by Rebecca Knight
You’ve worked hard all your life, and now you’re on the brink of retirement. Trouble is, the things you looked forward to all those years — mornings on the golf course, afternoons puttering in the garden, trips to exotic places — don’t feel like they’ll be enough to sustain you. Encore careers — jobs that blend income, personal meaning, and often some element of giving back — are becoming an increasingly popular alternative to full-time retirement. But where do you start?
What the Experts Say
According to Encore.org, a think tank focused on Baby Boomers, work, and social purpose, nearly 9 million people ages 44 to 70 today are engaged in second-act careers. “People are leading longer and healthier lives and so leaving full-time work in your mid-60s means that you’re looking at a horizon of 20 to 30 years. That’s a long time,” says Marc Freedman, CEO of Encore.org and the author of The Big Shift. There is, he says, the financial question of how you’ll support yourself, “and then there is the existential question: Who you are going to be?”
On one hand, it’s daunting to contemplate embarking on a new career at this stage in life. On the other hand, it’s liberating to “let go of the past” and forge a new identity based on “things that you find exciting, stimulating, or interesting,” says Ron Ashkenas, a senior partner at Schaffer Consulting and an executive-in-residence at UC Berkeley’s Haas School of Business. “It’s an opportunity to think about how you want to contribute to society, your community, and your family.” Karen Dillon, coauthor of How Will You Measure Your Life?, agrees: “Life doesn’t necessarily get simpler after you leave a full time job,” she says. “But it can become more rewarding — if you’re willing to hold yourself accountable and work for the new goals you’ve set yourself.” Here are some things to think about as you prepare to for this new phase.
Lay the groundwork early
If you’re confident that your job won’t be in jeopardy, tell colleagues about your plans to officially retire while you’re still gainfully employed. “Then it’s not out of the blue, and it also gives them a chance to figure out if they have contacts or a network you could leverage,” says Ashkenas. It’s also important that you leave on good terms with your company and indicate if you are open to occasional projects and assignments — which is a good way to keep your hand in your profession. Adds Dillon: “You can’t just stop working and expect the phone to ring. Plant seeds early so that once you’re in circulation, experiences and opportunities will come to you.”
Don’t rush
Once you leave your job, give yourself a period of time — ideally months in duration — to reflect on what you want to do next. “Give yourself time to rest, renew, and restore,” says Freedman. Navigating this transition will take some time. “You’ve been working and juggling family stuff for decades and likely haven’t had the time to think about this next chapter of your life. Recognize that finding work that is significant and fulfilling could take two to three years.”
Ask yourself: what’s really important?
Make a list of all the things “that feed you emotionally” and then drill down to figure out exactly what it is about those things that inspires you and makes you happy, suggests Dillon. For instance, you might list spending time with your kids or doing work that’s challenging, but “what you most enjoy is having new experiences with your children, like travel. And what you really like about work is collaborating with others and creating something,” says Dillon. “Push yourself to do the things that matter to you and be conscious of the choices you’re making and how you’re spending your time.” Your goal, says Freedman, is to “figure out what your priorities are at this juncture in your life.”
Be willing to experiment
Freedman advises taking a “try-before-you-buy” approach. “Find ways to dabble in things that interest you,” he says. Seek out internships, fellowships, or part-time jobs; give back by volunteering to serve on a board of a nonprofit; take on different kinds of professional assignments; or sign up for a class at a community college. “If it sounds fun and interesting and it seems as though you will learn new things, do it,” says Dillon. Also look for ways to transfer your hard-earned expertise to new domains, says Ashkenas. “It’s not as if you stop being who you are. You are still you, and you still have the same skills; you’re just applying them to new situations and environments.”
Keep productive
After you’ve given yourself some time off, it’s important to return to some of the things that office life gave you: structure and community. “Just as you would look ahead to milestones in your work, you need things to look forward to and anticipate,” Ashkenas says. Consider joining a group or community like an alumni association, a volunteer or religious organization, a freelancer’s group, a book club, or even a virtual community. After all, “you need the stuff you get from the informal office environment: banter, chatter, laughter, and information,” Dillon adds. It’s also helpful to spend time with others who are “wrestling with the same challenges you are,” says Freedman.
Hold yourself accountable
As you’re navigating this transition, “you have to think about goals,” says Dillon. “Get feedback from those you care about — like your spouse or partner, children, and friends — about how you’re doing. And be honest with yourself about how you’re spending your time. Do a reality check by asking yourself, “Do I feel good and healthy? Do I feel stimulated? Don’t let outside voices dictate your answers,” says Dillon. And once you figure out where you want to focus, Ashkenas says, “you need to keep asking yourself: Am I adding value? Am I making a contribution? Am I learning something?”
Principles to Remember
Do:
- Find meaning in your new life by pinpointing how you most enjoy spending your time
- Experiment with different jobs and assignments to stretch yourself and learn new things
- Expose yourself to new perspectives and ideas by joining a community
Don’t:
- Be secretive about your intentions to leave your job — share your plans with colleagues and let them know you’re open to new opportunities
- Rush into a new job right away; give yourself time to relax and restore
- Squander hours away just because you can; hold yourself accountable about how you’re spending your time
Case study #1: Embrace your personal passions as the source of new opportunities
The day that Gail Federici sold John Frieda — the professional hair care company she co-founded with the British stylist — her mind reeled. “We hadn’t been planning to sell the company,” she says. “Over the years we had meetings [with prospective buyers], but we wanted to keep doing what we were doing.”
Once the paperwork was signed, she took a one-week trip to Venice with her college roommate then returned home to London. At first it was a tough transition. “We had been building this company for 12 years: I had a definitive routine; I had a plan for the future; I had goals. All of a sudden it was gone,” she says. Gail decided to dedicate her time and energy to a personal passion: music. It was a natural second act: Her husband is a musician and Gail used to sing in his band in New York. At the time, the couple’s twin daughters were interested in becoming performers. “It was a huge learning curve for me: I had to read the back of CDs to find out the names of producers and songwriters,” she says.
Over the next five years, she worked on albums and promotions with several musicians and boy bands, including Taio Cruz, the British singer-songwriter and record producer. “It was exciting and challenging to learn a new industry but I was still doing what comes easy to me: marketing, problem solving, and strategizing.” After signing the main act she and her team developed to Interscope, she decided to “go back to what [she] does best.”
Now in her 60s, Gail is the President and CEO of Federici Brands, another hair styling company. While she is happy to be back in the hair care business, she looks back on her years in the music industry fondly. “I was out of my comfort zone but I liked it.”
Case study #2: Leverage your expertise and connections to give back
Bill Haggett spent the first part of his career in the shipbuilding business — first as President and CEO of Bath Iron Works in Maine and later as the head of Irving Shipbuilding of New Brunswick, Canada. After leaving Irving in the late 1990s and returning to Maine, Bill wanted to give back to his community.
His first priority: building a new YMCA in his hometown. Bill helped raise funds for the Y and also helped design the new complex. “I grew up in Bath, Maine in the 1940s and I am from a family of modest means,” he says. “The YMCA was a terrific outlet for me and my friends.”
By 2000, the Y project was complete, but Bill wasn’t interested in “moving into retirement mode.” The Libra Foundation, a large charitable organization in Maine, approached him about a job. “They wanted to make a strategic investment in a potato company in northern Maine on the brink of bankruptcy. And they asked: ‘Would I be willing to serve as chairman and CEO?’”
Bill knew nothing about the potato business, and he had little interest in moving to northern Maine. But after reflecting on what he wanted out of the next chapter of his life, he realized the opportunity was appealing. “It was a way to help the economy by adding value and jobs in that part of the state,” he says. The job would be fulfilling on a personal level too. “I wanted the challenge of turning this business around. It was a way to learn something new, but I also thought I had some expertise I could bring to the party.”
The early years were a struggle, but after a while, business at Naturally Potatoes improved: Sales increased by 40%, and the company returned to profitability. By 2005, it was sold to California-based Basic America Foods (BAF). Bill, meanwhile, went on to run a meat company. But Naturally Potatoes fell short of BAF’s expectations, and when, in 2010, a team led by Libra bought the company back, Bill resumed the role of CEO.
At the age of 80, Bill — who is chairman and CEO of Pineland Farms Natural Meats and Pineland Farms Potatoes — has no plans to stop working. “I feel energized,” he says. “One of the great pleasures of being my age is that everyone I work with is younger than I am. They have bright ideas, skills, and technology savvy that I don’t have.” Learning a new business every few years has been “stimulating,” he says. “I like to be useful and to make a contribution.”
REBECCA KNIGHT
Rebecca Knight is a freelance journalist in Boston. She has been published in The New York Times, USA Today, The Financial Times, and The Economist.
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