EP. 1786

06/18/25

Oliver Widger

“Find the point of no return and then cross that point. As soon as you cross that point, that’s the hardest part. As soon as you cross that line, it’s, it’s, you’re all in, you’re, it’s, you go for it.”

Sailing With Phoenix: "I Quit My Job To Sail The World & Discovered My Purpose" – Here's The Secret To Finding Yours

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What happens when a spine diagnosis worse than you can imagine forces you to confront your mortality at 29? Oliver Widger went from working a corporate job he hated to sailing solo across the Pacific Ocean with nothing but his cat Phoenix and an unshakeable belief in chasing impossible dreams. After learning he had the spine of someone over 120 years old, Oliver spiraled through three years of partying and self-doubt before accidentally posting a video of himself in his work uniform declaring he “absolutely hated this life” – a mistake that changed everything when it went to all his bosses. Now weeks into a solo voyage from Oregon to Hawaii, Oliver has gained nearly a million followers while proving that the most below-average person can achieve extraordinary things through pure determination. This conversation reveals how facing your mortality can become the greatest gift, why crossing the point of no return is the only way to truly live, and how anyone brave enough to spin a globe and jump can transform their biggest fears into their greatest adventures.

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"I literally completely came to terms with possibly being completely broke for the rest of my life until I die. Like being just poor and dying poor, I could, I absolutely became like completely content with that idea and once I became content with that idea, it was freedom."
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And now let’s jump into episode 1786 of The School of Greatness!

Some Questions I Ask:

  • How did you overcome the fear of being worried about what everyone thinks about you by doing some crazy idea?
  • What’s the biggest lesson about yourself you’ve learned in the first 12 days of traveling from Oregon to Hawaii on a sailboat alone with your cat?
  • When do you feel the most loved in your life?
  • If you could go back to your 21-year-old self knowing everything you’ve been through in the last almost decade, what advice would you give?
  • How did you not have an option but to succeed when you quit your job with $10,000 in debt and no plan?
  • What is it about your relationship with your family that you appreciate so much?
  • How does it feel going from nothing 12 days ago to having a million followers and people so invested in your story?
  • What’s your greatest fear?

In this episode, you will learn:

  • How a devastating spine diagnosis became the catalyst for the greatest adventure of Oliver’s life
  • Why accidentally posting your breakdown video to your bosses might be the best mistake you ever make
  • The simple strategy Oliver used to overcome overwhelming self-doubt: solve only the problem directly in front of you
  • How to find your purpose by asking yourself one ridiculous question: what crazy thing do you actually want to do?
  • Why becoming completely comfortable with dying poor is the secret to unlimited freedom
  • Plus much more…
The School of Greatness Podcast
The School of Greatness Podcast

The School of Greatness Show

The School of Greatness shares inspiring interviews from the most successful people on the planet—world-renowned leaders in business, entertainment, sports, science, health, and literature—to inspire YOU to unlock your inner greatness and live your best life.