Learn to Win Without Feeling Guilty

Recently I was playing a card game with my husband and realized how truly hard it is for me to lose at something.

Honestly, this should not have been a new realization. I’m incredibly competitive. But if you would have asked me before this particular game I would have said losing wasn’t that big of a deal.

photo credit: shikiro famu, Creative Commons
photo credit: shikiro famu, Creative Commons

Instead, we played the game several times—and each time I lost (which was most times—I wasn’t very good) I found myself acting more and more like a sore loser.

At first, I tried to ignore it.

I would feel frustrated after losing, but I would try to play it off. I would say “good game,” and tell myself move on. But I wouldn’t move on. I would be in a bad mood about it, sulking around, not really able to explain why.

So the next few times we played, I paid specific attention to what was going on while I played. The game requires speed and quick-on-your-feet thinking, which are not exactly my strengths, so most of the time, I would start to feel powerless and frustrated—like no matter what I did to get better at this game, there really was going to be no winning.

But I also noticed something totally opposite, but equally as interesting.

Every now and then I would win. The cards would be dealt in my favor, or a strategy I tried would work, but as soon as we would near the end of a round, and I would notice I was ahead, I would catch myself slowing down—considerably—so I didn’t beat my husband too badly.

This didn’t make a ton of sense to me, because like I said, I’m really competitive. But I couldn’t ignore what I saw was true:

I was not only scared of losing. I was scared of winning, too.

The more I thought about it, the more I realized there is a really strong connection between winning and losing.

First of all, if I’m not willing to lose at something, I’ll never be able to win at it.

I’m about to release a video course for writers and I’ve invested tons of time, energy and money into getting it ready. It’s something that has been stirring inside of me for a long time and I’m really excited about it, but in order to move forward with creating it, I had to be as willing to “lose” at it as I was to win.

I had to be willing to get started and realize I had no idea what I was doing, or invest all of my time and energy and get a poor response.

I had to be willing to face the critics.

I also had to be willing to face the “crickets”—the less-talked-about response of silence which can often be more painful than the criticism we talk so much about.

This is what we have to face as people—wives, husbands, creatives, business owners, students, job-searchers, friends, sons and daughters—every day of our lives. We have to be willing to put everything on the line, to lose it all, if we’re ever going to be able to get to the place and have the things we so desire and want.

Second, if I’m a sore loser, I’m going to be a sore winner, too.

I think part of the reason I found myself hesitating when it came to winning is because I could feel internally how important winning was to me. By that I mean, somehow in my heart (not so much in my head) I had come to the conclusion that if I won, I was a winner. If I lost, I was a loser.

There is something so very inhumane about that conclusion, I think that must have been the reason I was hesitating.

Winning doesn’t make us winners. Losing doesn’t make us losers. Winning, if anything, makes us responsible. When we are the strongest, savviest, most successful person in the room (not necessarily at a card game, but you get the picture) we have an incredible responsible to notice, provide, care, reach out, back off, understand, and share our “power”.

To whom much is given, much is expected.

Likewise, losing doesn’t make us losers. Losing gives us information. Some of it might be uncomfortable information: I’m not good at this like I thought I was. I’m not all-powerful, all the time. I’m not the center of the Universe. But all of that information—comfortable or not—can be valuable to us if we let it be.

Here’s the craziest thing about all of this: When I can make “winning” and “losing” not about me, but about information and responsibility, I actually believe I can “win” more of the time.

I don’t have to be afraid of winning; and I don’t have to dread losing.

Obviously, when it comes to playing card games, this is not a big deal. My life probably won’t be made or lost in the number of times I win at cards (I’m not very good anyway) but when it comes to “winning” in life—getting a promotion, having a great marriage, accomplishing a lifelong dream, making a comfortable living doing what I love, creating beautiful art—winning matters.

I have to be willing to lose those things if I’m ever going to have them.

And if I’m scared to “win” because I think “winning” at what I really desire puts me above other people or makes me “better” than them, I’ll hold myself back and cut myself off from the incredible power inside of me that was made push and create and cultivate and go after and grow and become something amazing.

I don’t know about you, but I want that.


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Allison Fallon

I write books. I help people write books. I believe a regular practice of writing can change your life.

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