Ep. 107 – Lynn Cherry – Learning the Game of Pickleball

Have you heard of the pickleball sport? It’s a sport that you might find interesting if you’re getting close to or are already in retirement. 

Pickleball with its low entry cost and easy accessibility into the community is the perfect sport for your retirement plan. The sport has many social and health benefits, which include weight loss, and is increasingly becoming popular with people of all ages.  

In this episode of the Secure Your Retirement podcast, we have Lynn Cherry talk about pickleball as the perfect sport to join pre and during retirement. Lynn is a pickleball player and enthusiast who enjoys the sport and even has a podcast to help others understand it too. 

In this episode, find out:

  • Lynn on how she got into pickleball and found it interesting.
  • The similarities and differences between tennis and pickleball sports.
  • How the pickleball court size allows less movement and is perfect for people with knee issues.
  • Why pickleball environment and technique make it a great social sport.
  • Lynn describes the double bounce rule in pickleball. 
  • The low entry cost and accessibility into the pickleball sport and community. 
  • How Covid has prompted younger generations to start participating in pickleball.
  • The history of the name and game of pickleball. 
  • How to set up the net plus where to get the pickleball equipment. 
  • Lynn’s Pickleball Fire podcast where you can learn more about pickleball.

Tweetable Quotes:

  • “One of the greatest things about pickleball is even if you’ve never played a sport, you can pick it up the very first time and have a good time.”– Lynn Cherry  
  • “Pickleball is one of the sports or activities that cut across generations.”-Lynn Cherry  

Get In Touch with Lynn:


If you are in or nearing retirement and you want to gain clarity on what questions you should be asking, learn what the biggest retirement myths are, and identify what you can do to achieve peace of mind for your retirement, get started today by requesting our complimentary video course, Four Steps to Secure Your Retirement!

To access the course, simply visit POMWealth.net/podcast.

Here’s the full Transcript :

Have you heard about pickleball, how to play it? What does it mean for retirement? Well, by the end of this video we hope you’re going to gain clarity for your personal retirement plan and have action items to secure your retirement.  
To learn more about securing your retirement and all the different elements you need to know, subscribe to our channel and hit the bell to be notified when we post a video every Monday. We have helped hundreds of our clients gain clarity and get on the path to a comfortable and happy retirement. Now it’s your turn. Let’s dive in.  
Welcome everyone to our Monday podcast, where we are trying our best to always bring somebody that can enlighten you, whether it be in financial things, legacy or lifestyle. Today is a lifestyle show. And we have with us Lynn Cherry, who is a pickleball expert. So, Lynn, thank you so much for coming on and talking with us today.  
It’s great to be on. Happy to be here today.  
So this idea of pickleball, I’ll tell you a quick story. We have a client of ours, in particular, that he loves playing. He started playing a little bit, I think, before he actually retired. But then he got his wife into it and then they now play together. And it’s actually been fantastic throughout the COVID scenario because they were able to get out and be outside and do things. So, I don’t know how big of a topic this is with a lot of folks, but I’m hearing more and more about it. So could you just give us a little bit of background, maybe about yourself, how you got into it, and then I know you have a whole podcast on it. So can you give us a little bit of background about that and your world of pickleball?  
Absolutely. Honestly, I had never heard of pickleball until I moved to Connecticut in 2018. And I had been in North Texas for 25 years, had never heard of it, was always really athletic. And so, when I moved to Connecticut, I’m like, “Well, what am I going to do indoors during the winter?” Because with my knees and stuff, I couldn’t ski or do anything like that or snowshoe. So I just looked at the local recreation center to see what they were offering. And I’m like, “Wow, there’s something called pickleball? How weird is that?” But I looked it up on YouTube, of course, and I’m like, “Wow, that looks great.” Because I played open level racquetball, played a little bit of tennis and I’m like, that’s the perfect game. So I went to the rec center here in central Connecticut.  
And there was people playing in the gym. And as soon as I peeked my head in the door, they’re like, “Hey, you want to play?” And I’m like, “Oh no, no, no. I’m just going to watch.” And they come over, they hand me a paddle and say, “Come on, come on and get on the court.” And so, I hit the ball a few times and it was being addicted to the sport immediately. And you’ll hear that from just about everybody who plays the game. That pretty much the first time they got on the court, they became addicted to the sport.  
Yeah. I have some friends that are a little bit younger than, I guess, the typical demographic that’s playing pickleball. And they walked up to a court kind of like you did. And they said everyone was so nice and inviting. And so they joined in just to learn the game and everyone taught them the game pretty quickly. And they said they had so much fun. So, I’m excited to learn more about it and to eventually pick it up. From what I have seen and just some YouTube clips and stuff like that, it seems like, I think there’s, I mean, a few aspects to it. One, I guess, we could start with is, could you compare it to maybe someone has played tennis all their life and if you look at a pickleball court, it looks kind of similar, but maybe a little bit smaller. So could you compare some of the differences between maybe pickleball and tennis, I think, are probably the most comparable just from a view perspective.  
Absolutely. And you’re right. The pickleball court does look a lot like a tennis court but it’s much smaller. A pickleball court’s only 20 feet by 44 feet. So it’s half the size essentially of a tennis court. But the net’s about the same height, fairly close. But the interesting thing is that, there are so many people who come in to pickleball who have never played a sport before, but then you do have tennis players who come in and they immediately are pretty darn good at the sport. Now, with that being said, tennis players like to hit the ball hard. And there’s much more to pickleball than that. There’s a soft game which is with soft shots, dinks, drop shots, like you might see in tennis and things like that.  
And sometimes it takes a little bit for the tennis players to actually learn the game of pickleball because it’s not just all about hitting the ball hard. I mean, think about it. We’re essentially hitting a wiffle ball, which is essentially what a pickleball is, not with a racket with strings, but it’s actually just with a paddle typically made out of graphite. And it’s also much smaller than a tennis racket. Most pickleball paddles are maybe 15 by 8 inches and with a fairly short handle. And so, those are some really the biggest differences between the two games. And pickleball is a little bit more about not making errors if you really want to do well and win. Whereas in tennis, you might go for an ace on a server or something like that. Well, in pickleball, you only get one serve. So, you’re trying to be much more consistent and get the ball in the court.  
So, you mentioned something a little bit earlier, you talked about your, I think you said your knees, and playing other, doing other stuff. I have bad knees too by the way. My knees are getting worse and worse, and my question is, if you play pickleball, I’m assuming then that you can play at a pace that in my mind, tennis, I think I’m running all over the place to play. So with pickleball is it a ton of movement that way? I mean, how active do you get during play?  
It depends on the level you play, certainly. But I’m with you. I actually have no ACL on one of my knees because I tore it and then I never had it surgically repaired. So I hadn’t played a court sport until I found pickleball. Because I looked at it and I’m like, “Wow, this court is so much smaller than a tennis court. And so, I do have a much smaller area to cover.” But one of the things that pickleball is because so much of the game is near the net, will say. There’s actually a line called the non volley zone line. And you cannot go into that area and hit the ball in the air. If it bounces, you can go into that area.  
But what it does, essentially, is it puts you most of the time, seven feet away from the net. And it becomes a very fast game, bang, bang, bang, you’re hitting shots hard at each other. And you do have a certain amount you have to move. And just like tennis, somebody can lob over your head. So, because the court is much smaller, that’s really why you’re not moving so much, but you still have to move some.  
I got you. So, I’ve read about this sport and it seems like there’s a social aspect to it as well. It seems like every time I’ve seen it, I know that it can be played in a singles version, I think, but it seems like you see it more in a double style type of format and you’re in a much smaller court. So is there a social aspect to it that makes everyone want to play this, that makes it so much fun?  
I think there absolutely is. I mean, that’s one of the greatest things about pickleball is, even if you’ve never played a sport, you can pick it up the very first time you go out and play and have a good time. Because it’s easy to learn. You don’t have to spend all this time with technique like you do with tennis, just to even get the ball over the net and in the court. So, that’s what makes it so appealing and what’s great too. And one of the things that I think makes it really, really social is that, you can walk onto a court and play with people who, you’ll see beginners and we’ll call them experts playing together.  
Whereas in something like tennis, I hate to say it, even though I played tennis for a few years, it’s a little bit more elitist, where people only want to play with people of a certain level because otherwise it’s not fun. But that’s what’s great about pickleball is that, it’s fun really regardless of what level of person that you’re playing with. And so, because of that atmosphere and people being so inviting, that’s really what makes it a great social sport.  
So I know, I’ve never played tennis, but I play ping pong. If you’re playing as a team in ping pong, you’re supposed to be an every other hit. Is that the same in pickleball, is it only if it comes into your zone you can hit it again, or when the ball comes back to you, you’re supposed to trade off as far as your team mate?  
No, actually in pickleball, you do not need to trade off. So, the server does have to hit to a certain person and they have to return the ball. But once that occurs, either partner can hit the ball. So it is not limited like it is in ping-pong.  
And you said something about a no volley zone. So, I know we’re doing this over audio, so it’s going to be hard to turn this into something people can grasp, but we can try. And so, let’s say I have to serve to you Lynn, and I serve it over to you. What is your response? I know there’s something about, there’s a certain area that there’s something that you cannot do and I know there’s certain amounts of times that the ball has to bounce, maybe, before you can return it. So, take us through that because it’s a little bit different than any other sport I’ve ever played.  
That’s true. That’s called the double bounce rule. So, say I’m serving the ball to you. Okay. So the server is one, your return is a second hit, and then that third ball it’s coming back to the serving team, but they cannot hit that ball in the air. They have to let it bounce on the court. So that’s the second bounce. So that’s why it’s called the double bounce rule. So you’ve got to have the two bounces before and then you can do whatever you want with it.  
So, now I know you said this is easy to learn and you can come in and pick it up. I guess, you got to have at least somebody that’s got a little bit of an understanding of the rules, but is there like, I don’t know, a quick, easy way, let’s say that me and Murs have never played, but we take our wives and we decide we want to go play. Is there something that we could do to could give us like a little bearing on what the rules are and how to get set up and all that kind of thing?  
Yeah, that’s actually a great question. I mean, you’re talking, I think there are about rules and equipment too. So, obviously, the first thing is to… I priced it out the other day, you can basically buy four paddles, a couple balls, and even a net for about $100. So the economics of the game really make a lot of sense. And then in terms of the rules, you can find the rules on the USA pickleball website. So there actually is a, we’ll call it a governing body for the sport in the U.S. and there’s actually a couple ones internationally too, but you can go on there and find the rules. But the game is pretty simple, and you can just watch a few YouTube videos or pretty much just go show up wherever they’re playing pickleball near you. I mean, because nowadays there’s probably 3000 plus, 4,000 places that you can go play pickleball. And with your audience, if they’re thinking about retiring and maybe traveling around an RV, there’s probably a couple hundred RV resorts which have pickleball courts too.  
Hmm. Yeah. I think that’s really important. The cost of entry into the sport is, I mean, next to nothing, when you compare it to something like, a retiree that says, “Hey, I’m going to retire and I’m going to pick up golf.” And all of a sudden, you’ve got the equipment that you have to buy, the lessons that you got to take, all the balls that you’re going to lose. And then the green fees, cart fees, all this stuff adds up to thousands of dollars just even to get to the point where you can decide, “Hey, do I like this sport or not.” Pickle ball like you said, $100, and you can learn it relatively quickly. There’s definitely a health aspect to it. It gets you out there, it gets you moving around, and probably not as much impact as a lot of other sports out there.  
And then there’s a social aspect to it too. You can make a ton of new friends just by showing up on the court. And then, I assume you just hang around with them and you start setting weekly pickleball dates and stuff like that. So, it seems like a win-win in every direction. And I can understand why it’s gotten so popular in the U.S. and probably all over the world. Is there anything that we’ve left out that we should be asking you while we have a pickleball expert in front of us about the sport, maybe about the uniqueness of it or anything like that?  
Well, one thing I do want to say is that pickleball was really known as a sport for people who are over 50. And even the statistics back in 2019, 75% of the regular players were 55 and over. Well, due to COVID, and like we had mentioned with the game being very COVID friendly, that number actually has dropped significantly. You have so many young people now coming into the sport, only about 60% of the participants now are over the age of 55. And just on the weekend, I was over at the courts, and a couple of people came onto the courts who I didn’t know, but it was probably like a young guy who was maybe a freshman or sophomore, I guess, in high school, and he came with his grandmother. And you just see that because it’s one of the best sports or activities that really cuts across generations.  
Yeah. And we’ve talked about it as far as learning it, but say you learn it and you do get pretty good. I assume there’s leagues as well. Leagues around and tournaments that people could enter if they wanted to get into more competitive nature of it.  
Oh yeah, absolutely. There’s hundreds of tournaments, probably thousands in 2021. But there’s two professional pickleball tours, which are now being broadcast on CBS ESPN. And then, of course, streaming. So, some people are a little bit reluctant to play pickleball just because even the name of the sport. And there’s many people who basically, guys who basically said, “I don’t want to try a sport with that silly name.”  
Well, that is a good question. Do you know why it’s called pickleball? We haven’t really touched on that.  
Yeah. Well, there’s a couple different stories when it comes to why they call it pickleball. But pickleball was actually invented a long time ago, back in 1965. And there was three families who got together. And honestly, the sport was started because you had these three families and their kids were bored. And, I guess, they brought out the badminton net and then they realized that they didn’t have a shuttlecock to play. And so, they found a wiffle ball and they’re like, “well, that won’t work with a racket or string.” So they grabbed some ping pong paddles. And then they lowered the net because there was kids. And that’s how the game got started.  
Now, there’s a couple stories about the name itself. And with the name, one story is that the sport was named after one of the founders of pickleball named after their dog. Because when they played pickleball, the dog would go grab the ball and run away with it. It’s a wiffle ball. But if you think about that, a wiffle ball wouldn’t last long with a dog. But the other story is that apparently one of the wives of the founders was a competitive rower. And apparently there’s something in rowing where I guess, the last boat that comes in is called the pickle boat. And basically the pickle boat can often be just a group of people who aren’t used to rowing together. So, it’s just a mismatch, we’ll call it. And that’s how pickleball is. I mean, it’s a mix of ping pong, tennis and badminton. So, everybody really likes the dog story. And now pickleball’s popular enough that it doesn’t look like the name pickleball is going to go away.  
So you mentioned something earlier about getting a couple of four paddles and a couple of balls or whatever, and a net. So that part now makes me think, if you buy a net, where would you set that up and how would you, if you go to a court, I guess, do you need to have a net? I don’t know. I mean, I’m trying to think of how that would play out that you would need a net.  
There’s obviously different places to play. A lot of people during COVID were playing in their driveway. So yes, they needed a net. And then you can just take chalk and create the lines. But nowadays there’s dedicated pickleball facilities where there might be 8, 10, 20 courts. So, no, you would not need a net there either. And sometimes if you go to a place where you’re not really set up for pickleball or it’s on a tennis court, because sometimes they drop the lines for the pickleball court on a tennis court, and there’s a place near me where you do need to set up a net, or if you’re in a gym you do need to set up a net.  
Okay. And I guess the nets come with stabilizers on either side that you, I don’t know, poles or whatever that you would do to hold the net.  
Yeah. Yeah. And honestly, nets like that nowadays they’re designed really well. But, yeah, they’re easy to set up.  
And where’s the best place to get that equipment. I mean, would you order it online, or would you go to like a sporting goods place, or what would you recommend on that for somebody who’s listening and going, “Oh man, I might want to try to get this.”  
Yeah. That’s a great question. The first time I went and bought a pickleball paddle, I actually went into, I think, [inaudible] sporting goods, but there’s lots of options for paddles on Amazon. But yeah, when you’re starting to play, you can just even buy a couple paddles, a couple balls that comes as a set, and for $30 or $40, you’re good to go.  
Well, Lynn, this has been great. Before we go, I know you have a pickleball or a podcast that is dedicated to pickleball. So for anyone that is intrigued about this conversation that we’ve had, tell us a little bit about your podcast and how they could get to it.  
Right. I’ve got the Pickleball Fire Podcast, and you can just go to pickleballfire.com/podcast to find it. And they’re at little play on Apple or iTunes or Spotify or what have you. And you can also get more information on the sport, on the pickleballfire.com website too. So, it’s a pretty good resource for all your pickleball needs.  
Very good. And how often do you have a new podcast come out?  
I actually do two podcasts each week. One of them, I talk to a coach or professional player or an instructor. And so, that just gives more information on both the physical and the mental game. And then on Thursdays, I talk to different people in the industry. They could be pickleball paddle manufacturers. They could be people who run tournaments, just a variety of people in the industry. And also, the one other thing I should mention is that pickleball is a great sport for weight loss. I’ve got somebody coming up on my podcast who lost 100 pounds from playing pickleball. And then there’s actually even one of the pro players that I talked to on the podcast, I think her name is Cassandra Gerkey, she lost like 60 pounds playing pickleball. So, it’s such a fun sport to play. I think if you need some activity, not only will it be fun, but you can really burn some calories if you need to or want to.  
Well, fantastic. Well, thank you very, very much for coming on our podcast. I know that our listeners will enjoy listening to this as well as maybe doing some research and seeing if they want to get more into this idea of playing pickleball. So, thank you very, very much. We certainly do appreciate it.  
All right. Thanks so much.  
We hope this video has given you some confidence and clarity as you plan for a worry-free life in retirement. But what else do you need? We have created a complimentary video course called 3 Keys To Secure Your Retirement. This video walks you through step by step, what you need to do to get ready for retirement. You can also check out our podcast called, Secure Your Retirement. You can subscribe below.  
For more retirement tips, watch this video, Create Your Retirement Income Plan. Also, click here to subscribe to our podcast, Secure Your Retirement. If you like this video, hit the like button and be sure to subscribe and share it with your friends.