Gomperts suggests looking at the new technologies and skills as an opportunity rather than a negative barrier. Taking a hiatus between the hustle of the corporate world and the new challenges of the encore career can also be helpful.
"Leaving the hurly-burly of a big national company on Friday and then arriving on Monday at a nonprofit would make somebody's head spin -- no matter what age or stage of life they're in," Gomperts says.
Stephen K. Orr, a onetime investment banker at Goldman Sachs (GS), handled that challenge in a unique way. Orr left that role at Goldman in 1991 to help with a youth mentoring program the firm was setting up. The transition was somewhat of a culture shock, and Orr spent a lot of time visiting charities and nonprofits in New York, Washington, D.C., and Los Angeles to become more familiar with how they operate.
"I got tired of just doing deals and making money through transactional events on Wall Street," says Orr, who is now 55. "I loved it, but it ends up losing a lot of its meaning. What I'm doing now is incredibly meaningful.
Orr discovered that his talents didn't lie in reading books with children or playing pickup games in the schoolyard. But, he was able to build a successful nonprofit structure, raise funds and recruit executives to join a group's board.
In light of that, Orr transitioned from the Goldman youth group to start a nonprofit called Youth, I.N.C., which researches small youth charities in New York -- a task Orr refers to as "due diligence." The group chooses a handful of nonprofits, then helps them raise funds, recruit board members and run their operations more efficiently. It also teaches Wall Street executives how to get involved in charities and how those boards of directors differ from corporate boards.