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How to Win at Anything

Last year I started as an assistant coach of the local varsity high school tennis teams and this year I took over as head coach.  Yesterday I got some feedback I cherished. A parent of a team we played against contacted me to say “I am truly impressed by your teams character and disposition. I wish all athletes had that sort of positive attitude”. This hit me in the feels because it struck a nerve with my outlook and it’s exactly why I volunteered to lead the teams.

After starting back playing tennis about seven years ago I wrote an essay on Collaboration vs. Competition1 explaining some of my outlook on sports, education, and life.  Although I’m sure there is a myriad of reasons why I started playing, part of the reason I took up tennis began with me quitting football. My father had always wanted to be a football coach and he attended the University of South Carolina with that in mind. His first job was given to him by Bob Fulton who was the announcer for the Gamecock football games.  Needless to say, he got pretty involved in my early football days. I remember vividly being completely knocked unconscious during a football practice. The coaches pulled me up off the ground by my face mask, patted me on the ass and said something to the extent of “get back in there Windham”. I was still dizzy seeing ‘stars’ and I took my helmet off, slammed in on the ground, and started to walk off the practice field. My father said “if you walk off this field, you’re never playing football again”. Needless to say, I never played football again. 

I had a childhood friend who’s parents were really into tennis who introduced me to junior leagues and tournaments.  I got good enough to compete at a regional level so I stuck with it. Loosing at tennis is still fairly tough mainly because it’s a drawn out process and it’s just you out there shouldering all the responsibility of a loss. I remember my father coming to one particular junior match I was losing. I was already acting defeated midway through the match and he disappeared even though I had expected that he was my ride home. I apologized for my attitude when I got home and he said something along the lines of “I left because I didn’t enjoy watching, you didn’t embarrass me at all, you embarrassed yourself”.  Years later I saw an interview with Roger Federer where he shared a very similar story2

I’ve never been one to hype the motivational type ‘sports is life’ metaphors because I mostly find the majority of them relatively shallow emphasizing competition in life. Needless to say, I’ve taken that lesson to heart and I learned something really valuable in the process. If you’re giving it your best and having fun in the process, you never really lose. Part of the having fun in the process means that you’ve gotta feel good about what you’re doing and the key to that is being honest and fair to yourself. In a lot of ways, I think sports are an achievement of humanity alongside of the arts.  In a world of constant competition for resources, we’ve decided to take the time to play games with very little consequence. I often joke when folks get into conflicts on the court to imagine if we were playing this game with guns where we just shot at each other from the other side of the court. And although I’ve seen grown men swinging their tennis racquets at one another, It’s not exactly Roman gladiator games and the only thing we actually stand to lose is ego.  If you can put that aside and have fun, you never really lose. 

You can apply that same approach to almost everything. Sure, there are cases in life where you lose and it’s very serious. Even if you’ve been diagnosed with a terminal illness or can’t afford to feed yourself, I’d argue that keeping your chin up and giving it your best will still get you much farther than the alternative. I’d even go so far as to suggest that doing so may actually give you an advantage. I’d imagine it’s extraordinarily tough to ‘have fun’ under those sorta circumstances, but I’ve personally seen folks do it. I apply it to even the smallest of challenges. I can smile right through the most contentious of business meetings knowing I’ve done my best and realizing the consequences are generally minor. I can let someone vent in an argument without needing ‘win’, I can look at my work contracts not as a competition but as collaboration, I can look at life hurdles not as losses but as challenges, and I always try to find some fun in it. It is how I try to play the game. 

Our final match is next week against the strongest team in the division. The girls varsity team this year was made up entirely of beginner players so we’ve managed to lose every match this season. I noticed that it started to wear on the players late into the season.  I started the practice season this year with just two rules: always try to have fun and give it your best effort. I ended the season reminding the players that challenging yourself to try something new and giving it your best is the epitome of success and in that regard, they are all winners. I’ve watched the players exemplify that attitude on the tennis courts.  They all thanked me for introducing tennis to them, asked to continue the practice season, and committed to coming back next year. I’ve had fun coaching so I already felt like a winner, but when I got that message yesterday afternoon, I knew we had really won the season. 


  1. Collaboration vs. Competition – https://davidawindham.com/collaboration-vs-competition/
  2. Roger Federer Interview – https://player.vimeo.com/video/170668278?#t=1m5s