How Do You Win?

Bryan Hendley
7 min readOct 29, 2018

I don’t do this nearly as much as I used to, but when I was a kid, I used to be the Grand Poobah of making up games. This part of me still exists, but I certainly miss the frequency with which I used to display it.

Pretty much anything could turn into some sort of game, complete with an absurd scoring system. I was reminded of this recently when talking to one of my childhood friends who reminded me of how I used to make up games for him when we were practicing hitting in the baseball cage. He went on to play baseball at the University of Georgia, where he had a very successful career, but mentioned that one of his favorite drills was when we created some sort of (seemingly) nonsense game that allowed him to practice his hitting a little more creatively.

Part of it was the fact that it was more fun to attach some sort of value to things that otherwise could have been monotonous. Rather than taking a cut, and having the ball fly into one of the four nets (side, side, top, or back), and then settling in for another cut, over and over again, there was an element of play and fun attached to the work we were doing. So when you finished your turn, you would be able to determine that you had fifty points, or scored three runs, or hit a double, or whatever it was. There was a value attached to each repetition.

Another part of it, was the desire to compete. Sometimes the game was played all alone, with no one else around, and I would compete against myself, or the (imaginary) field. Other times it was played with a friend, or a group of friends. And even though there were other people around, and we might like to measure our score against the score of others, mostly the competition was simply us trying to do better than we had done the time before.

No matter what game we made up, or whether we were competing against another individual or against the field, it was always important to clarify one question before we began,

“How do you win?”

In order to avoid significant frustration, and potential ruining of friendships, the method of scoring, and in turn, determining a winner, had to be established before the game began. To illustrate this point: at a friend of mine’s bachelor weekend I got involved in a pretty intense game of bocce ball. I had never played bocce ball before, so I was a little unclear on the rules but picked up on it fairly quickly and was having a great time playing.

But there were some rules that weren’t fully clarified before we began, so some arguing ensued, which led to me being called an ***hole for the first time (and so far the only time that I’m aware of) in my life. So, clarify the rules before you begin, unless you are comfortable being on the giving or receiving end of strongly worded and false accusations.

You could always add a rule or create an opportunity for bonus points — “all right, if the ball lands in the bucket, it’s worth 100 points” — but everyone had to agree on it. This was not always an easy thing to accomplish once the game began and the competitive juices started flowing. Outside of some rare instances, it is always best to know how to win the game before you start playing.

What about you?

At some point (and it’s likely you’ve already done so), you will attempt to take some sort of measurement of where you are in your life. Maybe you even find yourself doing this daily. We are all well aware of the stress, pressure, and noise that we must navigate throughout our lives. It’s easy to get consumed by those things. Perhaps you’ll find yourself asking those questions we asked ourselves as kids when we were playing those made up games.

How do you win?

This is a really important, and often frustrating question. I won’t dive into why we might ask ourselves this question. For now, it’s enough to acknowledge that the question is asked, either internally or even out loud from time to time. How do I win?

It depends on the answer to another critical question.

How are we keeping score?

Remember, you have to decide this before you start playing, or risk the chance that you become an ***hole, or at least be seen as one in the eyes of those around you. Or worse, in your own eyes. The importance of determining how you are keeping score cannot be overstated. We have to decide how we are going to keep score, and get very clear on that, before we can determine how we are going to win.

Of course, you may decide, at some point, that you want to change how you are going to keep score. Maybe you want to add some bonus points, make some things more important than others, or get rid of certain scoring opportunities altogether. This is allowed, for sure, but it must be done with clarity and with an explicit understanding between all parties.

It’s all invented

The games I used to play and the scoring system that we used was completely fabricated. The roof was worth three points, or thirty points, whatever I decided. You got one shot or five shots. You stood on one leg or closed your eyes.

We just made it all up.

When it comes to answering the question, “How are we keeping score?” you get to decide. It’s all invented any way, so figure out how you want to keep score, and stick with it.

What’s important to you?

What do you value?

What is worth your frustration?

Who do you want to be?

This is how you keep score. Seriously. It’s that simple. It takes some thinking, and some time dedicated to making some determinations about these things, but it’s not as terribly complex as we’d like to make it. Just decide how you want to keep score, then keep your eyes on your own paper. Other people’s scoring methods may look neat, or exciting, and maybe from time to time you test some of them out. But don’t stray to far from your own scorecard.

Decide what to be and go be it.

-The Avett Brothers

You do have to settle in on something and decide. But you get to decide, not someone else. Let’s assume that if you are reading this you have some sort of moral compass. So there are some adopted rules that you have based on morality, or spirituality, or faith, or whatever it is for you, that are sort of foundational. You know, treat people well, understand that your actions affect others, be a good human being (by whatever acceptable metric you use), etc.

But beyond that, (and those things are certainly important) what determines your score? How do you know if you had a good day? What is a success? For YOU.

You gotta figure this out. Without it, you will find yourself in great frustration, or feeling like an ***hole, or looking like one, as you chase things that don’t matter, or drive yourself crazy trying to figure out if you are winning, or wondering if you are playing the right game, or if the game you find yourself involved in is even worth playing. You’ll wear yourself down and wear yourself out. You’ll keep changing the rules, and adjusting the scoring system, trying to find something that works so that you can win, or at least find some enjoyment, but you won’t. You can’t.

Not when you don’t know how you are keeping score.

You gotta figure this out.

Maybe you have read all of this and you say, “This is MY frustration. I don’t WANT to keep score!!!” Great! You don’t have to. Your choice of scoring system is that there isn’t one. You are playing for fun. Again, let’s assume that there is some sort of inner compass that you are living by, and fun doesn’t mean you turn into Veruca Salt and you just do whatever you want whenever you want because, “Hey, I’m just playing for fun”. But perhaps you need to release yourself from the pressure of “winning” and, at least for a season (or maybe forever) allow yourself just to play the game.

Anyhow, I don’t know that I believe that you can win, not in the traditional sense that implies beating someone else. And there is no great scoreboard in the sky. These are all analogies for sure. But I think you can “win” in terms of your measurement of success. And therefore, you can “score” in a way that relates to what you deem important and what value you place on things. In those games that we used to make up, there was no pressure, and mostly, we were playing for fun. So, go for it.

It’s all invented anyway, so invent and settle in on something that works for you. Give yourself the time and space you need to decide what matters to you (what really matters), who matters to you, and what is important to you in this life.

Check out the following resources if you need a little jump start to figure out how to determine your scoring system.

Writing Your Roots

Who Matters/What Matters

If you have any questions about these, don’t hesitate to reach out.

Much Love,


Originally published at on October 29, 2018.



Bryan Hendley

Coach, Teacher, Author, Encourager. - I write words of encouragement focused on personal growth, parenting, and leadership.