It's OK to Get Lucky

I couldn't write this post. I'd tried three or four times. I knew there was something I needed to say about feedback and track records and the way both of those quietly poison each other, but every draft came out either smug or evasive. So I did something I'd been circling for a while: I let an AI interview me about my own blind spots. I sat on the receiving end of the questions instead of generating the answers I wanted to look good. What I learned from that exercise turned out to be the post. Not the conclusions I went in with — the thing that happened during the process itself.

Let me start where the exercise started, with a phrase I've been using with coworkers for about ten years.

When a developer freezes up before speaking in a design review — when you can see them holding a real objection and swallowing it because the room is full of people with longer resumes — I tell them: it's OK to get lucky. I mean it as permission. Your idea doesn't have to be backed by twenty years of war stories to be worth saying out loud. You're allowed to be right by accident. You're allowed to have stumbled onto the good answer. The work is the work regardless of how you arrived at it.

I believed that about other people for years before I turned it on myself. But turning it on myself is old news — seven or eight years old. The interview didn't pry that gap open; I'd closed it long ago, and I've been living inside the closing of it ever since. What the interview was for was something else. I had been trying to get this lesson onto the page for a long time and failing, and what I actually wanted to know was whether an AI could help me do it without quietly telling me what I wanted to hear — whether the voice that came out the other end would still be mine. That question is where the honesty has to start, and it is about my own conduct, not advice for yours.

The scene I didn't want to write about

Here's the one I led with when the questions got pointed.

I built something. I brought it into a review. The feedback was negative — these developers, the ones in front of me, didn't think it was right. And I remember the exact shape of the thought I had, because I'm not proud of it: Do you honestly think I would come into this meeting, with my track record, and show you code that didn't work?

I want to be careful here, because the easy version of this story is a redemption arc where I turn out to have been wrong, learn humility, and grow. That's not the story, and the AI kept trying to make it that story, which I'll get to. The truth is I still think my approach was sound. I'd defend it today.

And that is exactly why the scene matters. The problem was never whether I was right. The problem was the argument I reached for. I didn't answer the objection on its merits. I answered it with my history. I heard "this code might be wrong" and translated it into "these people can't understand me," and that translation is the whole disease. My track record is not evidence about the artifact sitting on the screen. It can't be. The work in front of you is either sound or it isn't, and nothing I did five years ago changes a line of it. The moment I let my past stand in as an argument about my present, I stopped being able to hear feedback at all. The merit of the work and the worth of the person came unglued from each other, and I welded them back together backwards.

Resentment, and the thing it was hiding

My first honest reaction to other people leaning on their track records wasn't insight. It was resentment. It's OK for him to get lucky, I'd think, but somehow not OK for me. Which meant my arguments always had to be a little stronger than everyone else's. I always felt I was risking more by opening my mouth. I had built a private ledger where seniority was a currency other people got to spend and I had to earn twice over.

It took months for the obvious thing to land. The slogan I'd been handing out for a decade was supposed to apply to me too — and not as comfort. As discipline. "It's OK to get lucky" doesn't just absolve the person whose project failed. It also indicts the certainty of the person whose projects succeeded. Maybe I got lucky on the work that built my track record. Maybe a good chunk of that record is survivorship. If that's even possibly true, then my arguments have no business carrying the weight of history into a room. They have to win on their own, today, the same as everyone else's. The resentment had been hiding a flattering assumption: that my wins were earned and other people's were luck. Turning the slogan around dissolved that.

I'd love to tell you that realization set me straight. It overcorrected me, which is its own scene.

The punch I pulled

Reacting to the meeting where I'd been all track record and no listening, I swung the other way. I went quiet exactly when I shouldn't have.

A junior engineer was working on an a new module in an automation application. The automation could only be testing using captured sessions internally--meaning we were automating against a system we were not supposed to access directly. He wanted to prove a piece of code correct by instrumenting which branches got selected — enumerating the paths to demonstrate they all behaved. It's a genuinely appealing idea until you notice the branches multiply on you, and you're suddenly pressed up against a wall that has a name. He was, without knowing it, wading into NP-hard territory and an workable solution was very unlikely to emerge.

I saw it. And I said almost nothing. I said something like, "I think your solution is turning into an NP-hard problem and you should be careful." And nothing more.

I told myself I was respecting his agency. I was so busy not being the guy from the meeting — not bludgeoning a room with my opinion — that I skipped the higher-level conversation that actually needed to happen. He spent weeks on it. The tests kept not proving what he wanted, because the branches kept fanning out faster than he could pin them down. In the end he came back and recommended abandoning his own approach for the one I'd suggested at the start.

Everyone called that a reasonable outcome. I felt that I failed as a leader, and here is the part I need to state precisely so it doesn't curdle into a brag: my failure was not that I turned out to be right. Forget whether I was right. My failure was that I left him no room to be anything but governed by my being right. By staying silent on the actual structural problem, I didn't give him freedom — I gave him a maze with one exit, and the exit was my original suggestion. He had no choice but to absorb every consequence of my correctness, weeks of it, the slow way. Restraint that removes someone's real options isn't restraint. It's the same authority I'd misused in the meeting, just wearing a quieter costume.

What the correction actually looks like

The fix, when I finally found its shape, is behavioral, not internal. You can't fix this by feeling more humble. You have to do something different in the room, where it can be seen.

It looks like externalizing the decision into a negotiated plan instead of issuing a verdict from authority. It looks like asking the other engineer, directly, what action they would take given the same fork in the road — and meaning it. It looks like putting an alternative on the table that includes the live possibility that I'm the one who's wrong: what if I just got lucky when I hit this exact problem before? That sentence does real work. It hands the other person back their agency, including the part I'd been quietly confiscating — the freedom to be wrong on their own terms. And to lead that way I have to be willing to be wrong first, out loud, before I ask anyone else to be. You don't get to assert your genuineness here. You demonstrate it by offering a choice that's actually a choice.

I want to be clear about a boundary, because "who's right should matter less" is easy to misread as "never trust experience," and that's not it. Under real time pressure, with real stakes, you still act on your judgment. Of course you do. The discipline isn't refusing to act — it's holding your judgment as a possibly-lucky guess while you act on it, rather than as incontestable proof. The high-stakes room is where this thesis matters most, not where it breaks. Admitting "I may have just guessed right again" doesn't devalue the win or the experience behind it. Refusing to admit it — that's the bias, and the higher the stakes, the more expensive it gets.

There's a softer version of the same lie worth naming. The vast majority of AI projects fail; you hear the figure thrown around. Suppose you ship one of the rare successes into production. That doesn't certify your team as top-tier — you may have gotten lucky. And if your next project lands in the failure pile, that doesn't invalidate the talent on your team either. The outcome is not a clean verdict on the people. We desperately want it to be, in both directions, and it isn't.

The bias was strong enough to capture the review

Here's the part that kept me honest, and the opened I began with the process I used for my writing in the first place.

Twice during the AI-assisted interview, the structured critique — and the human steering it — got pulled onto the exact bias this post is about. Twice it fixated on but was the code actually right? The correctness axis. The one thing the whole argument says to set down. And separately it pushed me toward a high-stakes "silver bullet" exception, a room where surely the veteran's judgment just wins. Both times the process had to be dragged back to first-person introspection — back to my conduct, not the verdict.

I sat with that for a while. The tool I'd reached for specifically to catch my blind spot walked straight into it, in real time, while we were examining the blind spot. The gravity toward "who was right" is so strong it bent the instrument built to measure it.

The cheap move here is obvious, and I'm refusing it: see, even the AI did it, so I'm off the hook. No. It runs the other way. If the bias is pervasive enough to capture the review process itself, then my falling into it isn't some personal defect I should have outgrown by year thirty — it's a current you have to swim against constantly, on purpose, knowing you'll drift. That makes my susceptibility more understandable. It makes it no less mine to own. The whole reason to build friction into the process is that the bias is too strong to catch by feeling careful.

So I'll end where I started, with the phrase, pointed correctly this time. It's OK to get lucky. It's OK if some of my track record was luck — that costs me nothing real and frees me to actually hear the work in front of me. And it's OK if the junior engineer, or the new hire, or the AI, gets lucky too. The work is the work. Who turned out to be right should matter less than whether we judged it honestly. I don't always manage it. But I know now which direction to point the humility, and I know I can't trust myself to do it by instinct.