When Winning is Losing

Ah, I thought I had finally found a topic on which several books had not already been written.  Wrong again.  When I searched Amazon for books entitled “When Winning is Losing”, several popped up.  But surely, I thought, Google Gemini won’t be able to generate any ideas on this topic!  Bingo.  In one second it came up with several examples.  Oh well, I consoled myself, at least I can still provide my unique view on the subject.  Even though my effort may not offer anything significantly new to the literature, at least I will have tried.  And maybe it will help to preserve my soul a little longer in this increasingly complex and chaotic culture in which we live.  As I said to a friend recently, it’s better to focus on the content of our lives given the context in which we are currently living them.     

Indeed, I’ve started to think about my posts in much the same way as Margaret Renkl, one of my favorite NYT columnists, thinks about her Sisyphean, environmental efforts to save the plants and animals on our planet.  While she often feels like her work does not seem to make any difference, she finds that trying nurtures her soul.  I understand why it’s a discouraging and depressing time.  It seems like we are losing on multiple fronts:  the environment, liberal democracy, DEI, human rights, justice, equality, housing, etc.  So I thought it might be helpful to flip the script – to ask, “when is winning losing?”  Looking at the win-lose phenomenon from another perspective may not only give us insights, but also kindle some hope.  So here we go. 

There are several easy examples to illustrate when winning is losing.  One of the books that came up in my search on this subject was, When Winning is Losing:  Thin enough can never be achieved.  This book illustrates how anorexia and bulimia are losing propositions even if the person with an eating disorder thinks she/he is winning.  In this case, “Winning” the battle with weight means losing your health in the process.  When a person gets into this cycle, it can result in an obsessive mindset that lasts for years.

Gambling was another example.  In the book, Counseling Problem Gamblers:  When Winning is Losing, discusses how wins at the casino only fuel the obsession and often result in significant financial losses, relationship challenges, mental health problems, legal issues, etc.  Winning at Roulette, black jack, or craps once in a while may provide just the right amount of intermittent reinforcement to trigger a downward spiral that is hard to escape.

Title: Winning. | Credit: spyderella | Source: Flickr | License: CC BY-NC 2.0
Title: Winning. | Credit: spyderella | Source: Flickr | License: CC BY-NC 2.0

Winning at video games is more recent manifestation of this paradox.  When kids get hooked through seductive algorithms to win virtual tokens for their successful mastery of the game, they begin to lose perspective on what is real in life. In many ways, the generation that has grown up in this virtual world has been groomed for material obsession instead of artistic innovation. Perhaps we should focus more on real threats, like how social media platforms are reprogramming our kids to be obsessive and unhealthy, instead of freaking out and imagining that LGBTQ teachers are trying to groom kids for a gay lifestyle. I also wish leaders in fields like the social media and the gaming industry would take more enlightened approach to creating games that foster innovation and healthy cultural norms as much as shareholder value. 

In the TV series Friday Night Lights, the idea of “winning is losing” is clearly apparent. It shows the downsides of young athletes dedicating their lives to football only to end up sacrificing their grades or their bodies in pursuit of glory. I was so moved by the series that I did some research and wrote a post on the topic. Here is one paragraph from that post. 

  • According to the Department of Veterans Affairs and Boston University, where researchers studied the brains of 165 people who played football at the high school, college, or professional level, 79% of the 131 studied had evidence of CTE (chronic traumatic encephalopathy). Of the brains studied, 91 of them belonged to former NFL players, and 87 of those 91 (96 percent) had signs of CTE.

These jarring statistics make the case—we may think we are winning when we are really losing. 

In a recent Heather Cox Richardson letter, she discusses how the relentless and ruthless pursuit of winning by a few (mostly white men) has resulted in significant losses for most of humankind. In the letter she shares how Eleanor Roosevelt chaired the United Nations committee on Human Rights after World War II to address that issue. Here is a paragraph that captures the point of this post as well as any I could imagine:

“The final document began with a preamble explaining that a Universal Declaration of Human Rights (UDHR) was necessary because “recognition of the inherent dignity and of the equal and inalienable rights of all members of the human family is the foundation of freedom, justice, and peace in the world,” and because ‘disregard and contempt for human rights have resulted in barbarous acts that have outraged the conscience of mankind.” Because “the advent of a world in which human beings shall enjoy freedom of speech and belief and freedom from fear and want has been proclaimed as the highest aspiration of the common people,” the preamble said, “human rights should be protected by the rule of law.”

Yup, when winning is achieved through barbarous acts and contempt for human rights, the whole community loses. 

Winning, in the traditional sense, implies achieving a desired outcome, surpassing competitors, and reaping the rewards of success. Yet, there are instances where the pursuit of victory, the relentless drive to be the best, and the intoxicating taste of triumph can lead to unintended consequences, transforming a perceived win into an eventual loss. As a result, winning paradoxically becomes losing.  Here are some principles underlying this paradox:

  • When the means used to achieve victory compromise ethical principles or moral values, then winning morphs into losing.   For example, a business that engages in unethical practices, such as exploiting workers or misleading consumers, might experience initial financial gains, but ultimately faces legal repercussions, consumer backlash, and irreparable damage to its brand image.
  • Similarly, when the pursuit of status, wealth, and power becomes all-consuming, it can lead to neglect in other vital areas of life. The workaholic who dedicates every waking hour to climbing the corporate ladder might achieve professional success, but at the cost of their personal relationships, physical health, and overall well-being. The student who prioritizes academic excellence above all else might earn stellar grades, but miss out on social interactions, extracurricular activities, and the development of essential life skills. In these cases, the imbalance created by an obsessive focus on winning in one domain leads to significant losses in others.
  • Winning can also become losing when it creates unrealistic expectations and a fear of failure. The individual who has become accustomed to winning might develop an intense aversion to losing, leading to anxiety, avoidance of challenges, and an inability to take risks. This fear of failure can stifle creativity, innovation, and personal growth, ultimately hindering future success.

The most current and dramatic example of winning = losing is the victory of Trump in the presidential election. Many of his followers are reveling in the win, even those who will be the most likely ones to lose if he is able to implement what he promised regarding tariffs, mass deportation, and cost cutting. Also, his intentions to extend tax breaks for the wealthy and reduce regulations for big business will only increase inequality and jeopardize the safety of all of us. And, if Pete Hegseth, his appointee for the Secretary of Defense, wins confirmation, America could suffer catastrophic losses in our geopolitical conflicts with Iran, Russia, North Korea, and China. In the Trump administration, for all but the wealthiest few, winning means losing. 

I know, I know.  This post now looks like a big set-up to deliver another shot at Trump. Even though there may be some truth to that criticism, I will still stand by the overlying principle: some wins result in big losses. 

In a time when it feels like we are confronting the loss of so many of the values and norms that we cherish, I thought it might be helpful to ask, “What price do the “victors” pay when winning at any cost drives their decision-making?” The same could be said about the dialogue and discourse we witness in daily interactions. When does “winning a debate” result in failing to understand more fully the perspective of the other person? The intent is not to bask in the smugness of defeat but to inspire us to make a small difference where we can simply to nourish our souls during this avalanche of soul-sucking experiences. And yes, small wins feel good.

I’m hoping we can connect with people who hold similar values and form small communities that advance the common good. I’m hoping we will be able to focus more on the content of our lives than the context of our culture. I’m hoping for small wins and a few moments of joy over the coming years. Finally, I’m hoping we can soothe our souls by continuing to try. May it be so. 


Also published on Medium.

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