Pajamas, Stairs, and Everything in Between

Person wearing sneakers and jeans relaxes with feet up on a railing in a rustic setting. Text reads KEEP IT FUN.

There’s a pair of stairs in my house, and honestly, they’re a disaster. I walk past them every day, and every day I think, “I should clean those.” But I don’t. And you know what? It doesn’t matter. Not because I’m lazy—though I am—but because there’s always something more important. Like figuring out how to live a life that doesn’t make you want to scream into a pillow at 3 a.m.

I used to think about these imaginary people who had it all figured out. The ones with perfect houses, perfect stairs, perfect lives. They didn’t exist, but that didn’t stop me from comparing myself to them. Even now, I catch myself wondering if I’m “doing life right,” which is hilarious because, honestly, I’ve spent the better part of my career in pajamas.

Pajamas are a weird thing to aspire to, aren’t they? But for me, they’re a symbol. They mean I get to call the shots. I don’t have to put on a suit or commute or do any of the things people think you’re supposed to do to be successful. I can sit here, unshowered, drinking coffee that’s gone cold, and still feel like I’m winning.

But you don’t get to pajamas without a few stumbles. Actually, a lot of stumbles.

Like the time I thought making money was the answer to everything. Turns out, it’s not. Don’t get me wrong, money’s great. It keeps the lights on and buys fun things like a house with stairs you forget to clean. But it’s not the thing. You know, the thing. The reason you get out of bed, the reason you care, the reason you keep going even when the world feels like one giant Monday morning.

For me, the thing was fun. Stupid, unproductive, childlike fun. The kind that makes people roll their eyes and say, “Shouldn’t you be more serious?” Except I never wanted to be serious. Serious people look miserable. They follow the rules and do the right things, and somehow, they still end up stressed, overworked, and wondering why life feels like a treadmill.

Fun, though? Fun gets you through the hard stuff. It’s why I started making videos, even when they were bad. It’s why I took risks, even when they didn’t make sense. It’s why I learned to do the things other people avoided, not because I loved them but because I knew they’d lead somewhere interesting. Fun keeps you curious. It keeps you creative. It keeps you from becoming one of those people who sits in meetings and says things like, “Let’s circle back on that.”

God, I hope I never become a circle-back person.

But here’s the thing about fun: it’s sneaky. It doesn’t always look like fun in the moment. Sometimes it looks like trying something scary or doing something messy or failing so hard you want to crawl into a hole and never come out. Like the first time I charged money for something I made. I thought, “What if nobody buys it? What if this is dumb?” And you know what? It kind of was dumb. But it worked. Not perfectly, not without hiccups, but it worked enough to make me think, “Maybe I can do this.”

That’s the thing I wish people talked about more—not the perfect end result, but the weird, awkward, uncomfortable middle. The part where you’re not sure if you’re making progress or just making noise. The part where you look at your stairs and think, “Yeah, that can wait.” Because it can. It really can.

So, here’s what I’ve learned: stop trying to get it right. Stop worrying about what everyone else thinks or what they’re doing or whether your life matches up with some imaginary Pinterest board in your head. Clean your stairs when you feel like it. Wear pajamas to work. Take a risk, even if it feels like the stupidest idea you’ve ever had.

You’re going to mess up. You’re going to make things that don’t work. You’re going to look back and think, “What was I even doing?” But you’re also going to have fun. Real fun. The kind that makes life worth living, even when it’s messy and imperfect and your stairs are still covered in dust.

If this makes sense to you, or even if it doesn’t, there’s a video I made where I ramble about some of this stuff. I’ll leave it here. Maybe it’ll click, or maybe you’ll just think, “That guy should really clean his house.” Either way, enjoy.

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