It's Only Lonely at the Top If You Can't Be Yourself There

Brian Chesky built Airbnb into a hundred billion dollar company. In an interview, he described what it was like at the top:

"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."

He described the day after the IPO. He woke up, put on his sweatpants, sat down at his iMac, and did ten to twelve hours of Zoom meetings. "My work was my life. I didn't know at that time that I was lonely. I knew I was isolated, but I didn't know that also meant loneliness."

The founder of a company whose mission is belonging, surrounded by thousands of employees, felt alone.

He's not the exception. A Harvard Business Review study found that half of CEOs report feeling lonely in their role, and 61% believe it's hurting their performance.

For example, the moment in the car. You've pulled into the driveway, done being the confident leader, and you're a minute away from walking inside to be steady for your family. So you sit there. That minute is the only part of the day that belongs to the person underneath both roles.

So the question worth sitting with is this: how and where can you be more fully yourself? Some answers are obvious once you look. The one underneath them all almost never is.

Nowhere to Set It Down

For many founders, the honest answer is almost everywhere. And it happens gradually, for reasons that make sense.

You feel like the only one bearing the full burden of responsibility for the company, its employees, and its investors. That weight seems to demand a strong, confident face. It feels like you have to hide your humanity and be superhuman for your team, with no luxury of admitting you're scared, doubting, or disappointed.

Then it goes further. You start taking more than 100% responsibility, as if your job is to protect everyone around you from any challenge, setback, or hardship. You absorb it all so nobody else has to feel it.

Meanwhile, everyone else is posting their glory days, so it looks like everybody else is crushing it and you're the only one struggling.

The people you could be fully yourself around, your oldest friends, get squeezed out of the calendar. You spend most of your time with the people you feel you can't be fully authentic with.

Then you come home to your family. Your absence has been building resentment for months, and when the company hits a rough stretch, a new fear moves in with it: all of this sacrifice, and the thing might not even work. The shame of that possibility makes you even harder to reach. Some founders arrive at a point where they can't fully open up to their own partner.

Nowhere to set it down.

Deep connection comes from feeling like you can totally be yourself and be seen and loved for who you are. If you're not being fully yourself, you can spend all day surrounded by people and feel none of it.

Loneliness is the distance between what you're actually experiencing and what you let anyone see.

The Belief Underneath It

The mask is usually older than the company.

Chesky said he felt guilty whenever he wasn't working, because so much of his life was about being successful, and deep down he believed success would make people love him.

Most entrepreneurs hold some version of that belief: I'm not inherently worthy and lovable, but I can become worthy and lovable by achieving enough.

I certainly felt that and believed that for a long time. In my years as a founder, any given hour presented the same choice. Should I go home and spend this hour with my wife and young kids, or do one more hour of work? The extra hour of work always felt like the more beneficial thing, because it had a tangible outcome. It wasn't even a conscious choice. I didn't know it at the time. I only saw it much later, reflecting back. I was so busy trying to become worthy of my family that I almost lost them.

A founder at my last retreat put it this way: "I've struggled my entire life with the belief that I have to 'earn love' in life and working hard so that I can be deserving of my existence."

That belief is itself a kind of loneliness. If love has to be earned through achievement, you can never trust that anyone loves you for you. And chasing the proof pulls you away from yourself: your own feelings, your own knowing, your own wants. When we're disconnected from ourselves, we end up feeling disconnected from everyone else.

The Way Back to Connection

1. Find two or three people you can fully share with.

You don't need to announce every fear to the whole company. Your job with the full team is to steward its collective creative energy, and unloading everything on everyone rarely serves that. A question I often ask leaders: are you sharing this for you, or for them? If it's for them, share it with whoever needs to hear it. Letting your team know you're scared too can give everyone permission to feel what they're feeling.

And if it's for you, that's the antidote to loneliness working. Find specific people on your leadership team you can be more real and vulnerable with, and more fully known by. Most people wildly overestimate how invulnerable they need to seem. With them, you don't have to carry it alone.

2. Allow work to feel like play.

Play is how humans connect. Kids connect by playing together, and the same is true on a team: the more work feels like play, the more connected you feel to the people you're building with. The more serious and heavy it feels, the more everyone pulls away.

When a team is checked out, numbed, or escaping into screens and scrolling, the instinct is to prescribe more willpower. A famous addiction experiment found a different lever: rats housed alone took the drugs, while rats in a rich, social environment mostly ignored them. The environment was the difference.

So look at your environment and ask what's making work feel heavy. Anytime work is feeling serious, you're making it mean something it doesn't mean, usually something about you. A missed goal in a rec league soccer game means nothing about your worth, and you still play hard and play to win. A missed target can work the same way.

Play and connection are a performance advantage: more trust, faster decisions, better collaboration.

3. Have the conversation you've been avoiding.

Avoiding a hard conversation means swallowing what you actually think, feel, and want. That's disconnection from yourself, and every avoided conversation manufactures a little more distance between you and the other person.

The hard conversation with your co-founder, the honest one at home, the direct one with a team member: each one reconnects you twice. To yourself, because you finally said the true thing. To them, because now they know the real you.

4. Get in person, with people on the same path.

In person beats video, video beats phone, and all of it beats Slack, which abstracts away the human connection layer.

Prioritize the friends you can be fully yourself around. Join a forum or CEO group. Do offsites with your team. Go to retreats.

It's a big part of why I host a founders retreat every January. In those rooms, you get to connect in a way not related to business: the mask comes off, everyone's open to share, you have permission to experience and release emotions in a safe environment, and you're seen, held, and supported by people on the same path as you. The belief that you're the only one struggling doesn't survive a room like that. You get to be human again.

(Enrollment for the January retreat opens Tuesday. Only twelve spots are available. Click here to learn more and apply >>)

We're All Human

Some founders harden their hearts on purpose, keeping their team at a distance because they might have to fire someone someday.

But the distance doesn't make those moments easier. Ironically, the more connected you are, the more people know you care about them, and the easier it becomes to give hard feedback. If you ever do have to let someone go, the connection is what allows you to do it in a way that feels humane and dignified.

Closing your heart doesn't protect you from the pain of leadership. It just guarantees you carry that pain alone.

Chip Conley said, “The most neglected fact in business is that we're all human.” Underneath all of it, I think we're afraid to love one another because we're afraid to get hurt, or to hurt others. That's a bad trade-off.

The willingness to feel whatever comes is the price of admission for everything on the other side of it: a team that trusts each other, friendships that hold you, a company that moves faster because the people building it feel connected, and a family you can truly feel at home with.

It's only lonely at the top if you have to be someone else the whole way up. And that minute in the car doesn't have to be the only one where you can take off the mask and just be yourself.

With love,

Dave Kashen

P.S. Enrollment for the Sun Valley Founders Retreat opens Tuesday, 48 hours from now. January 20th to 24th, twelve spots, four days of transformation with people who understand the weight, where you're seen and loved for who you are. Spots will fill up.

​Click here to learn more and apply >>​

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