You get good at going deep. You get terrible at keeping it easy.
A guy I grew up with stopped inviting me to things and I didn't notice for six months.
We used to watch football on Sundays. Talk shit about nothing. Eat bad wings and argue about whether the Chargers would ever figure it out. It was never about anything. That was the whole point.
Last time I was home I met him for tacos. Somewhere between the second beer and the salsa verde I asked how his marriage was going. Not "how's Sarah." How's your marriage going. Like I was hosting a podcast nobody subscribed to.
He looked at me like I'd asked to see his tax returns.
That's what happens when you spend two years reading about attachment styles and emotional intelligence and listening to podcasts about having better conversations. You get good at going deep. You get terrible at keeping it easy.
The trap is turning yourself into someone who can't just hang out anymore.
I did this to myself. After I sold my company and suddenly had all this time, I filled it with self-improvement. Books about meaning. Journaling every morning. A therapist I actually liked, which made it worse because I started talking like her. Long voice memos to friends at 1am about what I was "learning about myself." I thought I was evolving. And maybe I was. But I was also becoming the guy nobody wants to get a beer with because every conversation turns into a confession booth.
You know this version of the trap. Maybe you haven't lost people over it yet. But you've felt the moment. Someone tells a funny story and you respond with something about how humor is actually a defense mechanism. Someone mentions their dad and you ask what that relationship did to them. You say "that's interesting, say more about that" to a person who was making small talk and watch their whole body shift back.
You've noticed people getting quieter around you. Shorter texts. Fewer invitations. Not because they're mad. Because being around you started to feel like work. Like they needed to show up with something real or you'd look at them like they were wasting your time.
The people who are best at just being easy to sit with, they don't work at it. They don't read books about it. They show up and talk about the game or the weather or some dumb thing that happened at the grocery store. And those people have slowly pulled away from you. Not with drama. Just with distance.
My friend didn't blow up at me. Didn't say anything was wrong. He just stopped texting. Stopped sending the group thread about Sunday plans. Because I'd turned every hangout into something he needed to decompress from after.
When I was running my logistics company I didn't have time for any of this. I was too wiped to go deep with anyone. I'd show up at a barbecue, drink three beers, talk about absolutely nothing important, and drive home feeling better than I had all week. Those were some of the best nights of my twenties and I had no idea.
The self-work wasn't wrong. I needed it. I was delivering Chipotle at 35 and sleeping in my childhood bedroom wondering what the hell happened. Therapy pulled me out of that. The books helped. I'm not sorry I did any of it.
But I didn't know when to stop. Or honestly, I didn't want to stop because working on myself gave me something to work on. And I have always needed a project. Take away the company, take away the seventy-hour weeks, and I just found a new one. The new project was me. And I went at it the same way I went at everything else. All in. No off switch.
It followed me overseas too. I'd meet someone at a hostel or a bar and within ten minutes I'd be asking what they were really doing with their life. People don't want that from a stranger. They want to talk about the food or the music or where to find a good meal. They want easy first. I forgot how to give them easy first.
I turned my own personality into something to fix. And then wondered why people felt like they were being studied instead of talked to.
I called my friend last week. Didn't bring up anything I'd been processing. Didn't ask anything heavy. Just asked if he'd seen the game. We talked for twenty minutes about nothing and it was the best conversation I'd had in months.
He said we should do it again Sunday. I said yeah.
The most important people in your life don't need you to be deep. They need you to be the kind of person who can let a silence just be a silence.
— Best, Jose
