I'm a crazy person.

A buddy who used to work for me just had his first baby a few months ago.

Jennifer and I met him and his wife out at a winery when the baby was just seven weeks old. It was a beautiful Saturday afternoon, and we were so happy (and pleasantly surprised) that our friends were up for some socializing with a newborn in the picture.

They showed up a bit late after struggling to get the baby to eat. And my friend looked tired as his eyes darted between our conversation and the baby every few seconds.

When I asked how he was sleeping, he laughed and said it's about three hours a night.

But here he was. Out on a Saturday, newborn in tow, making time to be a good friend on top of everything else. He told me he wakes up at 4 a.m. to help with the baby, get the house moving, and fit in a workout before he heads to work. He runs revenue at an early-stage AI company in the Bay Area.

I hired this guy almost a decade ago. And right when I met him, I knew he had something most people don't. A gear that doesn't turn off.

Watching him describe his life now, I realized he couldn't slow down, even if he wanted to. His family needs him. His company needs him. And the version they need is the one that does everything at 100%, all the time, no exceptions.

Sounds exhausting, I know. But I'm not worried about my friend.

Because I recognize him.

The mirror

When people ask my wife to describe me, she says (without fail), "He's a crazy person."

She doesn't mean it as an insult, but more like a doctor giving a diagnosis. Something she's observed over the years about my personality and finally accepted and stopped trying to fix.

Jennifer's not wrong.

I'm a control freak who obsesses over my work. When a day goes poorly, I can't let it go. I'll fixate on whatever went wrong until I figure out how to make sure it won't happen again. And even though I know every business has ebbs and flows, I'm not good with ebbs. I need every day to go as planned, and I have a hard time letting anything get in the way of that.

A few weeks ago, I had a piece of important content scheduled to go out at 4:48 a.m. Pacific Time. That's when I've released content for six years. But normally I'm on East Coast time, so it's much easier to manage. But here I am in California, so I woke up at 4:00 a.m. Not because I set an alarm. Because my brain wouldn't let me sleep. I was too wired, thinking about this content existing out in the world without me being there to make sure it went well. So I lay there awake in the dark, waiting, and grabbed my phone the second it went live.

But here's the thing (in defense of my crazy):

The obsession that wakes me up at 4 a.m. to micro-manage social media is the same obsession that built this business in the first place. The perfectionism that drives Jennifer nuts is the same perfectionism that keeps my open rates above 60% with 180,000+ weekly newsletter readers. My inability to let a bad day go is the reason my business has improved for six years straight.

I can't separate the flaw from the fuel. They're the same thing.

The pattern

It's not just my buddy with the new baby and me who are wired like this. I see crazy people all over the place when I study successful folks.

I have a founder friend in Austin who checks his Stripe dashboard before he checks on his kids in the morning. Because he physically can't start his day without knowing his numbers. Sure, the business wouldn’t change if he just skipped it for a day, but he needs to know if there’s a problem immediately. Like the moment his eyes open. Sounds crazy to most, but to me it sounds totally normal.

Successful people like him don't have better habits than everyone else. In fact, they probably have something a bit wrong with them, by average standards anyway. A weird compulsion, or an inability to do things at 70%, or an engine that runs hot whether they want it to or not.

People will (admiringly) roll these personality quirks into terms like "determination" and "grit." They've "got strong priorities," "rigid boundaries," and "disciplined morning routines."

But the people I know who are like this? Most of them aren’t as disciplined as they are obsessed. They have a monster chip on their shoulder that never went away, or an inability to be satisfied, even when they've hit every milestone on the dashboard. From the outside, it looks like ambition, but on the inside, it feels more like an addiction.

And I used to think these kinds of people succeeded, despite the thing that was off about them. But now I think they succeed because of it.

They can't separate the flaw from the fuel either.

The cost

There's a huge toll to pay for these kinds of behaviors, and that darker side doesn't get talked about much, especially on social media. Because most people will notice the success part without imagining what it takes to get there.

People congratulate me on my business all the time. But my mood often swings like a pendulum based on how my work is going. A newsletter that underperforms can wreck a Saturday, while one that everyone loves makes me feel invincible. And when my content bombs for days on end, I can easily convince myself that everything around me is crashing down.

When I'm being logical, I know to zoom out and look at the big picture instead of any singular event. But I can't help it. I rise and fall with the daily numbers, and I struggle to insert logic into situations that could threaten everything I've worked so hard for.

There's a physical cost to this behavior, too. I carry around intense stress, struggle to relax, lie in bed overthinking things at night, and worry about work during moments I should be fully present with Jennifer.

A few months ago, she looked at me after a particularly rough week. She put both her hands on my cheeks and looked me in the eyes. Not as a casual check-in, but the way you ask when you're scared of what the answer’s going to be. I said I was fine. We both knew it wasn't true. She kept her hands on my face for a moment, and we just sat there quietly. I didn't feel better exactly, but I certainly felt a little less alone in the moment.

At the end of the day, I chose to build this business. I love the work I've created for myself. And I love how I'm wired. But obsession costs something. It always does.

Sometimes I wonder if I would trade this crazy personality for an easier-going one if I could. Someone who lets things go, or has a bad day and shrugs it off. Someone who operates at 70% and sleeps fine anyway. My answer is still no. But it used to come easier.

The bottom line

Jennifer will forever call me a crazy person. And we both finally get that my crazy is tangled up with everything else, that you can't extract it without losing something important. So now we just try to pay attention to where the crazy is focused, and we (usually) make the most of it.

So here's something that might be worth pondering this week:

Do you have something slightly wrong with you? A compulsion you can't turn off? An obsession you've learned to aim at something productive?

If so, I'd love to hear about it. Tell me what it costs you, and what it's built.

I'm inviting you to help me feel a little less crazy. Or maybe by knowing my story, you can feel a little less crazy about yourself.

While we can't reply to every email we get, we love reading your responses.

And that's all for this week.

See you next Saturday.