Photograph by Biggie Productions—Getty Images

Answering these five questions will help.

By Anne Fisher
November 4, 2015

How do you want to spend the rest of your life? Most of us choose a career when we’re too young to know beans about our options, or ourselves. Now, even the youngest members of the 77-million-plus Baby Boom generation, born in 1964, are over 50. They’re nowhere near ready to hang up their spurs and, after decades of working in the same field (or even in the same company), many are hankering for a second act.

The trouble is, the possibilities can seem bewilderingly vast. You could start a company, or a charity. Or you might take your skills and experience to a nonprofit, or to another company in the same industry, or to an entirely different business. What about going back to school to train for a career that’s always intrigued you, or turning a hobby into a job? Career coaches and successful 50-plus career changers say the answers to these five questions can help you decide.

Have you written down a wish list?

Here’s where you get to do some blue-sky thinking. “Stretch your imagination,” suggests Robert Dilenschneider, author of 50 Plus!: Critical Career Decisions for the Rest of Your Life. “Don’t pigeonhole yourself as a ‘marketing person’ or a ‘finance person.’ Instead, think hard about what really matters to you. What makes you get out of bed in the morning?”

“People often want to start with their resume,” says Nancy Friedberg, president of coaching firm Career Leverage. She uses a step-by-step method called “Now What?”, developed by Laura Berman Fortgang (whose TED talk on getting started is a must-see for career changers). “But what’s on your resume will not help you make a real change. You have to begin with a deeper dive into not just what you’ve done, but who you are.”

Putting it all down on paper helps. Robert Hellmann, head of Hellmann Consulting and a coach with the Five O’Clock Club’s national career-counseling network, encourages people to make a spreadsheet with columns listing the pros and cons of each possible move they’re weighing. “Once all your ideas aren’t just floating around in your head, it’s much easier to see your way forward,” says Hellmann. “One thing I suggest that people ask themselves is, ‘What will I regret most in 10 years if I don’t do it now?’”

Have you looked around your own company for fresh challenges?

Many people itching to make a leap to something new “completely overlook the chance to stay with the same employer, but in a very different job,” says Friedberg. One of her clients, for instance, was a U.S. bank executive who yearned to quit his job so he could travel more. Friedberg suggested he ask around in-house first. He did, and ended up moving to a new position with the same bank. He’s now based in Hong Kong, and often on the road throughout Asia.

 

Some companies have launched “phased retirement” programs that help longtime employees go into teaching or community-development work. IBM, for instance, started Transition to Teaching in 2008, preparing hundreds of former IBMers to teach math and science in public schools. Intel sponsors Intel Encore Fellowships, which connect employees to new careers with nonprofits. Your employer may not offer anything similar, but it’s worth asking.

When did you stop doing what you loved?

Maybe you really wanted to be a photographer, but you took a job 30 years ago in accounting to pay the bills and relegated photography to the weekends. Or you went into sales because you got a kick out of solving problems for customers, but you’ve spent the past 20 years managing salespeople who do what you used to enjoy.

“After age 50, so many people have been promoted beyond what first appealed to them about their fields,” notes Dilenschneider. If that sounds familiar, he suggests, “think about how you could go back to what you loved. Knowing what you know now, how can you use that passion in your next career?”

This can lead in surprising directions. About eight years ago, Terry Harlow decided it was time for a second act after 25 years at Citibank, Marsh & McLennan, and AIG. So she moved back to the rural community where she grew up and signed on with a local real estate firm. Harlow had earned her real estate license way back in her twenties, but didn’t yet have savings and investments to draw on while she built a customer base. “Living on 100% commissions,” she says, “is tougher when you’re young.”

Would you be happier living somewhere else?

If you’ve been longing to move to a completely different place, a second-act career might be the perfect time to do it. In 2013, when Alix Pelletier Paul relocated to Gulfport, Fla., near St. Petersburg, she had put in almost 30 years as a manager at the New York Times Co., and she’d had more than enough of her three-and-a-half-hour daily commute to and from New Jersey.

In Florida, she and her husband noticed “a niche that was not being served,” she recalls. So they started a business called Nestwatch Homecheck, taking care of property, plants, and pets for absent clients. They now live, Pelletier says, “near the water, with a warm breeze coming in the window, and boats sailing by.”

Is your family, especially your spouse, on board?

“Your spouse or significant other absolutely has to support your decision,” notes Roger Ferguson. A few years ago, he left a long career in HR and operations management at Chase and then at Fluor. He now owns and manages real estate, and started a consulting company called Big 5 Performance Management, in Houston. Ferguson also runs a local church-based organization for job seekers, many of them over 50.

“Especially if you’re going from a sizable corporate paycheck to a smaller one from a nonprofit — or to no steady income while you start a business — your spouse has to be 100% behind you,” he says. “And even then, he or she may have misgivings as you go along. It can be difficult day to day. There probably is no way to prevent that. But it’s important to be prepared for it.”

One more question: Have you asked trusted friends and colleagues for their thoughts on what your next move could be? “Often, people who know you well see strengths and talents in you that you don’t see yourself, and they can make suggestions you wouldn’t think of,” Robert Dilenschneider says. “So use them as a sounding board.”

As you’re mulling over possible second acts, he adds, “Make a list of the 10 people you’ve helped the most in your career. It might be time to ask them to help you.”

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