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Wynning Your Way

May 12, 2021

Season 2, Episode 19


Your current thinking around winning is messing you up.

Chances are your definition of winning is influenced by others’ definitions. Maybe you picked up a piece from a leadership book, a section from corporate goals, maybe a smattering from a mentor or from playing a team sport. 

How’s that working for you?

I want to talk to you about the difference you can make in your life by redefining what it means to YOU to win at work and in your life. I’m not talking about winning at all costs and smashing unrealistic goals set by people with little skin in the game (or understanding of the game in some instances.) I’m talking about how you define what it’s like for you to feel like you are operating at your best, showing up as your best self in situations that matter to you, and feeling like you’re participating according to your own rules. I’m talking about Wynning Your Way. Listen to what it takes to Wyn Your Way and how you can define it and live it on the latest Champions of RISK episode. Season 2, Episode 19





Michael Kithcart: 

Hello, I'm Michael Kithcart.

I'm a high performance leadership coach, entrepreneur and creator of the Wynning Your Way framework.

Welcome to the Champions of RISK Podcast, where we examine the many aspects of risk. So we can all navigate uncertainty with more strength, courage, and humor together.

The main reason why I chose to have a podcast on risk is because it's a term that's used broadly, it's experienced by everyone.

It's measured differently.

It's defined differently. It's subjective.

So today, I want to talk to you about what's the risk in staying the same- as in what's risky about the ability to acknowledge that what you're doing isn't getting you the results that you want. It's not getting you where you want to go.

But you continue doing the same thing. There is no judgment in my questions here. I'm bringing it up, because it's a pattern that I'm seeing.

And quite frankly, it usually starts at the beginning of a conversation when I'm first starting to work with a leader or their team.

And it sounds a little something like this isn't working, but I don't know what isn't working, or how to go about changing it.

Or it sounds like I can't keep operating the way that I am. But how do I go about doing things differently? It also sounds like, look. I am dog ass tired, I'm frustrated.

And quite frankly, pretty pissed off that I can't seem to figure out how to change. Does any of that sound like you?

Someone who's successful by many, many standards, right?

Someone who likes to win, but feels like they aren't winning at anything right at the moment, like not winning in business or in life as a leader.

Look, fundamentally, you can understand that a lot of that risk by staying the same, right. And if you're operating full tilt all the time, you know, that's not sustainable, right.

So logically, we're all lying there, we can agree on these points.

But the other piece of this is that people aren't willing to do anything about it, because they're too exhausted, worn out or overwhelmed. Or they don't know what steps to take to get themselves going in a different direction.

So you want to win.

But in the moment, when it doesn't seem possible, it can actually feel like well, hopeless.

So today, I want to go deep with you on the risks that you're taking, by operating the way that you are with the definition of winning that you currently have.

Now, this episode comes with a disclaimer, I'm going to make an ask at the end of this podcast, okay, I just want to be fair and let you know about it in advance, we're going to provide value, maybe shift your perspective on a couple of things here.

And then I'm going to also tell you how you can take back control of your situation and start Wynning Your Way.

So if you're not ready to get a little uncomfortable here, if you're not interested in getting different outcomes, if you're not the kind of person who wants to set that thriving badass version of yourself free, then stop listening now. You still with me?

Okay, let's get into it. Your current thinking around winning is messing you up.

Let's just call it what it is.

So chances are your definition of winning is influenced by other people's definitions.

Maybe you've picked up on a piece of winning definition from a leadership book, maybe it added another piece of your definition from corporate goals, maybe added a smattering from a mentor.

Or maybe your definition of winning comes from playing a team sport. How's that working for you?

I want to talk to you about the difference that you can make in your life by redefining what it means to you to win at work and in your life. I'm not talking about winning at all costs, or smashing unrealistic goals set by people with little and I'm talking little skin in the game here.

Or maybe like people who don't even understand the game at all. We're taking all that off the table. I want to talk to you about how you define what it's like for you to feel like you're at your best that you're operating at your best.

You're showing up your best self in the situations that matter to you most.

And to get you to feel like you are participating according to your own rules. I'm talking about Wynning Your Way, not anybody else's way, your way.

And you may think that, yeah, I Well, I am winning my way.

But are you really?

Like, are you letting the environment that you're working in dictate to you how you're feeling about whether or not you're being successful?

Are you looking at maybe what other people's expectations are of you and letting that influence whether or not you feel like you're winning?

Or have you created some type of unattainable definition for yourself, that just makes you feel like you're not getting ahead, no matter what you're doing.

That is a problem. It is. And I just want to break you free from any of the thinking that you've had before, around what it means to be successful.

I'm using successful and using winning, I get that some people get turned off by the word winning, I happen to love it.

I love winning, I love helping people win. I like watching other people win. I like to feel like I'm winning. Full disclosure, it's also my middle name, Wynn it really is.

So it might be a little bit biased. But hey, if winning isn't a word that connects for you, no problem. Stick with me, okay?

Because the point is still there. Every time you hear the word winning, replace it with a word or a phrase that works for you.

Maybe it's mastery, continuous improvement, thriving, reaching a new level, leading by example, being a warrior being in the zone, whatever it is, that connects for you. Stick with me and use that word.

Okay. I also want to give you an example of how I define winning my way, because maybe that will connect for you.

Here's how I define it. I define it.

That's the first step. Nobody else does.

Nothing else does. It looks like I choose the way that winning is going to look what success looks like for me, based on my outcomes.

My focus, the definition also bends and flows, it changes over time.

So let me give you an example. When I have led teams, it's been a collective win, right?

Like, what is it that we as a team are going to define as winning? Forget the budget that was handed to us, and we didn't, you know, have influence over it or perceived expectations that others might have?

What are we as a unit going to determine as a win for us. And then that's what gets focused on that's what the actions are around. And that is what we celebrate at the end. Not anybody else's definition, but what we set for ourselves.

And you want to know what?

That approach has kept people engaged when goals and budget numbers weren't achieved. And it's also expanded the reach far beyond any corporate goal that was set.

I mean, goals get shattered with this approach. It works on both ways.

And my guess is that you've got an example that comes to mind in your mind of when you have been hugely successful as a team. And it was because of what you all collectively decided was going to be the benchmark, am I right? Now, I'm just going to admit here that I started being better at helping others wrap their arms around what would be deemed successful, then I was at doing it for myself.

Okay, but at the same time, I can point to key moments in my life when I made a shift in how I was seeing my circumstances, and I redirected my thinking to how I wanted the situation to be, how could I make it work in a way that would feel inspiring and appealing and energizing. I know that when I did a few things differently, I started getting different results, results that I wanted results that mattered to me, and every time I did this, it was like I took back my own power, it removed challenges, and it created a possibility. It was freeing. It was empowering. And you know what I achieved better result.

Each time I redefined what winning looked like to me and got back on track and I reached a new level of success.

Success according to me.

Now the patterns emerged and that lead to a framework that I could consistently go back to and revamp what it meant to win for me in that moment. So became repeatable, right?

So I just want to know for you, like, do you have a go to when you need to recalibrate?

Do you have a go to method that pulls you out of your funk? helps you examine what's important to you, and provide a path to taking the steps that will get you where you want to go?

It's okay, if you don't I mean, I'm I met, I didn't have it either. But I found it. I found this way.

And I just want you to stop down and think for a moment. What is your current method for winning your way? Is it working for you?

Is it designed for you, and by you?

Or if you really think about it, is your definition of winning, based on someone else's expectation, or kind of forced upon belief that you've just kind of absorbed? Here's the thing, winning by someone else's definition or expectations can and often does lead to disappointment.

There's a huge opportunity to reconfigure what you've been doing, and more importantly, how you've been winning. Look, I want this for you, I want you to win your way.

But of course, I can't want it for you more than you want it for yourself, I have a way to help you based on my own experience and the outcomes that clients have received.

There is another way of being of thriving, of contributing in life. Look, this isn't for everyone. But it could be for you, it could be for you.

If you've been saying there's got to be a better way. It could be for you if you're feeling that something has to change, or you won't be able to keep going.

Or if you've noticed that you've lost some of your stamina, your motivation, or even what you're doing isn't that meaningful to you anymore.

If others have commented on your mood being more caustic, agitated, or maybe have been short tempered, or it could be for you if you want to get back on track with the goals that you set back in January, and when the back half of the year.

If any of those rang true for you, then chances are the new Wynning Your Way course is right for you.

Okay, fair warning, I'm about to tell you about my new six week Wynning Your Way course because it starts May 20th.

And I'm super excited about it.

It's designed exactly for those of you who have not given up on the year who are ready to redirect your thinking and your actions in a way that energizes you, is aligned with what you want to make happen in a way that fits your values, your priorities, your strengths, your way of winning.

So if you connected with anything that I said In this episode, then you are going to love my new Wynning Your Way six week course to transformation. This course is action oriented, we're not messing around here.

Each week is going to build on the last week so that you have discovery options and actions every single week.

It guides you to redefining and designing your own version of Wynning Your Way so that you get more time back, experience more freedom, and lead the way you want in life. It is living life on your terms. So here's a quick breakdown.

I'm gonna be brief.

Each week, there's a 90 minute live workshop to learn and practice each element of the Wynning Your Way framework, you'll better understand the impact your thinking and actions have on your success, and how to align that to better achieve results regardless of your current situation.

Then you're going to get exercises or short videos that really lock in the concepts that can guide you to define what will work for you.

Now, this is committed you time it's designed to energize you not shut you down or overwhelm you.

It's at just the right pace. It's engaging, encouraging, actionable and sustainable. It's practical. Look, I was once you and some days, I'm still that exhausted achiever doesn't listen to my own coaching. I use this framework, and I want to share it with you.

This is not about perfection. It is about progress.

And that's what you're going to see. At the end of six weeks, you're going to see progress.

After the first couple of weeks, you're going to have some wins racked up, you'll see results from shifts or maybe even just an absolute overhaul that you've made, and you'll know how to sustain the newfound energy that you have from Wynning Your Way.

Become the thriving badass I know you can be and register for the Wynning Your Way course through the link in the show notes or go to

Thank you for listening to this podcast and I look forward to seeing you win your way!


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