MONEY Second Career

How to Jump from a Second Career to a New Dream Encore Job

Senior painting in studio
Lynn Koenig—Getty Images/Flickr

You aren't limited to a second career. Be ready to embrace a third or fourth career as opportunities come along.

Most of my boomer friends tell their adult children to plan on multiple jobs and careers. The era of corporate loyalty and the organization man and woman is long gone, they (and I) say—due to a hypercompetitive global economy and their likely desire to embrace new opportunities throughout their work lives. Good advice.

But boomers ought to heed this insight, too, embracing multiple acts during the second half of life. I think you shouldn’t just plan on a second career, but maybe a third or a fourth.

Linda Lyman: On Her Third Career

That’s also what Linda Lyman told me with a smile when we met at a Phoenix breakfast event for UMOM, a nonprofit helping families break the cycle of homelessness. She’s exploring her third career in what I call Unretirement (also the title of my new book on the trend).

Lyman moved to Phoenix 31 years ago, eventually managing legal services for a land developer. On the 17th anniversary at this job, a colleague congratulated her and asked: “What will you do for the next 17 years?” The thought of spending another 17 years at one place jolted Lyman, then 46.“I have to get out of here,” she thought. “I am going to do something more meaningful.”

Lyman next began working at a small nonprofit that mentored at-risk kids, New Pathways for Youth, and ran the group successfully for a decade. She loved the work, but decided it was time to “retire” earlier this year. “Ten years is a long time,” Lyman says. “I needed to have more life balance. I left on my own terms. It’s good.”

Now Lyman, 58, is eager to teach in an inner-city school. “I want to do something that I’m passionate about,” she says. “Teaching is what I thought I was going to do when I was in high school. It’s nice to be circling back.” Her husband is 65 (he’s retired from Intel) and the couple is open to relocating for Lyman’s teaching job, with Wisconsin and Minnesota high on her list.

Ginia Desmond: Heading Toward Career No. 5

Ginia Desmond is now on her fourth career and may be heading towards No. 5. My sense is that she has danced from one adventure to another.

Desmond was a serious artist early on, with a Masters in Fine Art. She painted in Argentina while living there with her first husband and then in the Phillippines, where her second husband—Charles Kepner, founder of the Kepner-Tragoe consulting firm—worked.

Desmond brought some Philippine fabrics back when they moved to Tucson about a year later and sold them to a local boutique. The store owner wanted to buy more fabrics, so for her second career Desmond created Sangin, a trading company importing baskets, fabrics, lighting fixtures and similar items from the Philippines and elsewhere in Southeast Asia.

She ran the business for 27 years and sold Sangin in 2003. “I never got rich,” she says. “But we didn’t go broke and I employed a lot of people.”

Time to return to her first career, she thought. So Desmond again picked up her charcoal, oils and watercolors and worked at becoming an established artist.

But Desmond took a screenwriting course at the University of Arizona in 2004 and fell in love with writing screenplays, which led her to career No. 4.

She’s since written a dozen-plus scripts; some have been optioned and she has been hired to write a few others. One of her scripts is Lucky U Ranch, about a bullied boy living in a trailer park in the ‘50s who is helped out by an angel appearing in a Cadillac that’s pulling a shiny silver trailer. A local director liked it and offered to turn the script into a movie if Desmond could find a producer.

She thought about the offer and finally landed on a producer—herself. Could this be career No. 5?

“I could buy a home or I could make a movie,” says Desmond, now 72. “I’ve bought several homes. Why not make a movie?”? She put up the money, is hoping for a winter release and is now working on another screenplay, Singapore Fling, about revisiting the island nation late in life to meet up with an old flame.

While Lyman and Desmond have led very different lives, they’ve both taken a savvy approach in approaching their encore careers.

For example, Lyman took advantage of her retirement from New Pathways for Youth to think through her options. When she kept coming back to becoming a teacher, she reached out to a few that she knew to glean insights about the job.

At the moment, Lyman is thinking about applying to Teach for America. The program is best known for hiring young college graduates and placing them in schools in low-income communities, but the organization has been increasingly opening its doors to midlifers.

Desmond has a talent for finding intriguing opportunities, but was careful to ensure that she could afford her latest venture: movie producer.

She didn’t let her enthusiasm for the project put her finances at risk. An unusual source of income helps: she gets royalties from her songwriting father, whose best known hit is Here Comes Santa Claus.

Turns out that for many of us, our Unretirement may not be our encore career but encore careers. Pretty cool.

Chris Farrell is senior economics contributor for American Public Media’s Marketplace and author of the new book Unretirement: How Baby Boomers Are Changing the Way We Think About Work, Community, and The Good Life. He writes about Unretirement twice a month, focusing on the personal finance and entrepreneurial start-up implications and the lessons people learn as they search for meaning and income. Tell him about your experiences so he can address your questions in future columns. Send your queries to him at cfarrell@mpr.org. His twitter address is @cfarrellecon.

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