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June 1, 2025 26 mins

If you were diagnosed with a rare condition that could leave you paralyzed, would you leave corporate America, and liquidate your 401K to buy a boat and sail around the world?

This is the story of Oliver Widger, or sailing_with_phoenix on Instagram and Tik Tok—a man who decided to follow his dreams and set sail from Oregon to Hawaii with nothing but YouTube tutorials, his cat Phoenix, and a dream. And the internet took notice. This is for anyone who’s ever dreamed of leaving the 9-to-5 grind . . . or just needs a little push to start that “someday” goal.

You’ll learn:

  • What it really takes to make a major life pivot—financially, emotionally, and mentally
  • How documenting your journey (even imperfectly) can turn into a brand, a community and even a possible income stream
  • Why brands like e.l.f. Cosmetics won the internet with their unexpected marketing move
  • What this story teaches us about career clarity, freedom, and choosing aligned risks over safe regrets

If you’ve ever felt the ache to change your life, but didn’t know where to start—this is your sign to press play.

#sailingwithphoenix #viraltiktoksailor #leavingcorporateamerica

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Music: “Sugar Groove” by INPLUSMUSIC — Licensed via PremiumBeat (License #6849247, Order #5428551) for Jeans With a Blazer podcast. Used with permission.

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