Pickleball Adventures: Fun, Fitness, and Friendship with Lori Gillespie

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In this episode, Lori Gillespie, a top-rated pickleball player with a 4.1 DUPR rating and multiple gold, silver, and bronze medals, joins the show to share her journey in the sport. As the pickleball coordinator for Prolific Sports House in Calgary and owner of Pickleball Retreats for Canadians, Lori organizes leagues, tournaments, lessons, and clinics. She shares her transition from tennis to pickleball, discusses the differences and challenges in the sport, and recounts both positive and negative experiences, including a particularly tough rating evaluation. Lori emphasizes the importance of communication, inclusivity, and fun in pickleball, and gives insights into building relationships through the sport. She also talks about the transformative impact of pickleball on players' lives and fitness, including her own experiences with pickleball vacations and handling unexpected challenges like heavy rain in Costa Rica.

00:00 Introduction to Lori Gillespie

01:06 Lori's Pickleball Journey Begins

02:30 Challenges and Triumphs in Pickleball

05:58 Building Relationships Through Pickleball

09:46 Funny and Memorable Pickleball Moments

11:22 Pickleball Camps and Vacations

13:58 Adapting to Challenges On and Off the Court

17:20 Creating Inclusive Pickleball Communities

24:16 Advice for New Pickleball Players

27:52 The Transformative Power of Pickleball

29:30 Conclusion and Contact Information

Key Takeaways from today's episode with Lori:

1. Embrace New Beginnings – Just like Lori transitioned from tennis to pickleball, stepping out of your comfort zone can lead to unexpected passions and opportunities. Stay open to trying new things.
2. Persevere Through Challenges – Whether in sports or life, setbacks and obstacles (like Lori’s rating struggles) are part of growth. Keep pushing forward, and don’t let temporary roadblocks define you.
3. The Power of Connection – Strong relationships are built through communication and shared experiences. Whether on the court or in life, surrounding yourself with supportive people makes the journey more enjoyable.
4. Adaptability is Key – Weathering unexpected challenges, like Lori’s rainy Costa Rica trip, teaches us resilience. Learning to adjust and find the positive in any situation helps us thrive.
5. Prioritize Fun and Play – As adults, we often forget the importance of play. Finding joy in the moment, whether in pickleball or everyday life,

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Transcript

 Hello. Hello. Today I'm joined by Lori Gillespie. Lori is the most amazing pickleball player. She has a DUPR rating of 4.1 Woo, celebrating you, Lori. She has won five gold medals, two silver medals, and two bronze medals in pickleball brackets tournaments.  She's also the pickleball coordinator for Prolific Sports House, which is in Calgary, Canada, where she organizes leagues tournaments, lessons and clinics with the pros.
And she is the owner of Pickleball Retreats for Canadians.. Welcome, Lori. Thanks so much for joining us here today.
Thank you so much for that beautiful intro. 

You're so welcome. That's amazing.  You have quite the medals there. I hope you have a board where you've put them up and you are showing them off. I've been meaning to get one.
They sit in a drawer for now, but I'll get aboard one day. 
Absolutely. . So Lori, just share with our listeners what first drew you to pickleball and can you tell me about your earliest experiences with the sport? 
Oh sure. Basically it started with tennis because I lived in Texas for a year and I didn't have a work visa.
So what I did was I learned how to play tennis and I played in two different leagues and I loved it. And then when I moved back to Canada, nobody was playing tennis. So my friend Dina, actually, I remember her saying, come out to play with us. So I went out to play with her and I just had a blast. I took some lessons and I was like, yes, I love this.
I love that. What do you think the difference is for people who are perhaps playing tennis now? What are the differences that you found between pickleball and tennis and would you go back to tennis? 
Ooh, that's a great question. I think for me, the big difference is you are a lot closer in pickleball and a lot more people play pickleball, so you're going to get a beautiful variety of some fierce competitors, and you're going to get some people that are like, Hey, I come out maybe once a month on Saturday, and you're gonna get to play with all of those people in pickleball.
And it makes for a really great time and a great laugh. 
I agree. Absolutely. Can you share perhaps some of your earliest experiences of pickleball?   Were they all positive? Were there some perhaps more challenging 
moments? Yeah. Oh, absolutely. , I remember signing up for lessons and taking those lessons and just being very unsure with myself and maybe I didn't sign up for the right level and I.
Especially remember when I went out to the Red Deer Club, I was a very new player. But I played with the three oh ladies in round Robin, and they're like, you shouldn't be playing with us. You should be playing at the higher level. And then, so I was like, thank you, first off, and then I went the next week for the three five ladies and they're like, you can't play with us.
You are not welcome here. You have to get rated to play with us. I was like, oh, how do I get rated? And they're like, oh it's a process. So that was tricky and humbling itself. 
Yes. That does sound like quite a challenging experience that you had. Does it, how did it feel like the experience of almost feeling excluded.
Definitely. So yeah, for new players, if you do feel excluded in pickleball, you are not alone. That happens in this sport, and I just want new players to know that and to feel you can get past that because I remember going for the rating so that I could be welcome to play in a round robin and it was. Six hours.
And basically they had a referee there who was evaluating every type of shot that you did. There were at least 10 different types of shots and it was the serve and it had to be in a specific box that they had taped off deep in the court. 'cause everybody wants a deep serve. And I remember this lady that was evaluating my LOBs and she was a short lady, so she's your lob has to be above my paddle where I'm standing.
So I was like, okay. So I did that. And she's your LOBs were terrible. So I passed the test, but she's your LOBs were terrible in a game. I would jump and I would smash you. Oh my gosh. So it's, but it's like TSA pre-check. You cannot argue with these people. If you wanna play, you gotta put up with it.
Absolutely. Yes. You have to bite your tongue and oh my goodness, that was harsh. 
Yes. Yeah, it was rather traumatic. And then at the end of the evaluation, like I said, it was six hours. So you get a card from a deck, and then these are random people that you're assigned to play with. And then the points Are tracked. So you have that random component of whoever you draw, that's your partner for your evaluation, and then your score is calculated in to determine if you are a 3.5 and worthy to play in that category. And so it was rather stressful, and I remember. Myself and my new bestie Cheryl, who we bonded over the trauma.
We made it and then two of the other people didn't make it right. And so you, then you feel bad because these other people are like, Nope, you're not good enough. And so it, it was very traumatic to be evaluated to see if you can play round robin. 
that does sound like quite the experience, but it sounds like something positive came outta that.
If nothing else, your friendship with Cheryl. And just thinking about that, thinking about friendships and any sport, but pickleball in particular. Has pickleball helped you form new relationships ?  Or perhaps even strengthened existing relationships, and if so, how has it brought people closer in your life?
Absolutely. I like to say communication for the win, and that is in regard to so many different things. So for example, when you're playing in pickleball, there's the divorce line, that centre line. That spot where I'm not sure, is it mine? Is it yours? Is it your forehand? Are we going cross port? How are we doing this?
So it's a tricky thing to navigate. But communication for the win, it really helps. And when you see your partner going for that out ball, it's clear as day and you gotta say no or out. And you're allowed to say that before the ball bounces and pickleball. And it's so helpful 'cause when that shot's coming at you, somehow it doesn't.
Exactly. Oh, I know. , I have sworn blind, Nope. That was out or it wasn't out. And three other people disagree with me. Absolutely, yes. So yeah, communication for the win, it really helps to be clear. It really helps to ask for what you want and ask for what helps you. 
And I'm just curious about building those relationships in pickleball.
Do you find that pickleball has strengthened existing relationships or have you met lots of new people playing pickleball? 
I've met a lot of great, fantastic people playing pickleball, so it's just been an absolute joy in my life to meet new people and to play with them. 'cause sometimes as adults, we forget to play and it's so important to play and it makes us all feel so happy.
To play. And sometimes when we're in a tournament, we forget that pickleball is fun. We forget that, Hey, we're actually here to have a good time. We're here to enjoy ourselves. Absolutely. Oh my gosh, yes. 
Even you mentioned tournaments. Tournaments for sure, but also even just playing games.
I think sometimes our competitive edge gets the better of us. 
That's right. And you wanna be able to. Have that carved out time that you've set aside to play and play your game well at the best level that you can play without your side life. Everybody has their traumas, everybody has their issues.
Everybody has their work that they're addressing, but have that time where you can just focus and play and have a great time. So if we can give ourselves that gift of time in that window where we can play, we can have. Fun and do our thing. It feels really great. 
I agree with you. I think, there, there are definitely a lot of serious moments in life, and life can be challenging and stressful and busy, and I think you're spot on.
When I've had my most enjoyable games is when I have put. All of that aside and walked onto the court. And I always say to Neil as well, my husband, I, and I remind myself every time when I cross that line and walk onto the court, you put everything else behind you. He and I, we laugh about it, now and it still happens.
But we could have had the biggest argument. We could absolutely. Dislike each other. But when we step onto that court, you are putting all that,  behind you. Talking about funny moments. I'm gonna put you on the spot now, but perhaps you can share a funny or an unexpected moment from your pickleball journey that still makes you laugh.
Okay. I was doing a pickleball camp and I was asked to do a demo. So you're put on the spot of okay, you're gonna demo this. And it was like, how to handle a banger, someone who hits the ball really hard, and it might not be going in the court, but they're hitting the ball hard and sometimes they're winning.
And so I was asked to be the banger and just hit the ball as hard as I could at this guy. And this guy's a skilled and strong player. So I felt comfortable hitting the ball as hard as I could at him, and so you never know how a demo's gonna go, but I just hit the ball really hard and the ball flew up straight in the air off of his paddle and the look on his face was quite funny. The ball went up and he wasn't sure where the ball went, so then he's looking all around and then it hit his arm on the way down and it was just very joyful to see such a high end player have that response to my shot, which is normally very gentle. 
Oh that's priceless. I'm just imagining the look on his face now.  It's those moments in pickleball, isn't it? When you can, even if you are the best player there, or the worst player there. Just to have that moment of, oh, we are all here for fun, for fitness,  we are not all trying to be pros  that's for sure
yeah, that's right. Although if there's an opening, just let me know. 
Love that. So it sounds like a, and I know Lori 'cause you and I have chatted and we've played pickleball together, but you've attended various pickleball camps and training environments. I wondered if perhaps you could just walk us through some of the most memorable experiences, either positive or challenging.
So I somehow convinced my buddy and business partner Ruth to come with me to Costa Rica, and we experienced a pickleball vacation and I loved it. And thankfully she loved it too. So we basically did zip lining, we did ATVing, we did all sorts of. Activities like a catamaran and a snorkel, an island exploration with monkeys.
We did all of these activities every afternoon and the mornings we played pickleball. But it was a level of luxury that I had never, ever experienced before. And sometimes as a woman, it's okay, we're gonna go camping. Guess what? On your vacation, you're gonna be cleaning the camper, you're gonna be packing this food, you're gonna be packing the stuff.
You're busy. Whereas this vacation was not like that. This vacation was there was a personal chef, there was someone to do your laundry after pickleball, so it was absolutely. Amazing and such a treat to go to and experience. 
everyone is gonna want to know exactly where you went and who you went with.
That sounds amazing. Yeah, I think and you are right. I think as a woman, when we go on vacation and I think about the years and years of camping that we did as a family and the preparation for that, and even while you are there, . It's not relaxing, but to have a personal chef and have someone to do your laundry for you.
yeah. I had never experienced that before. It was an absolute treat. Yes. 
That's wonderful actually I talked to a couple of ladies who played a lot in Costa Rica as well, and although we've played quite a bit of pickleball in Mexico, but not Costa Rica, but that sounds yeah, a really good place to put on my bucket list to go and play.
Yes, I would highly recommend it. Ruth and I are planning to go back every year and we seem to tack on an extra week every time we talk about going. So we're gonna be there and we're gonna have trips for friends that we coordinate. And we're also gonna plan trips for new friends. So people that we don't know they can go to the website, they can come on the trip as well.
 Now, I know you recently were in Costa Rica and the weather didn't quite cooperate, did it? 
It did not. It was like a hundred year rain. we kept on looking at the forecast. It was about 10, 12 days of rain. So we're thinking, surely it's gonna stop, but let's check in.
Let's see. And the forecast kept on giving us a little happy prediction that it was gonna clear up. Sure enough, that didn't happen. It just rained nonstop and usually the rain rainy season ends in October, but this was November and it was through and through. Hardcore rain, it was to the point that the airport was closed.
We have videos of my friends walking in the streets. The water's like up past their ankle in the streets. It was epic. It was something to experience. . So in a situation like that, it was great to have a local person there so we could modify what we did based on the weather, we could modify where we played and we went to covered courts.
Definitely not as fun as playing in the sunshine, but we were able to do modifications. It was absolutely difficult though, and a learning experience. 
Yes, it sounds like it  and good for you. Like it really sounded like you were able to pivot and just be very flexible and work with the conditions.
'cause you obviously, none of us can change the weather. How do you think that mindset, that flexibility, that ability to pivot, has influenced the way you approach life and relationships on and off the court? 
Yeah, I have found that when you argue with reality, you lose so, so I have to be very accepting of what the reality is.
And is that difficult? Absolutely. And I struggle with that every day. But yeah, we have to accept things, how they are. But definitely see the bright side and the upside to everything. 'cause there is an upside to everything, like even in a situation like that. I found I really liked cards. I really liked playing cards.
And playing different games like that, I really valued the covered deck and watching the rain and seeing what was going on. So absolutely there's an upside to everything. So when we find ourselves in those problematic situations, it's look for the upside because it's there. You just have to look really hard sometimes.
Sometimes you do. I agree. You have to uncover a lot of. Stuff before you find it, but it's always there. That's amazing. I love that you shared that with us.  Thank you. So you are currently the pickleball coordinator for Prolific Sports House in Calgary where you host numerous tournaments.
Leagues lessons and clinics. Yeah. And I know I've been part of several of these and I always enjoy the connection with other women. We always have fun. It's always a very relaxed and supportive atmosphere. I love that. So based on your. Experiences at both welcoming and unwelcoming venues that you've been part of.
What advice would you give to communities or organizers who want to create a more inclusive environment for players of all levels? 
Yeah, I think that's an absolutely great question and an important one. And I think there has to be a spot for all levels to play where you can go for players who are unrated, who just wanna play for fun.
And in that group there'll be some new competitive players, right? And then some opportunities for different different things and more competitive and structured games. 'cause eventually, I get it, you do want. Your competitor to give you a difficult game. You wanna have a battle, right? You wanna have a good game.
That's challenging on both ends. Ultimately, that makes the best games. It's hard to organise that. It's hard to make that happen, but I think DUPR is making that a bit better. So how it used to work in pickleball brackets. Is you just rate yourself and then you are stuck to that rating. And most of us are pretty modest and humble, and we don't know, and we're new, so we rate ourselves really low.
And then it's really hard to move slowly and incrementally. And plus some of the people that you're playing they're getting better too. And so the rating wasn't really. Reflective of the truth, whereas with DUPR the dynamic universal pickleball rating, it's getting better because based on that, you can say I only got two points, but I played a really challenging team.
And so then I think with DUPR, we're getting a much better. Shot at how people play and who should be playing with who, right? So I don't want anyone to go through a six hour evaluation when you know you're stressed out and you're being evaluated and told, oh, you're no good. And I would've smashed that at you.
I don't want that for new players. I'd rather just, you go out for fun and eventually your DUPR, figures it out. It'll go up. It'll go down for sure, but eventually you'll know where you should play at. 
That's great advice and I think, it's not necessary for you to have a DUPR rating, if anybody's debating whether they should play pickleball or not, it doesn't need to be, perhaps that regulated or that serious.
You can just go and play pickleball without a rating, but absolutely. Yeah.   And I think that must be a very challenging aspect of the sport for like yourself that organises leagues and clinics for people in a formal environment. 
Yeah, , it is progressing.
It is getting better. And if you do find yourself as a player playing against really challenging people, well great. Sometimes I throw on the mindset of, wow, this is a great learning opportunity. I'm losing really badly, but what a great learning opportunity. And then sometimes it's the other end of the 
Spectrum where you're a lot more experienced than your opponents, then you can work on your shot placement. You can work on different things or a certain skillset that you're doing. You can work on your drop shot if you're worried about, your opponent now is, this beautiful, wonderful, talented 85-year-old lady, and you don't want a body bagger, right?
So you wanna do some nice shots too, but you can still have a great time and you can have a fun game with anybody. 
Yes. It's read your opponent, right? Yes. Like you say, you're not going to , mind you, I have played,  , I think she was 83 and definitely, you tone down your shots, you're not banging them at people.
But I've also played with 80 year olds who gave me a run for my money, and that was a very, oh my worry. 
Yeah, experience. It's intensely humbling. I played against a lady with double knee braces. She beat me profusely 
And so you really cannot pass judgment when you are playing against opponents who you've not met before and you haven't played with before.
That's a good reminder for me. Do not judge a book by its cover. Oh, absolutely not. I think this lady was even wearing a bucket hat. I'm like, who wears a bucket hat and plays pickleball? . She was a phenomenal player. 
I hope that's me when I'm 80, 90. I plan on still playing.
Absolutely. Me too. So looking back at your pickleball journey so far, what aspects of the sport have changed the most for you? Whether that's perhaps how you play or how you approach it, or how you feel about the sport? I. 
It changes every day, and I've gone through moments where I've hated the game and I'm like, oh, I'm so frustrated.
I feel so down and so low. And then other moments where. I feel really good and I feel some confidence about oh, I'm really happy with how I played that game. I was really happy of the thought process that went into that game. So it evolves and it changes. I. Every day, every shot. But yeah, I'm interested in continuing to being a student of the game and keep on learning, keep on trying.
And when I get those bad shots, which happen to all of us, just be like, oh and not let that linger inside and just go on to the next rally and go into the next game. And just remember, we're doing this for fun and we live a life of luxury. When we have pickleball problems, you're living a good life, 
oh, I agree with you. And aren't we the luckiest to be living at a time when there is pickleball? Can you imagine if we weren't living in 20, 24, 25, you know that without pickleball, I dunno what we would do. 
Yes, absolutely. We are intensely lucky.  I highly encourage people to play and to have fun and feel lucky when they get those opportunities to play.
And you're so right. You bring up a good point about pickleball , and that's definitely something that I have experienced that one day you can go on the court and you can play the most amazing games and you think, yes, I had it all together. My mind was in the game. I was focused, the shots were going where I intended them to.
And then you can get on the court like I did last. Night and think, have I actually ever played before? What the heck is going on? And, I find there are so many variable factors that, we talked about this earlier, about leaving things off the court, but there seem to be so many variables and I wish I could just pin it down.
What exactly is that equation that I needed to play the great games and what happened when I wasn't? If you find out, please let me know. 
I'm gonna sell it because I think that's my way to a million dollars. Absolutely.  Lori I'm curious, what advice would you give to somebody who's hesitant to try pickleball or feels intimidated by the learning curve?
Because let's face it, the learning curve is huge. 
Yes, the learning curve is huge and it is intimidating. So just know that when you're going in, know that there will be people that are better than you, but how you get better is by putting in your time, putting in your practice, playing lots of games. I.
That's how you get better. Those people that are beating you, they've probably been playing for many years and they might have even had a different racket sport going in before they started playing pickleball. So just know that and be gentle with yourself and protect yourself. Definitely wear your eye protective wear.
You don't wanna get an eye injury. I had a game last week where, it was a hard drive to my partner. He caught the edge of it and the ball went like whizzing, right? Probably. About an inch in front of my eye. It can happen. So protect yourself and don't go for every ball. Initially I saw a lot of men especially, we'll pick on the men 'cause we're women.
So men especially, sometimes they'll just dive and slam their bodies on the ground. It's not worth it. Keep playing. Keep your body fit so that the next rally, the next shot, gonna get it. Sometimes you need to say. Nice shot. 
That's great advice. I love that, Lori. And I think, when we were first starting out, when Neil and I and we actually did an episode on pickleball and fitness and our personal injuries, but I think, we forget.
When we start to play pickleball that our bodies are not used to this and you may not think that you're actually moving as much as you are, but yeah, we remember those pulled muscles and some painful next day.  That we were experiencing. So I think that's great advice to to take it one step at a time and not throw yourself into it.
And I agree. 'cause , Neil is definitely a culprit for throwing himself at the ball. But yes, leave it. Let that one go. It's okay. . And the thing I love about pickleball is that it is so accessible for everybody. We see people of all ages. We see, very young children playing with their parents.
We see, people in their twenties, thirties, forties, fifties, all the way up to your eighties. It really is accessible for everybody, and you need very little. I love that you mentioned the eyewear. I'm an advocate of that too. And really quite an inexpensive paddle and a wiffle ball and you are off.
it's very accessible for lots of people and I would encourage everyone to go and at least go and try it and see if it's something that you want to get into. For sure. 
Yeah, absolutely. Keep it easy, keep it fun and just keep trying and keep playing. And if your kids are like, no, I don't wanna try this welcome to the club.
But if they do come out every once in a while, yeah, just keep on encouraging, keep on inviting them out. Maybe, bribe them with some fries afterwards. But that's a great idea. It's super fun. If you can get the whole family out and all ages out to play, you can have a super fun time.
So Lori, , I'm curious also if there was a future episode of Pickleball and Partnership Podcast, what would you like to see it about and why? I. 
Oh, I would love to see about some of the transformations that have gone on because I have visually seen some of my friends and people that I've played with just really transform themselves.
A fellow that I play with has a lost. Probably about 60 pounds. And all that he really changed was he added pickleball to his life, and he , kept going out and he kept trying and playing and he's a really great player. And when I see pictures of before, I'm just like, oh my gosh.
Wow, what a transformation. It really is a great way to stay fit for me. I hate cardio, I hate intentionally exercising. So I really get my cardio in a better way. 'cause in the past, probably in my thirties, maybe my twenties, I just really ignored my cardio health. So I'm grateful that I do have that workout going on right now in my life.
I love that.  I think of in my thirties I hit the gym quite a bit and it felt laborious. It felt like a real chore. And I have to be honest,  I wanted to go because I wanted to be fit and healthy, but did I ever really enjoy it? I can honestly say no because now that, like you say, I get my cardio from pickleball, I love it, and I don't even feel like I'm working out.
And that is what makes it sustainable and that's what leads to the life changes, the lifestyle changes. 
That's interesting.  If  we have that future episode of the podcast, we will dedicate it to you, Lori, for sure. Yay. Thank you so much. Oh, it was so lovely chatting with you today.
I really appreciate your insights into pickleball. Where can our listeners find you? 
They can go to the website . It's pickleball retreats for canadians.com and it's the number four. You can message me there, you can ask questions about retreats and things like that, and we'd be happy to have you we're planning trips for friends, but like I said, we're open to new friends as well.
That sounds incredible. I'm going to put that website in our show notes so that people can find you there, and I will definitely be checking that out myself. Thank you, Lori. 
Awesome. Thank you so much and I'm so proud of you for starting up this podcast and doing it. 
Thank you so much, Lori. I really appreciate you taking time out of your busy schedule to come and chat with us. That was an amazing conversation, and thank you all for listening.
And if you know someone who would also enjoy this conversation, please feel free to share this episode of Pickleball and Partnership with them. But before you go, wait, here's the key takeaways from today's episode.
Here are six key takeaways that apply to both playing pickleball and life. One, embrace new beginnings. Just like Lori, transition from tennis to pickleball. Stepping outta your comfort zone can lead to unexpected passions and opportunities. Stay open to trying new things. Two, persevere through challenges, whether in sports or life setbacks and obstacles like Lori's rating struggles are part of growth.
Keep pushing forward and don't let temporary roadblocks define you. Three, the power of connection. Strong relationships are built through communication and shared experiences, whether on the court or in life. Surrounding yourself with supportive people makes the journey more enjoyable. Four. Adaptability is key.
Weathering unexpected challenges like Lori's Rainy Costa Rica trip teaches us resilience. Learning to adjust and find the positive in any situation helps us all to thrive. Five, prioritise fun and play. As adults, we often forget the importance of play, finding joy in the moment, whether playing pickleball or in everyday life keeps us engaged, happy, and balanced.
Six. Health is a lifelong investment. Staying active doesn't have to feel like a chore. Find activities that you love and fitness will naturally become a sustainable and enjoyable part of your life. Thanks for listening.
Thanks so much for listening today. I hope you enjoyed that conversation as much as I did. Anything mentioned, including links, notes, and a full episode list, will be over on our website at pickleballandpartnership. buzzsprout. com. Com. If you got something outta this episode, be sure to follow or subscribe to Pickleball and Partnership on Apple Podcasts, Spotify, or wherever you listen so that you are notified of new and upcoming episodes.
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Thanks again for listening. Please tune in next week for another exciting episode of Pickleball and partnership.  📍 Remember, we're all learning, growing, and showing up in our own ways. And that's what matters most.