I stared at my ceiling, sleepless in San Francisco, knowing that I would have to fight my battles all over again tomorrow, even more exhausted.

“What’s wrong with me?!” That was the question that haunted me in my mid-40s. I hated my life, partly because every piece of it was falling apart. Yet I clung to those pieces as if they were a tattered life preserver.

Worse still, I felt completely alone. An idiot without a village.

Midlife is when we begin to worry that life isn’t turning out the way we expected. We may feel a sense of lost opportunity and frustrated longing. Or feel that we’ve sold out and are living someone else’s life. It’s when we can look in the mirror and see a stranger.

But once we settle into the transformative opportunity of midlife, something profound and beautiful awakens inside us. For me, this life stage has been the tale of two midlifes: one very bad followed by one very good. Life does get better with age.

I deeply believe that society doesn’t understand the upside of this era. We’ve come to think—and accept—the notion that midlife is one endless sand trap on the golf course of life. Pop culture’s most common stereotype about midlife is that our only option is to imitate Kevin Spacey in American Beauty: Buy a red 1970 Pontiac Firebird and lust after your teenage daughter’s seductive best friend. I know, not a great look!

In short, midlife has a colossal branding problem.

The English word midlife dates back to 1818, but it didn’t enter the pop-culture lexicon till the mid-1960s. And it was less of a state of life than a trait. Yes, there were twentieth-century midlife markers—menopause, empty nest, parents passing away, twenty-fifth anniversary at work—but to be experiencing midlife was also thought to mean feeling stuck, bored, and dissatisfied. Hence, it was seen almost as an affliction… and a lousy excuse for crazy, selfish behavior.

Is any other era of life yoked so consistently with the term crisis, defined as “a time of intense difficulty, trouble, or danger”? Sounds rotten, right? Interestingly, however, the word crisis is derived from the Greek word krinein, which means “to make a decision based upon one’s judgment.” In other words, we have agency in our lives. This sheds a different light on the midlife brand, doesn’t it? Maybe midlife is not something that happens to you, but a life stage that happens for you, one that unlocks a whole new world of choices. Wow, that just wiped my windshield clean!

Yale’s Dr. Becca Levy has shown that when we shift our perspective on aging from negative to positive, our health outcomes improve. Better balance, more openness to new experiences, better cognitive functioning, more satisfying sex life, and all kinds of other benefits.

She’s also shown that we’re granted seven and a half years of additional life when we reframe our mindset on aging. Remarkably, this is more additional longevity than if we stop smoking or start exercising at age 50. Where are the public service announcements (PSAs) on the health benefits of reframing aging?!?

This book is meant to be your midlife PSA: a wake-up call (appropriate from a former hotelier, right?) to the unexpected pleasures and joys of midlife. On average, we’re becoming wiser, less reactive, more generous, and happier as we get older. Our life has gained a rich patina.

I know this may sound blasphemous in our ageist society, but aging can be far more aspirational than most people realize. Instead of an era one has to endure, midlife can be a time to adore. In the pages ahead, you’ll learn why.

Your Midlife Chrysalis

So when do you hit midlife? I know it crept up on me like a lurker in a back alley.

Midlife is generally defined as the years 40 to 65. A growing number of social scientists believe midlife has grown longer recently, as many young knowledge workers feel obsolete earlier due to artificial intelligence and many of us are staying in the workplace longer by choice or necessity. The most conclusive study ever done on midlife development in the United States (Midlife in the United States, or MIDUS) studied people 25 to 74 years old.

In my opinion (and that of a growing number of sociologists), in a world with more and more centenarians, midlife may last from 35 to 75. Just as adolescence is a transitional stage between childhood and adulthood, maybe part of midlife’s role is to be a transitional stage between adulthood and elderhood.

I believe there are three stages of midlife. During early midlife (years 35 to 50), we tend to experience some of the challenging physical and emotional transitions—a bit like an adult puberty. We realize we are no longer young, but not yet old, and we can feel it’s time to metaphorically shed our skin. The core of midlife is our 50s, when we’ve settled into this new era and are seeing some of the upside—which you’ll read about later in this book. Later midlife, which might last from 60 to 75, is when we’re young enough to still be working and living a very vital life, but old enough to see and plan for what’s next: our senior years. At 63, I am just getting acquainted with this third stage, but I do know it’s also when our body reminds us it doesn’t want to be forgotten.

Of course, not everyone experiences these three stages on the same timeline. Midlife is less of an age than it is a feeling. And just as with any other stage of life, your mileage may vary.

Taffy Brodesser-Akner is someone whose mileage definitely varied. She is the author of the midlife book and TV series Fleishman Is in Trouble and says her midlife crisis happened earlier than most. As Taffy told NPR’s Fresh Air, at 33, with a one-year-old baby in tow, she wasn’t experiencing the wild, professional success she’d imagined for herself: the success her other classmates from film school appeared to enjoy. She says, “The start of middle age hit me like a truck.”

On the other hand, my dear old dad, Steve, says his midlife lasted through his mid-70s when he started winding down his career.

Regardless of what age defines it, for many of us, life begins at 50. Before that, life is just a dress rehearsal.

Fortunately, a more life-affirming description of midlife can be found in the dictionary. Go to the Cs, and you’ll find chrysalis, defined as “a transitional state.” When a caterpillar is fully grown, it uses a button of silk to fasten its body to a twig and then forms a chrysalis. Within this protective chrysalis, the transformational magic of metamorphosis occurs. While it’s a bit dark, gooey, and solitary, it’s a transition, not a crisis. And, of course, on the other side is a beautiful, winged butterfly.

If you yield to the chrysalis call, it means that the incessant accumulating (the caterpillar consuming) must come to an end. This means dropping mindsets, habits, identities, stories, and choices made when we were younger, which no longer reflect who we are or who we’re meant to be. As David Bowie is reported to have said before he passed away, way too young, “Aging is an extraordinary process whereby you become the person you always should have been.”

This is a rich time for introspection, a journey through stillness into freedom. We must transcend the caterpillar if our midlife calling is “to butterfly.”

A caterpillar consumes. A chrysalis transforms. A butterfly pollinates. Early midlife is when much of what we accumulated dissolves, just before we’re ready to transform and pollinate our wisdom to the world in our 50s and beyond.

The Midlife Unraveling

Midlife is the initiation into a time of massive transitions. A drizzle of disappointments. Parents passing away, kids leaving home, financial reckonings, changing jobs, changing spouses, hormonal wackiness, scary health diagnoses, addictive behaviors becoming unwieldy, and the stirring of a growing curiosity about the meaning of life. Author Brené Brown calls this era the “midlife unraveling.”

Let’s unravel this word unravel. My initial reaction to hearing the word was, “Geez, I don’t want that to happen to me!” It sounds like something is falling apart.

The more I thought about it, though, the more the word made sense. I experienced that unraveling, as well as a large dose of anxiety, in my mid-to-late 40s. I felt that I had less time to “correct” my life than I had a decade earlier.

Between 45 and 50, I felt like a failure on so many levels. My long-term relationship was ending. My company was falling apart due to the Great Recession. My adult foster son was going to prison for a crime he was wrongfully accused of committing.

It was also a time when I came face-to-face with mortality. I was losing friends and my health was failing. My life was one big unraveling.

“Slightly wounded and tightly wound” was how I described myself to a longtime friend just a couple of weeks before I had my NDE (Near Death Experience) at age 47. My self-esteem was so raveled up and tangled with the way others perceived me that I felt like the hunchback of San Francisco, and not just in my physical body.

For many, midlife can feel like a run-on sentence without any punctuation. It can be a time of deep disappointment in oneself and the world. This might be part of the reason I lost five male midlife friends—most in their 40s—to suicide, right when I was going through my own midlife challenges.

One of them, Chip Hankins, was my mirror. Not only did we share the same preppy nickname, but we were born the same year and were publicly extroverted but had an introverted, melancholy side. Our friends felt comfortable taking quiet counsel with us, and, in fact, Chip was a bit of a spiritual adviser for me.

However, though he was often helping his friends, he didn’t admit to himself that he, too, was in a dark tunnel of his own mind’s making, silently experiencing deep emotional and physical pain.

Hearing “Chip stories” at Chip’s memorial service was surreal. His friends weren’t talking about me, but I felt hyperconscious that I might be the next one to join this private club of those who checked out from life way too early.

It was then that I started telling friends about my nightmares of cancer and car crashes. I felt trapped by the momentum and monotony of my life and was looking for an escape. I was yearning for a midlife pit stop, an off-ramp from an endless freeway where I felt I was running on fumes.

Less than two months after Chip’s memorial service, I experienced a miracle disguised as a crisis, a severe allergic reaction to an antibiotic I was taking for a broken ankle and septic leg. I died multiple times onstage just after giving a speech in St. Louis.

My NDE helped me to see how silently unmoored I was from what brought me joy, which was psychologically awkward for a guy who’d started a company named Joie de Vivre (joy of life). My wise, thoughtful friend Bruce Feiler calls the wreck of my world a “lifequake.” (Excuse my French, but I called it a clusterfuck. Sorry for swearing, Mom!)

But after experiencing the dark side of early midlife, I found myself in the light around age 50. Within two years of my NDE, I’d sold my company at the bottom of the market, ended my problematic romantic partnership, gotten my foster son exonerated and freed from prison, and realized that my own suicidal ideation was based on the prison of my own constricting identities. And while it wasn’t easy, I was able to move on from a career that had defined my identity for two dozen years: being founder and CEO of my boutique hotel company.

With newfound time affluence, I hung out in my backyard hammock listening to Rickie Lee Jones and studying a series of topics that had always fascinated me: the nature of emotions, the growing popularity of festivals, the geophysics that create hot springs.

I got in the best shape of my life, partly because I was in dating mode again. But I also started wondering whether I was irrelevant in the working world. In the film The Intern, Robert De Niro says, “Musicians don’t retire. They stop when there’s no more music in them.” I knew I had some “music” to share, but I wasn’t sure with whom to share it.

It was around that time, at 52, that I got a call from the cofounder and CEO of a fledgling, fast-growing tech start-up named Airbnb. Brian Chesky asked me if I wanted to help him and his cofounders “democratize hospitality.” I initially thought home sharing was a terrible idea. Boy, was I wrong! I wasn’t the only hotelier who didn’t see this Millennial disruptor sneaking up on us.

I decided to come on board as Brian’s in-house mentor and a senior leader, and more than seven years later, Airbnb had grown into the world’s most valuable hospitality company, and I was crowned its “modern elder” because they said I was as curious as I was wise. Thank you very much, but less than a decade earlier I’d felt like a “modern failure.”

After my challenging transition into midlife in my 40s, I found my 50s to be a revelation. A time when I developed into the man I was always meant to be. It wasn’t a perfect decade, but it was a time when I joyfully shed so many of my identities that were no longer serving me. I felt like I was being birthed into a second adulthood.

It was also when my curiosity once again led me to the newest topic I wanted to explore: one of the three life stages that was born in the twentieth century. But, unlike the other two—adolescence and retirement—midlife felt unloved and unstudied. And, when it was studied, it was mostly men studying men. Midlife was a life stage constrained with a bad brand—“midlife crisis”—a term that had been around almost as many years as I had.

Brené says,

This is part of the reason I kept so much of my life dissatisfaction to myself. I didn’t want to sound whiny and ungrateful. A “midlife crisis” seems so damn self-indulgent, right? Hence, I often suffered alone, despite the fact that so many of us—not just a privileged few—experience what I did. Silence no more! What we’re going through is normal.

I often wonder about my five friends who didn’t realize that early midlife, like adolescence, is just a bridge over troubled waters. But you don’t have to die and come back to life, as I did, to realize that this bridge leads to a safe shore.

Yes, your midlife unraveling can be tricky, and it requires a healthy dose of support and love from those around you. But it also offers you the first glimpses of a life less ordinary.

Seeking Your Midlife Atrium

We’re living longer than ever before. Some people think this means we’re going to be old longer. Anthropologist and author Mary Catherine Bateson says we’re thinking about this all wrong. Our extra longevity means we’re not old longer but in midlife longer. Middle age has expanded, just like our waistline. She suggests that we’re not adding a metaphorical extension to our home in the form of a couple extra bedrooms in the backyard of life. We need to introduce what she calls a “midlife atrium” to support our longer lives.

Creating a midlife atrium means changing the blueprint for the whole home, or the rest of our life. This suggests we’re moving the walls and, in the center of our life, creating an atrium filled with fresh air and sunlight. In a world in which some estimate that half of all children born into the developed world today will live till one hundred, it’s time to re-architect our societal life blueprint by creating space for people to reflect on how to consciously curate the second half of adult life.

More than a century ago, psychologist Carl Jung asked, “Are there perhaps colleges for forty-year-olds which prepare them for their coming life and its demands as the ordinary colleges introduce our young people to a knowledge of the world?” In other words, where might we find that light-filled atrium? And are we in need of a midwife for midlife epiphanies that might emerge from this atrium?

In some ways, the sheer volume of middle-aged employees who took a break from working full-time during the COVID pandemic suggests that a collective midlife atrium is dawning. Millions of midlifers left their jobs and the cubicles that confined them and “went atrium”!

And more and more people are seeking this kind of reflection space in the company of others. Peer-to-peer midlife professional networks like Chief (for women) and Vistage are seeing huge increases in their membership. Midlife transition programs affiliated with universities, such as Stanford (Distinguished Careers Institute), Harvard (Advanced Leadership Initiative), and Notre Dame (Inspired Leadership Initiative) have grown steadily under the loose network of the Nexel Collaborative.

A version of SoulCycle, F3, pushes midlife men physically but also allows them to bond emotionally and spiritually. And even intentional communities—a communal vestige of the hippy-dippy ’60s and ’70s—are making a mainstream comeback focused on midlifers who are more interested in the belonging that comes from “we-tirement” than the isolation that often comes from retirement. Midlife atriums abound!

Over the past few years, I’ve had the great fortune of closely working with thousands of midlifers ranging in age from 28 to 88 (the average age being 54) who came to the Modern Elder Academy (MEA) to reimagine and repurpose themselves: to create a life that’s as deep and meaningful as it is long.