Here is how I would handle it. First background and then the answer.
I had a teacher tell me in 9th grade that it's not all about winning. She was a nice lady but didn't agree with a paper that I wrote on competition. I forget the details including the grade but remember that I essentially said that it's all about winning. Now let me move the clock forward 50 years. I still think that it's all about winning. Now though, I tell students that it is how you define winning and success that give you the most benefit and ability to move forward. Of course we want to win by the score if possible, but to even be on the playing field is a win if you are improving, learning, and competing. I only left the court unhappy after a loss if I let myself down for some reason.
Think of the future
Sometimes surviving to fight another day can be a win especially if you're in a life and death circumstance like cancer or war. I think almost tennis player would agree that to come up short against Rafa in a final anywhere at any time would be a win. I'd take it. Call me number two or three. " I'm good." The fact that I could honestly say that I was in his league or at least was there to be crushed by him would still mean I was better than 99%+ of all the other players out there. This would be especially true if I took games off of him since he doesn't give away gift points or games to anyone that I've seen. If could walk around saying that I met Rafa, Fed, or Novak on the court for a match and wasn't leaving in a wheelchair or on a stretcher and had taken some points, games or even a set would make me feel like winner. If you can't say that, well I suggest looking closely at how you measure success which is another way to say winning.Set Your Own Definitions of Success and Winning
I made it through 40+ years of teaching a sport that I love though I never played professionally. I don't consider myself anything but a winner since I came out of the other side with a lifetime of pleasure on the court, a solid income, respect from those who wanted to learn tennis, and am able to share some lessons to others like this.So when you hear, Winning isn't everything, it's how you play the game." I'd add , no it's how well you play the game. Well enough to call it winning. To quote Vince, "Winning isn't everything, it's the only thing." Then go about defining it for yourself so you can claim success and a win by the standard you set and not those set by others including misguided teachers. Even on the court a score loss can be a win for the future.
What I'd say to the kid.
I'd tell the kid that his teachers must not understand winning and the if they never talked about how to define it or how to measure success then they needed to study the concept further. Otherwise, they are setting up anyone in this competitive world to have their delusions crushed. Did the teachers not chase a win by getting their credentials to become teachers and if they hadn't they wouldn't be there parroting such a false truism since credentials are everything in the realm of Education.
2 Mental Shifts Highly Successful People Make
This is good reading with some concise information.
