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Playing to Win—Not Playing It Safe

playing-to-win“Playing to win” is a phrase often associated with sports. If you’ve watched a good number of games, you may have heard commentators mention that individuals or teams are either playing to win—really going for it—or “playing not to lose”—taking a more conservative approach. The same terminology can apply in the business world.

Those who frequently get out of their comfort zone are certainly playing to win, while those who aren’t challenging themselves are playing not to lose, i.e., playing it safe. I find that people who don’t stretch themselves and get uncomfortable ultimately go backwards, since they’re essentially “marking time” rather than pushing themselves forward.

Can you tell where you fall on the “play” continuum? When I work with clients who are stuck and need some guidance to ensure they’re playing to win, I ask them what they can do differently as well as what they’re willing to change. Then, to dig a little deeper, I suggest they ask themselves the following questions:

  • What are some of my irrational beliefs or fears that limit me?
  • Am I afraid of failure or success?
  • What stops me from setting the challenges higher and achieving them?
  • Is this a job or a career?
  • What am I passionate about?
  • What motivates me?
  • Am I having fun?
  • What are my current strategies—and are they limiting me or helping me?

This is a lot to ponder. Our perceptions are reality, so I can’t stress enough how important it is to think positively and stop feeling like a victim. It’s also invaluable to define what success means to you and what sacrifices you believe you need to make to achieve it, along with what makes you nervous about success.

You must understand whether you’re pursuing a vocation or an avocation, and be aware of what you love about it—the challenge, the work, the money, etc.—as well as what you gain from it: self-confidence, self-respect or something else.  Finally, are you doing things to limit your progress? Remember that in this “game” you’re actually competing against yourself.

Years ago I worked with a client who faced a crossroad in her career; she had a good job, but she felt professionally unchallenged and didn’t see a bright future ahead if she continued in her current role. After a lot of soul-searching, she decided to take the biggest risk of her life: leaving her high-paying job (and its benefits) to become a freelancer.

Five years later, this woman is enjoying the life of an entrepreneur—something she never dreamed she’d have the guts to do—because she realized that without stretching herself by playing to win, she’d be stuck in a rut, playing not to lose. She won her game, and you can win yours, too.

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