“Winning” in leadership can become a trap when it defines your identity instead of your impact.

Remember Charlie Sheen’s very public meltdown in 2011? That’s when we were introduced to the “Tiger Blood” that supposedly ran through his veins.

When someone asked if he was bipolar, he said, “I’m bi-winning!”

One of the most recognizable celebrities. The highest-paid actor on television. And completely unraveling. Drug abuse. Imploding marriage. Life out of control.

“Winning!” became a meme.

Who doesn’t want to win?

Almost all of my clients are hard chargers. High performers. They want to win—in other words, to be winning in leadership in every season.

I like winning too. I understand that winning isn’t everything, even winning in leadership. But it can become a trap.

It tricks leaders into trying to live up to their own personal “Mythology of Being Me.” It’s the core ingredient of the hero identity. It’s the Instagram image of a person—well-posed, edited, and without context.

Some begin to believe they actually are larger than life.

Others know they aren’t but feel the need to maintain that image.

I’m bringing this up for two reasons:

• There are leaders who need to win. But no one can win everything, all the time. So when they don’t win, they deny it, blame others, cheat, or do something else to protect how they see themselves. Their worth.
• Then there are leaders who want to win. But “winning” all the time feels unachievable. So they feel discouraged or overwhelmed. And they give up trying to be effective at the things within their reach.

First, a Definition

I’m not sure Charlie Sheen knew what he meant by “winning.” I doubt he did either.

But “winning” is a comparative term. It implies outperforming someone else. It’s the opposite of losing.

When “winning” becomes our primary feedback loop—how we gauge our worth—it becomes dangerous, especially when you confuse it with winning in leadership.

Why?

Because when it becomes your identity, then losing—or even “less success”—isn’t just an experience. It’s an attack on your self-worth.

And no one wants to be a loser.

That’s how capable leaders implode in full public view, convinced they’re still “winning.” Or scrambling hard to convince everyone else.

The 3 Deceptions of “Winning”

I’m not against winning. I’m very pro-winning.

But “winning,”when your identity and worth are tied to being the best, all the time – that’s dangerous.

Here are three lies leaders start believing when “winning” becomes the point:

1.The Deception of Applause or Approval

• External validation feels like success. It starts to define success for you.
• Danger: You start performing for others’ reactions instead of leading from conviction.

2. The Deception of Activity

• You confuse being busy with being effective.
• Danger: Activity becomes a proxy for progress.

3. The Deception of Winning Past Battles

• You believe past wins make your judgment unimpeachable now.
• Danger: You stop learning. You stop growing. You avoid new challenges.

Charlie Sheen as a Parable

Sheen didn’t start talking about “winning” until his life was clearly in free fall. Publicly. Spectacularly.

He needed to believe he was winning. So he made that his only metric.

Until he hit rock bottom.

That’s the trap: when you’re addicted to momentum, you can’t recognize the warnings.

Redefining “Winning” in Leadership

Here’s the irony: the better some leaders get at “winning,” the more they lose.

Over a third of Olympic gold medalists experience the “Gold Medal Blues.”

Successful entrepreneurs, after selling their companies for millions or billions, often report depression. (Over 70% of business owners who sell report this.)

In the big “win,” they lost clarity. Or connection. Some lose their families.

To be clear—I’m pro-ambition. I like winning. But some forms of “winning” warp your perspective about what winning in leadership should look like.

When it becomes your identity, you stop making decisions based on conviction. You make them for optics, likes, or numbers on a spreadsheet.

You protect a personal mythology. You chase applause, activity, or outcomes that signal success—but have nothing to do with purpose.

The Metrics That Matter

“Winning” isn’t the problem. It’s what you call winning, and how you measure it, that matters.

I won’t define that for you. But I’ll say this:

Vague goals and self-validating stories burn leaders out.

You need a way to track progress that makes sense of your life—not just your business, especially when you think about winning in leadership over the long term.

Here’s a tool that helps:

• Create clear, values-aligned goals: What do you want in terms of family, contribution, impact, health, growth, friendships?
• Define progress. Otherwise you’ll chase moving goalposts.
• Build consistent, honest input from people you trust. You can’t see your blind spots. But they might.

If you want to win, especially if you care about winning in leadership, make sure you’re in the right game.

The Real Win

I never followed Charlie Sheen. I don’t think I ever saw a full episode of Two and a Half Men.

But I recently heard an interview and thought, “I didn’t know he was still alive.”

Turns out, he’s been in recovery since 2017. And he sounded like a completely different person.

He acknowledged that he didn’t just wreck his life, he hurt a lot of people. He sounded humble. Like someone who’s owning it and trying to make amends.

That caught my attention.

When “winning” was his catch phrase, he wasn’t winning at anything. Not even things that didn’t matter.

Now? Maybe he is. I hope he is.

Your Turn

What are you calling “winning” right now? And is it what you really want to win?

Is it for applause or approval? Is it just keeping you busy?

You can’t win everything. But you can win the right things. Make sure you do, especially when it comes to winning in leadership.

Take good care,

Christian