will come from unpredictable places.
• You'll need to look for startup ideas in the right places, but I can't tell you the right places because the right places are (1) specific to you and (2) at least somewhat contrarian.
• If this is a "find your next startup" sabbatical, you'll need to be kind of deliberate about it. If you have marketable skills, the market is inevitably going to pull you towards lower-risk roles.
• Getting to conviction on a new startup idea will take months. Anyone who tells you otherwise doesn't understand the creative process that founders need to go through.
• Definitely do not rush into anything: “Don’t start a startup because you can. Start a startup because you can’t not.”
• Founder skills go stale, so don't wait too long before diving back in—it gets harder the longer you wait.