oops! I'm better at earning things than receiving them

The opportunities, relationships, and moments I nearly missed by trying to earn them twice.

I prefer to be a big fish in a little pond, but sooner or later, I’ll need bigger rapids.

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I’ve been reading The Big Leap.

The main idea of the book is that everyone has an upper limit. A kind of internal thermostat for happiness, success, love, money, attention, whatever. When life gets better than what we’re used to, something in us gets uncomfortable and starts trying to restore balance.

Some examples:

One couple eloped against their families’ wishes and ended up covered in poison ivy after laying a blanket down in the woods. Another story is about a PhD student who lost his voice right before the most important presentation of his life. Both situations arrived at moments when their lives were expanding in ways that challenged what they believed they were allowed to have.

The idea has been rattling around in my head all week because I’m visiting Los Angeles as I write this.

A brand flew me out to speak at an event. It was a great opportunity. I got to spend time with creators, see old friends, wander around neighborhoods I like, and eat a frankly irresponsible amount of food.

Objectively, everything’s going well.

And yet I noticed how quickly my brain starts trying to turn it into a problem:

Should I move here?

Should I get management?

Should I be scaling faster?

Should I be taking content creation more seriously?

The funny thing is that none of those are bad questions. They’re probably reasonable questions. But I noticed how quickly I moved from appreciating what was happening to trying to optimize it.

Instead of it being just a good trip, I kept turning it into some existential crossroads.

I started wondering if that’s what an upper limit looks like in my life:
My inability to leave something alone once it starts going well.

The thought followed me for a few days before I realized it wasn’t just about work.

It was about dating.

A few months ago, someone I was interested in happened to be passing through town. They were only there for a few hours, so we made plans to hang out.

We spent time together, talked, laughed, and eventually went our separate ways.

It wasn’t until afterward that I started replaying the afternoon in my head.

I realized how hard I had been working.

I had spent hours making sure he was comfortable. Making sure he was having fun. Making sure there was always something interesting happening. I was suggesting checking in, reading the room, trying to anticipate needs before they were even expressed.

At one point I laughed because the entire thing felt like a Destiny’s Child “Cater 2 U” music video.

None of it felt fake, I genuinely wanted him to have a good time.

I couldn’t just enjoy his company, I had to manage his experience.

But that gag is,

He already said yes.

He already chose to spend the afternoon with me.

He already showed up.

But I was still behaving like I needed to earn it.

I’ve started noticing that whenever something enters my life that I genuinely want, I immediately shift into proving mode.

If someone likes me, I become accommodating.

If an opportunity appears, I start justifying why I deserve it.

If something succeeds, I start wondering how long it’ll last.

It’s as though I never fully register that the thing has already arrived.

Part of me keeps acting like I’m still standing outside the door trying to get in.

What’s especially interesting is that my friends don’t get this version of me.

The people who know me best would probably describe me as opinionated. I have preferences. I ask for what I want. I take up space. I can be demanding and self-involved.

And yet when romance enters the picture, I often become remarkably easygoing.

I become the version of myself that is easiest to choose.

I think that’s the key to my upper limit.

When I reach a certain level of being wanted, I immediately become uncomfortable with it.

And then I start earning something that has already been given.

I don’t know if I’ll move to Los Angeles. I don’t know if I’ll get management. I don’t know if the creator career I’m building will eventually become something much bigger than it is now.

What I do know is that I’m becoming more interested in my reaction to good things than my reaction to bad ones.

I’m starting to suspect that some of the most important work isn’t learning how to get what you want.

It’s learning how to stop earning it after you’ve already received it.