Oregon man leaves job, sails with cat to Hawaii, becomes a social media star

(MAY 29, 2025) Oliver Widger is 29 years old. He used to work as a manager of a tire company. Recently, Oliver became a social media star. Why? He quit his job and sailed from Oregon to Hawaii with his cat, Phoenix. 

Oliver was tired of working for a company. He also had a medical condition that could cause paralysis. Paralysis means you are unable to move all or part of your body. So Oliver decided to chase a new deam. 

“You can be making $150,000 a year, and you still feel like you’re just making ends meet,” he said. 

His story has inspired over a million followers on TikTok and Instagram.

Oliver had no sailing experience. He taught himself using YouTube. He spent months fixing up a $50,000 boat. He used his retirement savings and started his journey with $10,000 in debt and no plan. 

Oliver shared the highs and lows of the trip on social media. Fans watch him battle rough seas, enjoy sunsets, and talk about life on the ocean.

There were challenges. He got seasick. The boat needed repairs. Some nights he didn't sleep. Oliver faced danger, too. For example, one time he got trapped in the engine room.  Another time he had to deal with a broken rudder during a storm.  Oliver tried to be safe. He used a satellite phone and an emergency beacon.

As Widger nears Hawaii, he’s also making sure his cat won’t need to be quarantined, arranging a vet check upon arrival. Now juggling life at sea with managing merchandise and social media fame, he says his journey is about more than sailing. “Everything I’ve done I thought was impossible,” he said. “Whatever your dream is, just go, just do it.”