A Nonprofit Leader Builds His Encore Career

For the first time in 35 years as an educator, I am not facing the start of a new academic year this fall — but I am anticipating a new phase in my life as a nonprofit leader.

Having just retired as the founding headmaster of Sage Hill School, in Orange County, Calif., I have given myself a year to come down from a nearly decade-long adrenaline rush and gear up for my next creation. Yet, already, as I set up shop in my son’s vacated bedroom and learn to fend for myself, I am starting to feel the itch.

The endless string of meetings, the impromptu encounters with students and faculty and parents, the athletic contests, the theatrical performances — the stuff and the routines of keeping school — are beginning to fade into memory.

My e-mail messages, once a flood, have now slowed to a trickle. Those heady months in start-up mode, the 80- and 90-hour workweeks when the school itself was a vast strategic plan covering three walls in my office, are all ancient history. So are those years when we could barely keep up with our growth.

There is, of course, the inevitable sense of loss from leaving such a creation, but along with it comes a deep and lasting sense of satisfaction. My yearlong hiatus is a pregnant pause in my career, and because I don’t know what form the next venture will take, it is a pause that is punctuated by moments of anxiety and uncertainty.

But mostly it is a moment brimming with promise of liberation and possibility. Personally and professionally, my wife, Carla, and I are officially in transition.

Now, like the adolescents under my care for all these years, I, too, am going into the world. It is time again to drape my office walls in another strategic plan, but like the students I have taught, all I know is school. I am a kid all over again. What was I thinking?

I am 60 years old and haven’t yet found my new niche.

As I wrapped up my time as principal, I reflected on what it has meant to spend my entire adult life in the good company of teenagers, and what I will miss most is my students’ infectious sense of idealism.

We built Sage Hill on this very teenage idealism — on how teenagers, more than adults, hold each other to the highest standards when given a meaningful voice in the community.

As I got ready to leave, I realized how important it is to nurture this spirit while students are in high school, for it only fades with age. And I concluded that this spirit of idealism is their greatest gift to the world, the very fuel that powers positive social change.

Old enough to see injustice all around them but still young enough not to accept it, teenagers have always been masters at rooting out any inconsistencies in my logic or my actions, quick to uncover any pretense as hypocrisy. Accepting nothing short of the ideal, they always kept me sharp and honest and humble. That explains my addiction to them.

As a teacher and school leader I prepared many generations of young people for an ever-changing world. And this generation of students — well, they are a very special breed. I never doubted that they would seize this unique and dangerous moment in human history and clean up the mess that my generation is leaving them.

But would I, myself, be ready?

“The only way you can manage change is to create it,” I told the graduating seniors at our commencement, quoting the late Peter Drucker.

Could I follow his admonition?

My first stirrings started harmlessly enough, with some vacation reading two years ago. I devoured Marc Freedman’s prophetic book, How Baby Boomers Will Revolutionize Retirement and Transform America, and I immersed myself in the demographic trends.

Three-quarters of the 77 million baby boomers will work well into their 70s, either by design or by default; a majority of them would like to “give back,” and we will have a life span far longer than any previous generation. Add this all up, and we are sitting on a stockpile of potential human capital waiting to be unleashed.

Engage baby boomers for the common good: what a brilliant way to deal with the looming Social Security crisis and realize the promise of a generation that has not exactly lived up to its self- proclaimed billing. It is what Mr. Freedman calls the “experience dividend.” I was inspired.

My interest piqued, I began steeping myself in economics, a subject I had avoided in college and graduate school. I thought about getting an M.B.A. I started connecting with others like me, fellow travelers who had founded their own organizations.

All the while, I was focused on the most effective ways to unlock this treasure trove of human capital. How can I best take advantage of my own skills to reinvest in this “experience dividend”? What would be my role?

As an educator, I naturally thought of a school. This time around, however, it would not be a school for teenagers but rather one for experienced professionals, especially those who want to become high-impact leaders in the nonprofit world. It would also be an innovative school, but it would look far different from the one I had just led.

I could seek investors rather than donors, and generate revenue in excess of our expenses, then reinvest the surplus in research and development, or spin off other ventures, or spawn other schools, or pay back our investors.

In brief, my school could take on a hybrid organizational form — part nonprofit, part for-profit — what some are calling “the fourth sector,” a social-benefit enterprise that would generate renewable assets for the community.

But one major question remained: Would the baby boomers now reaching 60 have enough fire in their bellies to actually take on this challenge? Would they actually want to give up a life of leisure for a life of more work?

From my unscientific polling of the fiftysomethings I know, the answer was an immediate, enthusiastic, and nearly universal yes. “Sign me up,” they say.

In asking the simple question “What do you want to do next?” I seemed to open up some deep wellspring of potential energy.

Nearly every person I polled revealed what the gerontologist Gene Cohen calls the “inner push,” an ineffable life force that drives one forward and that is the key to health and creativity in older adults.

This all has great potential, I thought. The demographics are compelling. The market is ready-made. The human spirit is there. And my school promises to be financially viable. This could be the encore career in public service that I had always entertained but never fully envisioned.

So, here I am, at the fuzzy front end of my next venture, having jumped off into thin air, not knowing where I will land. But after a year of talking with experts, I am already beginning to draw some conclusions and home in on my emerging role. If the promise of baby-boomer civic engagement is to be fully realized, the solution lies primarily in the organizational mechanisms we will need to create. This is, after all, where the rubber meets the road.

Ideas for new efforts abound. A group of seasoned business executives could attack poverty by setting up a series of microlending institutions, while a group of school principals could create a version of Teach for America that trains mid- to late-career engineers and retired military leaders to teach math and science to high-school students, thereby opening a new front on our campaign to regain national competitiveness.

Baby boomers, both in number and in spirit, are poised on the threshold of a new movement. But the moment is fleeting. Just as there is a narrow window of opportunity for teenagers to realize their own spirit of idealism, we boomers, given our age, are ourselves a time-sensitive asset. And this time around, we cannot go it alone. We will only be as effective as the intergenerational partnerships we can fashion.

Clint Wilkins, who retired as headmaster of Sage Hill School last spring, plans to write regular updates as he seeks to build a new way to engage the baby boomers in social enterprises. His e-mail address is clintwilkins@gmail.com.