I Went to a Pickleball Ladder League Alone. Here’s What Happened.

Pickleball kind of fell into my lap. When I first heard about it, I didn’t really know what it was. I wasn’t a competitive athlete. I didn’t grow up playing racquet sports. But suddenly, I found myself in a full-time role… spending my days learning about pickleball, talking about pickleball, and eventually, making it my entire life (and let’s be honest—my personality).

If you’re wondering why the hell someone who didn’t even know what the sport was is writing about it now, well, six years ago, I landed my first job in pickleball—and everything changed.

How I Got Started in the Pickleball Industry

I got lucky. My first responsibility was helping to run one of the largest indoor pickleball tournaments in the country at the time. Six years doesn’t feel that long ago, but in pickleball years? That’s ancient. The sport changes fast.

And here’s the other thing: I was an introvert. I didn’t like small talk. I wasn’t great at public speaking. I had a solid core group of friends, and I stuck with them. I’m not the person who walks up to strangers at parties or volunteers to lead the group icebreaker. I listen. I observe. I wait. 

But when you work in pickleball, especially in tournaments, you don’t get to sit on the sidelines. You’re thrown in. You meet a lot of people. They'll tell you their life stories. They’ll hug you after five minutes. They’ll ask for your number to play later in the week. 

For someone like me? Terrifying. 

But also… kind of incredible. 

How Pickleball Helped Me Break Out of My Shell

I still don't love small talk. But I can talk to just about anyone now. It didn’t happen overnight. It took years of tournaments, conversations about paddles, gear, gameplay, and listening to people’s stories.

Pickleball didn’t just shift how I work—it changed how I connect. And if it weren’t for the people who made me feel welcome early on, I honestly don’t think I’d still be here. 

Which brings me to the first time I really played.

What’s a Pickleball Ladder League?

Since I was working in the industry, I knew I needed to actually play the game—not just talk about it. So I signed up for my first ladder league. 

If you’ve never done one, here’s a quick explanation:

A ladder league is a structured way to play pickleball where players are grouped by skill level. You move up or down the “ladder” based on how you perform each week. It’s doubles format, and the idea is to keep you playing with people at a similar level so it’s competitive and fun.

This one took place every Sunday for a few weeks in the summer and ended with a tournament. I signed up alone.

Showing Up Alone—and Being Welcomed Anyway

The first week, I showed up early. I remember listening to the organizer’s intro while everyone else chatted and laughed like they’d been playing together for years. I stood off to the side. Alone. Awkward. Trying to breathe through the anxiety creeping up my spine. 

Then they called the matchups. I walked to my court, met my first group of ladies—and just like that, everything changed.

The women I played with were kind, welcoming, and encouraging. One in particular—we’ll call her Jayne—stood out. She made a point to say hi every week. Checked in on me. Remembered my name. Made me feel like I belonged.

Years later, Jayne still says hi when we bump into each other at events. 

She probably has no idea how much that meant to me. 

What I Learned from Playing in a Pickleball League

Not every experience in pickleball is perfect. There are cliques, bad sports, and the occasional ego on the court. But 90% of the time? You’re welcomed with open arms. People invite you to play, ask about your life, cheer you on, give tips if you’re new—and sometimes, offer to grab a margarita after.

That first ladder league didn’t magically make me outgoing. But it was a turning point. A reminder that I could be myself in this sport and still feel like I belonged. It showed me how strong pickleball communities really are. And how often, the hardest part is just showing up.