I turned 50 and decided to take a break. After 25 years of working, it seemed like a good idea. Honestly, I was feeling depleted. I still cared about my career and realized, amid a worsening economic climate, that I was lucky to have one. But that appreciation felt more lodged in my head than my heart.

One day, United Airlines sent me a card, along with some new luggage tags, offering congratulations on having flown 2 million miles. Quick arithmetic translated all those zeroes into the equivalent of flying from one side of the country to the other every single day – Sundays, holidays, birthdays, sick or well – for more than two years.

Maybe the card from United should have offered condolences. It all added up to an abiding fatigue. And a question: Did I want to fly 2 million more miles over the next 25 years of my life?

Was I having a low-grade midlife crisis? I had no red sports car, reckless affair or other obvious sign something was amiss. Instead, there seemed to be internal bleeding – a sense that the energy and optimism were ebbing out of me. My hope was that a three-month sabbatical would cure all that, bringing needed rest and clarity.

After 10 years of running the organization I’d founded, I thought I might be able to arrange some combination of vacation and leave. My board, perhaps a little worried about me as well, was happy to oblige.

I resolved to get away, far away. Soon I was looking at hotel reservations in Australia, contemplating time in Southeast Asia, marking off several months in the calendar. I purchased plane tickets, for myself, my wife and our kids. Then the reality set in – the cost, the time away, living out of a suitcase for weeks on end. It all sounded eerily like one more business trip.

A down payment on the road to 3 million miles? Do they give you the actual luggage when you hit that milestone?

I canceled the Australian hotels. I called the airlines to say forget it. They informed me that not taking my trip would cost $1,000 in penalties. I contemplated returning my luggage tags in protest. Soon, however, to my surprise, liberation was replacing disappointment.

The lightness reminded me of research findings suggesting one of life’s great joys was not taking a big vacation after the pleasures of anticipating one. Planning a trip, basking in the possibilities, experiencing the entire journey in one’s mind – those were the fun parts.

Lugging bags, dealing with surly employees, battling airport security, spending more money than budgeted and eventually returning home exhausted and confronting a pile of mail and accumulated obligations – in other words, taking the actual vacation – were much less enjoyable. The perfect combination, at least according to this research, turns out to be planning fantastic adventures and then bailing out at the last minute.

Yet, research notwithstanding, I still wanted to get away and clear my head. My three-month sabbatical Down Under was downsized into a two-week car trip in a dented Prius up the Pacific Coast from San Francisco, where I live, to Oregon. After consulting the map and locating the midpoint for our journey, I got on the phone with the Homewood Suites in Medford, Ore., to make reservations for our first stop en route to the Pacific Northwest.

In the spirit of frugality – after all, I was already out 1,000 bucks before our trip had even started – I asked about discounts. The AAA rate knocked off 20 percent. Great. Then it dawned on me. I was 50 years old, after all. I had shelled out for the AARP card when prompted. What about the “senior” discount?

It was the lowest rate. Book it, I told the 20-something clerk, and hung up the phone triumphant. I was already beginning to envision the new trip, when I remembered my wife’s injunction about requesting cribs for our two boys, ages 1 and 3, part of the reason we weren’t checking in at the Sydney Marriott.

The same clerk answered again. Yes, I was the guy he’d just talked to, with the senior discount. I’d like to request two cribs in the room, I said. Yes, that’s right, an AARP discount and two cribs. Was that the fraud alert beeping in the background? I know I heard something. I fully expected to be carded by the clerk upon check-in, perhaps flanked by local law enforcement.


The Homewood Suites of Medford provided a memorable moment: Our 1-year-old took his first steps on the hotel room’s recently laid carpet, as we followed him around with the video camera. The stay was significant in another way as well. In that moment on the phone with the reservation clerk, a series of truths about my quiet crisis became evident.

The odd combination of discounts and requests – signs of what once indicated distinct parts of the life cycle separated by decades – made one thing abundantly clear and personal: The old map of life, which guided us for generations, was rapidly becoming an anachronism.

Until not long ago, the 50s and 60s meant retirement, grandparenthood, senior discounts and early-bird specials. Possibly contemplating a retirement community free from school taxes and frequent visits by anyone under 18. Maybe even an end to working. My own father took the early-out package at 57, with 80 percent of his top salary guaranteed for life.

Now 23 years into retirement, he has a decent shot at being retired for as long as he worked and earning more money for not working than he earned for getting up and going to the job each day. That won’t be possible – or sustainable – for me.

By the time my dad was 50, I had already graduated from college, and my sister was nearly done. By the time my third son – yes, we had another one since the trip – is through college, I will likely be closing in on my 80th birthday, my father’s age today.

Like so many others, I delayed parenthood until my second marriage. It’s a joy and I have no regrets, but I wonder how I’ll wrestle with my kids without wrenching my back and how I’ll pay college tuition in my 70s. I wonder what it will mean for my working life.

There’s also a question of identity. What’s the category for people like me? There are a growing number of us who can be classified as neither-nors. Neither young nor old. Neither retirees nor of traditional parenting age. Tired, perhaps, but neither ready to be retired nor able to afford it. The truth is, I will probably be working for another 25 years, the second half of my adult life.

What’s more, this isn’t just about me or my boomer colleagues. New research suggests that children the age of my kids, growing up in the developed world, can reasonably expect to see their 100th birthdays. The odds of doing so, by some estimates, exceed 50 percent.

In other words, those of us hitting 50 today are simply the first generation to inhabit an emerging life course, one that is in flux but will be a permanent change, not a passing aberration.

My Medford moment brought with it another juxtaposition. For me, the personal and professional were merging in a way I hadn’t seen coming, even though it should have been excruciatingly easy to spot.

In my 30s I started Civic Ventures, an organization focused on helping America make the most of the coming demographic revolution by enabling people to move into new jobs for the greater good after age 50. We call these “encore careers,” a kind of practical idealism at the intersection of continued income, deeper meaning and social impact.

For some time, I’d been promoting all the benefits to be reaped by more individuals making the leap from the desire to find a new calling in the second half of adulthood to a life built around these aspirations.

Burned out? Do something else, especially since you’ll probably have to work for decades more. May as well find something you can look forward to doing when you get up all the many mornings to come. Not sure what you want to do next? Consider taking time off to experiment. The expense? It’s worth it if you plan to work in your encore career for another 10, 15, 20 years. Facing economic downturn? Education, health and public-sector work are the most recession-resistant sectors, full of jobs that might appeal to people looking for work that matters.

I had a lot of advice for others, all those folks presumably older than I was. Now the person looking back in the mirror not only qualifies for the AARP discount but also looks like he qualifies. (I did not get carded when I showed up at the check-in counter at the Homewood Suites.)

What about taking my own advice? Not so easy while supporting a family of five, weighed down by a mortgage acquired at the height of the real estate boom. And then there’s health insurance. For a whole set of practical reasons, I felt stuck. What wisdom did I have for myself?

Sure, I was at a natural transition point. Twenty-five years laboring in, essentially, the same vineyard. I had established some standing as an authority on finding meaning in the second half of life, particularly through career change. But here I was facing all the barriers to making a shift – psychological inertia, financial risk, the reality that my search for happiness was inextricably intertwined with the dreams and happiness of four other people (also known as my family ... three of them still shy of kindergarten).

I started resenting the easy advice dispensed by lifestyle magazines – and experts like me.
Then an additional element entered the mix. Several years ago a colleague noticed my hands shaking and suggested that I go see someone about it. I was convinced the tremors were the result of too much coffee, but after several others offered similar counsel, I made an appointment with a neurologist.

She put me through a battery of tests, including an MRI of the brain. The test revealed nothing worrisome. The doctor diagnosed “benign essential tremors,” with an emphasis on the benign over the essential – and a recommendation to cut back on the caffeine. I was instructed to check back in a couple of years.

It took me three, but this time when the neurologist ran through her routine, which I assumed would be routine, the concern on her face was evident. She advised me to see someone who specialized in Parkinson’s disease. Starting to panic, I asked her to level with me. I wouldn’t hold her to it, but what was she really thinking? What were the chances I had Parkinson’s? She told me they were 50-50.

A week from the due date for our third child, I found myself rewriting the future in my head. A sense of dread began forming, aided by Internet searches revealing grim prospects, plus a very long wait to see a doctor. After three months, I was finally able to see Parkinson’s specialists at the University of California at San Francisco, who examined me thoroughly, for hours.

Their conclusion was that I didn’t have the disease. An enormous weight lifted. Still, there was a residue, a new perspective, a sense of the finiteness of life and the precariousness of health. And, at the same time, the recognition that I’d likely be healthy for decades to come. Time had been compressed and had then expanded again. The question of how I was going to spend the next 25 years took on a new cast.


Of course, I knew that I was hardly alone in my unease. In logging those millions of miles, I’d heard the same refrain dozens of times from people I’d once considered “aging.” But now, I was hearing it from my friends and colleagues, from my own mouth. We weren’t old, but we were all navigating similar challenges, similar changes.

One friend first survived a bout with melanoma, and then a few years later his wife asked for a divorce just as the second of their two children headed off to college. He was left with a new sense of insecurity after the settlement. Marriage over, kids grown, house sold, savings depleted.

“My life imploded,” he told me.

What’s more, his commitment to his job as a lawyer was also wavering. He had been just about the only person I knew who loved being a lawyer. After surviving turns representing Hollywood clients, a final barking-dog case pitting one misanthropic neighbor against another ended his romance with private practice.

Within months he moved from Los Angeles to Washington, D.C., to take a job as assistant general counsel at a federal agency, renting a modest apartment, taking a substantial pay cut and starting over in a line of work that he hoped would provide not just a change of scenery but a new sense of purpose.

A few months earlier, I’d picked up the Sunday New York Times to read an article in the Business section about an acquaintance from college, whom I remembered as particularly driven and brilliant. She won a prestigious international fellowship in our second year.

Soon after graduation, she landed a lucrative job on Wall Street, where she by all accounts prospered for decades. The Times article was her personal reflection on being laid off, stripped not only of her livelihood but also a major part of her identity. She was now in the throes of trying to make a transition, at last liberated by being tossed out of work that had lost its appeal.

Yet she was still interviewing for banking jobs while trying to convince nonprofit organizations that her skills would translate to a new role.

“I found myself struggling with one path that looked backward to what I knew and another that would go forward in an unfamiliar direction,” she wrote.

I soon realized that one after another of my 50-something friends were themselves wrestling with a shift, feeling a growing pull not only toward a new phase of work but toward a different kind of life and a new set of priorities as well. Many likewise felt stymied by a variety of barriers. For every one who’d been visited by a health crisis, a divorce, a layoff, there seemed to be several more who were thinking that a new direction was needed.

Yet we were all unsure of the path from what’s past to what’s next. We lacked a language even to talk about this change, which felt for many simultaneously self-indulgent and imperative.

They were asking the same questions gnawing at me: How can I find rest and renewal? How do I make a change? How do I get started? How do I finance this transition? What if things don’t work out? Will I be any good at something new? Can I take a big risk in my life when my situation is so intertwined with the well-being of others? How can I live a life that has greater significance, that leaves the world a better place? If I don’t make that change now, will it be too late?

I’d heard it all before, yet it all seemed new to me, so puzzling when at earlier points in my life, it had all seemed so simple.

This book grew out of a desire to make sense of what was happening in my own life, in the lives surrounding me, in the circumstances of many others at a similar juncture, especially in the context of economic pressures that were forcing more and more people to rethink assumptions about the future, about what’s next and what matters most.

My instinct was toward stories. What could the role models just ahead of us on this journey impart about their experience, both the more uplifting moments and the times of despair? What lessons had they wrested from their encounters? Perhaps, most significantly, why is this transition so hard if so many people are feeling the same thing, at the same time, in sizable numbers?

I put on more miles, talking to hundreds of individuals in dozens of places all around the country, across the socioeconomic spectrum, all moving beyond midlife and reflecting on their odyssey. This book set out to impart their tales. I even thought of it as an homage to Studs Terkel’s collection of first-person narratives, Working.

My goal was to let them speak. But as the narratives piled up, the many stories – in all their idiosyncrasies – insisted on telling a larger tale. The individual odysseys were part of a bigger migration – not only from one job to another but also from midlife to an emerging period between the middle years and anything resembling either retirement or old age.

It’s the story of a generation’s movement into unfamiliar terrain, an often awkward adventure that carries with it the potential to be one of the greatest transformations of the 21st century.


What is it that I learned from these numerous conversations over many months? We need a new map of life. We’ve been making do with one that was fashioned for an expected longevity of threescore and 10. We shouldn’t knock that legacy. At one time, that constituted progress.

But we can’t stuff a 21st century life span into a life course designed for the 20th century – or stretch the old model so that it accommodates a task well beyond its intended capacity. The story starts with the numbers, but it is really about the nature of lives.

In 1900, the life span in the United States was 47. Today, it is approaching 80 (although great disparities persist across class and race). Overall, that’s an increase in 100 years approximating all the gains since the beginning of time. And the length of life may well be headed toward the century mark. Some think the upward rise will be even more precipitous.

Yet while we’ve been remarkably adept at extending lives, our imagination and innovation in remaking the shape of those longer lives have been struggling to keep pace. In the words of anthropologist Mary Catherine Bateson, we’re “living longer and thinking shorter.”

The situation is beginning to fray, especially in the period of life that is emerging between traditional midlife and what used to be occupied by retirement and old age. It’s fair to say that this condition constitutes a long-standing problem, one that existed even before longer lives and changing demographics made it a much bigger one.

The territory between middle age and old age has long been shaky ground, “unstable social space,” in the words of cultural historian Thomas Cole.

Remarkably, the first recipient of Social Security, a bookkeeper named Ida May Fuller, started to collect her checks in 1940. She proceeded to live another 35 years, long enough to witness the ascent and disbanding of The Beatles and the landing of the man on the moon. (For her total $24.75 contribution, she received $22,888.92 in benefits, perhaps qualifying her as the nation’s first de facto lottery winner, as well as its inaugural Social Security recipient.)

Indeed, the time between the end of work and the end of life was already starting to raise uncomfortable questions in the decades following the establishment of Social Security and mass retirement – most fundamentally, what do you do with yourself during this period? Medical experts were advising a quiet existence, rocking peacefully in Whistler’s Mother-like fashion.

What role would this population in their 60s and beyond play in American life, especially as their numbers grew? How was it that increased economic security at the personal level was producing a purpose gap for many of those individuals, their growing years spent dangling, in what one scholar of the time called a “roleless role,” on the margins of society?

It’s no wonder labor leader Walter Reuther described this period in 1949 as “too old to work, too young to die.” It was a very awkward time, an “inbetween” period. It took ingenuity to redesign lives to keep up with changes in longevity and society in mid-20th century America, but we rose to the occasion.

We plugged the purpose gap with something called the “golden years,” a stunning innovation that almost overnight turned an arid economic institution, retirement, from an anteroom to the great beyond into a core component of the American dream.

We did such a good job of making virtue out of seeming necessity that soon retirement at 65 wasn’t enough. Even as lives were already lengthening, we wanted retirement earlier and earlier. We couldn’t wait to stop working and start playing in a period that was fashioned by financial marketers and housing entrepreneurs as a kind of second childhood.

Golf became the new symbol of late-life success. A new deal was struck around shorter working lives that turned the push out of the labor market into a powerful pull. The golden years shored up the postmidlife purpose gap for 50 years and then some, filling the unstable space with something aspirational and attainable.

This was a dream for average Americans, not just the elite. But as lives lengthened and careers shortened, this fix grew shakier and shakier, especially as the vast wave of boomers began approaching.

Kurt Andersen, in his book Reset, provides a useful context of broader changes in American life over the past quarter century. Andersen suggests that we are in the aftermath of what might be characterized as the bloating of America, a mass overextension that occurred between 1980 and the late 2000s.

Mortgages mushroomed, debt ballooned and our houses expanded, along with our waistlines. We could easily add the golden years to the package, as they went from an assumedly brief proposition at the end of life, a well-earned respite, to a 30-year McMansion of a stage, inflated until it literally constituted the second half of adulthood.

But it became both unattainable, for most individuals, and unsustainable, for a society soon to have more people over 60 than under 15. (And we’re relatively young in the community of nations – Japan, South Korea, Germany, Italy and Spain will see over-60 populations approaching or exceeding 40 percent by the middle of the 21st century.)

Unsustainable and unattainable, the old dream dies hard, as a recent ad from Allstate illustrates. Advising readers to “consider this: Hallmark sold 85,000 ‘Happy 100th Birthday!’ cards last year,” the ad asks, “How long of a retirement should you plan for?” It then answers its own question. “The average 65-year-old woman can expect to live until 87, and the average 65-year-old man to 84. So it’s easy to understand why workers today should plan for a 30-year retirement.” It then concludes: “Let’s save retirement by saving for retirement.”

Thirty-year retirements, in the era of the Great Recession? Let’s face it, that is simply not going to work, nor is it desirable. Does it make much sense for society to throw away the most experienced segment of the population when it is a long way from obsolescence?

This book argues that the way to make the most of coming 100-year life spans is not to stretch and strain the contours of a life course set up for a bygone era. That’s like plastic surgery to make a 70-year-old face look like a 40-year-old one – the result is unnatural and the intention wrongheaded.

Likewise, the answer to the unsustainability of 30-year retirements is not substituting endless middle age for endless old age, the alternative some are proposing to the much longer life. Middle age, like all good things, eventually must reach an end. No use denying it.

In Nora Ephron’s words, “There’s a moment when people know – whatever their skills are at denial – that they have passed from what they can delude themselves into thinking is middle age to something that you could call the third act.” Ephron, now 69, declares, “I’m definitely in the third act.”

As the “third act” notion suggests, the reality is that the end of middle age is no longer, for most people, attached to the beginning of either retirement or old age. (It’s like the transcontinental railroad, started at both ends, designed to eventually meet. However, the two ends of this project – life – don’t meet anymore.)

Individuals left in that lurch, in this unstable space that has no name, no clear beginning or end, no rites or routes of passage, face a contradictory culture, incoherent policies, institutions tailored for a different population and a society that seems in denial that this period even exists.

Daphne Merkin describes the unease of this predicament: “Sheer dread lies in wait: the fear that we’re fast gaining upon that demarcation line where you stop being young and you start being something else entirely, someone belonging to a different order of nomenclature.” Merkin adds, “Middle age becomes a life raft that we can’t afford to fall off.”

Her observation is timely. We’re in the early stages of a great migration, but it is not the old retiree migration that literally saw millions travel from north to south, from cold, drizzling places like Michigan and Pennsylvania and Oregon to warm, recreational states like Arizona and Florida.

The new migration is across time and the life course, as tens of millions (8,000 a day, one every 10 seconds, are turning 60) reach the spot where middle age used to end and old age once began, the new territory where a resurgent purpose gap, and gulf in identity, stands. Opportunity is there as well. The surge of people into this new stage of life is one of the most important social phenomena of the new century.

Never before have so many people had so much experience and the time and the capacity to do something significant with it. That’s the gift of longevity, the great potential payoff on all the progress we’ve made in extending lives. Realizing these possibilities will require the courage to break from old and familiar patterns that once were our friends but just don’t work any longer.

This book is a plea for mustering the imagination and the will to forge a new map of life fitted to a new length of life and to the particular circumstances and opportunities of the 21st century. It argues for the creation of a new stage between the end of the middle years and the beginning of retirement and old age, an encore stage of life characterized by purpose, contribution and commitment, particularly to the well-being of future generations.

The ensuing chapters seek to tell the stories of a new group of pioneers who aren’t waiting for permission from anyone to begin fashioning this new phase. They are harbingers from a land that has yet to be realized, signals from a future we would be happy to inhabit. As the science fiction writer William Gibson states, that future is already here, “it’s just unevenly distributed.”

Throughout, the book is animated by a simple premise: that the challenge of transitioning to and making the most of this new stage – while deeply personal – is much more than an individual problem. As such, it’s just too hard, the exclusive province of the heroic, lucky or loaded. No glib talk from advice mongers or exhortations from the optimistic will do the trick.

What we’re facing is not a solo matter; it’s a social imperative, an urgent one that must be solved as the great midlife migration gathers scale and momentum. Inventing a new stage of life is a conscious decision that won’t happen by itself, easily or automatically, even as the soil becomes more fertile and conditions increasingly ripe.

This book issues a call to action for creating the new stage and offers a set of prescriptions for realizing this opportunity. If we act, the new stage could well become a destination, even the new crown of life, and the individuals flooding into it the human-capital solution to much that ails us in this society. As we confront significant challenges in areas like education, the environment and health care, this windfall of talent could help carry us toward a new generation of solutions.

We are in the position to make a monument from what used to be the leftover years, a second chance for people of all stripes to ascend the ladder of contribution and fulfillment, and an opportunity for society to “grow up” along with its population. This amounts to nothing less than changing the pattern of lives, and with it the nature and possibilities of every stage along the way.

It’s time, once again, to rise to the occasion. It’s time for a shift – a shift in thinking and in culture, in social institutions and public policies, a shift from what worked in the past to what can carry us into the future.

Return to the Big Shift page.