This is 63: Entrepreneur and Theorist Chip Conley Responds to The Oldster Magazine Questionnaire

"I got comfortable in my own skin, just as it started to sag."

From the time I was 10, I’ve been obsessed with what it means to grow older. I’m curious about what it means to others, of all ages, and so I invite them to take “The Oldster Magazine Questionnaire.”

Here, author, entrepreneur, and theorist on aging, Chip Conley, responds. -Sari Botton

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Chip Conley, 63. “I love writing and reading as a way of honoring my interior life. “

New York Times bestselling author Chip Conley is the boutique hotel entrepreneur who helped Airbnb's founders turn their fast-growing tech start-up into a global hospitality brand. Chip is the founder of the Modern Elder Academy (MEA), where a new roadmap for midlife is offered at a beautiful oceanfront campus in Mexico. MEA will be opening up their first two U.S. Academies and Regenerative Community in Santa Fe, New Mexico soon. His seventh book “Learning to Love Midlife: 12 Reasons Why Life Gets Better With Age” has just been published as has his third TED talk, this one on the topic of the Midlife Chrysalis. 

How old are you?

63.

Is there another age you associate with yourself in your mind? If so, what is it? And why, do you think? 

I do not identify as having a fixed age or being part of a specific generation. I guess I consider myself as "age-fluid.” In the past, people might have called me “ageless,” but that compliment suggests that age is a bad thing. I’m perfectly content to be both younger and older than my chronological age. I look at ages (or stages of life) as identities or costumes we can don or shed. We can now measure biological, cognitive, and even psychological ages, so maybe we have many ages that define us, not just our chronological age.

As social science research has shown, the U-curve of happiness is real…it felt like my life began at 50.

Do you feel old for your age? Young for your age? Just right? Are you in step with your peers?

In some contexts, I feel older than my peers and in other contexts, younger. I’m less focused on whether I fit in with my peers and more focused on this rental vehicle I was assigned at birth, my body. I cared a lot about what that rental vehicle looked like during my first 40 years on the planet, but I’m more focused on what it feels like now. I got comfortable in my own skin, just as it started to sag. LOL. Today, I’m more focused on the long-term maintenance of my body than my short-term vanity. 

Conley at 30, in The Phoenix, the hotel he opened in San Francisco 37 years ago, which he still owns.

What do you like about being your age?

I like that I’m all the ages I’ve ever been. I’m that shy and introverted teenager, that rambunctious and rebellious 20something, that ambitious CEO in his 30s and 40s, and that sage in his 50s and beyond. I believe that my painful life lessons have been the raw material for my future wisdom, so I appreciate that I’m able to metabolize my experiences in ways that serve me and allow me to share with others. 

What is difficult about being your age?

I’m having more physical issues and am in my sixth year with prostate cancer which has metastasized, so I’m on testosterone blockers and doing radiation. I’m having all the symptoms of menopause: hot flashes, night sweats, etc… No fun, but I see cancer as my teacher as this journey has helped me become more awake and aware. I’m just ready to graduate now and retire from cancer.

I look at ages (or stages of life) as identities or costumes we can don or shed. We can now measure biological, cognitive, and even psychological ages, so maybe we have many ages that define us, not just our chronological age.

What is surprising about being your age, or different from what you expected, based on what you were told?

I’ve come to love midlife, a life stage with a terrible brand. I see it as not a “crisis,” but a “chrysalis.” Yes, my early midlife years (45-50) were difficult—dark, gooey, and solitary—but that’s where the transformation happened, just as we see from the caterpillar to the butterfly. And, as social science research has shown, the U-curve of happiness is real, as it felt like my life began at 50. I regularly review the 12 reasons why life gets better with age (the topic of my new book) as our ageist society doesn’t realize the unexpected pleasures of getting older. 

What has aging given you? Taken away from you?

Age has given me a life patina, a sense of how the world works and, more importantly, how I flourish best in the context of the world. Aging has helped me get clearer on what’s meaningful and important in my life and I’ve learned to edit out that which doesn’t matter. The only thing that aging has taken away is my ability to compete in athletics as effectively as I used to. 

Conley at work in his 30s. “I had time-poverty during my 30s as I was growing my business and stoking my ego.”

How has getting older affected your sense of yourself, or your identity?

Long ago, Oscar Wilde wrote, “Be yourself, everyone else is taken.” I wish I’d learned that in my teen years when I was doing my best to keep up with my friends and be carbon copies of them. Over time, I became an “admiration addict” but by midlife, I realized these people (whose opinions I probably shouldn’t have cared about) were renting space in my brain and it was time to evict them. I like that I own my age and that I no longer feel so ego-identified with my roles or personality. I’m more focused on what will survive me and how I can serve others. It’s a big relief. 

I’m having more physical issues and am in my sixth year with prostate cancer which has metastasized, so I’m on testosterone blockers and doing radiation. I’m having all the symptoms of menopause: hot flashes, night sweats, etc… No fun, but I see cancer as my teacher as this journey has helped me become more awake and aware.

What are some age-related milestones you are looking forward to? Or ones you “missed,” and might try to reach later, off-schedule, according to our culture and its expectations?

One of the reasons I started the Modern Elder Academy, the world’s first midlife wisdom school, was to create adult rituals during “middlescence” to mirror all the rites of passage we have in adolescence. I’ve now created “Life Begins at 50” rituals as well as something called the “Great Midlife Edit” as a way to let go of that which no longer serves me or those who come to MEA. I’m looking forward to being 75 years old in a dozen years, as that’s when I think midlife ends and true elderhood begins. 

What has been your favorite age so far, and why? Would you go back to this age if you could?

I loved my 50s, as I was old enough to be wise and young enough to become a beginner in all kinds of ways: learning to surf, learning Spanish, traveling the world to 36 festivals in 16 countries in one year. I became the “modern elder” to the founders of Airbnb, which they defined as “someone who is as curious as he is wise.” My 50s were also a decade when I realized I have “no more fucks left to give.” It didn’t mean I didn’t care about life—it just meant that I was more judicious about what I did care about. 

Conley meditating. “After a frenzied early midlife on the Hedonic treadmill, I'm really appreciating spaciousness today.”

Is there someone who is older than you, who makes growing older inspiring to you? Who is your aging idol and why?

Our oldest MEA alum, Jim Flaherty, is 88 years old and came to our Baja campus for two workshops in 2023 while also learning how to surf. He will be one of our leaders of our MEA Blue Zones workshop program and will be going through the facilitator training program for that in 2024. He has a huge sense of “joie de vivre.” 

I regularly review the 12 reasons why life gets better with age (the topic of my new book) as our ageist society doesn’t realize the unexpected pleasures of getting older. 

What aging-related adjustments have you recently made, style-wise, beauty-wise, health-wise?

I don’t eat much red meat nor drink alcohol as much as I used to (which is a bummer living in Mexico part-time). I’m much more diligent about my sleeping habits and go to bed by 8:30 pm, week or weekend, because I tend to wake up very early (4 am) and do some serious meditating before journaling and writing each morning. 

What’s an aging-related adjustment you refuse to make, and why?

I refuse to let go of my sophomoric sense of humor. Yes, I regularly make inappropriate jokes—mostly at my own expense—because I believe growing older is about gravitas as we age, and levity. Our sense of humor is something we carry with us until we die and laughing has proven to be a variable correlated with living a longer, healthier life. 

Order the book.

What’s your philosophy on celebrating birthdays as an adult? How do you celebrate yours?

I’ve enjoyed being a “social alchemist,” a mixologist of people. Since age 30, I’ve celebrated a multi-day birthday party in far-flung places around the world every five years: Kauai, Bali, Las Vegas, Marrakech, Burning Man, and Baja. I loved introducing my diverse collection of friends to each other and celebrating in places that many of my friends have never experienced. I was supposed to do my 60th birthday party leading an all-campus workshop at the Esalen Institute in Big Sur, but Covid canceled that plan. For my 65th in a couple years, I will likely do something more subdued and intimate with a dozen friends instead of 100 folks. Being a Halloween baby, I do love a reason to get dressed up.