#1493 Learning-Wins

How to Operationalize Winning or Learning


Emerson’s newfound passion for chess has given us an opportunity to go to the next level in our relationship.

It’s hard to put into words just how fun it has been to use his passion for chess as the context to teach him all the stuff you and I talk about all day every day—from dominating the fundamentals to forging antifragile confidence.


His passion for playing and competing in tournaments has ALSO given us an incredible opportunity to spend more time together.

A couple weekends ago, we went on a roadtrip to the Texas State Chess Championships. It was just the boys while the ladies got some girl time together. 5-hour drive on Friday. Games on Friday night, Saturday and Sunday, then 5-hour drive home on Sunday.

We had so much fun on the first day that I fell asleep with tears in my eyes as we played footsie in our shared king-size bed. (And, I just got tears in my eyes typing that as well. Target swipe: Savoring a Micro-Moment of Awesome… 🎯 )


That’s not quite what I want to talk about Today.

Today I want to talk about how we are moving from Theory to PRACTICE with the whole “Win or Learn” ideas we talk about so much.

First, a little more context.

As we’ve discussed, Emerson got REALLY into chess about 7 months ago.

He spent hours and hours and hours a day hanging out with FunMasterMike at ChessKid.com—who is INCREDIBLE. As in, from my perspective, one of the best teachers in the world incredible.

He entered his first informal tournament and won something like 3 games and lost 2. Then he entered another informal tournament and almost won it. Then he entered his first “real” tournament (the Texas Regionals) and won the Novice division.

Then we went to the State Championships.


Emerson and I are DOMINATING our new chess tournament protocol. (That’s like us! 🤓)

Of course, we did our best to get great nights of sleep. We packed all our food so we could eat well. We meditated to mommy’s 7-minute peak performance visualization-meditation and rocked out to her 1-minute declarations before each match.

We even invented a new workout called “Skippy Ball” in which we side-skipped across a huge empty parking lot while tossing a little ball to one another as I tried to find a way to make our 30-minute a.m. workout fun. (It worked. He LOVED it.)


It’s Sunday afternoon.

Emerson is 6-0 as he heads into the FINAL match of the tournament.

If he wins…

He’ll be the Texas State Champion for his JV division.

Note: I started sweating a bit just typing that (lol) (seriously) feeling into how I felt waiting for him in the car after sending him off with a hug after walking into the room whispering “Breathe in through your nose… Chest up, chin down. Calm confidence… You’ve got this, Buddy. LET’S GO!!”


I got off a FaceTime call with Alexandra and reflected on how I would practice my philosophy and MAKE SURE that he felt REALLY (!!) supported whether he WON or he LEARNED.

Then it hit me.

Every time he lost before, we IMMEDIATELY 1-2-3’d it—celebrated what he did well, reflected on what he could have done differently, and made a commitment to use that wisdom to play differently next time.


Each of the times he TRULY did Learn, and the lessons he learned DIRECTLY led to him WINNING as a result of the Learning opportunity.

I wanted him to SEE the connection and that it TRULY is “Win or Learn!


I made a little note file thing on my iPhone.

Title: Chess: Top Learning-Wins

Then I typed: We Win or we Learn and Learning is Winning so we LOVE the winning AND the learning. OMMS!! Let’s go!

Here are the first top Learn → Wins so far!

Learning-Win #1:
Loss = Learn: Very first informal tournament. After accidentally touching a piece, his opponent said he had to move piece. He didn’t know the rule to say “Adjust.” And, he didn’t know the rule that you could call the tournament director over. He lost the game. And he cried. 😕 😢

Learning-Win: On Saturday (and Sunday!) at the State championships, an opponent said that he needed to move a piece that he didn’t need to move. Now he knows the rules so they brought the tournament director over. Had zero fear. Was right. Won game. Celebrated.

Learning-Win #2:
Loss = Learn: He felt tired in the final game of second tournament. Had he won that match, he would have won the tournament. He lost the last game. Cried.

Learning-Win: We decided that we’d do our best to make sure that that was the last time he’d be tired in his final match. Started dominating Fitbit and went beast-mode with our Energy protocol before, between, and during matches.

Learning-Win #3:
Loss = Learn: In his first official tournament (Regionals), an opponent badgered him to accept a draw—asking him over and over and over. He finally did—when he was up a couple points. Cried. Only game he didn’t win as he won the championship.

Learning-Win: Opponent offered draw again and again. He refused. And won. Now knows that an opponent offering a draw is showing weakness and a fear of losing. With rare exceptions, that’s a trigger to be aggressive and win.


As I experience the wonderful eudaimonic joy of waiting to see how my beloved 10-year-old son did in his big match, I’m prepared to Win or Learn…


Emerson comes out beaming.

He won the match.


We celebrated.

Then we MADE THE CONNECTION between each of his Losses and how they DIRECTLY led to his Learning-Wins.

THAT is how we moved from Theory to Practice to (aspirational) Mastery on one sacred weekend in which the game of chess gave us an opportunity to play the ultimate game of life.


That’s Today’s +1.

Got kids? Grandkids?

Nieces? Nephews?

How can you practice your philosophy a little more in YOUR life and help them practice it a little more in theirs?

We Win or we Learn.

And Learning IS Winning so…

We Win or we Win.

Day 1. All in.

With Love…

Let’s go, HERO!