Unlocking Success: How Mindset and Self-Awareness Empower Teens for College with Coach Sherry Win

Coach Sherry Wynn, a two-time Olympian and CEO of Winning Leadership Company, explains how self-talk shapes outcomes. She uses the formula E + R = O (event plus response equals outcome) to show how limiting beliefs like "I'm not fast enough" become self-fulfilling prophecies. Only 15% of people are truly self-aware, she says.
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Hello, this is Shellee Howard with Parents, Is Your Teen College Ready? And I have a wonderful guest tonight, Coach Sherri Wynn. Welcome to the show.
Hey, thanks, Shellee. Really appreciate it.
So let's talk a moment. Maybe you can share with our listeners a little bit about your background because I was so impressed when I read it. So please share.
Okay, we'll do a pared down really quick thing. So I'm a two-time Olympian, national championship basketball coach. I was an All-American in college, valedictorian in college. And so now in the last 12 years, I've been the founder and the CEO of the Winning Leadership Company, where I speak to folks all over the country like Adobe, Dell, McDonald's, those kind of companies.
And you just breezed right by that two-time Olympic champion. And since we just had the Olympics and everybody is like, wah, let's talk a little bit about the leadership, the mindset, that goes into being an Olympian, right? I mean, I think it's important for student athletes to hear at that whole next level, did they prepare you mentally for the challenge?
I'm laughing because no, because this is like 1984 and 1988. So we've really progressed in a lot of different ways. But, you know, what I noticed when I was even playing, what I would hear myself say things like, oh, I can't play I can't play against this player because she's taller or she's faster or any of those numerous things we tell ourselves that stop us from being our best. And so to be the best, you have to recognize the words that you tell yourself really affect your outcome, right? So what you say to yourself really matters. And then change those words, change that into the positives. You have to believe it. You can't just say it. You have to believe it, right? You have to believe it is something that really feels true to you. And you have to really understand that when you say to yourself, I'm not, like, I'm not fast enough, I'm not strong enough, I'm not smart enough, that will become your reality. Yeah.
So did you learn this on your own? Like, this is your world now. How did you go from really not having support mentally going through the Olympics to where you're at now, where you're teaching corporations?
Well, so at the age of 35, I developed chronic pain. I couldn't sit, stand, or walk without intense pain. I mean, intense pain. So if you've ever had whatever you've ever you had. Let's say you broke your ankle. At the moment you break, break your ankle, that intense pain, that's what it felt like to me every day for year after year after year. So during that time, I went to 17 different medical professionals, had every test known to mankind, and now had zero answers. And so I was like, okay, so I don't trust— like, you guys did your best you could, I believe there's an answer. And so I started looking over at alternative medicine, and then I met these people and they said, well, you know, this chronic pain is body, mind, and spirit. It's not just physical. And my response was, that's a bunch of crap. Like, there's no way that there's, you know, there's no way that the mind has— it plays a part in this. Well, come to find out, yes, it does. Like, and so it was, it was the years of going through that intense— I'll call it therapy because it was. I mean, it wasn't like you're going to a therapist, but it was a mind-body-spirit therapy. Um, I had to change, like I did change some diet and I changed some other things, but it's really about learning the power of the mind and learning about the things that I'd built, my beliefs that I'd had that weren't positive and that were harming me in different ways. And then I started reading tons of books, listening to different people speak, and really understood, you know, and I'm still understanding the depth of this is insane of what we, what we do to ourselves. And yet we blame other people for the life we're living, and it's really what we're doing to themselves.
That is so fascinating. So we have— in, in the world of college planning, test anxiety is a very big thing where a student prepares, prepare, prepare, and then they sit down and then it's blank, right? It just is all— it's just not there. So we actually have worked with a similar thing where it's the power of the mind and how to prepare them the night before and what they need to do the day before. And it's just like very much a pattern. So have you been able to help in that world as far as, you know, helping students overcome that mindset?
Well, I've helped a lot of people overcome different mindsets, right? So there's all kinds of limiting beliefs that people have that stop them, so— but they don't even recognize they have the belief. That's the, that's the problem. That's the first challenge you have to do is to figure out the beliefs that you have. So right now I'm working with a golfer, right, that's in college, and I don't normally work with student athletes, but her parents heard me speak one time at their company event. And so I said yes. Wonderful, wonderful lady, young lady. And what she does is she tells herself, like, I'm not good enough. Like, she will know, like, she'll start, like, she'll play well and then she'll go, oh my gosh, I'm not very good at the short game. I'm just really terrible at the short game. I'm like, okay, so let's look at this. How can you have, how can you tell yourself I'm not good at the short game and then go think that you're going to be good at the short game. And we had to unravel everything around that. And so, you know, it was things that she learned as a child. Now listen, her parents are— I'm not blaming her parents. Her dad really wanted her to be good, so he would force her to work harder and harder and harder without ever saying, hey, that's really good, or you did great, or that was awesome. Let's step away from the golf course feeling good. It was always, you got to get better, you got to get better, you got to get better, you're not good enough, you're not good enough, you're not—
this kind of thing.
Well, When you're— when you hear that, it becomes really embedded in your brain. Like, our brain is a computer, if you will, and it—
and it—
whatever is wired in your brain becomes a way that you view the world. And so you literally have to change that your brain is wired, your neural networking, so that you get a new experience. And most people are like, well, it sounds like work. Well, it does. It is. And do you want to live a different life, or do you want to stay stuck in the same story? Because you're going to stay stuck in the same story, whether it's test anxiety, becomes some other anxiety, that becomes some other anxiety. Like, you have to get the root cause and unravel that. And when you get to the root cause and you unravel it, like this young golfer who's had remarkable improvements, then you can have a different experience. But if you keep telling the same story, you're going to get the same results.
Makes so much sense. So when you're working with these corporations, and obviously they, they bring you in because of your background and your knowledge, Um, are there any things that you do in corporate America that maybe the families could help support their child or children overcome, you know, the COVID mindset, like 2 years were taken away from me and, you know, that type of thing? Is there something that you can recommend that they might be able to, to support their child with?
Well, first of all, let's stop telling that story.
Right?
So whatever story we tell is the experience we're going to have. And so people go, but it's real. Okay, so it's also— other people had experienced COVID as well and they don't have the same outcome. How is that possible, right? How is that possible if they experience COVID but they don't have the same outcome? Why is that possible? And there's a great— and this is not a formula that I created, but there's a great formula that says E E plus R equals O. The event plus your response to the event equals your outcome. So look, if you want to have a different outcome, you got to change your response.
Okay.
So you have to change the story you're telling yourself. And people say, but it's real. I'm like, it's real because you keep telling yourself the story. Change the story and you'll have a different experience. And so it's the stories we tell ourselves that create the life we're living, right? That's why I say that the two most powerful words of the universe are the words, "I am," because whatever you say after those words becomes your truth, right? So you can't say, "I'm not fast enough," and then go play somebody and think you can beat them. There's no possibility. You have to convince yourself of something different, like, "I'm smarter than the other person. Even if the other person's faster, I'm still smarter." And so I know the shortest distance on the court, or whatever it is you're telling yourself, you know, that will enable you to do something different. And so the power of our mind is so more powerful than most people could ever imagine, ever imagine. Um, and we learn these, like, we have these truths, but it's not the truth, it's a truth. So it's a truth that you've chosen to believe versus what is the truth, right? So there's different things that we believe, and just unraveling that and really getting to the, the core, the core issue, unraveling that, is that a belief Let me give you a short, a really short story. So when I was growing up, my mom sang me a song, and I don't know the title of it. I just call it the worm song. And the song goes like this: nobody likes you, everybody hates you, you need to eat some worms. First you get the bucket, then you get the shovel. Ooh, how they wiggle and squirm. Now listen to the words: nobody likes you, everybody hates you. Nobody likes you, everybody hates you. So what did I believe? I believed that nobody liked me, everybody hated me. Oh, that was a belief. So, but I didn't know it was a belief. Like, I hadn't examined it. I didn't know it was a silly song. I accepted it as truth. But what happened is, okay, so elementary school comes along. I start playing little teams. I start thinking they don't like me. Then I started separating myself. And then they start thinking, well, she's really good, so she thinks she's better than us. That happens in elementary. It happens in junior high. It happens in high school. It happens in college. Well, what's the common denominator? It's me. It's me. And it was never the truth. It was never the truth. It was a truth that I accepted from a silly song. And once I understood what the root cause was, I changed my thinking. And guess what? People liked me.
That is so fascinating. Now, what about affirmations? So that was a big thing when I was playing softball in college. And I don't know if that was just the timing of things, but affirmations, they would record positivity, these types of things. Is that still something that is working and available?
So yes, and let me say the and part. If you say something but you don't think it's true, then you don't believe it. So it's the person that's saying, well, I'm an Olympian, but you're like, I'm really not even started on my high school team. So, so it's, it's a stretch. It's too far stretched. You have to say things that you actually believe. So I'm a hard worker. I'm always getting better. I'm very coachable. I am like— all of those things are truths. Say the truth. Say the things that are really true that you experience. If you say something and you don't believe it, it's only harming you. So the affirmations have to be in alignment with the truth that's already there. And once you believe that truth, you can stretch the truth a little bit more, right? You can increase that level. But saying something that's not true, that you feel like is never going to be true, is not going to get you the result.
Okay, that makes sense. They have to believe it to be true. Okay. Now, what about— are there tools that you use or that you can work with people to get them through tough times? Before we got on the call, you were saying how life is just full of tough times. Maybe you can share a little bit of that.
Well, look, it's really important that people develop resiliency, right? Because here's why this is so essential. Is because our experience as a human being means that we're going to be hit with challenges. In fact, we're going to be hit by about 48 life disruptions. So a life disruption is something that affects your life for 6 weeks or more. You got 48 of those in a lifetime. That's on average for every single person. Then you have 3 to 5 lifequakes. So a lifequake is a life disruption on steroids. So a lifequake is like the, the injury or illness that alters your life forever. It's the lifelong dream that blows up in your face. It's the person that you love, the loved one that betrays you in such a way that seems unforgivable. You're gonna have 3 to 5 of those. So this is the human experience. So trying to put somebody in a bubble or rescue them from these is not the answer. That's not going to help them because another one's going to come and another one's going to come and another one's going to come. What the answer is, is finding the right tools to meet these challenges, right? So how you think about the challenge is going to be changed to your outcome. We went through that E R O, right? So what is your response and how do you get to a better response so you can have a better outcome, right? That's the, that's the whole thing. Well, for me, it goes back to this: you don't get what you want, you get who you are, right? To get what you want, you have to change who you are. So that means you have to change your thinking. Change your thinking around challenges. What does challenges really mean? It means an opportunity. That's what every challenge is, it's the opportunity. So how am I growing from this? What is it that this is giving me that's going to prepare me for something even you know, even more challenging, or preparing me for the life I want to live. How is this helping me? Versus, oh my gosh, this happened to me, it's terrible, it's a tragedy, it's awful. Stop, stop. No, it's an opportunity. It's going to give you the way for you to progress. It's going to give you the way for you to become even better human being than you are today.
Wow. And so when you're working in these corporations, are— is this some of the tools that you're sharing with them? What does that look like?
Oh yeah, absolutely, absolutely. So, you know, it depends on, you know, there are different ways for me to work with somebody. We can do, for example, we'll do team building, and in team building we'll put forth things that make people, you know, very challenged. So they have to challenge it, and then how did you respond to that challenge? What were the things going, thoughts going through your head? Let's examine those thoughts. Are those thoughts helpful or are they harmful, right? Most people don't even recognize that they repeat harmful thoughts again and again and again. Let's change those thoughts. Let's change your thinking. So there's team building, there's, you know, one-on-one coaching where I do a lot of one-on-one coaching with individuals and folks to help them recognize the things that they're doing that harm themselves, right? Because look, that's your controllable factor. There's only one controllable factor that you have, and that's you. That is your controllable factor. You cannot control, you know, your classmates, your teacher, your professor, your coach, your teammates, your parents. You have no— but you can control you.. And by controlling you, you're gonna get different, you're gonna get better results, right? And so when we stop trying to control everything else and stop blaming everything else and take responsibility upon ourselves, we're gonna have much different outcomes and much better outcomes.
Yeah, it all makes sense. But what about for the people who are not coachable? Those ones that are like you said, oh, I don't know if I believe in all of that. That's just a bunch of you know, uh, mumbo jumbo. Is there hope for the, the non-coachable?
I'm gonna say no. Only hope for the non-coachable is that they, they hit the pain deep enough, right? So we're only motivated by two things and two things only. One is to avoid pain, and the other is to gain pleasure. That is where we're motivated. So the pain gets deep enough, then they may change their tune. They may be willing to look for other answers, or if they're— or if the reward is big enough, right? And for me, I think it's a combination of the two, right? So that your pain gets deep enough, you want to change, and you see the reward as something over here that you really want. That will create the opportunity for that person to change. But if you're unwilling to be coached, if you're unwilling to listen, to examine, to think, to self-reflect, look, you're going to keep living the same life over and over again, and you will blame other people. That does not change your outcome.
That makes a lot of sense. I mean, it really all— you're saying it all comes back to you and your thinking. So what would be the first step? Maybe a parent's listening and they have a teenager that's really hard on themself, and maybe it stemmed from, like you said, a book or a saying of someone. What would be like the first or easiest next step to, to try to help make a better situation?
Well, you know, again, I think the first thing is, is to get them to self-reflect. Look, only 15% of the population are self-aware. One-five, 15%. That means 85% of the people never examine what they're doing, right? So they'll never say, why do I do this? Why do I think this way? Why do I react this way, etc.? So when somebody is beating themselves up, the first question is Is this helping you or is it harming you? And they might say, it's helping me. It's okay, give me all the ways it's helping you, right? Yeah, give me all the ways it's harming you. Like, when you're beating yourself up, are you a better player or are you a worse player? Well, I'm worse. Oh, so it's helping you? No, it's not, it's harming me. Okay, so, or even if it's not even that, maybe it's just there, it's, you know, taking a test and you make a B instead of your A++ or whatever, and so you get mad. So in that, how's your thinking when you're mad? Like, where does that lead you? Are you able to think clearly when you're mad?
Well, no.
So is it helping you? Is it harming you, right? I mean, what's the benefit? What's your true— how does it benefit you? Because it always benefits us when we behave a certain way. How does it benefit you to behave this way, right? How does it hurt you to behave this way, right? So is it— is it not beneficial to you? What would happen if you changed? What's going to happen if you don't change? Like, it's that self-awareness thing, Shellee. You're really trying to tap into getting people to think and examine why they do what they do. And really, is it helpful or is it harmful to them?
That's so powerful. We do a program that's called Passion with a Purpose, and it's helping students start with what they're passionate about and change something they want to see changed. And I see a lot of limiting beliefs around this. And so I'm just taking notes to see you know, how can I help reflect back to them that is that helping you to think that you have no passion, that you have no purpose?
Well, it is in some way, right? So it might be protecting them from like fear of failure because we only do something if it benefits us. We just don't examine how it benefits us. And do we really? So in other words, let's say that somebody goes, well, you know, I don't have any passion. Okay, well, how does it benefit you? Well, then I'll never get hurt. Oh, oh, right.
Sure.
So, so is that true? Like the next thing you say, is it true that you will never get hurt? Well, yeah, no, I don't know. Yeah, you don't know, right? Because we're not— that's part of the human experience. So just really helping people understand why they do what they do and understand if they do something different, they're going to get a better result. I mean, it sounds really simplistic. It's actually very challenging, as you know, if you go through this with your students, you know how challenging it is. And it's very possible. And if you do it, like, your life is going to be totally different. I mean, you're going to spend less time in drama and unhappiness and depression and more time in happiness and joy and serenity and peace and, you know, all the things, and passion, all the things that we love, all the things you really want over the other side.
So when these, these thoughts come to these students and they're, I can't, I, I don't, I won't, I'm not good enough, what would be something that you would recommend saying back to them to help them to see that that's, that's not serving them well?
Right. Well, it depends on what they say, right? So again, you're looking at what they say and If, you know, is it— is this a truth you're willing to live? Basically, is this the truth that you want to live? So if I'm not fast enough to make the team, is this the truth you want to live, that you're not fast enough to make the team? Well, no, but it's true. No, I'm not asking though. I'm asking if this is what you want to live. Well, no. Okay, let's look at something else, right? Because you don't have to be fast. You can be smart. You can be deceptive. You can be, you know, like There's so many different ways to meet life, and we think that there's only one way, and then we tell a story and repeat the story a thousand times, and we want a different result, and we know that's called insanity.
For sure. That's exactly what I was thinking. Well, it has been such a pleasure getting to hear your stories. And is there any last thoughts you would share with a parent of a teenage or college student Sure, look, you know, always happy to help people.
Like, one of my things is, you know, I've got to this position in life, and so many, many— I had many mentors that helped me get to where I am. So if you'd like to have a free discovery call with me, that's F-R-E-E. Now here's what it is, everybody goes, oh my gosh, that's not true, there's a catch. Yes, it is. Here's the catch, folks. If you want to have that call with me, if you want to discuss, you know, with your child, about your child, or you want to discuss some of the things you can do, Here's what I would want back from you is that you'd be willing to rant and rave about me to other associations, organizations, and people. If you want to do that, what you can do is you can email me at sherry@thewinningleadershipcompany.com, sherry@thewinningleadershipcompany.com. And I'm happy to help you find some tools that you can use to move your child forward.
Mm, that is such a generous gift. Thank you so much for your time, and it has been a pleasure. Parents, this is something super powerful. You could change their life forever. So thanks so much, Sherry, for being on the show.
Thank you, Shellee. Much appreciated.
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