by Chip Conley, Co-Founder and CEO, Modern Elder Academy
Embracing Life’s Changes
If my younger self could see me now, he would indeed have a good laugh.
Here I am, age 62, living in Baja, Mexico. To be honest, present-day Chip is also smiling. It was an improbable journey that brought me to where I am today. Some days, I hardly recognize the person staring back at me in the mirror, and not just because of my sagging body parts or the life wrinkles etched on my face. It’s also because of how far I’ve come and how much I’ve changed.
However, I am happy to say I’ve reached a point where I proudly embrace this metamorphosis as a badge of honor. It is an acknowledgment that I’m constantly evolving into who I want to be in the second half of my life.
When the Joy is Gone, It’s Time to Make a Change
Of course, my younger self knows better—how I wanted nothing to do with midlife. As I approached my late thirties and early forties, the idea of midlife filled me with dread. It seemed to offer nothing more than a bleak future of disease, decline, and death.
And so, I ignored it, kept my head down, and followed the conventional path of youthful ambition. I continued to grind, build, and achieve, all fueled by the ego of my younger self. I started a successful boutique hotel company, Joie de Vivre, which I named to reflect our company’s mission to celebrate the joy of life.
I genuinely loved what I did…until I didn’t. After 24 years as CEO, I sold my company. The joy had disappeared.
Around the same time, the Great Recession hit, coinciding with the loss of five midlife male friends to suicide and my own struggle with suicidal thoughts. I also had an unexpected near-death experience. Suffice it to say, I sunk into despair and discontent, a perfect recipe for falling asleep to life’s possibilities.
Thankfully, one of the gifts of discontent is that it can serve as a wake-up call to embrace what truly matters and look for who we are and what we were put on Earth to do.
Midlife Can Be a Time of Transformation
In a twist of fate, the three young founders of Airbnb approached me to become their in-house guide and mentor—an opportunity I happily embraced for the next seven years. They called me their “modern elder,” someone who is as curious as they are wise. During this time, my curiosity and passion for midlife gradually expanded. I wondered what if midlife wasn’t a crisis but a “midlife calling” or a “chrysalis,” that time of magical transformation?
And with that thought in mind, I decided to leave Airbnb to embark on my next venture, Modern Elder Academy, to help others navigate midlife with a renewed sense of purpose and possibility.
Life truly does get better with age. While there are many reasons the best years of your life are still ahead, I offer you three. And, honestly, the best reasons you’ll find are always the ones you discover for yourself.
Three Reasons Life Gets Better with Age
We Are Finally Stepping Off Life’s Treadmill
Shedding Old Identities to Become Who We Want to Become
The first half of life is often defined by the question, “What does the world expect of me?” It’s the pursuit of happiness through validation. In this stage, it’s easy to play the I Am Game.
I am what I do (achievements). I am what others say about me (image). I am what I have (status). I am what I control (power). I am my physical body (self-perception).
Fortunately, if we’re curious enough, around midlife, many of us start to see through this foolishness. We realize these mantras are roadblocks to living a good life. We know we don’t have to stay on the treadmill of life if we don’t want to. Why do we need to sprint towards some distant and imaginary destination? We can get off the treadmill and allow ourselves to stand still and appreciate where we are in the present.
And most importantly, we can finally shed all those I-AM identities that no longer serve us (or bring us joy). Once free of old labels and identities, we can explore other possibilities and paths to become who we always wanted to be. We are also free to focus on those closest to us, our community, and the legacy we will leave behind.
We Are Becoming Happier
The Great Midlife Edit leads to Peace, Joy, and Happiness
Attend a 50th birthday party, and you’ll see all kinds of birthday cards with tired clichés about how life goes downhill at 50 or becomes infinitely dull. You might chuckle at the jokes but don’t buy into them for a second.
Research on the U-Curve of Happiness reveals a fascinating trend. Happiness tends to reach its lowest point in middle age (around 47.2) but steadily climbs as we age. Statistically speaking, people tend to feel happier in their fifties than in their forties. This growing life satisfaction continues each decade.
By age 50, we find ourselves young enough to embrace new experiences while understanding what truly matters. The “Great Midlife Edit” of our forties creates space, granting us a sense of “time affluence.” With this newfound space and a growth mindset, we can focus on improving ourselves, learning new things, and turning fear into curiosity. In short, we are invited to become beginners again, re-engaged with life while stepping towards a happier life.
As Charles Schulz, the creator of Peanuts, once said, “Once you’re over the hill, you begin to pick up speed.” And, I’d add, happiness as well.
We Are Discovering What Matters
The Shift from Ego to Soul
When we are finally off the identity treadmill—and on a new path to happiness—we are free to look up into the stars and deep into our hearts.
Midlife allows us to become less driven by the trappings of ego and more directed by our soul (spirit, heart, inner nudge…call it what you will).
And when we shift from ego to soul, we innately start searching for deeper truths—discovering what matters to us. This search leads to a more authentic life and a deeper understanding of our place in the universe, which leads to more mindfulness, peace, and life satisfaction.
Then, when we finally begin to understand what is truly important to us, we can recalibrate and design the life we want to live. And once we settle into the transformative opportunity of midlife, something profound and beautiful awakens inside us.
The Bottom Line
Yes, my younger self might be laughing and looking at me now. However, I’d also like to believe he would be more confident about his future, less driven, and perhaps more inclined to slow down long enough to look for deeper truths.
I’d also like to think my younger self is smiling because he knows how beautiful life will be.
All of it.
About the Author: Chip Conley
Chip Conley – Co-Founder and Chief Executive Officer, Modern Elder Academy, is on a mission. After disrupting the hospitality industry twice, first as the founder of Joie de Vivre Hospitality, the second-largest operator of boutique hotels in the world, and then as Airbnb’s Head of Global Hospitality and Strategy, leading a worldwide revolution in travel, Conley co-founded Modern Elder Academy in January 2018. Inspired by his experience of intergenerational mentoring as a ‘modern elder’ at Airbnb, where his guidance was instrumental to the company’s extraordinary transformation from a fast-growing start-up to the world’s most valuable hospitality brand, Modern Elder Academy is the first-ever ‘midlife wisdom school.’ Dedicated to reframing the concept of aging, Modern Elder Academy supports students to navigate midlife with a renewed sense of purpose and possibility. LEARN MORE
Conley’s upcoming book, Learning to Love Midlife: 12 Reasons Why Life Gets Better with Age, about rebranding midlife to help people understand a life stage that is misunderstood, will be released in January 2024.