The Pros and Cons of Playing with Better Pickleball Players

Why Stepping Up Can Sharpen Your Game—or Shake Your Confidence

The other day I played a few games against Michelle, probably the best female player on our town courts. I was amazed by the consistency of her topspin drops, and it took me several misses into the net to figure them out. But eventually I did to some degree, and it helped me in later games against other friends. Losing isn’t as bad when you feel like you learned something.

Playing pickleball with players who are better than you can be a game-changer—but it’s not without its challenges. Let’s break down the pros and cons.

The Pros

The most obvious advantage is the opportunity for growth. When you play against stronger players, you’re pushed to adapt and raise your own game. You’re forced to be more strategic, and you quickly learn what works—and what doesn’t. This environment accelerates your learning curve. Better players tend to hit cleaner shots, move more efficiently, and make smarter decisions, so you can observe and absorb those habits.

Another pro is that it builds your resilience. Facing tougher competition can be humbling at first, but you’ll develop mental toughness and patience as you weather longer rallies and trickier shots. Over time, you’ll find your confidence growing, even if you don’t win many points right away.

Finally, it’s a huge motivator. Watching those polished volleys and perfect dinks up close is inspiring. It’s a reminder of what’s possible if you stick with it, and it often reignites your enthusiasm for practice and drills.

The Cons

Of course, it’s not all upside. Playing against much stronger opponents can be discouraging if you’re not in the right headspace. It’s easy to get stuck focusing on mistakes or feeling like you’re slowing the game down. That frustration can sap your enjoyment if you’re not careful.

Another downside is the risk of injury or burnout if you’re constantly pushing beyond your physical limits. Better players might play at a faster pace or hit harder shots, so you need to listen to your body and rest if you feel strained.

And let’s not forget the social dynamic—sometimes, playing with better players can feel intimidating. If you’re worried about being judged or not “pulling your weight,” it can mess with your focus and keep you from playing your best.

The Bottom Line

In the end, playing with better players is an invaluable tool for improvement, but it takes the right mindset. Instead of measuring yourself by wins and losses, treat each game as a learning experience. Ask questions. Watch closely. And most importantly, don’t be afraid to make mistakes. After all, growth in pickleball—and in life—often comes when we step outside our comfort zone.