We Quit Our High-Paying Tech Jobs to Buy a Sailboat and Live Our Dream Life

A couple in their 30s quit their jobs at Amazon and Business Insider to buy a sailboat and travel. Here's how they made it work and why they have no regrets.

The Decision

Bianca Chan, a senior finance reporter at Business Insider, and Charles Boddie, a software engineer at Amazon, were living in Seattle and enjoying successful careers. However, visa issues and a desire for more freedom led them to consider a drastic change. In April 2025, they decided to quit their jobs and buy a 42-foot sailboat named Windsong.

Financial Planning

They were financially conservative and wanted to be debt-free during their "first retirement." They sold their Seattle condo, budgeted for living expenses and boat maintenance, and ensured they had enough savings for post-retirement life. They also decided to stay with family when not traveling to keep costs down.

Career Risks

They worried about the impact on their careers, especially with AI and layoffs in tech. They gave proper notice, left on good terms, and prepared for difficult conversations. They also discussed what they hoped to achieve during their time off.

Life on the Boat

Twelve months in, they have cruised over 1,000 miles along the Pacific Northwest, traveled to Japan, Vietnam, French Polynesia, and Mexico, and taken spontaneous trips. They've spent more time with family, learned new hobbies (Bianca plays bass guitar, Charlie is becoming an amateur electrician), and experienced less stress and better health.

What's Next?

They are considering freelance work or small business ownership and hope to be working again by the new year. They are open to pivoting careers but are not worrying about future work yet, focusing instead on enjoying their current freedom.