Are You Playing To Win?

“As you all know, first prize is a Cadillac Eldorado. Anyone wanna see second prize? Second prize is a set of steak knives. Third prize is you're fired.” -Blake, as played by Alec Baldwin, Glengarry Glen Ross

I like winning. It’s a good feeling when you gave your level best and that was enough to put you ahead of all the other competitors. There’s also something special about winning that makes you feel clever, qualified, and worthy.

But the honest truth is that pretty much every human on this earth will rack up more losses than wins over the course of their lives. Losing is a huge part of life. It permeates every single thing that we do. Whether it’s our jobs, our hobbies, or just our everyday lives. We will experience losing, and we will likely experience it frequently.

I have this friend named Ken. He’s literally one of the nicest and most caring and considerate people that I know. He designs games and he also hosts epic game nights at his house every month. Recently, I attended a special game night that he calls, Kencon. It’s a birthday celebration where we play games, and have fun, and even donate food to those in need. Ken had these special acrylic chips made that said Kencon 2019 and also included what has come to be his mantra for games, “I play to grin.”

It’s a great mantra to play games by, right?

For me, it also serves as a nice reminder that even when I am getting completely stomped while playing some board game, I can still enjoy myself. As I mentioned above, I do love to win and there have been times in my life when I haven’t always been the best sport when I am losing. I don’t mean to be frustrated about losing, and for the record I am not upset with the other players. In general, I am annoyed at myself for not being a better player.

Here’s a question I have asked myself before when upset at having lost. “Would you have played the game if you knew you were going to lose?” Without hesitation, I can say that my answer is yes nearly 100% of the time. The reason behind that fact, is that I honestly love playing games with my friends. Win or lose, it’s about the experience.

Now back to Ken’s catchphrase, "I play to grin.” While I love it, I think it’s wasted if we only apply it to board games, because as I said at the beginning of this article, we are going to lose at a lot of things in our lives. I believe it’s imperative that we start asking ourselves questions like, I am playing to win at my job, or am I playing to grin?

Are money and success my only goals? Or am I also in it for joy and fulfillment?

I know for a long time in my career, I was in it for money and success. I didn’t enjoy most of what I was doing but I was good at it and I kept getting promotions. If you are only playing to win, then being promoted at your job will very likely scratch that itch of more money and more success.

When you are playing to grin, that doesn’t stop money and success from being good things. It does however put those things in the back seat and take away the power they have over you. Playing to grin means that you won’t stay on a career path for the wrong reasons. And I’m not saying that money and success are the wrong reasons to stay at a specific job. Unless you can truly say that those are the only two things that keep you there. In that case, I am saying that you’re doing it wrong.

On average, Americans spend at least 1/3 of their lives working. That’s a whole lot of your life to spend being unhappy. The fact is that the old saying is correct, money doesn’t buy happiness. Neither does a fancy title. I used to say that the amount of unhappiness that I would be willing to suffer at my job was totally proportional to the amount of money I was paid. And it wasn’t untrue. I can honestly say that my least happy points in my work life were without a doubt when I was being paid the most. Slowly but surely as my job got less fulfilling, I was also getting paid more and more. And that fact helped me push aside my feelings and stick with something I didn’t want do.

Eventually, with some help from my wife, and my coach, I wised up and moved on so that I could do work that I found more fulfilling. Studies show that as many as 80% of people don’t even like their job. That’s a startling number. Don’t get me wrong, I know when I talk about leaving a job that made me unhappy — despite it having short term financial consequences — I am speaking from a place of extreme privilege. I understand that not everyone in who is unhappy in their job is there because they are playing to win. Many of them are in that job because it’s a job, and they need it.

Here’s my challenge to you. If you find yourself a job where you are only playing to win and you aren’t getting fulfillment, then I encourage you to consider your options. Think about the things in life that bring you joy and take a step towards making the needed changes to move in that direction. Even if you are in the position of needing the job and feeling trapped in it, there may be other options…

Reach out to me and let’s see if we can’t work together to figure out the path that gets you where you want to be in life and work. You can reach me at jason@yourturncoach.com.

If you’re one of the people like me who has already found themselves in job that allows you to “play to grin”, then I ask that you do your level best to help those around you do the same. It’s absolutely achievable if we all help one another out.

-Jason

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Jason Slingerland