How to Move Beyond the DIY Transition to Encore Careers

After 25 years of climbing her first ladder at Hewlett-Packard (HPQ), Gina Cassinelli knew it was time for a change. "All of a sudden, you wake up and you say … I can’t believe I’ve been here 20 or 25 years," she recalls. "I loved what I did, but I don’t want to do it for 20 more."

Cassinelli took early retirement, then tried to open a new career door with few guides and little help. "You get to a point in your life where you have to feel like what you’re doing matters," Cassinelli says. "But how to do it? That’s hard."

The road used to be much easier. For 50 years, the average fiftysomething American was headed inexorably toward a clear-cut career and life transition: the transition to a leisure-based retirement.

The path was well-marked, with familiar rites like the retirement party and the gold watch. Employers offered enticements for early retirement, starting with pensions and health care. Policies like Social Security and Medicare were true safety nets.

Then the mad men of marketing went to work. On TV and in magazines, insurance firms trumpeted a shimmering vision of the good life. Whole communities with names like Leisure World were set up to cater to a full-throttled golden years’ lifestyle, filled with golf and shuffleboard.

Too Often a Do-It-Yourself Project
Today an unprecedented number of Americans are coursing through their 50s, bound for a dramatically different destination. They’re headed not to the golf course but to a new stage of life that, for most, includes work. Like Cassinelli, a great many want jobs that supply money and meaning, especially if they’re going to have to do them for another decade or two.

But the paths to find this kind of encore career range from dimly lit to nonexistent, and the search is all too often a do-it-yourself project made all the worse by tough financial times.

There’s no getting around reflection and initiative. And there are an increasing number of consultants—life coaches, financial planners, and headhunters—who are willing to help for a fee. But when millions of people are confronting the same transition, their struggles are no longer personal. They constitute a social imperative.

Think back. When millions of soldiers were crossing over from World War II to civilian life, we invented the GI Bill to help them move into a new chapter. Now, with 10,000 boomers crossing over the half-century mark every day, it’s time to tackle their transition not just one at a time, but as a society. At stake is the continued productivity of the largest, healthiest, longest-living, and best-educated generation in American history.

Making the most of this opportunity will require four changes.

We need a collective attitude adjustment. We must recognize that this isn’t merely a vocational shift—it’s not just a transaction (to a new job) but a transition (to a new stage of life stretching between the middle years and true old age). It’s not just about what you’ll do, but who you’ll be, for a period that could last a quarter-century or longer.

We’ll need to invent and adapt a whole range of social institutions, beginning with the two routes we offer young people preparing to start careers—internships and education.

Gina Cassinelli was lucky enough to take advantage of an Encore Fellowship, essentially an internship for grown-ups, being piloted in Silicon Valley. (For more information about Encore Fellowships and other emerging opportunities, see

She spent the past year working for Citizen Schools, an entrepreneurial nonprofit that provides apprenticeships for young people led by volunteer "citizen teachers." The experience not only provided a foot in the door but left her brimming with ideas for how to transform education and eager to plunge into a new nonprofit career.

In Portland, Mark Noonan faced a different kind of transition, one born in tragedy. At 52, after his wife died in an accident, Noonan decided to leave an unsatisfying management job and look for something more fulfilling.

He headed back to school at Portland Community College in Oregon. Through a one-year program, he earned an associate’s degree in gerontology and launched a second career with Elders in Action, helping Portland tackle both the challenges and opportunities presented by an aging society.

Cassinelli’s and Noonan’s paths approximate a kind of "gap year" for adults—the chance to catch their breath, test the waters, and fashion a new chapter of life and work.

We’ll have to invent new ways to finance this transition. Even with more ways to try on and train for new roles, underwriting this shift is a formidable barrier. One solution: Instead of telling boomers to save for an unsustainable 30-year retirement, the financial-services industry would do well to develop and market new products aimed at the midlife transition.

How about IPAs—Individual Purpose Accounts—to go along with the retirement-focused IRAs? IPAs could be set up to provide tax breaks for savings focused on education, training, or fellowships after the age of 50. Vehicles of this sort could help individuals invest in their own future by covering the costs of midlife transitions.

Finally, innovations in public policy will be essential, not only in creating tax incentives for savings mechanisms like IPAs, but for fashioning a midlife transition superhighway to replace the rickety routes that currently exist.

Here we won’t have to start from scratch. The new Serve America Act establishes the prospect of federally funded encore fellowships in all 50 states. That’s a start. But given the size of the boomer generation, we require nothing less than a national human resources strategy and policy agenda for the second half of life, one that includes health coverage for the midlife shift.

If we replace the DIY transition with a sturdy passage that helps boomers find new meaning, continued income, and the chance to use all they have invested in their human capital, we can make a virtue out of longer working lives over the next 50 years just as we made a virtue out of shorter ones in the past 50.

In the process, we can turn the demographic wave already washing over us into a new tide of individual and social renewal.


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