When we are talking about playing to win in the adventure of our lives, the traditional definitions of winning and losing don’t hold up. Of course, there may be times when we need to call on our competitive natures to accomplish what we set out to accomplish. But competing to defeat someone is only one way of responding to the events we encounter. In fact, in the great adventure of our lives, there is no one to defeat.

The first step in redefining winning and losing isn’t determining whether you’ve defeated all comers or won all the prizes; it is more fundamental. The deeper question is: “On this adventure of your life, what is the game you’re playing?”

We are going to consider two “games.” The first — and more common — game we call Playing not to Lose. The second and rarer game we call Playing To Win.

PLAYING NOT TO LOSE

Playing not to Lose is ultimately about avoiding fear. Having said that, if you ask people if they experience fear in their personal or professional lives, they will most likely tell you no. Here is why.

We are bright people, and most of us learned long ago to avoid situations in which fear (defined differently for each individual) might come up.

In many situations, this makes eminent sense. We avoid going down a dark alley because we might be confronted by muggers — or worse — and experience fear. We have a built-in early warning system that alerts us to these kinds of situations so that we can avoid them and thereby avoid experiencing fear. Unfortunately, this precognizant ability often leaks over into other areas of our lives where we aren’t at true risk.

Avoiding situations where we believe we are at risk often starts early in life. A friend tells his version of an archetypal story.

He was in third grade. Like most third-graders he had a vivid imagination and lots of energy, and he loved to draw. One day in class, he was drawing away, oblivious to everything but the smell of crayons, the feel of them on the paper, and the wild and wonderful colors they produced.

All of a sudden, he noticed that the other kids were laughing at him and making fun of his drawing. It stung. The well-intentioned teacher admonished the other children for laughing, but reminded him that the assignment was to color inside the lines.

He felt deeply embarrassed and decided at that moment that he never wanted to experience that kind of embarrassment again. He made a simple decision never to draw again. Even though he enjoyed drawing, it became more important never to risk being “humiliated.”

It’s not important to know whether our friend wanted to be an artist and his aspirations were destroyed in third grade. We will never know — because he chose a path designed to avoid situations where he might be embarrassed like that again. His early warning system went on alert at that moment and it generalized. It no longer warned him simply about drawing; it helped him avoid situations where embarrassment might occur. It influenced all kinds of choices he made later in life.

Our early warning systems are put on full alert early in our lives to help us avoid situations in which our status or sense of belonging might be threatened. And so when we are asked whether we experience fear, the reasonable answer is no, because we have often spent a lifetime avoiding those situations where fear or embarrassment might result.

We call this strategy Playing not to Lose. Playing not to Lose is like playing tennis against eight-year-olds who have never played before. We are in no jeopardy of “losing”; we can declare ourselves winners after every match . . . but we are not playing (or living) anywhere near our potential because we are afraid of losing.

PLAYING FOR SURVIVAL

We often Play not to Lose because we believe that the consequences of embarrassment, or “losing,” are awful. “Awful,” according to psychiatrist Dr. Maxie Maultsby (a man we will meet in the next part of this book) means “100 percent bad.”

Ask yourself:

In our imaginations we believe that the consequences of being rejected are so awful that they are akin to psychological death? “I’ll be embarrassed to death.” When we Play not to Lose, the game is about survival. To survive we need to avoid the awful stuff that we have imagined over the years might happen to us if we take a risk.

This avoidance leads to the regret that Dick Leider’s seniors were talking about. They chose not to take the risks required to grow in relationships or at work because they were afraid of what might happen. So you avoid telling people you love them because they might not say it back. Avoid striking out on your own because you might fail. You play it safe.

PLAYING TO WIN

In its simplest sense, Playing To Win is consciously choosing to not automatically avoid situations in which we might fail, be embarrassed, or be rejected. Why on earth would we consciously choose to do something that could lead to failure, rejection, embarrassment, or worse? Because our goal is to grow. Playing To Win is concerned with engaging with life, with the desire to thrive on the adventure. Emotional, spiritual, and intellectual growth are the game’s payoff.

This is easy to see in the area of emotional growth (although easy to see doesn’t mean easy to do!). Take a key component of emotional maturity: bouncing back from failure and rejection. There are no doubt some genetic aspects to the ability to “bounce back.” Yet, even so, the way we are going to truly improve on our ability to bounce back is by experience — by trying something out, failing, getting over it (“I didn’t die!”), trying again, and so on. Remember how you learned to ride a bike? The human being is wired to learn by experience. This is especially the case for emotional and spiritual growth.

Playing To Win means consciously choosing to experience those situations that will help us grow. Further, it means going into those situations wholeheartedly, committed to going as far as we can with all that we have.

A CONSCIOUS CHOICE

We choose to Play not to Lose because we believe our emotional survival is at stake. We choose to Play To Win in order to learn, grow, and thrive. Although it is not often that black and white, the critical moments of our lives and careers often come down to a choice between the two: Am I going to Play To Win or am I going to Play not to Lose?

Ask yourself:

• Where have you chosen to take risks and, as a result, grown — often in ways you didn’t expect? That’s Playing To Win.
• Where have you given 100 percent regardless of the potential for failure — and been satisfied with the effort regardless of the outcome? That’s Playing To Win.

Playing To Win is about making choices — especially the important ones — consciously rather than simply letting our early warning system direct us away from possibly difficult situations. As we will see, consciously choosing requires us to know what we want, to understand how we want our lives or a particular decision to turn out. Consciously choosing requires us to think more clearly and objectively about how to get to the game’s payoff. Being more conscious of our important choices also means that we are constantly asking ourselves: Are there real things here to fear (do I really need to fear embarrassment, for example), or am I just following the herd by balking at another painted cattle guard?

TO BE COMFORTABLE BEING UNCOMFORTABLE

Playing To Win also asks us to take on this ability: to be comfortable being uncomfortable. Often the desire to be comfortable is how the choice to Play not to Lose is made. I will be more comfortable if I don’t take this risk. I will be more comfortable if I avoid asking difficult questions: Am I doing what I want to do? Do my life and work have meaning? Am I in denial? Am I in love or am I just passing the time with someone?

Emotional and spiritual growth demand of us that we be uncomfortable, that we take risks when we are uncertain of the outcome. Playing To Win asks us to be comfortable in that uncertainty. Playing To Win asks us to be comfortable asking uncomfortable and difficult questions of our soul. This is a path to growth.

A while ago I had the opportunity to see this in practice. I was sitting with a senior executive team that had decided to embark on a significant change effort. They had all agreed intellectually to the need for the change. Now the launch moment was at hand. You could see that the emotional impact was just hitting them — we might fail, we might look ridiculous if we fail, and so on. The CEO spoke up first: “I am uncomfortable with going ahead.” A chorus of executives joined him in expressing their hesitation. They were all emotionally uncomfortable with taking the risk of doing what they knew intellectually was for the best.

Finally — in what was an act of courage — a woman in the group stood up and spoke her mind. In essence she said, “This is between choosing to be comfortable and continuing to do the same old stuff — which might in the long term put us out of business. Or we can choose to do the right thing and as a result accept being uncomfortable. As leaders, it is our responsibility to not avoid doing what is right because we want to be comfortable.”

There was an “uncomfortable silence,” but her impassioned words carried the moment. The group chose to go ahead. Playing To Win asks us to choose being uncomfortable in order to grow.

WINNING

Winning, then, does not mean defeating someone else or achieving a goal that doesn’t really stretch us. Winning in the adventure of our lives means that we are going as far as we can with all that we have. Goals are good — they make interesting benchmarks. Competition can help us push ourselves (the word competition comes from the Latin word competere, which means “to strive together”).

But are you really stretching yourself when you try simply to “win”? Are you growing? Are you pushing your limits? Do you feel alive? Do you feel excitement, the anxiety of trying something that really pushes your abilities, good exhaustion at the end of the day, an I-can’t-wait-to-get-up-in-the-morning sense of anticipation for each new day? Are you going as far as you can with all that you have? Are you Playing To Win or are you Playing not to Lose?

Clearly, Playing To Win is how we thrive in the adventure of life. Playing To Win becomes an easier and more natural response when we are emotionally mature, when we have access to and control over the emotions needed to respond optimally to life.

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