Don't Keep Pushing Your Dreams Aside
Community
Apr 22, 2026
Meet Xander
Meet Xander. He’s currently sailing around the world on his 1979 Gulfstar 37, with his rescue dog Phoebe a rescue pup from Puerto Rico.
From just nine months old until he was seventeen, Xander split his life between living aboard his family’s boat in Greece and spending the rest of the year ashore in Maine for school. It was his last summer on the boat before going off to college when he promised himself that somehow, he’d find a way to live on boats full time.
Despite his first hand experience of boat life, it never quite seemed practical within the “American Dream”, where climbing the corporate ladder is the standard. Not knowing any better, he went along with what we’re told: college, grad school, and a good corporate job.
He didn’t know any other people who shared his passion and felt crazy for wanting something so different. It wasn’t until covid that he stumbled across sailing YouTube channels and discovered a whole community of people already living the life he had always dreamed about.
An Engineless 26-foot Day Sailer
He bought an engineless 26-foot day sailer, fixed it up with his dad, and spent a couple of seasons sailing around Maine. Three boats later, after a major heartbreak, a freezing New England winter living aboard, and a full refit, he finally had a boat ready to take offshore and nothing was going to stop him.
Take The Risk
Four days into his longest offshore passage as captain, sailing from North Carolina to St. Thomas, he found himself 300 miles offshore in 30 to 35 knots of wind. Massive swells rolling through the ocean, the last golden light of the day hitting their peaks. He told himself, “I did it. I’m finally out here, exactly where I want to be, and it’s so gorgeous.”
As your deepest passions are not actualized, you will not be happy. Stop ignoring your dreams. Start that business, buy the boat, van, motorcycle, surfboard, quit the toxic job and find a career that calls to you. Whatever burns at your heart, make it real and take the risk.
His Advice
His advice is to start small - right now. There’s a lot to learn to be a safe and competent sailor, but it’s all very attainable. Take lessons, go racing, buy a dinghy, get as involved as you possibly can, and you’ll quickly be on the right path. You never stop learning, and what a privilege that is.
Would he do it all over again?
Without question.
