Hey!

I want to tell you the truth.

Not the polished version. Not the filtered highlight reel. Just the real, raw version of what happened over the last two weeks.

Because if I’ve learned anything from this sport—and from life—it’s that real transformation doesn’t happen in the comfort of certainty. It happens in what Scott Belsky calls the messy middle. The part we don’t usually share.

And this past week? I was deep in it. 

See. . .

Right after the US Open, I found myself asking a question I was afraid to say out loud:

“Is this even worth it?”

The whole thing—traveling, performing, chasing this dream of becoming a top pro pickleball player that sometimes feels so out of reach, I don’t even know what I’m chasing anymore.

I even had a few posts written up about this feeling, but I couldn’t bring myself to hit publish.

Because the truth was, I didn’t just feel off—

I felt a bit ashamed. 

Ashamed for not enjoying the life I worked so hard to build.
Ashamed for possibly wanting to step away from all this when so many people would give anything to be where I am.

And that shame is sticky. It doesn’t just sit quietly in the background.

It speaks in absolutes and it told me things like:

“You’re not enough.”
“You’re letting people down.”
“You’re not cut out for this.”

And it hit me hard after the US Open a couple of weeks ago.

I was partnered up with Patrick Kawka—someone I really respect and admire. I really wanted to show up, play free, and be the kind of teammate he deserved.

Instead, I spiraled.

I missed routine drops early, popped up some dinks, and that tightness crept into my chest. And if you’ve played for a while, you know the feeling. That rising pressure that whispers, “Don’t mess this up.”

Point after point, the opponents started targeting me. And instead of rising to meet the moment, I disappeared.

And by the end of the match, I wasn’t just disappointed. I was embarrassed. 

I’ve read a lot of author Brene Brown’s work over time, and she says:

Shame doesn’t need to be loud to be powerful. It just needs you to believe that your worst moment is your truest one.

And that tough match stayed with me for days.

Not because of the score, but because of the story I started telling myself afterward:

“I failed. I let PK down. Maybe I’m not cut out for this.”

DAYS AFTER…

 I skipped training, my body felt off, and my mind felt fragile.

In fact, I didn’t even want to go to Cincinnati last week for the APP tournament.

I just wanted to disappear. 

Have you ever felt this?

Now, in the days leading up to Cincinnati, I knew I needed to do something, and I did. 

It wasn’t anything dramatic. There was no Rocky montage or big hero moment.

Just some quiet, steady work that looked a bit like this: 

1. I watched highlight reels of myself, not to puff up my ego, but to remind my body of what it already knows.
   

2. I sat in stillness for five to ten minutes a day. Not to escape the noise, but to hear what was underneath it. To evaluate why I spiraled and what I’d do about it the next time I felt similar emotions. 

3. I simplified my plan - I cut away the one new shot I was trying to implement into my game (the topspin drop) and decided I’d go back to what I know works (for now) – the backhand cut drop. 

4. And I decided to lean into my superpower. My Movement. And for multiple days in a row, I just repeated this phrase to myself: “Active feet. Active body. Active mind.”

None of this is glamorous. And it’s not new.

But after your hardest moments, you either lean in deeper and face the music or run away.

I wanted to run away, but I chose to lean in. 

Off to Cincinnati

By the time I got to Cincinnati, I wasn’t excited to be there at all.

I was still unsure of my game. Feeling a bit shaky.

And like Brene Brown says, sometimes courage looks like just showing up. Not confidently, but just with your presence. 

My partner for this tournament was my old roommate, Casey. And when we looked at our draw, we liked what we saw. 

But still, the voice was there: “What if you lose in the first round?

Well, the 1st round came and we started off hot, up 7-0. But somehow, we lost that game. Then we were down in the second, and facing match points.

I was already writing the headline in my head:

“Another early loss. Maybe this just isn’t for me.”

But then we won a point. Then another. And something shifted.

Not just on the scoreboard—but in our bodies. We stole the 2nd game and then went on to win the 3rd pretty handily. 

Afterwards, we just smiled because we knew we escaped the loss and felt a weight lifted off our shoulders in that moment.

From there on…

Match after match, we climbed.

• Round two? Tough win in three.

• Quarterfinals? Another battle in 3 games. 

• Semis? We beat a team fresh off a US Open silver.

And then… we were in the finals.

WHAT!?!?

About 24 hours ago, I didn’t wanna be at this tournament, and was considering if I should stop playing tournaments.

Life’s funny this way. 

We ended up losing in the finals and getting 2nd, but gosh, we had a great run.

In fact, next week I’m going to release inside ThatPickleballSchool a match analysis of both our semifinal and finals match!

So if you want to see that next week, you can join here :)

A Crazy realization…

From the day I picked up a paddle—August 26, 2021—to May 11, 2025:

It’s been 3 years, 8 months, and 16 days. 

1,355 days. 

To win my first pro medal.

So this medal didn’t just represent a win last weekend.

But really, it was a reminder that everyone’s journey is different. Everyone’s timeline is different. And often when you’re at a place where you are genuinely thinking about quitting, you may be closer than you think.

As in 24 hours closer 😂.

Until next week,
-Kyle

PS: The more I play pickleball, the more I realize how much this game requires mental strength and resilience. And after coming off our “3.5-4.0 30-Day Challenge” inside Thatpickleballschool. I’m really considering creating some type of Mindset Challenge sometime soon. 

If you’d be interested in my team & me creating something like this, let me know here:

P.P.S. Want to see the match breakdowns leading up to my first ever pro medal? Join ThatPickleballSchool for Free right now.