Jonathan Ingham ’65 had a career many Yalies might find enviable — he was a successful investment banker in New York City for a decade before establishing his own banking firm and then starting a new career buying and selling other companies.

Having secured financial stability for the rest of his life, Ingham could have cruised to an early retirement and relaxed. But that was not what he wanted for himself. Instead, at age 55, he dropped everything.

Ten years ago, Ingham, who had always been an avid sailor, decided to travel around the world in a 41-foot boat. The trip took him three and a half years, his longest solo stretch in the water lasting about a month.

“You have to come upon something like that at the right time in your life,” Ingham said. “It’s like climbing Mount Everest. If you’re a sailor, you want to sail around the world. You’ve got to have that mindset that’s a little more open to things.”

Ingham set off from Oyster Bay, Long Island, and traveled down the Eastern Seaboard, through the Panama Canal, across the Pacific Ocean, and eventually through the Mediterranean Sea before returning to the United States. He took several breaks during the voyage, spending a summer in Bali and a winter wandering through Asia.

While the journey was physically challenging, Ingham said, his most difficult hurdles were psychological.

“The hardest part was learning how to let go,” he said. “As a New York businessman, I spent my life controlling things. When you get into the ocean, there’s some navigation, but beyond that there’s nothing you can do.”

Ingham’s friends and family were not surprised by his impulsive decision to circumnavigate the globe, he said. John Schenck ’65, a classmate of Ingham’s who has retired from a career in magazine marketing and currently dabbles in poetry, said Ingham’s decision fit his character.

“He’s always been a sailor,” Schenck said. “While he was out there, we always knew where he was. Every now and then we’d get calls and e-mails.”

Schenck, who first met Ingham as a fellow resident of Timothy Dwight College, said he does not believe the sailing experience wholly changed Ingham’s personality, though it provided an opportunity for soul-searching.

“We talked about it all at length when he got back,” Schenck said. “He spent a lot of time looking at the stars and probably triggered a mode of contemplation. But he’s exactly the same person now as when he left. He didn’t leave a Christian and come back a pagan or anything like that.”

Barry Preston ’65, who was Ingham’s roommate for three years, said Ingham had a vivacious spirit in college that he maintains today.

“He really enjoys life,” he said. “He has a love of adventure and people and has done so since the first time I met him. In college, he liked to have a good time, but he was able to combine his keen interest in his studies with his ability to kick back.”

Ingham’s decision to travel the world fit in perfectly with his character, Preston said.

“It was something he had wanted to do his whole life,” he said. “He lives his dreams.”

Ingham said he has been happier and more relaxed since he returned from the sailing expedition. He currently lives in Rhode Island and New York City, and serves on the board of the City College of New York. He said he still sails and fishes often, and continues trying to broaden his horizons.

“My wife and I travel a lot,” he said. “I think traveling and seeing the world and seeing how people live is something everyone should do more of. By and large, Americans don’t understand the world as well as we might think.”

Ingham said he was visited by his daughters, niece and nephew during his three-and-a-half-year trip, and he occasionally picked up hitchhikers along the way.

Schenck said he wrote Ingham a poem — which referenced an oceanography class the two had taken together at Yale — before he embarked on his journey.

“The poem references the course, and any information Ingham may or may not have picked up in it,” Schenck said with a laugh.

At Yale, Ingham was a member of the Duke’s Men of Yale, the Yale Whiffenpoofs, the Fence Club and the senior society Wolf’s Head.