It Doesn’t Matter if You Win or Lose When You Dare Greatly

Where there is no vulnerability, there is no courage

“At least she tried.”

I told my sister she can write that on my tombstone if I end up being a complete failure by all worldly standards.

She thought I was being hilarious, but I was being honest. I can think of a million worse ways to be remembered. For example, by the opposite: She never tried at all.

Let me give the context for where my mind was at when I said this. I had just finished watching the Netflix documentary Brené Brown: The Call to Courage, where Brown reveals the inspiration for her book, Daring Greatly, came from a famous Theodore Roosevelt quote.

“It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better.

The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again,

because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause;

who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly…”

I had heard this quote before, but this time it hit me like a bucket of ice water, startling me from a long slumber. I used to be a person who dared greatly.

What the hell happened?!

When I was young I was a risk taker. As a nine-year-old gymnast, I threw a back handspring on the high beam when I could barely land one on the floor. That skill was for girls two levels above me, but I didn’t care. I went for things even when they scared me — especially then!

In my early teen years something inside of me started to shift. Suddenly, I was unsure of myself, unconsciously holding myself back in sports, school, and my social life. I began choosing comfort over challenges, acceptance over authenticity, and making myself small over daring to be seen.

At times I shied away from participation for fear of external judgment, like when I refused to speak in my English class discussions even though I was one of the only students who read the books. Other times, I avoided trying new things because I was afraid of finding out I wasn’t any good at them.

I’ve spent many years playing it safe, avoiding the things I want by refusing to admit I want them, even to myself.

What no one tells you about dreams is they’re terrifying. It’s easier to never want anything at all than to want something desperately, just as it’s easier to care less than care deeply.

Caring means allowing yourself to be vulnerable. It means you have a reason to enter the arena where you know bruises and blood, embarrassment, uncertainty, and loss are inevitable parts of the good fight.

Brené Brown claims if you choose to dare greatly, it’s not a matter of if you will fail. It’s a matter of when. This is true, of course, if you look at failure as what happens when you don’t get what you want.

You won’t always get what you want, but sometimes you’ll end up with better. Other times you’ll fall short. That’s part of the process too. Brown reminds us,

“Vulnerability is not about winning. It’s not about losing. It’s having the courage to show up when you can’t control the outcome.”

We all get to define for ourselves what’s winning versus losing, success versus failure. Your definition can be this simple:

If I try today, I win. If I don’t try, I lose.

You might think trying isn’t enough, that it’s our outcomes that matter more than our efforts. I disagree. Effort is everything.

So many people settle for safe when they could be striving for something special. These kinds of people will always find reasons to stay on the sidelines, pointing, criticizing, and maybe even cheering, but never joining the players.

Sure, you can’t lose if you never play the game. Or do you lose by default?

One thing is for sure. Unless you enter the arena, you will never win. If you choose to fight, however, something else is certain. You will get hit.

You’ll make mistakes and fail in the eyes of onlookers. You’ll be attacked with sharp words and have to block them from piercing your heart. You’ll need to work when no one notices and stay humble when they do.

Playing with all of your heart means risking heartbreak and opening yourself up to both joyful triumphs and devastating losses. If it sounds scary, it is.

It’s also much scarier to spend your entire life sitting on the sidelines, where you can neither win nor lose, where you can never freely live.

In the worst-case scenario, if you enter the arena and all you face is failure, at least you failed daring greatly. At least you tried.

I can think of a million worse ways to be remembered.

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