Walking Contradictions: I Hate Managing. I Keep Leading.

People have a habit of reading me as someone who is chasing something I’m not. they see the startups I’ve been part of, the teams I’ve found myself inside, the communities I’ve helped shape, and they conclude: entrepreneur. business minded. someone with their eye on the market.

That reading has always been a little off. I was never the one who applied. I was nominated, referenced, recommended. I got pulled in. and the reason that distinction matters is because it points to the actual motive, which was never money, and never the feeling of being supreme over others. I don’t love controlling people. I genuinely don’t. not out of shyness, not out of some performed humility, but because responsibility is something I fear, and because I have always preferred being a contributor over being a manager. a contributor does the work. a manager mostly speaks about how the work is progressing. I despised that image of leadership since I was young.

The first time I built something, the advertising agency at sixteen, the motive wasn’t financial independence or market opportunity. it was simpler and less impressive than that: I could see talent around me, I could see a gap that talent could fill, and I wanted to connect the two. the fact that it generated money was secondary. almost incidental.

The Slow Accumulation

What I didn’t account for is that experiences don’t care about your stated preferences. they accumulate regardless.

By 2024 I had been leading communities for years while being in active denial about it. I kept stepping back from the spotlight, kept framing my role as supporting rather than directing, kept telling myself that what I was doing wasn’t really leadership — just coordination, just being organized, just being around. and then slowly, through the forced honesty that comes from doing something long enough, I had to admit it. I was leading. I had been leading. and the world hadn’t ended.

What shifted wasn’t that I started loving it. it was more that I started to recognize it wasn’t destroying me. responsibility still felt terrible, the way a weight feels terrible when you first pick it up — but I was holding it. people were trusting me. I still had room to contribute as an individual, not just as the person pointing at the work other people were doing. and around this time I came across a video of Steve Jobs talking about the difference between managers and leaders — about how the best leaders he knew were people who had deep individual expertise and happened to be running things, not people who had climbed toward management as an end in itself. that framing gave me something to hold onto.

What Leadership Actually Cost

I should be honest about the cost, because I wasn’t honest with myself about it for a long time.

During those periods I was anxious in a way that ran beneath the surface of everything. full of stress. mostly on autopilot, driven by a combination of perfectionism and a fear of not delivering, which is its own particular kind of exhausting, because perfectionism doesn’t tell you when you’re done, it only tells you what’s still wrong. my standards were high and my rhythm was fast, and I think that made me harder to approach at times. I was restless in a way that probably read as intensity or impatience, and I wasn’t always generous with the people around me when I was moving at that speed.

I was trying to hold two things at once: the clarity of the working environment, meaning, no unnecessary tension between me and others, and the drive behind everything, the forward momentum. most of the time I managed both. sometimes I didn’t. and here is the honest part: I don’t actually know how well I did, because I never stopped to assess it.

What I did instead was keep moving. I would feel something unresolved at the end of a difficult period and then fill that space with more work, more busyness, anything to avoid sitting with the question of whether I handled it right. I have a debt, experiential, of days that stretch back across a couple of years, where I deferred the processing entirely. not out of denial exactly, and not out of carelessness. I overthink small things compulsively, and the only way I’ve found to stay functional is to quarantine the larger ones and file them under later . the problem is that later always arrives.

What I Can See But Can’t Believe

This is the part I find the hardest to write. because it requires me to admit something that sits in direct tension with everything I’ve described above.

There are parts of this I’m good at. I know that on some level. I can read a room well. I can sense the dynamics forming before they fully form, the way I could sense at fifteen whether a new person’s chemistry would fit or fracture the group. I can hold people together while also holding myself together. I have been trusted repeatedly, not by accident, and not because I positioned myself to be.

The problem is I can see that evidence but I can’t give it real weight. it registers and then I discount it, the way you might register a compliment and immediately find three reasons it isn’t true. the negative has gravity in a way the positive doesn’t, which, if I’m being precise about it, is just negativity bias doing what it always does. but naming it doesn’t automatically dissolve it.

That is still where I am. not resolved. still trying to figure out how to let the evidence of competence sit in the same room as the fear of responsibility, without one canceling the other out.