Winning and Losing

You Can’t Win Them All

Most driven people tend to see their work as a winner-take-all scenario, in which the only favorable outcome is a win. A “win” could mean a successful sale to a big customer, it could mean securing funding for your company’s next round, or it could mean winning the upcoming football game. The benefits of winning greatly outweigh those of losing in almost every scenario, but I’m going to play devil’s advocate here and say that there are positives that come from every loss and negatives that come from every win.

Positives of Losing:
1. Reality Check. It is human nature to want to believe all the wonderful things people and the press say about you or your company. Instead of riding the rollercoaster of emotions that go along with defining yourself by the current opinion of others, put your earplugs in, your blinders on, and your nose to the grindstone. Ultimately, the strength of your product will determine how successful you are, not the positive stories on a website or the negative tweets from some creep in his mother’s basement.

2. Friend or Foe. With each success comes more bandwagon fans. Friends and coworkers that are there, and willing to improve after a win or a loss are the ones you want to keep around.

3. Tax write-off. Some losses have tax implications. I couldn’t think of a better number 3 at the time of this writing.

Negatives of Winning:
1. & 2. Group Think & Resting on Your Laurels. “Whatever has worked in the past will continue to work in the future.” You’re probably right, but it will be progressively less effective as competitors improve. Any forthright financial advisor will tell you that past performance does not equate to future success. Learn. Improve. Grow. Innovate. Evolve.

3. It’s easier to overlook mistakes when you win. “Winning makes everything better.” The quote is true… until you lose. Don’t change your attention to detail or your willingness to correct mistakes because of the outcome.

It’s difficult to talk about winning and losing without listing millions of cliches. I’ve been trained in cliche-use since I began organized sports, so forgive me, but it’s not whether you win or lose, it’s how you play the game (and how you learn from it afterward).