Oswald Letter

Are you measuring the risk or the reward?

by Dan Oswald

I read something the other day that asked, “Are you playing to win or not to lose?” It’s an interesting question. You may be wondering what the difference between the two exactly is. You may think that if both strategies are successful, the result is the same. But is it? Winning is winning, but not losing isn’t necessarily winning. Not losing doesn’t ensure victory. Things like tie games pop up. It’s not losing, but it isn’t winning, either.

So what’s the difference between playing to win and playing not to lose? Playing to win includes taking some risk to achieve the ultimate goal. It means working harder and smarter to get the prize. And sometimes playing to win—really putting yourself out there—can result in a big loss. To achieve the big win, you often have to risk that big loss.

Playing not to lose means taking less risk in what you do. The result may be victory, but often it means a small victory. You won’t ever hit it big, but you won’t risk the big loss, either. You don’t really put everything on the line and roll the dice, so the payoff tends to be less than it is for those who play to win.

Think for a moment about the football team that jumps out to a 21-point lead in the first half. They have been marching up and down the field, taking risks that have paid off. With the lead firmly in hand, they change their strategy. They begin to get very conservative on offense in an attempt to avoid a big mistake and hope the clock keeps running. On defense, they begin to back off to avoid giving up the big play. Suddenly, they’re not advancing the ball, and the other team is methodically moving down the field. Momentum swings, the 21-point lead disappears, and an apparent victory becomes defeat—because the team with the big lead started playing not to lose.

I think this happens in business just as it does in the sports world. Companies get away from the strategies that helped them grow to where they are and spend more time defending what they have. Individuals do it, too. Instead of taking the risks that have helped them move up the corporate ladder, they get comfortable and then complacent because they have reached a certain level they’re afraid they could lose. It happens all too often. And in many ways it’s understandable, even though it may not be admirable.

I believe that during the recession, many companies went from playing to win to playing not to lose. When times get tough, you start thinking about survival and forget about growth. When times are difficult, more focus goes to cost containment, and there is less focus on initiatives that will drive the business forward.

I understand there are good reasons for this. If you can’t survive the downturn, everything else becomes irrelevant. Sometimes you need to focus on survival so you can live another day. But playing not to lose becomes a habit. Years of managing the expense side of the business instead of the revenue can be habit-forming, too. Many of us are trapped operating in a way that was dictated by the recession. We forget about growth or how we achieved it. We don’t recall or are unwilling to take the risks associated with achieving the big win and settle for small gains that require less risk. The problem is that we’re sealing our own fates.

I’m always impressed when I meet entrepreneurs who have invested all of their time, energy, and money into a new venture. More often than not, they’re burning with a passion for their business—a belief that they are creating a company that will make a real difference. Their passion is palpable in their body language and every word they utter. They’re taking the big risk, and they’re expecting—no, believing—that they will win. It’s how we all should feel about what we do each and every day.

Elbert Hubbard once said, “The man who knows it can’t be done counts the risk, not the reward.” So I ask you, are you counting the risk or the reward? Are you playing to win or not to lose?

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