I Wish I Had Your Problems

When things are bad, everyone wants to listen.

Lose your job, and people check in. Go through a divorce, and the meals show up. Get a scary diagnosis, and suddenly everyone has time for coffee. We’re built for that. We know how to show up when someone is low. We’re encouraged to share our struggles, to be vulnerable, to ask for help. There are entire industries built around it.

But try talking about things going well, and watch what happens.

You’re allowed a certain amount of success. Make money, but not too much. Get promoted, but don’t leapfrog anyone. Start a company, but don’t bring it up at dinner. There’s an invisible line, and it moves depending on who you’re with, but it’s always there. Cross it, and people don’t get angry. They just get quiet. Or worse, they get dismissive.

“I wish I had your problems.”

That’s the sentence that ends the conversation every time. Five words, and you’re boxed out. Whatever you were about to say about the actual complexity of what you’re going through, it’s gone. You’ve been reclassified. You’re not someone with a problem anymore. You’re someone who should be grateful. And those are two very different things.

Here’s what makes that response so strange. The person saying it is almost always doing fine themselves. By any global measure, the vast majority of Americans are wealthy. We have clean water, electricity, roofs, cars, and grocery stores with 40 kinds of mustard. By the standards of most humans who have ever lived, the person saying “I wish I had your problems” already does have your problems. They just don’t see it that way. Wealth is always relative to whoever is standing next to you, not to the species.

I move through four social groups. Church. Work. The tech community. Family and old friends. Each one has a different ceiling for how much success they’ll comfortably sit with.

At work, the ceiling is whatever your boss is doing. Be good, but don’t be too visible. The moment your name appears more often than theirs, people who used to collaborate start competing.

In the tech world, ship a cool project, and people celebrate. Make real money from it, and they get quiet. The maker community loves the craft but gets uncomfortable with the commerce, as if building something useful and getting paid for it are in conflict.

At church, ambition itself is suspect. Start talking about building something, and the temperature drops. People hear “I’m trying to do something” and interpret it as “I think I’m better than this.”

With family and old friends, the ceiling is wherever you were when they last formed their picture of you. Succeed past that picture, and they don’t update it. They just stop asking. Or they ask in a way that’s already dismissive. “Still doing that computer stuff?”

The thing is, your problems don’t go away when things are going well. They just change shape. When you’re broke, the problem is money. When you have money, the problem is what to do with it, who to trust, how not to screw it up, how to keep the thing that generated it from consuming everything else. New money brings new decisions. New visibility brings new exposure. New freedom brings new ways to fail. These are real problems. They keep you up at night the same way the old ones did.

But you can’t say that out loud. Not in any of the four groups. Because the moment you do, you get the line. “I wish I had your problems.” And the conversation is over before it started.

I’m heading into a high-temptation environment across three endeavors over the next few months. I’m not going to say what they are to any of my groups, because that’s exactly the kind of thing that triggers the response. People hear certain opportunities and stop listening to everything after. They skip straight to “must be nice,” and they’re done.

So what do you do?

You find people who are ahead of you. I wrote something 20 years ago about how it’s great to be the worst musician in the band. You get better almost immediately just by playing with people who are better than you. You don’t even have to try. You just rise to where they are. Success works the same way. Find the people who are further along. Not to network with them or name-drop them. To be around someone who won’t punish you for winning. Someone who’s already past the part you’re going through and can say, “Yeah, that happens. Here’s what I did.” They’re the only ones who won’t flinch when you tell them what’s actually going on.

That’s the thing nobody prepares you for. When things are hard, the world opens up. People lean in. When things are good, the world closes down, and you’re supposed to just be thankful and shut up about it. The loneliness isn’t about the climb. It’s about the people who are still at dinner, still at church, still in your life, but who can’t meet you where you are anymore. Not because they don’t care. Because your success costs them something, and neither of you knows how to say it.