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Shark Tank's Kevin O'Leary says if he were 25 today, he'd chase these two booming opportunities in the world of AI

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Travel & Leisurework-life balance

Tire company manager who quit to sail to Hawaii becomes social media hero to people tired of earning $150,000 and feeling like ‘you’re just making ends meet’

By
Jennifer Sinco Kelleher
Jennifer Sinco Kelleher
and
The Associated Press
The Associated Press
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By
Jennifer Sinco Kelleher
Jennifer Sinco Kelleher
and
The Associated Press
The Associated Press
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May 16, 2025, 5:43 AM ET
Oliver Widger talks to the camera somewhere in the Pacific Ocean as he and his cat, Phoenix, sail from Oregon to Hawaii.
Oliver Widger talks to the camera somewhere in the Pacific Ocean as he and his cat, Phoenix, sail from Oregon to Hawaii. Oliver Widger via AP
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Midway while sailing across the Pacific with just his cat named Phoenix, Oliver Widger reflected on why he thinks his many followers — more than a million on TikTok and Instagram — are drawn to his story of quitting his 9-to-5 job and embarking on a journey from Oregon to Hawaii.

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“The world kind of sucks and, like, I don’t think I’m alone in how I felt with my work,” Widger, 29, told The Associated Press on Wednesday via Zoom. “You can be making $150,000 a year and you still feel like you’re just making ends meet, you know what I mean? And I think people are just tired of that and working really hard for nothing and want a way out.”

People are inspired by someone who found a way out, said Widger, who is among a growing number of people who have undertaken such voyages in recent years.

Being diagnosed four years ago with a syndrome that carried a risk of paralysis made him realize he hated his job as a manager at a tire company, a job requiring him to be clean-shaven and wear pressed shirts. He heard about people who sailed from California to Hawaii and decided that was the life for him.

He abruptly quit his job with “no money, no plan” and $10,000 of debt.

“I knew one thing: I’m buying a sailboat,” he recalled. “I’m sailing around the world.”

He liquidated his retirement savings, taught himself to sail mostly via YouTube and moved from Portland to the Oregon coast, where he spent months refitting the $50,000 boat he bought.

Now, Widger is harnessing the power of social media to fund his round-the-world sailing dream.

Since he set sail in April, followers have been tuning into his “Sailing with Phoenix” social media posts to view videos of him and his feline first mate battling the waves and bouts of seasickness, enjoying dazzling sunsets, recounting tricky boat repairs or just reflecting on life at sea.

As he discussed his journey with the AP, a netted bag carrying bottled water and snacks swung wildly over his head as the boat rocked.

He recalled highlights of the voyage so far, including marveling at the speed dolphins cut through the water and finding flying fish on the deck. There have been stretches when there were no birds in sight for days. It can be a struggle to sleep when the boat is creaking while being buffeted by waves or to steady a boiling pot for the MREs he has been subsisting on.

There have been harrowing moments like when a rudder failed and the boat tilted sideways in the surf for three hours as he made repairs, and the time he locked himself in the engine compartment and pried his way out with a wrench.

Widger acknowledged he is relatively inexperienced as a sailor, but he has implemented safety measures and communication backup plans, including a satellite phone and an emergency beacon.

Lt. Cmdr. Jesse Harms of the U.S. Coast Guard in Hawaii hasn’t been following the journey closely, but said he is relieved to hear Widger has the Emergency Position Indicating Radio Beacon, known as an EPIRB.

It’s a critical tool for rescuers to locate a mariner’s position during an emergency, especially in the Pacific, the largest ocean, Harms said.

Widger’s journey provides a good opportunity to educate the public about sailing safety, such as the importance of wearing a personal flotation device whenever topside on the boat, monitoring the weather closely and registering emergency tools like the EPIRB, Harms said.

“That’s a really critical piece for anybody that’s getting motivated by his story to go set off on their own adventure,” Harms said.

Until his arrival, likely in Honolulu, Widger is making sure everything is in place to avoid Phoenix having to undergo Hawaii’s animal quarantine. A mobile vet will sign off on Phoenix’s health when they arrive, he said.

Widger wasn’t aware of the deadly danger of cat feces to the endangered Hawaiian monk seal, but he has been keeping all his trash, including kitty litter, on board. Even though he said he is legally allowed to throw it overboard, seeing so much plastic in the ocean motivates him not to.

In addition to managing the practicalities of daily life on a boat, he is coping with going viral in the middle of the ocean by creating social media content and making decisions about merch his fans want to buy.

He credits it all to his neck issue, which “shook up my world and it changed my perspective on everything.” He also hopes he can be an inspiration for anyone who’s in a rut.

“Everything I’ve done I thought was impossible,” Widger said. “Sailing around the world is such a ridiculous dream. Whatever your dream is, just go, just do it.”

The Fortune 500 Innovation Forum will convene Fortune 500 executives, U.S. policy officials, top founders, and thought leaders to help define what’s next for the American economy, Nov. 16-17 in Detroit. Apply here.
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