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Have Patience When Considering an Encore Career

A college reunion prompts the author and her classmates to consider their next act

By Maggie Jackson and

In a new world of elongated lives and career fluidity, we need to have patience — with ourselves.

That was perhaps the most poignant and startling point articulated by a panel on “Second Careers, Doing Good,” held at my Yale college reunion. I put together the event to explore the trepidation and the liberation that we all seem to feel about the gift of a longer life.

Like other boomers, we are eagerly planning or pursuing new careers, which often involve social impact. But reshaping our lives doesn’t occur with push-button speed or ease.

The world has changed in startling ways in the 30 years since my class of 1982 graduated from college. In that year, Sony introduced the first compact disc player and Time magazine’s Person of the Year was the computer (desktop, of course). Life expectancy was 74, a huge uptick from the 61 years allotted to the average person born in 1935.

Today, the smartphone is our teddy bear and cognitive prosthetic — and we’re apt to live to nearly 80, with more of these years than not spent in good health. Gender roles and work-home boundaries have blurred, and we can work anywhere, anytime.

The idea of a second or even a portfolio of careers builds on this culture of fluidity, as much as on the potential of a longer life. Otherwise, we’d simply be hoping for longer time on the golf course. Voltaire once said it’s better to wear out than rust out. My classmates and I don’t want to do either.

But amid lives of flux, we need patience, said panelist Scott Gelband, a lawyer turned co-founder and executive director of Seattle Music Partners, a nonprofit that gives free music lessons to schoolchildren.

After burning out on corporate finance law, Gelband went home to a “year in my pajamas.” He told 175 of our classmates and spouses that he had to think long and hard — while facing raised eyebrows from family and former colleagues — about what to do next.

As a father, panelist Fred Leone told of wrestling with the question of whether he should take a steep pay cut to lead a nonprofit that builds playgrounds for children with disabilities — until his 12-year-old son urged him to make the leap.

“Those children need you,” Leone’s son said.

Leone, former chief executive officer of Boundless Playgrounds, made the leap, and is now hoping to make another change and start a new nonprofit.

Moving into an encore career does not come easily or without leaps of faith, said panelist Harriet Rogers Linskey, a marketer who became co-founder of Hands Across the Sea, a nonprofit working to improve child literacy in the Caribbean.


At first, Linskey and her husband, Tom, did not recognize how many skills they could bring to their new lives. He is web savvy and a good writer. She is a great networker and marketer. Their past job descriptions hardly did justice to all their talents.

Encore careers drive to the heart of who we are, and who we want to be. We can’t Google the answers to such dilemmas. Earlier in the day, I’d attended a rehearsal at the Yale School of Drama for Waiting for Godot. Asked how she prepared for a role, one student said: “I look for the character’s super-objective. What is the essence of what this character seeks?”

I shared her words with my classmates, because in an age of career fluidity, we are always shaping and reshaping our life roles.

Today, 31 million workers ages 44 to 70 want an "encore" career that combines income, impact and meaning, according to the think tank Civic Ventures. On average, they take 18 months — and often a pay cut — to make the change. Twelve million in this age group are interested in starting nonprofits or social ventures. In this time of invention and insecurity, we need to take the time to think about our next steps. We need to have patience with ourselves.

Intriguingly, when I mentioned to my classmates that we now likely have about as many decades left on earth as we’ve had since graduation, the room erupted in murmur, chatter and moans.

Did the merest hint of the M-word — mortality — shake things up? Did the glass look depressingly half-empty or wonderfully half-full? I don’t know. But in that moment of tension and excitation and chaos, we all were most wonderfully alive — together.

Maggie Jackson is an award-winning author and former Boston Globe columnist. (This essay also appeared on The Huffington Post.)

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