Winning Can Stand In Your Way Of Winning

​If we’re not careful, winning can quietly sabotage our future.

Winning feels like proof that what I’m doing works. Which is great, unless it freezes us there. Unless it makes us stop experimenting, stop questioning, stop being curious.

Complacency rarely shows up as someone who is lazy, it more often shows up as someone who thinks they have it all figured out. I have heard it said that success breeds success. This is sometimes true. But it is also true that success can breed stagnation.

Losing begs you to have some conversations winning never begs for. Where am I weak? What am I avoiding? What habits do I have that are not sustainable? What coaches or mentors in my life have I stopped listening to?

Losing strips away the illusions we build around ourselves. It removes the idea that “I must be fine because it worked.” Sometimes winning can be dishonest, while losing tells the truth we don’t want to hear but desperately need.

Why am I writing this?

Because many of us are in the first week of a new year, already committed to “win more.” I don’t want us to become overconfident with the first win and assume we’ve arrived. And I don’t want us to be undone by the first defeat and assume we never will.

Sometimes losing is a better path to winning than winning is. Maybe even most of the time.

And maybe winning isn’t even the best goal. Maybe the better goal is becoming. Becoming demands that whether we’re winning or losing, we keep examining ourselves.

There are valuable lessons in both winning and losing. It’s just been my experience that we tend to ignore them when we’re winning, and we’re afraid to face them when we’re losing.

I truly hope you experience many wins in 2026. Just don’t be caught off guard if, along the way, you occasionally feel like a loser.

That feeling might be the very thing that grows you.