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The School of Greatness

Sailing With Phoenix: “I Quit My Job To Sail The World & Discovered My Purpose” - Here’s The Secret To Finding Yours

The School of Greatness

Lewis Howes

Entrepreneurship, Fitness, Inspiration, Greatness, Health, Money, Celebrity Interview, Self Care, Celebrity, Success, Mental Health, Relationships, Mindset, Health & Fitness, Education, Alternative Health, Business, Self-improvement

4.821.6K Ratings

🗓️ 18 June 2025

⏱️ 52 minutes

🧾️ Download transcript

Summary

A 29-year-old man with a spine condition worse than a 120-year-old's quit his corporate job and is now sailing solo across the Pacific Ocean, inspiring millions with his authentic journey of courage over comfort. This conversation reveals how facing mortality can become your greatest teacher and why the scariest dreams often lead to the most extraordinary life.

Transcript

Click on a timestamp to play from that location

0:00.0

I went to a doctor and they took some x-rays and the doctors that she was like,

0:04.0

your spine is like somebody who's over 120 years old.

0:08.0

After the diagnosis, I spiraled completely and then I finally one day I was like,

0:13.0

My name is Oliver. I work a corporate job at a tire shop.

0:18.0

I absolutely hate this life. Yeah, I'm going to buy a sailboat

0:22.6

and I'm going to sail around the world. That's Oliver Whidger who quit his job after he

0:28.6

posted that video, liquidated his 401k, bought a sailboat and started learning how to sail.

0:33.6

Our guest for you guys today is the one-only Oliver Widgeer. I haven't told anyone this, but I was in special ed from first grade to a senior in high school.

0:44.3

There's only, there's one thing in my life that I could do well, and that is I can grind.

0:48.3

I can work so hard. If I lean into that, I can do, I can do anything.

0:52.3

I tell people this that are young all the time that like message.

0:56.0

I tell them, dude, if I could go back in time and I was 18 or 20 or whatever,

1:00.0

I would literally get a globe and I would spin the globe and then I would stop the globe with my finger,

1:07.0

and I would buy a plane ticket, a one-way plane ticket and go there.

1:09.0

If there's somebody that is looking to chase their dreams,

1:13.3

find the point of no return.

1:21.2

So I'm so excited, man, because I've been watching your journey over the last few days.

1:29.2

My friend Tim was here, showed me your videos.

1:33.1

And since three or four days ago when I started watching you, I think your audience has exponentially grown.

1:40.0

And I love seeing what you're doing.

1:42.5

And so we have, if you can, share your full name because

1:47.4

on Instagram, you're sailing with Phoenix and you are changing and inspiring the world in a

...

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