Oliver Widger, 29, quit his corporate job, liquidated his 401(k) and took a leap into the unknown.
Just a man, a boat and his cat, Phoenix.
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Widger, who worked at a tire company in Portland, left it all behind last year. He bought a boat and relocated to Warrenton, Oregon, to prepare for what he says is “a wild, impossible dream: to sail around the world.” He had no sailing experience and “just blind faith in a better future.”
What made Widger decide to make such a drastic life change?
From diagnosis to departure
The turning point came when Widger received shocking news. A few years ago he was diagnosed with Klippel-Feil syndrome, a rare skeletal disorder involving the fusion of vertebrae in the neck. This condition can cause paralysis.
“It took three years of battling fear and facing the reality that, as a result of my cervical spine condition, I’m at risk of paralysis,” he wrote on his GoFundMe page, “That truth pushed me to finally choose a life worth living.”
According to the Cleveland Clinic, the prognosis for Klippel-Feil sufferers varies widely depending on severity and complications. For Widger, it sparked his big leap out of the office and onto the ocean.
After learning how to sail on YouTube, according to AP, and preparing his boat, Widger launched his odyssey from the Oregon Coast. His goal was to undertake a 2,400-mile crossing to Hawaii.
“On April 30th, 2025, at 8:00 a.m., I left Warrenton Marina on the Oregon Coast,” he posted on Instagram. “And if you are reading this, it means I made it past the Graveyard of the Pacific, and I’m sailing for Hawaii. Ahead of me is the journey of a lifetime. Over two thousand miles of open ocean. No land. No help. Just wind, waves and a boat I prepared with my own two hands. And of course, my first mate Phoenix.”
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He said in another post, “For the next several weeks, I’ll face whatever the sea throws at me. Heavy weather. Long nights. Moments of awe. Moments of doubt. And maybe, moments where I find pieces of myself I never knew were missing. This past year broke me down and built me back up. It was the hardest year of my life. It was the best year of my life.”
Towards the end of May, he announced he had made landfall, and he is now taking a break.
Meanwhile, his story has been making waves online.
His GoFundMe page has raised $115,951 since December. Widger has also been documenting his journey on social media and made it possible for people to send him money, track his location with GPS and buy merchandise. His YouTube channel has over 56,000 subscribers, and he’s amassed more than 1.3 million TikTok followers rooting for him with his handle “@sailing_with_phoenix.”
Save for big changes
If you’re considering a major life change like Widger, you need to think about the impact on your bank account and plan accordingly. That’s where a life redesign fund can come into play.
Unlike a regular emergency fund, a life redesign fund is meant for intentional changes, like career breaks, starting a new business or extended travel.
How much should you save? It depends on your plans and financial obligations. You should also speak to a financial advisor about your plans. Here are a few guidelines:
Living expenses:
- Plan for emergencies. Keep money aside for unexpected issues
- Cash flow estimates: Project your income and expenses to spot shortfalls early
- Bank account strategy: Divide your funds into categories (e.g., essentials, discretionary, emergencies) for more control of where your money is being spent
You’ll want to map out a clear financial plan that helps keep you on track during and after the transition. Think about things like:
- Income sources: Can you explore freelance work, side hustles, or passive income?
- Make a detailed budget: Spend within your means with a realistic plan
- Re-entry plan: What are you going to do when you decide to come back to work?
- Contingency plans: Be prepared in case things go sideways and you need backup strategies
As for Widger, he’s showing that sometimes, big money moves can lead to major life changes. “Feel free to follow the journey,” he says in one post. “There’s nothing but open ocean and a beautiful sunset.”
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This article provides information only and should not be construed as advice. It is provided without warranty of any kind.
