Your Life: One Photo That Defines Each Decade.

January 1, 2024

Your Life: One Photo That Defines Each Decade.

May 29, 2023

Here’s an alternative inquiry to the tired New Year’s Resolution habit. Find one photo from each decade of your life and write about who you see in that photo and how it ties together with the human you’ve become. Think of it as a pictorial assembly line of the raw material that has made you who you are. Sounds tough? Let me be the guinea pig.

This is me at 2, a cheerful little dude with light in his eyes. I don’t remember much from this period other than my life seemed to be an alchemy of joy and fear. In my first decade, I was a bit of a loner and found great joy in creating imaginary friends on sports teams that I curated. Of course, there was the fear of making real friends who weren’t as compliant. I tended to win my imaginary games but wasn’t always winning the real-life games, especially when I was the starting pitcher on my Little League baseball team. This little introvert did his best to compete but definitely preferred shooting baskets by myself and playing electronic football in my bedroom with the door closed. I liked to compete but in a world of my own making.

Boy, do I look happy in this photo! There were many times in adolescence that I felt defeated and then I’d come back. I shocked everyone in 7th grade when the quiet, shy dude (me) became a starter on our really good school basketball team while also becoming 7th grade Student Council President. I was coming out of my shell, but I was also weighed down by being Stephen Townsend Conley, Jr., a "chip off the old block." I lived in the shadow of Dad, who loved me very much and wanted me to be a better version of himself. A Marine Captain in the Reserves and a hyper-extrovert, Dad felt different than me, and yet, as the oldest child and only son, I felt the obligation to live up to his expectations and I played along quite well.. I was the Eagle Scout, and Dad (also an Eagle Scout) was the Scoutmaster. I went to the same high school as Dad, played water polo and swam, and was Student Body President, just like him. I went to Stanford like my parents and studied Economics like Dad. And I joined a fraternity, just like Dad, but I didn't join my Dad's fraternity (LOL, this is when my rebel period started). And I went to graduate business school, but it was also different from Dad's. But, of course, Dad never worked at McDonald's, my first job at 15. I lasted a few weeks on the fries and shake section (the photo says it all). I realized I didn't want to be a cog in the machine.

My 20s were a liberating decade. On July 4, 1983 (at age 22), while working for Morgan Stanley during the summer between my two MBA years, I summoned the courage to enter my first gay bar, Uncle Charlie’s. I was taking a different path than Dad. Walking into that bar felt like The Wizard of Oz in Munchkinland - my life went from black and white to technicolor. Yes, it was a scary time to be coming out as, that summer, Newsweek had its first cover story on AIDS. From that point forward, I took a different path. I took the least impressive, lowest paying job offer out of Stanford Business School, but a position that gave me huge responsibility and would train me quickly to become a commercial real estate entrepreneur. At 25 with Dad as my mentor, I started cooking up my plan to create one of America’s first boutique hotel companies, and I called it Joie de Vivre because “creating joy” had become my mission after feeling my teens were full of joyless striving. This photo is me in Miss Pearl’s Jam House, the restaurant of my first hotel, The Phoenix.

My 30s were all about growing the business. I seemed to have a “chip on my shoulder,” as my career was all about how I could prove myself. And, it was a lot to handle, as evidenced by this photo about a decade after I’d started Joie de Vivre. My ambition was in overdrive. This was also when I started writing again. As a young teen, I’d wanted to be a writer when I grew up but it didn’t feel practical. As my company and I were gaining notoriety in my 30s, I was asked to give a lot of speeches and, voila, my writing career beckoned as more people wanted to hear my story. I was one of those few CEOs who loved both being a business operator and writing about it. The Prophet author Kahlil Gibran wrote “work is love made visible,” but this photo suggests workaholism is love made obsessive.

This was filmmaker George Lucas's private party's opening day to celebrate his new complex in San Francisco's Presidio. Yes, I'm sitting with Google cofounder and CEO (at that time) Larry Page, San Francisco Mayor (and now California Governor) Gavin Newsom, and San Francisco City Attorney (and now U.S. Vice President) Kamala Harris. This little introvert with imaginary friends was now hobnobbing with the rich and powerful. This was a heady time in The City's ascent on the world stage. As the hotelier with more San Francisco hotels under my belt than anyone else (21 in S.F. alone and, ultimately, 52 around the state) and an established author, I lived the good life, including mentoring the Mayor and acting as his consigliere. But, in the latter half of my 40s, I hit the darkest time in my life when I suddenly and desperately wanted off the treadmill. My midlife crisis (or chrysalis) caught up with me. Of course, it was hard to leave this perk-filled life behind.

It's hard to capture my 50s in one photo, so I offer two: one of me meditating in the entry hallway of my old San Francisco home and the other at a Burning Man fundraiser. I celebrated my 50th birthday party with over 100 friends at our Burning Man camp, Maslowtopia. For more than a decade, I'd enjoyed this annual pilgrimage's libertine, artistic spirit, so I helped launch the Burning Man non-profit Board around the time I sold Joie de Vivre. I was fascinated by the fact that the more digital we get, the more ritual we need, and I spent the early part of my 50s seeking collective effervescence, traveling to 36 festivals in 16 countries in 2013. That was also the year I joined Airbnb as their "modern elder." This was a decade in which I went internal, and my meditation practice became more central to my life, my fuel as I evolved into becoming an ambivert (an extrovert and introvert).

At 63, I know I carry with me all of my past, and hopefully, if I'm conscious enough, I can recognize my patterns and understand what intrinsic needs require tending. After my best decade ever, my 60s have been challenging - dealing with my cancer journey while also the time commitment to grow MEA. I'm doing my best to metabolize my past experiences to curate my life and lead MEA more wisely. But, as this photo shows, what I know I really need in my life is to learn how to be a great Dad to Eli (12) and Ethan (9) with Laura and Susan. As my lovable 86-year-old Dad observes me being a dad, I have much to learn from him, including his occasional regrets and lessons on how he raised me, which any parent will have (but he and Mom did quite a job and I’m deeply appreciative of that). I know that the ultimate legacy I can leave is one in which my boys feel loved and supported for being whoever they want to be.

-Chip

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 to 
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 to 
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 to 
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 to 
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Radical Transitions: The Courage to Reinvent Yourself with Stacy Peralta, Christine Sperber & Teddi Dean

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 to 
May 11, 2024
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