{Video} The Best Pickleball Singles Strategy For Beginners.

Feb 16, 2023


I read this in “The Art of Learning” and have been thinking about it ever since. 

While the weaker player would say, “I just had a feeling,” the stronger player would shrug and explain the principles behind the inspired move. This is why grandmasters can play speed chess games that weaker masters wouldn’t understand in hundreds of hours of study: they have internalized such esoteric patterns and principles that breathtakingly precise decisions are made intuitively…

While not the easiest to read, this paragraph is thought provoking for anyone in the pursuit of excellence.

More on this in the last section of today's newsletter.

For now, welcome back! Crazy to think 2,394 people are going to receive this email. I’m truly grateful so many of you read this on a weekly basis. :)

If you’re new to the newsletter and want to go back and check out past editions, go here!

Today’s edition has three parts: 

1. A Helpful Tip – Singles Strategy For Beginners {Video}

2. An Entertaining Video – Lee Whitwell's Hilarious Interview.

3. My Journey Playing Pro Pickleball – 6 Simple (But Not Easy) Ways To Level Up Your Game.

A Helpful Tip:

Pickleball Singles is hard. Like, really hard! It’s why I don’t play much. It’s hard on the body and requires so much running. Who wants to do all that? haha

BUT, I know there are a ton of people who love it, want to improve at it, and have asked me to make a singles strategy video to help them!

So, I did just that. 

Now, I personally don’t train singles much. However, I played a lot when I first started, even medaling at a 5.0 tournament. 

So, I’m not completely clueless! Haha, and not only that, but my training partners are all pro singles players, so I consulted them before I made this video. 

If you do what’s in this video, you’ll stop losing to your friends in singles. And, the best part is, they'll have no clue what hit them.

Tip #3 is by far the best strategy to put into play immediately. Seriously. Shoot, Tip #3 is also super helpful to think about in doubles!

Click below to enjoy! 👇

Entertaining Video:  

Pro Player Lee Whitwell was one of the first people I met at a pickleball tournament. And she’s become a good friend who’s hilarious to make videos with. 

In fact, this interview made me laugh so hard I’m reposting it on all platforms a year later. 

No one expected that last answer she gave. 😂


My Journey Playing Pro Pickleball: 

Ever had a day on court where you felt like, “it just clicked?”

Maybe the game slowed down or a shot felt good. Whatever it was, it just felt right. And it wasn’t like you’d never practiced that shot, or thought through that movement. But it finally felt like second nature. Like it was easy. 

See the thing is…

On any journey of improvement, you have breakthrough moments along the way. And no one really knows when they’re going to come. But the good news is, with intentional practice and a long enough time horizon —they definitely will come. 

To use Waitzkin words in his book, “The Art Of Learning”, “It's as if it became deeply internalized.” Second nature, if you will. 

People ask me all the time how to go from 4.0 - 4.5. Or how I’ve gone from playing 4.0 to pro. 

And the truth is, everyone basically knows the answer.  


  1. Invest more time drilling skills.

  2. Practice those skills in rec play with the best players you can find. 

  3. Watch the pros play on youtube and steal from them. 

  4. Ask players better than you how they think you can improve. 

  5. Notice the skills your opponents have that you want to add to your game, then add them.

  6. Play tournaments (if you’re into that) because tournaments make you feel pressure that rec play can’t. 


But as many of us know, the greatest distance in the world is the distance between knowing and doing. I know I shouldn’t eat ice cream at 11:00 at night if I want to be ripped, but... (you get the picture, ha) 

And here’s something else you can't forget. Everyone’s journey is different. Everyone's improvement cycle comes at a different pace. 

Sure, I get frustrated watching these tennis players come in and rise to the top quickly. But not for long. Because I remind myself they’ve been practicing these movements for 15 years. I haven’t. 

And here’s the thing, if you do those 6 things above, eventually, you will begin to internalize patterns and principles so you make decisions like their second nature.

And then all of the sudden, other players will look at you and say, “how did they do that?”

And sure you could just say, “practice.”  But you and I both know, it was a multitude of things added up over time and thought through intentionally, that led to that breakthrough moment where you can hit that ball and make that decision automatically. 

So if you’re sitting at home wondering, "How do I get to the next level?"

Remind yourself, you already know what to do. But it is up to you to execute. Go do it. Keep getting better. 

And someday soon, your breakthrough moment will happen.

Until next week,


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