After Chip Conley sold Joie de Vivre, the boutique hotel company he created and ran for about 24 years, his life took an unexpected turn. At 52, he was sought out by Brian Chesky, the then-31-year-old chief executive of Airbnb, for advice on how to turn the fledgling home-sharing startup into a major player in the hospitality field.
For the next four years, Conley worked at Airbnb, toggling between being a mentor and an intern in a sometimes baffling new role — a “modern elder,” as he put it. As a veteran hospitality executive, he was used to being the “sage on the stage.” But as a newbie in the tech sector, he was often the oldest person in the room, learning from colleagues who were young enough to be his children.
In “Wisdom at Work,” Conley writes that everyone working past middle age today needs to become a modern elder, simultaneously sharing wisdom while embracing fresh ideas and ways of thinking.
I think Conley’s on to something. It used to be, 50 was a time to begin thinking about retirement. But today, many people in their 50s — myself included — plan to work two or even three more decades. To become modern elders, we have to find new ways to stay relevant and keep our minds open, skills fresh and humility intact.
While I’m determined to become a modern elder, I know it won’t be easy. After all, most of us won’t be getting a phone call from a tech chief executive seeking our counsel. So I started looking for approachable role models I could learn from, and I found plenty.
Some did their homework and went back to school for jobs where there are known shortages — like nursing or teaching in STEM fields. Some found their way through volunteering or attending specialized fellowships or boot camps. Others teamed up with younger partners to lead new ventures. Most, it seems, did a combination of all these things.
Sharon Lewis, an independent consultant on consumer habits, was doing scouting work for the cultural forecasting firm sparks &honey when she heard about the company’s new cultural apprentice program. The apprenticeship was designed to bring together millennials and people with 30 years of professional experience to work on, among other things, a report on the future of work. Lewis decided to sign up for the 16-week program, which offered only a modest stipend, as a 60th birthday present to herself.
“The idea of working around so many younger people was exciting and invigorating,” she said. “I feel wiser, more well-rounded and updated, and I’m almost in withdrawal now,” she said. She especially appreciated the mutual mentoring. “We’re just not competing with one another because we’re at different life stages.”
Kevin Walker, 55, made several big changes after being laid off from a 24-year career in utilities in New York. He moved to Denver and started TurtleWise, a technology platform matching people seeking answers to life and career questions with mentors willing to provide advice. Walker met Kevin Freund, 31, at a conference hosted by Mentor Colorado. The two are passionate about the role of mentors and brainstormed ways to build Walker’s company.
“Being around Kevin is analogous to the kind of mentoring we’re doing with the platform,” Freund said. “I get little bits of wisdom dripped on me.” Within six months of their first meeting, Walker asked Freund to join the company as chief operating officer.
Shortly after that, Walker had to return to a full-time job to bolster his finances so he turned over the daily management of the company to Freund. Walker says he is still committed to the ideals that led him to start the company and remains only a phone call or video chat away should his younger friend need his counsel.
But with two young children at home, Walker has turned the company into a “side hustle,” something he said he learned from millennials. The two stay in close touch now that Walker lives in Los Angeles and Freund is still in Denver.
Kimberly Strong, 52, kick-started a career pivot by giving back. After retiring as head of diversity and inclusion at Target in 2016, she wanted to become an angel investor, supporting women-led initiatives and serving as a mentor to younger women, especially women of color. She discovered Pipeline Angels, which offers boot camps for people interested in supporting ventures led by women and nonbinary femmes, and she joined one of their cohorts this summer.
Strong says the program has provided speaking opportunities, judging roles at pitch summits, and the chance to hone her investing skills.
“My end game is to eventually be on a Fortune 1000 corporate board, and Pipeline gave me the opportunity to serve on startup boards and gain experience,” she said. And she has been able to mentor young female founders. “Basically, I’m the auntie to the startups,” she said, and the beneficiary of “reverse mentoring.”
Despite these promising stories, I hear a lot from people over 50, even over 45, who are doing all the right things but still not finding successful midlife transitions. Ageism is rampant — and internalized, with midlifers questioning our own ability to succeed in a world where youth is prized. And while there are many new offerings to help people make late-career transitions, moving into an encore career still requires an immense amount of creativity and persistence.
I have learned two things from my interviews about easing these transitions. First, and most obviously, it helps to have a financial safety net. Volunteering or refreshing skills while still employed, collecting severance or a pension, or having a partner who provides an income or health insurance can make a big difference. It is far more daunting without a cushion.
Second, the attitudes of younger colleagues are just as important as our own when we think about finding new roles in a rapidly transforming workplace.