When should you experiment, and what does that mean?
You should experiment any time you’re not in a competition. The idea is that in casual or recreational matches, you can really work on your dropshots, try to put things as close to diagonal corners as possible, work on the right side passing shot that is so successful when it goes right along the sideline, fool around with poaching, or find the right height for lobs that are unreturnable.
It is this experimentation that will make you a great player faster than anything else.
There are two downsides to experimenting: You won’t look like a good pickleballer to your friends and neighborhood players because you’re frequently missing your shots. Is that important? Maybe not in comparison to more rapidly becoming an accomplished player than everyone else. Plus, when you land that extreme diagonal, or drop one perfectly in the kitchen, you’ll look great then and there.
On the other hand, the pickup or recreational game may not be important to you, but your partner may be really hoping to win. Or, maybe you’re the kind of person who really wants to win every game. Can you give up the immediate games in order to become a better player? That little psychological shift may be harder than you think.
A really great game to experiment with on a recreational court is when your partner isn’t very accomplished, or the players you’re up against are weaker. This is a time to work on your subtler skills rather than slamming every shot.
You may find it’s great fun to return every ball gently, and watch the opposing team slam back every shot they can reach. When you get tired of that, aim for the feet of a player on their non-dominant side, but gently, and watch what happens!
The other downside is that you have to remember to play conservatively, to quit experimenting, when you’re in serious competition.