Education Opinion

Negotiating Winning and Losing: A Lesson From Serena and Venus

By Jill Berkowicz & Ann Myers — September 17, 2015 4 min read
  • Save to favorites
  • Print

American Pharaoh, horseracing’s Triple Crown winner, was defeated in his August race at Saratoga. Football season has begun. The US Open is just over. Last night was the second Presidential Debate. Winning and losing are everywhere around us. And, certainly, we can observe all different varieties of ways to do it.

We place children in a win/lose position every day. One child is chosen to be the line leader; the rest are not. One child receives the highest grade; the others do not. One child is chosen for the lead in the play; the others are not. Consider who sits alone at lunch and who is in the crowd. In many states, now, with teacher evaluations, even the adults are feeling the impact of the number or word that defines their performance.

There are many individual responses to being chosen, as well as many to not being chosen. The challenge with students’ and teachers’ being graded is complicated by the question of fairness of the evaluation methods and tools. For now, let’s put that aside. We want to talk about the emotional muscle that helps children and adults maneuver around their feelings as winners or losers.

This time of year, for most of us, the first days of back-to-school, are accompanied by the U.S. Open. For those who enjoy tennis, the spectacle of the competition can be enjoyed on television. It is not a team sport, except for doubles. It is a narrowing of the field to the one person who is the best. This year, in the women’s division, Serena Williams was on her way to winning the Grand Slam; that is winning the four major world tennis competitions in a calendar year. She had already won the Australian Open, the French Open and Wimbledon. All that was left was the U.S. Open, which she had won for the past three years. Expectations were high.

In the quarter-finals, her demeanor while competing against her sister was remarkable. The match was not an easy one for either of them. Both excellent players, it was clear they were truly competing, but it appeared there was an extraordinary amount of respect for each other. It was interesting to watch this dynamic considering they were both in serious contention for moving on to the semi-finals. It was moving to watch as they hugged at the end of the match, seeing Venus’ face during the hug as open and smiling, revealing real happiness for her sister. She had lost, but her sister had won.

Another observation came when Serena lost the semi-finals to 26th seed player, Roberta Vinci. That match, too, was riveting as the two competed for the win. Yet, in this match, Serena was less willing or able to hide her emotions. Her frustration with herself and her joy when she made a shot were more visible. We wonder at the love or the training that allowed her to contain that in the match with her sister. We can only imagine what that is like. Both women appear to have developed both as athletes and as emotionally nimble human beings. Managing winning and losing is an emotional challenge, and at least in public, they both displayed a stunning ability to do both well.

What are the expectations we hold for ourselves, our faculties, and our students? What are the skills and abilities we possess to manage our wins and our losses? And how can we help students develop as emotionally able to help us maneuver in an environment that hosts winners and losers? The answer is not to make everyone a winner, certainly. No, we celebrate them. It is also to remember that often there is only a day between a win and a loss.

“You tried your best”, “You did really well”, “Maybe next time”, “You can be the best second fiddle”, “Effective is a great standard to meet”, and other attempts at soothing a disappointed child or adult does little or nothing to uplift to the one feeling disappointed or embarrassed. Without the internal emotional skills to locate disappointment or embarrassment in a bigger context, the potential for developing risk-aversion is great. It is important for this to be recognized in classrooms. It can become the gradual ....or sudden....shift away from trying, from competing, from participating. How we deal even with possibilities comes from the manner in which we perceive them. A story told by Ben and Rosamund Zander comes to mind.

A shoe factory sends to marketing scouts to a region of Africa to study the prospects for expanding business. One sends back a telegram saying,


The other writes back triumphantly,


How to develop this in ourselves and others is truly an individual journey. Saying how someone else “should” be feeling is sure to shut him or her down. Inviting them to name the feeling opens the door. Sometimes, even a physical presence of proximity helps. Acknowledging the feeling they are experiencing is a beginning. It is disappointing to not make the grade, or not be chosen. Everyone ought to have the joy and excitement of winning, or making the grade, or being chosen for a leadership role. At its best, it brings the graciousness and the responsibility to be respectful to those who didn’t make it. There was a humbleness to Serena’s win over her sister that was palpable to the observer. Even though we were watching a winner and a loser, it felt like both were shared.

Zander, R.S., & Zander, B. (2000). The Art of Possibility: Transforming Professional and Personal Life. Boston: Harvard Business School Press

Connect with Ann and Jill on Twitter or by Email.

The opinions expressed in Leadership 360 are strictly those of the author(s) and do not reflect the opinions or endorsement of Editorial Projects in Education, or any of its publications.