What does semi-retirement look like?

This is the story of six-packs, high blood pressure, professional freedom and male-pattern baldness.

By request, y’all asked about my routines, rituals and habits.

We cover drinking, sleep, work boundaries and dark chocolate.

This episode of The Examined Life Podcast explores the question:

(I promise, I'm not starting an OnlyFans.)

🎧 Or listen on Spotify, Apple Podcasts or your favorite podcast app.

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My Top 3 Takeaways

Real financial trade-offs to owning your time
Bring out the tiny violins. If you want to own your time — pre-retirement — the opportunity cost is real. You really have to be sure of your “enough” amount.

→ Watch the clip

Giving up alcohol
I thought it would be a huge loss. A social loss. A loss of identity. Less fun. Never could I have imagined how much of a gain it was.

→ Watch the clip

We hate losing things
Yup, I have a six-pack. But I also hate the fact that I’m going bald. Since my early 20s. It consumes me daily. And while my schedule is “free” — until I come to peace with this "loss" - I’m definitely not free.

→ Watch the clip

My favorite quote: “We hate losing things.”

"We run towards pleasure and hate pain. We run towards praise and hate criticism. We love to gain things and hate losing them. And so, I don't like to look at myself in the mirror because I'm losing things—my hair, which is much more than that. It's like losing my sense of self and my identity.

And so, you could see how so much of my life is about gaining things: gaining fame, gaining notoriety, gaining followers, gaining a six-pack, gaining a body, gaining attention. That is, if you are beholden to that way of thinking, you're not free."

Why is this episode important to me?

I love my freedom. Full stop. And without a doubt, a large part of it comes from my financial security and high-earning days from Wall Street.

But if you look at the day, most of the activities don’t require much money. And much of the retired conditions don’t only come from owning my time — they come from knowing how I want to spend it.

Both are tricky, but few people talk about the latter part.