Oregon Man Goes Viral After Daring Job Quit, Boat Purchase, and Epic Cat-Sailing Journey to Hawaii

Oliver Widger, a 29-year-old from Clackamas, Oregon, is capturing hearts online as he embarks on a daring sailing journey across the Pacific Ocean. His only companion? A cat named Phoenix.

Widger’s voyage from Oregon to Hawaii marks a remarkable personal achievement. Three years ago, he was diagnosed with Klippel-Feil Syndrome, a rare spinal condition that puts him at risk of paralysis. Faced with this daunting reality, he decided to transform his life.

His spine was described by doctors as resembling that of someone much older due to the abnormal fusion of vertebrae. “I was told surgery could leave me paralyzed,” Widger recounted. This news prompted him to reevaluate his future.

In a bold move, Widger left his job, liquidated his retirement savings, bought a $50,000 sailboat, and began learning to sail. He leaned heavily on resources from YouTube and guidance from a neighbor.

A chance encounter with a customer at work, who wore a sailboat-themed shirt, inspired Widger. After sharing his dream of sailing around the world, he was merely reminded, “If you want to sail the world, what are you doing here?” This idea propelled him to take action.

Widger relocated to the Oregon Coast and dedicated ten hours daily to refurbishing his boat. His only constant was Phoenix, the cat he rescued years prior.

On April 30, 2025, Widger launched from Warrenton Marina, setting sail toward Hawaii—a daunting 2,400-mile journey that is expected to last about three weeks. It marks his first venture beyond river sailing.

Documenting the trip on social media, he shared insights into this life-changing experience, stating, “Day one of crossing the Pacific Ocean.” The journey has been filled with challenges, including storms and mechanical issues, but he remains positive. “It’s every single emotion you could imagine,” he expressed, calling it “absolutely awesome.”

Widger’s social media presence has surged, gaining nearly 800,000 followers on Instagram and about 600,000 on TikTok. With Starlink satellite internet, he provides real-time updates, even from the sailboat, aptly named Phoenix.

Reflecting on his unexpected internet fame during intense moments, he remarked, “I was fighting for my life and going viral at the same time.” His plans include a six-month stay in Hawaii before continuing onward to French Polynesia with dreams of circumnavigating the globe.