W – Winning and Losing in Tween Life

Dear Penguin,

We’ve discussed kindness. Curiosity. Money, moods, and even the cringe-worthy in-betweens. Now, let’s discuss something you’ll encounter repeatedly. Winning and Losing.

You’re at that age where there’s competition everywhere in class standings, school games, auditions, even among friends on who’s quicker, smarter, or cooler. And gradually, you’re discovering what it is to try very hard for something. and sometimes not receive it.

I want you to know this now, so that you can remember it when things get noisier in life.
Winning is great.
But it’s not all. And it certainly isn’t all.
Losing is awful.
But it’s not over. Not even close.

I’ve witnessed you radiate with happiness after winning that award for your art. I’ve also witnessed the tears after a quiz round did not favour you. And sometimes, my own behaviour has not helped.
I’ve said things in frustration. Pushed too much. Gotten too emotional over a report card or a competition. We’ve had our scream matches, and I’ve failed as a parent in those moments.

But then there are other times, when we celebrated effort, laughed over attempts that didn’t work out, high-fived even when we lost. I treasure those more.
Because those are the wins that matter most.

True success isn’t in beating someone else. It’s in beating your doubts.
It’s in showing up. It’s in doing better than you did yesterday.
I know the world is going to tell you to get to the podium.
I’m here to tell you that your value is not on a scoreboard.
Losing stings. Particularly when you’re giving it everything you’ve got.
But losing isn’t failure, quitting on yourself is.

You can lose a game, a test, an opportunity. But never lose your passion for learning, for playing, for attempting. That’s the sole true loss.
You’ll find people saying “it’s okay,” but occasionally, it’s not. And it’s okay to feel that, too.
Let’s cry if we have to. But then, let’s ask, “what did I learn here?”
Let’s discuss what actually drives you.

Occasionally, you create something incredible, then question me as to whether it’s good.
I adore that you want feedback. But I want you to believe in your own delight, as well.
You don’t require applause to know you’ve done a great job.
Some of the greatest things you’ll ever make will occur when nobody’s observing.
Do them anyway.

Winning and Losing in Tween Life

Outside rewards. Grades, applause, likes, trophies, will come and go.

But intrinsic motivation, aka doing something because it feels meaningful, will stick. That’s the kick you need.

I don’t care if you win the game, I care more about how you play it.
Did you assist a struggling teammate?
Did you shake hands even when you lost?
Did you not quit, even when you were scared you would?
That, my son, is success.

We’ll always celebrate your victories. But we’ll admire your courage, resilience, and kindness more.

I don’t want you to pursue a number or a title or the next big thing.
I want you to create a life you’re proud of.

That means being patient enough to fail.
The grit to attempt again.
The strength to leave when it no longer serves your joy.

Success isn’t about being the best.
It’s about being you, and doing it with your whole heart.

So, Penguin, whether it’s a cricket game, an art competition, a friendship, or a dream that you didn’t quite achieve this time…

You are not your victories. You are not your defeats.
You are the way you play, the way you grow, and the way you bring others along.

And in that… you’re already a winner.

Always rooting for you,
Maa

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