If you’ve spent any time on Wall Street, you’ve heard it. Bulls make money. Bears make money. Pigs get slaughtered.
I started on Wall Street in the ’80s. I worked my way up from a receptionist at Merrill Lynch to a sales assistant and ultimately traded S&P futures for a Swiss company. Futures trading was one of the fastest and least forgiving arenas in finance, and it taught you something about yourself very quickly: whether you knew how to take a loss.
I got good at trading. Not because I picked more winners than the next trader, but because I learned to close a losing position quickly. That discipline separates traders who last from those who burn out.
Pigs get slaughtered because they stay too long, wanting just a little more. I’ve come to think the lesson has less to do with the market and more to do with leadership.
The Trade Isn’t the Hard Part
Every leader eventually faces a losing position that isn’t a stock. A project past its useful life. A hire that isn’t working. A strategy the market has already answered.
The information needed to recognize the problem is often available before a leader acts. What delays the decision isn’t always analysis. It’s the story. We’ve come this far. We’ve invested too much. We can’t admit we were wrong.
The longer we’re invested in something, the harder it becomes to separate the decision from what it means about us. Leaders stop looking at the project and start looking at their reputation. A business decision becomes personal.
Why Leaders Hold On
A leadership team that struggles to take a loss isn’t necessarily undisciplined. Sometimes its members have lost the distinction between what’s so and what they’ve made it mean.
On a trading desk, when a trade goes wrong, you look at the position, the price, and the numbers. You decide what action to take. The market doesn’t care about your story.
Leadership teams don’t always maintain that separation. When a project fails, facts can quickly become interpretations. This means we’re not disciplined. This means leadership will lose confidence in me.
But those aren’t the facts. They’re conclusions about the facts.
What’s so is that the project didn’t produce the intended result. What that means about the people involved is another conversation entirely.
The Discipline of What’s So
The answer isn’t a pep talk about resilience. It’s developing the discipline of staying with what’s so.
When something isn’t working, begin with a clear accounting of the facts. What was tried? What happened? What did it cost? What remains possible?
No judgment. No immediate search for someone to blame. Just an honest examination of the situation.
From there, leaders can decide whether to continue, change direction, or close the position.
One question I find particularly useful:
If we were deciding today, knowing what we know now, would we start this?
That question shifts attention from defending the original decision to examining the opportunity as it exists today.
Hope has its place in leadership. But hope cannot substitute for examining the facts.
Pigs Don’t Get Slaughtered for Losing
Traders don’t necessarily get into trouble because of losing positions. Sometimes it’s the trades that were working. They stay too long, wanting a little more, and stop responding to what the market is telling them.
A leader keeps funding the project, defending the strategy, or waiting for the turnaround, even as new information suggests a different course.
I’ll give you mine.
In 1986, I bought 100 shares of Microsoft at its IPO for $21 a share. At $42, I sold. I doubled my money.
As I write this, after all the stock splits, those shares would be worth $15,370,272.
Where else would anyone second-guess a 100% return?
Forty years later, that decision still lives for me as a mistake. Yet nothing about the trade failed. That’s how much of failure is meaning.
And that meaning can be dangerous. Once you’ve watched one get away, every position can begin to look like the next Microsoft. You hold on longer, hoping this time you’ll get it right.
That’s how pigs get made.
The real lesson I took from trading wasn’t how to predict the market. It was how to stay available to reality.
A loss isn’t necessarily a failure. A win isn’t necessarily proof that the decision was right. Both require the same discipline: look at what’s so, take responsibility for the decision, and respond to what the facts now make possible.
Sometimes the smartest thing a leader can do is close the position—not because the original decision was wrong, but because the circumstances have changed.
Knowing when to change course is part of knowing how to lead.
And the story you tell about your last decision is shaping your next one.
