You trust your gut because it's been right before. But "right" is exactly the thing you've been measuring wrong.

A hitter never has this problem. His batting average is honest. It counts hits, nothing else, across a whole season, and he can't argue with the number. Your gut is supposed to work the same way: every decision an at-bat, every result feedback, a career sharpening your instincts the way a season hands a hitter a real number. But you keep your own scorebook. You mark every win as good judgment the second it lands. The trouble is that a skilled call and a lucky one produce the same win. In your book they look identical. Train your gut on that for thirty years and it grows certain about things that were never true.

I know, because I trained mine that way.

The Award and the Bankruptcy

At twenty-eight, I won, and the win felt like proof. I was at a company called ThumbScan, and I took a piece of government security technology and repackaged it for the business PC market. We called it PCBoot. PC World named it Security Product of the Year at COMDEX in Las Vegas, in front of the whole industry. I drew the obvious conclusion. My gut was good. I could see what the market wanted before the market did.

Except I didn't see it coming. In early 1988, computer viruses became front-page news. The New York Times ran it on the front of the business section, the story spread to nearly every paper in the country, and overnight every company in America decided it needed security. My product was already built and sitting on the shelf when the panic arrived. I had built a solution that needed a problem, and the people writing and spreading those viruses are the ones who handed it one. It was nothing I did. I hit the timing right, and the timing was luck.

It took an honest audit, years later, to admit that, and the same look turned up the opposite story. The other ThumbScan product was the one I was proudest of. It put fingerprint security on a personal computer, the first one under a thousand dollars you could attach to a PC. Your thumb instead of your password. The reasoning was sound and the technology worked. The market wanted none of it. PCs were barely in homes yet, biometrics sounded like science fiction, and the company bled cash and folded.

That product wasn't worse thinking than the one that won the award. It was the same thinking, aimed at an idea that turned out to be twenty-five years early. Today it sits on every phone, and hundreds of millions of people use it before breakfast. I wasn't wrong about the concept. I was wrong about the clock, and the clock runs mostly on luck. The award and the bankruptcy came out of one gut, separated only by the year each idea landed in.

What I did, years later, has a name. I ran the version of events that didn't happen, stripped the result off each decision, and looked at the call cold. That's counterfactual thinking, and it's the whole skill. It's uncomfortable, because the result already handed you a verdict and now you're reopening it. It's also the only feedback that makes you better.

Why Your Results Lie to You

None of this is your fault. It's a measurement problem. Your gut got trained on bad data, and it had no way of knowing. The more decisions you've stacked up, the more confident it's become, and confidence built on a bad stat is worse than no confidence at all. A junior person knows they're guessing. Twenty years in, the guessing feels like knowing.

Your own record is full of the same thing. Wins you credited to your own judgment when they really came down to timing, or to a competitor's mistake you had nothing to do with. Good calls you stopped making because one of them lost, even though losing was always on the table and the call was still right. None of that is carelessness. You recorded every result accurately. You just recorded the wrong thing, and then you trained on it.

The world isn't helping. Every outcome now arrives with its explanation already attached, ten confident takes by lunchtime, most written backward from the result. I covered that warning in "Hindsight Is Not 20/20."

So go back and run the audit on yourself. Rebuild what you knew on the day you decided, set the result aside, and ask whether the call still holds up without it. The hard part is doing this to wins, because taking apart a success while you're still proud of it feels like bad manners and bad luck at once. That's the reason your wins are where your worst lessons hide.

Read Your Competitors' Moves

You just watched me run this backward, over my own record. It points two other directions too. The first is sideways, at everyone else.

The same move works just as well on decisions that aren't yours. When a rival's bet pays off, the instinct is to copy it. When it craters, the instinct is to swear it off. Both stop at the result.

So rebuild their decision the way you rebuilt your own. Say a competitor ships a feature and it takes off, and three teams in your space scramble to copy it. What they miss is that the feature didn't carry the launch. It landed the week the category leader had an outage, and every angry customer went shopping. Copy that same feature into a calm market a year later and nothing happens, because you copied the move and not the moment. You're hunting for the hinge, the single thing the outcome really swung on, and it's rarely what the headlines credited.

Get this wrong and you don't copy a rival's strategy. You copy the luck that came with it, and luck doesn't travel.

Pressure-Test Your Next Decision

The other direction is forward, into a choice still in front of you, and it's where the skill pays you back the most.

Most of us pick options by their best case. You picture each road going well and take the one that goes best. Turn that around. Walk each option forward until it falls apart, because every option falls apart somewhere, and the one you can't picture breaking is just the one you haven't looked at hard enough. Pull in the alternatives you've already talked yourself out of, and count doing nothing, since that's a choice too. Then decide on the part nobody likes to look at: the downside you'd have to live with. A modest plan you can walk away from beats a brilliant one that takes you down with it.

Most decisions that seem obvious stop seeming that way once you walk the alternatives all the way out. The ones that still look right after that walk are the ones worth making.

Practice Exercise: Audit a Win You're Proud Of

This is the drill that matters most, and the one you'll want to skip. Pick a win from the last year. Not a loss. Something that worked, that you've been glad to take credit for.

Write down what you knew the day you decided. Only that, nothing you picked up afterward.
Run the version where it went the other way. How close did it come, and what would have had to break differently?
Answer straight. Good decision, or good result?

If it's hard to sit with, you're doing it right. The wins you can't bring yourself to examine honestly are the ones costing you the most.

A good decision and a lucky one keep looking identical until you do the work to tell them apart. Do that work often enough and you stop mistaking the breaks that fell your way for things you did well. Over a career, that is most of the gap between people who get reliably good and people who just had a good run.