Early in my career, I had the opportunity to work for a CEO who permanently shaped the way I think about business, leadership, and risk. This was the early 2000s, and our industry was clearly on the verge of major change. A lot of companies saw the signs. Most chose to wait, hedge, analyze, and reanalyze. Not him. A nod to him here…Mike O’Brien is his name.

He looked at what was coming and made a clear, bold call: We were going to move first. Act aggressively. Bet on transformation. That decision kept the company vital, relevant, different—and years ahead of competitors who chose caution over action. But what stuck with me most wasn’t just the action we took—it was a line he said that I’ve repeated probably a hundred times since:

“At the end of the year, I’d rather be 12-5 than 2-0. I’ll take the losses if it means I also stack up the wins.” (I’m paraphrasing this a bit).

That idea…12 wins, 5 losses…became a core operating principle for me; those who’ve worked alongside me can attest to this. It’s a mindset I’ve tried to carry into every team, project, and strategy conversation since. And it’s one I believe more business leaders need to embrace.

In too many organizations, we over-index on being right instead of making progress. We chase consensus, wait for the perfect data point, or delay action until the risk feels minimal. That’s how you end up 2-0. Undefeated, sure. But also underwhelming. And ultimately, irrelevant.

In today’s business environment where markets shift fast, innovation cycles compress, and competition is everywhere, urgency matters more than certainty. Acting decisively matters more than getting it perfect. No one remembers the cautious moves you never made. They remember the bold ones that changed the game.

Now, let me be clear: I act urgently but not recklessly. I only charge ahead with a plan and learning from past mistakes. The 12-5 mindset requires thought, discipline, and agility. You take calculated risks. You move fast. You absorb losses, for sure, but you also make sure you learn as you go. And then you keep moving: the goal isn’t perfection…the goal is progress. And progress is sometimes (often?) lumpy.

Look at the scoreboard you’re chasing. Are you trying to be perfect or are you trying to win? At the end of the year, what will you be more proud of a cautious 2-0, or a bold 12-5?

I know which one I’ll take.