Why Success Feels So Lonely: Inside a CEO’s Billion-Dollar Breakdown

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The Solitude of Success: A CEO’s Reflection ⛰️

Even a $100B IPO couldn’t fill the void. One CEO opens up about the hidden loneliness at the top behind massive success.

This essay by Brian Chesky explores his personal experience as a CEO who achieved significant professional success, including a hundred billion dollar IPO, but simultaneously grappled with profound feelings of isolation and loneliness. Despite their outward achievements, he felt a deep personal void and recognized that their life remained unchanged even after reaching the pinnacle of their career.

He recalls a conversation with a former Surgeon General, Dr. Vivek Murphy, who affirmed that loneliness is a critical health concern, underscoring its significant impact beyond emotional well-being. This essay suggests that professional ascent can surprisingly lead to personal solitude, and that loneliness is a widespread and serious issue.

Here’s His Thought Provoking Essay

“As I became a CEO, I started leading from the front at the top of the mountain, but then, the higher you get to the peak, the fewer people there are with you. No
one ever told me how lonely you would get, and I wasn’t prepared for that. I had this guilt about not working because so much of my life was about being successful, probably if I were to dig deep because I thought that would make people love me.

And the day of our IPO, we reached a hundred billion dollar validation. I remember after going public, I was like, ‘Oh my God, there’s this like amazing exaltation.’ It was amazing like I’d gone to the mountain and then I woke up the next day, and my life was exactly the same. I’m alone. I wake up, I put on my sweatpants, I go onto iMac, and I have like 10-12 hours of Zoom meetings and I just don’t really have much of my life outside of work. My work was my life.

I didn’t know at the time that I was lonely. I knew I was isolated, but I didn’t know that also meant loneliness. And I thought I have all these people around me, how could I possibly feel this way? There were a couple of people who entered my life that gave me some awareness and consciousness, one at a deeply personal level and one more at a professional level.

And the other person I met is the now and former Surgeon General of the United States, Dr. Vivek Murphy. We hired him during the pandemic because a lot of
people were afraid to go into Airbnbs and they were worried about germs on the surfaces. I remember having a conversation with him, and he said something to me. He said, ‘Brian, do you know what the number one killer in America is?’ And I said, ‘I don’t know, is it like heart disease? Is it cancer?’ And he goes, ‘No, the number one killer in America is loneliness. “‘

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