the curse of knowing how to win

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Jun 03 • 3 min read

I got wrecked at pickleball


I’ve got a buddy that travels the world spreading the gospel of pickleball.

He’s played on floating courts in the ocean.

In city centers under highways.

And last week he invited me to the Soho House of Pickleball venues to grab a few games.

The last time I’d played was last fall when I flew to Georgia to hang with a client. Got my ass handed to me.

No shock, because the time before that? High school.

We’re not talking rust. We’re talking derelict.

But, if you’ve been here more than 2 minutes, you know I’ve got no problem with looking like a fool.

So I dove in headfirst.

You play to 11. I got whitewashed a few times. Put up 4 points in my best game.

I told him not to take it easy on me.

I also solicited his advice after every other point, which he freely gave.

Gracious in victory, we grab some water, chat about his business.

He’s got the quintessential “looks good on paper” business. But his body language was holding back.

So, I do what I do. Asked a bunch of questions.

And it came to a head pretty quickly.

He’s good at what he does. But while that pays the bills, it’s not the work he wants to keep choosing.

So, I whipped up this exercise I’ve been testing with clients that’s yielded instant clarity, and quick results.

I still don’t have a name for it—and I’ll save you the nitty gritty—but basically we do this:

I put a list of values in front of them and tell them to pick anything their gut reacts to.

Then we force tradeoffs. This over that.

Again and again until the hierarchy gets obvious.

Then we explain what each value actually means in their life.

Takes a few minutes.

The clarity he got showed him his number one value was Wisdom.

And this is where the magic happened. Keep in mind, he’s not a client. This is the power of values, not how cool I am.

Although, obviously.

I asked, “What do you do with the wisdom you have?”

He didn’t understand. So I asked it another way.

Once he got it, he didn’t hesitate:

“I love to teach it to others.”

Bingo.

Your highest value is probably already pouring out of you somewhere.

The problem is you may not be letting it lead.

It’s not about repressing the value because “it’s too fanciful” or “can’t be monetized.” Hell, I know people monetizing bird watching lessons.

It’s about identifying what matters.

Letting it reject what doesn’t.

Then building a life that can actually hold it.

“When I asked about your serve (Wisdom) you told me what I was doing wrong (Teach) and it had a damn near immediate effect (Result).”

His face lit up like he’d written The Secret.

And it’s no different in business.

He just hasn’t figured out how to transition from misaligned ways to make money, to an aligned way to make money.

His lesson fixed my serve in a few seconds.

His own value altered how he saw his business in a few minutes.

I just made it obvious.

And now, he can look at everything in business, in life, and filter it through wisdom.

The question I had him walk away with:

Does this bring me closer to wisdom or further away?

A lot of his day-to-day stuff is “push button” unexciting stuff he’s good at, but doesn’t make him wiser.

It’s servitude to capability, not meaning.

Now he’s got a clear and obvious filter to tell him if he’s living in meaning or survival.

There’s a long road between recognition and result. But now the truth is doing the talking.

So, I might have gotten destroyed on the court.

But I left feeling pretty damn useful.

And can’t wait to see what he does next.

-C

P.S. Shameless plug now. This exercise I still need to name has been an unlock for all my clients so far.

Identify the value. Let it lead. Create evidence. That’s basically the play.

My offer has been private up until now. So far, the beta testers have…

One client 3X’d a previous result when creativity led.

Another eliminated an inauthentic relationship and saved $100K when authenticity led.

Another went viral numerous times when creativity led.

Three completely different people. None of their results promised by me. The space did what it is supposed to do: make the real thing harder to avoid.

That’s the power of what we do together. I call it “The Room.”

So, this is the first time I’m putting this in an email. If you’re interested in how this is happening, you can read about it here.


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