My Teenage Dream Was To Live On A Boat. Now I'm Doing Just That

How one bucket-list bullet point fueled a sweet second act.

- Elizabeth O'Brien

GARY BAKER was sorting through memorabilia in the basement of his Ann Arbor home about two years ago when he stumbled upon a bucket list he’d written as a young teen. Now 64, Baker didn’t recall making the list a half-century earlier, and he couldn’t believe what he’d written first: “Living on a boat.”

At the time, the IT executive was waiting to close on the 47-foot-long catamaran that would become his permanent home in Fort Lauderdale. He rents the yacht, named Shared Adventure, to day-trippers and overnighters on weekends and vacations, with the goal of expanding his side gig into a full-time adventure-travel company when he retires from his day job within the next few years.

“I just can’t imagine having nothing to do,” Baker says. “This will get me out of bed in the morning.”

Retirement experts often counsel folks to look back to their childhood interests for hints of what they might like to pursue as their second or third act. A lifelong sailor, Baker had followed their advice subconsciously.

“I always had friends who had boats,” Baker says. “Now I am that friend with a boat.”

Yacht life: Gary Baker on his 47-foot-long catamaran at the Bahia Mar marina in Fort Lauderdale.

PLAN METICULOUSLY