Are You Ready for Your Encore?

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Are You Ready for Your Encore?

If you’re thinking about a late-life career shift, here’s some advice from three people who did it right.
An older woman standing at her desk. Credit: iStock/Portra
Many older workers who’ve enjoyed successful careers are opting to pursue new careers that focus on personal meaning or social impact. | iStock/Portra

Americans are working longer and retiring later (if at all), and the opportunities for older professionals, and the companies that hire them, are substantial.

As the number of older workers in the U.S. continues to increase, many of those in their 50s, 60s, and 70s are asking a question their parents rarely did: What now?

Until recently, the answer was retirement. But today, many older workers who’ve enjoyed successful careers are opting to pursue an encore career — one that, in many cases, focuses on personal meaning or social impact. As healthy life spans increase, the concept of retirement becomes less relevant, says Rob Chess, a Stanford Graduate School of Business lecturer in management who teaches Longevity: Business Implications and Opportunities. “Our old map of life was to go to college, get a job, get married, have kids, retire — then people kind of forget about you and you go play grandparent,” he says. “Now, you do all those things and then go on, if you can, to an encore career that perhaps involves giving back based on your personal values and priorities.”

That’s good news for social impact organizations, but also for business, Chess says. Older professionals bring a maturity to the workplace, can mentor younger employees, and are often less concerned with advancement, preferring to be useful to an organization that reflects their values. “Mixed-age workforces can be more creative and productive,” Chess says. “Diversity in age is important because of the different perspectives it brings, and companies are starting to realize that.”

Here, three Stanford GSB alumni share their very different paths to their own encore careers.

Ron Morita, SEP ’15

Over the course of three decades, high-tech executive and entrepreneur Ron Morita founded one startup, served as CTO at another, and spent years leading engineering for large companies. His trajectory changed in 2016, when Morita, a VP at EMC, was laid off following an acquisition by Dell Computers.

“I’m thinking, ‘What do I want to do next?’” he recalls. “Go the VC route? The startup route? The big corporate route?”

Morita, 55 at the time, had recently completed the Stanford Executive Program at Stanford GSB and had been intrigued by a seminar on longevity.

“They made an argument that rather than saying, ‘OK, I’ve reached the end of my career and am going to retire,’ you can think about a continuous, lifelong career in which you find purpose and meaning,” he says. “That seemed really compelling.”

This pivot is not just a career pivot, but a shift in mindset about how I want to live my life and what I find joy and purpose in.
Ron Morita

That insight, along with conversations about social justice he was having with his teenage daughter, began pointing to a new — but uncertain — direction. Morita became a technical adviser at a VC firm, which allowed him to stay connected, watch for opportunities, and keep his hand in technology. He joined Stanford Angels and Entrepreneurs, and Princeton Alumni Angels, staying alert for possible investments or a job. He coached and mentored startup executives and founders at the Global Social Benefit Institute, an accelerator program at Santa Clara University.

Then a GSBI colleague introduced him to the Silicon Valley Social Venture Fund (SV2), which provides grants and impact investments in social ventures. After working with the organization for five months, he was asked to lead the impact investing group.

“This hits the things I was looking for; it’s interesting, dynamic, and not your old-school philanthropy,” he says. “I love the great community of partners I get to interact with — they come from all different backgrounds. It’s been really eye-opening and broadening for me.”

Morita’s new career has brought with it a fresh outlook that’s prompted him to examine everything from his personal development and financial expectations to his core strengths and values.

“For me, this pivot is not just a career pivot, but a shift in mindset about how I want to live my life and what I find joy and purpose in,” he says. “It’s a combination of career, keeping educated, learning new things, community, and, for me, travel. It’s trying to pursue all those things in a better balance.”

Jaehyang So, MBA ’88

When Jaehyang So returned to Stanford GSB in 2018 for her 30th reunion, she learned that only one person there had worked for the same organization longer than she had. A senior adviser at the World Bank, So had been at the financial institution for 30 years; she loved her job, but was also beginning to question her future.

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“I’ve always thought that applying my MBA skills in the public sector was basically my calling in life,” she says. “The World Bank is a wonderful organization, but I felt like I’d done everything I could or wanted to do there. I had almost no idea what my next thing was going to be.”

So, then 55, considered a range of options — returning to her native Korea to teach, accepting one of several job offers, retiring (either temporarily or permanently) — but none felt right until the day a colleague reached out with an opportunity. Would she be interested in working with a new organization devoted to climate adaptation?

“It was someone I’d worked with very closely before, also a former World Bank director, and almost without thinking, I said yes,” So recalls.

Today, as a member of the leadership team at the Global Center on Adaptation, So helps bring together governments, the private sector, intergovernmental bodies, and knowledge institutions to help make cities and communities around the globe more resilient to climate change.

“The interesting thing is that all the components of adaptation — water resource management, urban development, disaster risk management, and infrastructure — are all things I had done in my career,” she says. “So the move felt pretty natural, partly because it was a topic I knew something about.”

No one is more surprised than So herself that she seized the opportunity.

“I’ve always been a fan of big,” she says. “In my second career, I’ve gone from a large, formal, 18,000-person institution and am now working for a startup, which I’ve never been interested in before, so maybe I’ve matured enough in my own life that I can have the luxury of being in a startup. It’s a brand-new organization and I have a major hand in building it out, which is super exciting.”

So faces a range of new challenges. Her parents will have to wait a bit longer to spend time with her; she’s acclimating to working from home; and until she decides where to relocate, she commutes from her home in Washington, D.C., to the organization’s headquarters in Rotterdam, Netherlands. Yet she feels confident in the transition, and credits both her Stanford experience and years of leadership training at the World Bank with helping her recognize a worthy next act.

“I think I’ve started to understand what motivates me, how I contribute to the world and what really gets me going,” So says. “It’s to be useful to an organization, to be able to make an impact internationally. But the thing that made me accept this job almost immediately was the opportunity to work with people who share my passion and enthusiasm. I didn’t go looking for these people or this group, but I love it.”

So still dreams occasionally about early retirement, but she’s thrilled by the new challenge and eager to share her experience.

“This startup, like most, has a lot of young people,” she says. “They need some gray hair.”

David Heckendorn, MBA ’82

David Heckendorn veered from the traditional business trajectory twice in his life to follow his faith — once in his 20s, and now again in his 60s. Today, he says he’s come full circle.

After receiving his MBA in 1982, Heckendorn spent a year at a startup and two years in marketing at Hewlett-Packard before taking a position as the business manager for an organization smuggling Bibles behind the Iron Curtain.

“I had some exciting times traveling with a truckload or trailer-load of Bibles and Christian literature for the church there,” he says.

Heckendorn left that organization after three years, rejoining Hewlett-Packard — and staying on with its successors for close to four decades. He was a senior product manager at Philips Healthcare — and busy coaching soccer and mentoring youth at his church — when he attended his 35th reunion in 2017 at Stanford GSB. In preparation for a workshop on “Navigating Your Next Frontier,” he’d contacted friends and colleagues asking for their take on his strengths and abilities.

“What came back from several people was a message that I enjoyed investing in people coming along behind me,” he recalls. “Later on, when we were asked to imagine our dream job, what stuck in my mind was a job that would involve investing in those people still coming along.”

Heckendorn let the concept percolate for six months, until the day a friend and pastor told him that InterVarsity Christian Fellowship was searching for someone with his background to minister to international graduate students at Harvard University.

“I barely knew about InterVarsity,” he says, “But I filled out a summary of my background, spent a couple of hours in a Zoom interview, and filled out a 25-page application.”

Today, Heckendorn ministers to a wide range of international students and scholars studying, teaching, and working at Harvard, and is adapting to an environment where success is defined differently than in the corporate world.

“In business, decisions are made objectively based on the margin or the return something is going to generate; everyone can see how a business or people performed period to period. Here, it’s more qualitative or subjective in terms of whether we’re achieving what we want,” he says. “It’s less about revenue and profit metrics and all about building relationships and influencing lives.”

At 63, he’s also acclimating to working with a younger staff and students, and adjusting to his new salary reality (“‘sobering’ is a word I use a lot,” he says). He has no second thoughts.

“What helps is that almost 35 years ago I made a similar choice, so the idea of being a missionary didn’t seem totally foreign to me, because I’ve done it once before,” Heckendorn says. “The other thing that’s satisfying is establishing something that’s going to last, and that’s doing good in the world.

“I got to a place where I could hand off the work I was doing, and now it feels like I’m where I’m meant to be, and that’s immensely satisfying,” he says. “I haven’t had a single regret.”

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