Why I’m obsessed with surfing

I grew up in the concrete jungle of New York City.

Then spent 14 years on Wall Street.

And the whole time, I daydreamed about the day when the board meeting would become the board meeting.

At 35, I said, “I gotta make this dream happen now.”

I didn’t retire. Nor did I hit my “number.” But I had saved enough to make a bold pivot.

1,419 surf sessions later, I can say it’s pretty effing amazing to live life on your own terms.

This week, on a solo episode of The Examined Life Podcast, Khe asks the question:

Why do I love surfing?

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Do you want to make a bold pivot and live your passion every day? We’ve created a unique coaching experience where you’ll explore deep, introspective and provocative questions with Khe and other Post-Achievement Professionals.

My top 3 takeaways

Launch trial balloons

Many people think, 'when I retire, then I’ll do what I love.' A better plan is to test the waters earlier in life by trying out a hobby or interest. You may find that reality doesn’t match the fantasy.

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Progress and fun are a delicate balance

Pushing yourself to improve in surfing (or any passion) can be rewarding. But it’s essential not to lose sight of the joy in the process. Who’s always the best surfer? The one having the most fun.

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Don’t become a prisoner to mastery

Life teaches us to want to be great at what we do. We must be excellent at our hobbies. It’s why we obsess over the perfect running shoe or golf club. The next one will be the one. But it’s a lot more fun to just allow yourself… to not be great.

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My favorite quote: Surfing means connection

It's the rituals, it's the people, it's the aliveness in the water, it's the sense of progression without putting too much pressure on yourself and just really leaning into that aliveness and that presence of being in the ocean.

Why this episode matters to me

Surfing has always held this soft spot in my heart.

It represented an ideal: freedom, aliveness and a streak of rebelliousness.

I thought I’d have to wait until I started taking Roth IRA distributions (at age 59 and a half) to make this dream happen.

But it happened WAY earlier than expected.

Yet it wasn’t everything I thought it would be.

If you want to dig deeper

It’s hard to live on your terms without an identity earthquake. I love that surfing is a big part of my typical day. And of course, I wouldn’t be surfing every day if I wasn’t a post-achievement professional.

Love letters from our fans

“Exactly what I was looking for...Thanks for putting this out there."

Hope you enjoy the episode,


PS As we prepare our first IRL event, could you tell us which option best describes your career:

1. I currently work on Wall Street

2. I used to work on Wall Street but left

3. I'm trying to get a job on Wall Street

4. I'm not on Wall Street and have no interest

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