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How Jon Stewart and Obama Can Help You Change Careers

Their situations can be instructive for others at a crossroads

By Robert DiGiacomo

Planning a career switch after 50 is never easy, even if you're the world's most famous chief executive with a who's who of contacts and a Nobel Peace Prize on your resumé. Even President Barack Obama will have to figure out his second act when he is forced to “retire” from the White House.

If you’re at a career crossroads, here’s how to take a tip from Obama; the recently-unemployed TV talk show host Jon Stewart and Evan Wolfson, who is folding his Freedom to Marry nonprofit advocacy group:

The Professional In Need of Reinvention (President Obama)

Obama, who will be 55 when he leaves office, is a good example of a senior-level professional in need of a career reinvention. If that sounds like you, follow his lead and develop a plan based on your stature and career trajectory, says Robin Ryan, a Seattle, Wash.-based career counselor and author of Over 40 and You're Hired! Secrets to Landing a Great Job.

“You have to be realistic as to whom your potential employers are,” Ryan says. “When you're over 50, most hot tech companies are not going to be interested.”

An effective way to test the hiring waters is through consulting, teaching or some combination of the two. (Word is that Obama may teach at his alma mater, Columbia University.)

If you’re determined to find full-time employment, prepare for a job-hunting process that could last longer than you expect. “Many think it's going to take three months — it will take 12 months,” Ryan says.

Obama will likely be more than ready to leave the fishbowl of Washington, D.C., and you, too, should be open to the idea of relocating for the right position, especially if you were a CEO. “There are very few jobs at the top, and many have to go where the jobs are,” Ryan says.

Executives working in the for-profit sector may also want to take a cue from Obama, who has created a foundation for his presidential library: Follow more altruistic pursuits. “They are at a point in their lives where they can bring leadership to an organization and give something back,” Ryan says.

The Restless Type Ready for a Career Change (Jon Stewart)

Someone like Stewart, 52, who quit his role as host of Comedy Central's The Daily Show after 16 years, is probably “completely and totally burnt out” and should take at least six months to “recharge,” says Ryan.

After a suitable period, it will be time to explore how to use your talents, based on your values, strengths and interests. A great communicator like Stewart, for example, would likely find success appearing on the lecture circuit, writing a book or teaching — if he doesn't return to stand up.

Think, too, about whether you want to give back or if you envision your next career to be just (or mostly) fun. “It may no longer be about making the big bucks, but shifting to what is your legacy going to be,” Ryan says.


Stewart recently bought a New Jersey farm with his wife, Tracey, giving a home to rescued animals. But Ryan suspects he’ll be back on TV within three years.

When Your Job Gets Cut (Evan Wolfson)

In 2003, attorney Evan Wolfson founded Freedom to Marry at a time when few thought gays and lesbians would soon gain equal marriage rights. Now that the Supreme Court has legalized marriage rights for same-sex couples across the nation, Wolfson, 58, is shuttering the organization and putting himself out of a job. Slate calls him “the happiest unemployed person in America.”

If you’ve seen your job eliminated after 50 (even if you’re not as happy about it as Wolfson), challenge your preconceived notions about the possibilities, says career coach Julie Jansen, author of I Don't Know What I Want, But I Know It's Not This.

What type of lifestyle do you want? What would be your ideal constituency? What kind of recognition do you need?

“I think people when they're in a really successful career don't allow themselves to be excited about other things they're passionate about, even things they may have thought of as a kid,” Jansen says. “I tell my clients: Let's leave no stone unturned to think about all the things that interested you. Just because you were a great lobbyist for this cause doesn't mean you have to keep lobbying.”

Ultimately, a career decision at this stage should be about reaching your goals, not about satisfying others' expectations.

“I think prominent people allow the external world to drive a lot of decision-making,” Jansen says. “It should be about what you want to do.”

Robert DiGiacomo is a veteran Philadelphia, Pa.-based journalist who covers food and travel, arts and entertainment and personal finance. He has written for The Washington Post, USA TODAY,  The Penn Gazette and Fodor's. Read More
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