What Pickleball Taught Me About Kindness, Kaizen, and Culture
“Don't worry about your mistakes–you're learning.”
That's what an instructor said during my first 1×1 lesson at a local indoor pickleball center. It was my second time ever playing the sport. The first was about a week earlier–at a KaiNexus team-building event (hey, Kade!).
I noticed how frustrated I was with myself for mis-hitting shots and not being as accurate or consistent as I wanted to be during the lesson. After hitting a shot into the net, or sending it long, I'd cringe and my inner voice was being critical.
My instructor noticed my body language–and that's when she reminded me not to be too hard on myself.
That's the perfectionist in me–the part that remembers playing tennis on my high school team and still expects that version of myself to show up. But I'm 52, not 17. And this isn't tennis. It's a different sport, with different rules, rhythms, and angles. The phrase “rookie mistakes” is common for a reason.
But I was learning something deeper than just rules or form. I was learning how hard it can be to unlearn–especially when muscle memory and old patterns are so deeply wired.
Still, that comment from the instructor stuck with me. It's not just a friendly reminder. It's a leadership principle.
The Right Place to Make Mistakes
When I decided to start playing more regularly. I knew I had a lot to learn–so I made a conscious choice: my first real games after the lesson wouldn't be with strangers at “open play” sessions. I'd start with friends and neighbors. People I knew would be kind if (um, when) I made beginner mistakes.
And I did.
At one point during a friendly match, a neighbor called a timeout. She kindly pointed out that I wasn't serving legally. It wasn't intentional. I wasn't cheating or trying to push the limits of the rule.
I was dropping the ball and hitting it from waist height–a habit carried over from casual tennis hitting, but not compliant with pickleball's underhand serve rule, where you have to strike the ball at a height that's lower than your belly button.
And here's the kicker: I knew the rule. I had read about it. My instructor reinforced it. I thought I was following it. But my body was doing something different than what my brain intended.
That wasn't a judgment error, like a bad decision. It was an execution error–something I describe in The Mistakes That Make Us as a mismatch between intent and action. It was a physical “slip.” These mistakes are incredibly common–and incredibly human.
Mistakes, Safety, and Support
When my neighbor called this out, I was mortified. I apologized and immediately thanked her for speaking up. She said she almost waited until the end of our session to point this out. But I agreed that it was better to speak up in the moment so I could pay closer attention to correct form (and follow the rules).
After the match, I sent a text to again thank my neighbor–for playing and for speaking up. I told her that's exactly why I wanted to start out playing with friends–so I could make mistakes in a friendly setting. She replied:
“Of course! I'm glad you are okay with it. Not everyone is. My hope is that I always help in an encouraging and supportive manner. We're so happy to have a new player that loves PB as much as we do!”
That message meant a lot. It reinforced how much a supportive environment matters when we're learning something new. It's good to be learning something new, especially at 52.
Whether we're talking about Lean transformation, new software adoption, or trying to volley in the wrong part of the court, the principle is the same:
Learning stalls when people feel judged for not already knowing–and it suffers even more when kind, corrective feedback is withheld out of discomfort or fear.
Creating the Conditions for Kaizen
This is true far beyond the court. At work, too many people are hesitant to speak up, ask questions, or admit when something feels unclear. Why? They fear blame, embarrassment, or worse.
In a culture of continuous improvement, that fear is a barrier.
Psychological safety doesn't mean a lack of standards–it means people feel safe enough to say, “I made a mistake,” or “I'm not sure I'm doing this right.”
My neighbor's reaction wasn't just kind–it was constructive. I corrected my mistake without feeling ashamed. She recommended that I try the style of serve (also legal) where you drop the ball and hit it after it bounces. That really ensures that you're hitting the ball low and with an upward stroke.
And I got better. That's how improvement works. I still need to keep practicing to get more consistent!
Other Mistakes I Made
Where to begin?
I stepped into the kitchen to hit a volley–got a little too excited when a ball popped up and just had to be smashed. That's not allowed, of course. I realized it immediately and called the fault on myself. It was the right thing to do, even if it cost us the point. Accountability matters, even in rec play.
Old tennis habits crept in too. When my partner was serving, I kept wanting to position myself up toward the net–just like I used to do in doubles tennis, anticipating an opportunity to hit a quick volley. But in pickleball, that positioning sets you up for failure. Because of the two-bounce rule, the return of serve has to bounce before it can be played–so both players on the serving team need to stay back, not charge forward. I had to unlearn that instinct. I mean I keep working on it.
And when I did get a chance to put a volley away, I sent more than one wide. That might've been an execution error–but I think muscle memory played a role. A tennis doubles court is wider, and my internal compass was still aiming for that line, not this one.
Maybe I'm again being too hard on myself. I'd like to think I'm just reflecting.
Each mistake was frustrating in the moment–but each one helped me unlearn an old habit, replace it with something better, and move forward with more awareness.
Leaders Set the Tone
If you're a leader, consider:
- Are you treating execution errors as learning moments–or as personal failures?
- Are you being too hard yourself about your own slipups or mental lapses?
- Are your team members comfortable receiving feedback?
- Do they thank others for calling out mistakes, like I did? That's a strong signal of a healthy workplace culture.
Improvement doesn't happen in a vacuum. It happens in relationships–in systems–where mistakes are surfaced, reflected on, and used as fuel for progress.
Final Serve
I'm still learning to serve properly each time. I will still miss shots. And I still catch myself comparing today's performance to my high school self. That younger self was far from perfect when playing a sport after many years. My current self is just as human, and I can't expect myself to be perfect in this new endeavor (although I still have pretty good reflexes to return volleys!).
But I'm getting better at being okay with being new. And that's worth celebrating.
Growth often starts with unlearning–clearing out what no longer serves us so we can make room for new skills, better habits, and deeper understanding.
In pickleball and in business, it's not about getting it right the first time. It's about learning, adjusting, and showing up again–one improvement at a time. It's better when others speak up to help.
Keep the Volley Going
I'd love for you to share a comment below:
- And how do you try to offer helpful, respectful feedback when you notice someone else making an honest mistake?
- Have you ever discovered you were making a mistake you didn't realize in the moment?
- What helped you become aware–and how did you respond?
- Have you had to unlearn a habit from one context (like sports or a previous job) that no longer served you?
Please scroll down (or click) to post a comment. Connect with me on LinkedIn.
If you’re working to build a culture where people feel safe to speak up, solve problems, and improve every day, I’d be glad to help. Let’s talk about how to strengthen Psychological Safety and Continuous Improvement in your organization.
