sabbatical reflections
April 2025
I’ve been on sabbatical for about 7 months…
It’s one of the best things I’ve ever done.
And now I wanna reflect. Take stock. Muse a bit. Write something for “old man me” to read when he’s watching the sun go down and reminiscing about youth.
I was planning this for a while.
See, I spent the last few years dabbling. Law, tech startups, crypto. But I never found my “thing.” (Backstory here, if you’re so inclined.)
Christmas 2023, I read The Pathless Path. It got me good. I knew I needed to shake things up. Buy time to reset, experiment, and figure out what I wanna do.
Then, summer 2024, I read Shaan Puri’s blog posts about a “season of wandering.” 3-12 months to try shit and look for clues.
I’ve been in my wilderness period since September. Roaming Europe and Asia. Reading, exploring, and tinkering.
Some lessons so far…
1. Don’t rush, man
At first, I had grand plans for a business I was gonna start. Big mistake. I was just tryna fill the work void. After a few weeks, I scrapped it.
That led me down new rabbit holes. Then to the projects I’m working on now.
I like Jeremy Giffon's take: “a sabbatical is the unfettered act of following your curiosity until you’re grabbed by compulsion.”
Forget about feeling busy and productive. The entire point of this thing is to figure out what lights you up. Yeah, it takes time. But once you find it, you'll have the natural energy and drive to go hard. And it won’t feel like work.
Unless you’ve got that “compulsion,” don’t bother forcing it because (a) you won’t maintain it long-term, and (b) you’ll get beat by people who care about it more than you.
Project selection fucking matters. If you’re playing the wrong game, it doesn’t matter how hard you work. Your energy’s way better spent finding the right game vs. grinding your ass off in the wrong one.
I use 2 frameworks a lot:
“Avoid good opportunities” (h/t Auren Hoffman). Save your time and energy for great ones. They’re where the massive upside is (and downside too btw).
“Ignore the medium-term” (h/t Peter Thiel). Focus on what’s interesting to work on now and will be meaningful in 30 years. Don’t think about the next 5-7 years. That’s a one-way road to status games.
Basically: be patient. Do what’s exciting today and you can see yourself doing for decades. Everything else is noise.
2. You’ll look dumb and aimless to other people (and sometimes feel like it)
Just accept it.
If you’re committed to following your curiosity, people around you are gonna think you’re lost.
That’s fine.
Actually, it’s great.
Being misunderstood by the right people is a sign you’re thinking for yourself. Which, if you’re looking for your life’s work, is step numero uno. Anything great starts from within. With a strong sense of self.
Once you’re off the default path, there’s no script. You’re gonna meander, get overwhelmed with options, and think you’re being stupid. All par for the course, my friend. Trust the process. You’ll figure it out.
Being in the wrong environment turns down that little voice in your head that knows what you want. Being free helps you turn it back up.
Here’s a pep talk from Bezos:
“Wandering is an essential counterbalance to efficiency. You need to employ both. The outside discoveries, the nonlinear ones, are highly likely to require wandering.”
What looks like wasting time to other people, is actually an investment in yourself. You pay a status tax now to avoid a fat regret tax later. To butcher one of my favourite quotes: you risk wasting decades by refusing to “waste” a few months earlier in life.
Is it efficient?
No.
Is it worth it?
Yes.
“Longest way round is the shortest way home” and all that.
3. You’re gonna rethink your life
Sounds dramatic, but it’s true.
It only took a few weeks of being out on my own before I was saying to myself “no going back.” When you strip everything away, you start seeing things differently. Distance from traditional work sets your mind free. And travel puts this on steroids. You start remaking your whole concept of the world.
What matters to you? How do you actually wanna spend your time? What does your ideal day/week/month look like?
Paul said it well: a “true season of contemplation” lets you “re-engage with the world with a new bottoms-up perspective.”
You realise how many things you accepted top-down before. At least I did.
I don’t have all the answers yet… but I’ve got way more than I had.
4. Variance is your friend
Being out on your own feels like a different world.
There’s more risk. But more opportunities too. Your outcomes go from capped (Mediocristan) to unlimited (Extremistan). In a few years, you could be eating ramen 3 meals a day or sitting on 8-figures. Maybe it’ll take a while to make my old salary again. But once I do, there’s no ceiling. It’s all on me.
The price for such variance?
Uncertainty.
Shit loads of it.
It’s scary. But exciting. You feel alive. No one actually wants their life mapped out. I got a taste of that on the law track. Just put my head down for 7 years then make partnership or go in-house. No thanks.
And all this new-found opportunity…
The barrier isn’t smartness. It’s courage. Find the right vehicle and bravely go after it. The upside’s there for the taking.
“Always more audacity,” as Winston would say.
Parting thoughts…
There’s nothing to lose.
Worse case? Back to where I started but I know myself better.
Best case? I change the trajectory of my life and make “old man me” proud.
I’m pretty sure which one it’s gonna be.