How to Discover Your Encore Career

Undertaking a post-retirement career can be daunting—but rewarding. BusinessWeek asked experts for tips to help you start your second act

By Karyn McCormack

At age 55, Dorothy Mench opted to retire from her 26-year career in equity trading operations at a brokerage firm in Chicago when it reorganized. This fall, she's taking her first class about gerontology at the Center for Creative Aging at Harold Washington College.

"I want to learn more about me, and what I'll encounter in old age," says Mench, who is turning 59 this month and has a master's degree in social work. She's unsure if the class will lead to a new career in gerontology, but is seeking a job that's meaningful, a tenet of the encore career movement among baby boomers.

Trouble is, there's no definitive road map for early retirees' career transition. "If you want to get into social work, you go to college," Mench says. "But if you want to get into the rest of your life, it's a big question mark. How do you do that?"

These days, with the weak employment market, finding a new job or changing careers requires even more time and effort. Here are some steps to help with the transition, from career coaches, Encore.org and retirement experts.

Find positive experiences from your past jobs

Although it's natural to look forward and outward in the world for your future options, the first step, says John E.Nelson, co-author of What Color Is Your Parachute? For Retirement, is to look inward and backward. "The most valuable first step is actually counter-intuitive for most people," he explains. Ask yourself: What are some of the most enjoyable, challenging, and meaningful experiences of your career, Nelson advises. "By reflecting on yourself and your experiences, you're basing your exploration on real data, rather than flights of fancy," he says.

Understand the structure of those good experiences, Nelson explains, so that you can create a "template" for future positive experiences. "You're more likely to spot opportunities that will be fun and engaging and that provide you with a sense of purpose," Nelson says.

Identify your interests, strengths and values

From your work experiences, identify your interests, which can be fleeting and change over time. "What fascinated us in our 20s may not in our 50s," Nelson says.

Also consider your strengths and skills. These can range from your job responsibilities such as negotiating contracts, to the deeper layer of transferable skills such as social and interpersonal skills and being organized. Our character strengths and transferable skills don't really change—they're more like a foundation that is built and developed over time, Nelson says. For example, Mench developed problem-solving skills while working with high-net-worth clients during her career at the brokerage firm, as well as in social work. "I'm trying to use my skills and abilities from an older stage to go through this one," she says.

Our values are deeper than our interests, but they often change too, Nelson says. For example, after marriage and having children, you might discover that your values are different.

A new career might involve a different line of work, serve different values, and entail different job responsibilities. But it may use the same transferable skills and character strengths that you've spent a lifetime building, Nelson says.

"That's why knowing your skills and strengths is so important in creating that 'template' to identify opportunities that are a good fit for you," Nelson explains. "The goal is to find work where the subject interests us, the responsibilities make use of our strengths and skills, and the purpose of the work is aligned with our values."

Determine financial needs

When considering your next career, figure out whether you're going to work for fulfillment and a paycheck, or for fulfillment alone, Nelson says.

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