Oregon man quits lusterless tire company job to buy a sailboat and travel the world
“I absolutely hate this life.” Meet Oliver Widger. He’s sitting alone in his car, wearing a Discount Tire corporate polo. Recording himself, he tells no one (and everyone) his intentions. And they don’t involve his 11-year career track: His heart and mind are set on a dreamed-about sailboat he’d never set foot in.
“No money, no plan, no idea how to buy a sailboat.”
Like many Americans, Widger spent more than a decade living the typical corporate grind. Work long hours, party on the weekends “to fill a void.” But after getting a startling medical diagnosis that left him reeling, he questioned his cyclical, mentally fruitless routine.
A year ago, Widger pledged to himself and the world that he’d quit his tire company job and buy a boat.
No, he’d never sailed before. He’d learn. After that, he’d take a trip around the world. Within 30 days, he left his job. A month later, he purchased a sailboat, the Masswappii II, and moved into it. It needed work, which took some time. After fixing it up a bit, he started taking it out on the water.
“This is the start of my journey.”
By May 1, 2025, he successfully launched out to sea.
Yesterday, he posted a new video on social media. “This is Day One of crossing the Pacific Ocean,” he starts. “And this is my first time sailing outside of a river!”
You might think one would be near-frozen in fear (and incompetence). But Wider’s smiling and laughing to himself at a dream come true.
So, how much can you change yourself in a year?
“It’s corny to say you can change your life in a year,” he said in a reel posted back in December. “But you really can. Recognize the point of no return…and then cross that point. And that is where the magic happens.”
This first stretch in the sailboat, from Oregon to Hawaii, should take between 20 and 30 days. If you follow him, he says he’ll rely on Starlink to update us on his journey as he goes.
