I used to babysit for extra cash, and one of my regulars, Diana, was a single mom who was working her way up at a law firm. When I started, she was a senior associate putting in brutal hours. By the time I stopped, she’d made partner, and I was at her house most nights of the week.
The more she succeeded, though, the lonelier she seemed, and back then, I couldn’t make sense of it. She’d get home late, after the kid was asleep, and sometimes she’d sit at the kitchen island for a minute before going up. That’s when she’d say things I didn’t really get at the time. That she had a hundred people who needed her and no one she could talk to. That everybody wanted something from her. That she could walk into a room full of people who respected her and feel more alone than she did back when nobody knew her name.
I’ve thought about that a lot since, because I’ve seen it happen to other people who climbed. And I’ve come to think the success itself usually isn’t what makes people lonely. It’s a few things that come with it that nobody really warns you about.
The higher you go, the fewer people you can be honest with
When you’re starting out, everyone around you is in the same boat.
Same long hours, same cheap dinners, same complaints about the same boss. You tell each other the truth because there’s nothing to lose.
Then you get promoted, and the people you used to complain to now work for you. You can’t really vent to them anymore, because anything you say hits differently coming from the boss. And you can’t be totally honest with the people above you either, because you’re still trying to prove you belong. So the group of people you can actually be yourself with keeps shrinking the higher you go.
It’s not just a feeling. Surveys of CEOs keep finding that about half of them say they feel lonely in the job, and the people who study it point out something easy to miss: it’s usually not that they don’t have enough people around. It’s that the job takes away everyone they can be honest with. Near the top, there’s often no one left who isn’t also someone you have to manage, impress, or answer to.
People start treating you like a role instead of a person
Success changes how people act around you, and most of the time, they don’t even mean to do it.
They get a little more careful. They laugh a little faster at your jokes. They want things from you, even when they’re being nice about it. She used to talk about walking into a room and feeling everyone adjust, and once she said it, I couldn’t stop noticing it myself.
The problem is you end up around people who are reacting to your title, or your money, or what you can do for them. And you can never be totally sure which one it is. So you start wondering how much of it would still be there if the title went away.
That’s how you can be in a room full of people who admire you and still feel like nobody really sees you. Being admired and being known aren’t the same thing. People admire the part of you that did well. Being known means somebody sees the rest too, the doubts and the bad days, and the higher you go, the fewer people there are who get to see any of that.
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The drive that got you there keeps eating away at everything else
The habits that make you successful are usually the same ones that leave you lonely. The late nights. The travel. The weekends that turn into work. The friends you keep meaning to call and don’t.
None of it feels like a choice while it’s happening. It feels like focus. And for a lot of people, like Diana, a lot of it isn’t even optional. But you spend years pouring yourself into the work, and there’s less and less left for the people who keep you feeling connected. Those friendships don’t end with a fight. They just fade, slowly enough that you don’t notice until they’re basically gone.
There’s research on this, too. Psychologists spent years looking at what happens when people build their lives around money, status, and image, and they found that chasing those things tends to push out the stuff that actually sustains people, like close relationships and feeling like you belong. It doesn’t just take your time. It slowly changes what feels important, until calling an old friend keeps losing to the next thing on your list, and you don’t even notice you’re picking.
You keep telling yourself you’ll make time later
You tell yourself you’ll slow down after the next thing.
After the promotion.
After you build up your clients.
After you finally get to a point where you can breathe.
But that point keeps moving. The thing that was supposed to be enough just becomes the new normal, and then you’re measuring yourself against the next one. So “once things settle down” never comes, because things don’t settle down. And the people you keep planning to make time for someday don’t just wait around for you. They keep living their lives. That’s the part that’s easy to miss until it’s too late: the people you put off don’t stay put.
You never stop comparing up
You’d think getting to a certain level would finally quiet the feeling that you’re not doing enough. It doesn’t. You just start comparing yourself to whoever’s one step ahead, so the feeling never goes away. It just follows you up. And that’s part of why it gets lonely. When you’re always sizing yourself up against the next person, you’re never really there with the people in front of you. Part of you is somewhere else, doing the math. It’s hard to feel close to someone whose mind is always half on what they don’t have yet.
There’s some embarrassment mixed in, too. It feels stupid to admit you have a lot and still feel like it’s not enough, so you keep that to yourself, which just makes you feel more alone with it.
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What actually seems to help
The people who pull out of this don’t get there by working less or wanting less. They just stop assuming their friendships will survive on autopilot and start actually tending to them.
It’s small stuff, mostly. Hanging on to the friends who knew you before the job title, the ones who’d give you a hard time if you got weird about it. Texting back the person you keep meaning to text back. Treating dinner with someone you love like a meeting you can’t move, instead of squeezing them into whatever’s left at the end of the day.
None of that is hard, exactly, but it cuts against everything that got you here, the part of you that keeps saying you’ll get to the people later. Diana kept planning to slow down, too, and as far as I could tell, she never did.
That’s the thing worth sitting with: the success is rarely what’s making someone lonely, and it’s almost never going to be the thing that fixes it. You can climb your whole life and arrive at the top to find most of the people gone. What keeps you company up there isn’t the work. It’s whoever you bothered to hold onto on the way.
