I’ve always done pretty well. That’s the problem. I’ve had a standard amount of turmoil in my upbringing, a standard amount of heartbreak in my teens, and a standard amount of soul-searching in my 20s. I have found it relatively easy to “do the thing” - school, sports, tests, work. I’ve consistently gotten the acceptance letter, gotten the grade, the job, the girl.
I’m doing pretty well.
Once out of college and into the real world (if Silicon Valley can be considered this), the simple hierarchical ladder of achievement became more of a maze. Previously I’d been good at climbing this ladder, I now found myself pulled in multiple directions, unsure of what the world wanted from me. I had rarely considered what I wanted myself - instead deluding myself into thinking that whatever was considered to be most prestigious was, in fact, what I wanted.
From 24 until now, having just turned 29, I was slapped in the face by my indecision and self-delusion. The self-delusion was a direct consequence of previously being quite good at “life”. It was the subtle injury - “I’m good at this, I will be alright”. This is true. I am probably good at this, whatever this is, but I am not great. And that subtle injury has held me static for five years.
Patterns
I can imagine this sounds like BS. How can doing pretty well hold you back? It does so through conditioning. I’ve been conditioned to expect things to work out. This leads to helpful and harmful patterns:
Hurts
- No need to re-evaluate what already works
- Assuming things will turn out well because they have before
- Underestimating risk
- Overestimating capability
Helps
- Confidence from prior experience
- General wellbeing (no major health/situational obstacles)
Subtle Injury
Subtle - It is simpler to identify and correct things you have failed at than things you could do better. I often did not have a frame of reference for what better looked like. I knew what I was doing was good enough, but that it also wasn’t getting me where I wanted to go.
Carol Dweck’s research at Stanford showed that children praised for being “smart” - rather than for effort - later avoided challenges and gave up more easily. The mechanism is identity. When intelligence is your identity, struggle feels like evidence you’re a fraud. So you avoid situations where you might struggle. You stay in the zone where things come easy. You never get the signal that something is wrong.
As a thought experiment: imagine you were rejected for a job because you didn’t solve a technical question well enough. What do you do? You go study and get better.
Now you’re at a job, and you receive an “exceeds expectations” review. You’re doing great, on track. What do you do? What do you improve? Do you ask your boss? Are they better than you, and will they know what you should do? Maybe, if you have an excellent boss. But likely not.
This is subtle.
Injury - The injury comes from complacency. I was able to say to myself “you’re doing just fine, things will turn out just fine,” but I could twist that phrase to mean I was on the optimal path. This is clearly not true. But “you’re doing fine” was just true enough that my mind could sell the comfortable illusion to itself.
Andrew Huberman talks about “limbic friction” - the discomfort that precedes growth. The neural resistance you feel before doing something hard. His point: you need to learn to attach reward to the effort itself, not just the outcome. But if you never had to push through that friction, the pathway never developed. The muscle atrophied before it was ever built.
This is the injury.
I’m doing pretty well.
What I’m Trying
Many of my peers at Stanford or the Ivies are stuck in the same pattern. Here are some of the warning thoughts I’ve found in myself:
- Convincing yourself that the most prestigious “next thing” is really what you want. For me this was starting company #2. I considered it high status. I should not have done it.
- Believing that “if you wanted to” you could probably do X. You probably can’t, for all X.
- Telling yourself “I went to X school, I’ve worked at Y company, I’ll be fine regardless.” This is probably false, and it sabotages your drive.
- Romanticizing the “hero’s journey” you’re going to take. For me that was being a founder. There was nothing romantic about it. It sucked.
If you’ve read this far, you probably hoped this section would be a panacea. A simple mental trick to get out of this mindset. It’s not. I don’t know what works yet.
The way I’ve found to begin is to slowly, painfully, surround myself with people who are not like me. Pessimists, realists, people who actually picked themselves up by their freaking bootstraps. This includes my partner. She was the one who held the mirror up for me, for years before I was willing to take a look.
I’m doing pretty well.
It’s so much more comfortable to go back into our safe little delusions. And the dangerous part: living in that world is not bad at all. It’s actually quite wonderful. But it’s not what I want. I want to try for something beyond normal, and I can’t be normal for that to happen. I have been deluding myself for five years that I could be. Many of my well-educated peers are doing the same.
The only thing I can offer is a reframe: “I am doing pretty well” becomes “I can do better.”
Do better at what? I have no idea. That’s my next step. I’m starting by examining each action I take - each event I agree to, browser tab I open - why am I doing this? Do I want to be doing this? If not, what compelled me?
What I’ve learned so far: it’s easy to fall back. I catch myself returning to the same thought patterns:
It’ll all work itself out. I don’t want to disappoint X. It’s what I do.
They’re the scar tissue of the subtle injury, pulling me back to comfortable. But noticing them is just the start. The harder work is examining the beliefs underneath. What does loyalty to friends and family actually mean? What am I doing out of obligation that isn’t serving me?
Paul Graham says:
People who do great work are not necessarily happier than everyone else, but they’re happier than they’d be if they didn’t. In fact, if you’re smart and ambitious, it’s dangerous not to be productive. People who are smart and ambitious but don’t achieve much tend to become bitter.
I’m afraid of becoming bitter. I’ve seen it in older versions of myself, in peers who had every advantage and still feel cheated - by themselves, mostly. But I also don’t know what “achieve” looks like when you’ve optimized for the wrong game. I’ve identified the injury. The prescription isn’t clear yet. But at least now I can feel where it hurts.
I’m doing pretty well.