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Discover, define, and decide how to win your way

Keynotes that challenge leaders to expand possibility and take aligned action so they can create success on their own terms


You hold pretty high expectations of yourself and those around you. As a result? You love to win. A lot.


Sounds a great deal like someone I know … *cough* That’s me. *cough*

I’m assuming you haven’t clocked in this many hours and come all this way just to play small now, have you? Yeeeaahh, that’s a bit fat NO

But up to this point, what has all your success cost you? Healthy relationships? Personal wellbeing? Those are the few things in life that matter most and aren’t worth sacrificing.

There’s another way to get where you want to go. An easier way. A better way. 

It’s called Wynning Your Way.



“[Michael] inspired us to find our wins, use intention to break out of fear, and the persuasion formula was a big hit!”


Michael was a dream to work with. Everyone loved learning about the visualization and high-performance habits we can put in motion immediately.

Stephanie Theisen, VP Sales and Marketing, Leighton Broadcasting

Meet Michael Wynne Kithcart

High-Performance Executive Coach, Speaker, and Creator of the Wynning Your Way Method™


The Wynning Your Way Method is a framework I’ve used on myself, teams I’ve led, and hundreds of high performers I’ve served through my coaching business to accomplish breakthrough results. 

“Wynning” is spelled with a “Y” by the way, because it starts with YOU. 

According TO you, crafted BY you, and in support OF you. “Wynne” is also my middle name. So yes … you could say I was born to win.  ;)

Wordplay aside, I’m here for the people who make shit happen in the world. The overstretched achievers who are accustomed to “succeeding” by most standards, but want to experience joy in pursuit of their fullest potential. 

I spent years overachieving because I thought that was what success looked like and required. And in the process, I completely exhausted myself. When I finally set my own mindset, standards for success, and shared them with others, I realized how many other high achievers conform themselves to fit outward expectations of success. 

That’s why my greatest passion is helping high achievers transform into high performers, crush limiting beliefs, and show them they can truly have it all.  All the accomplishments, all the results, all the success — and feel good while doing it.

Photo of Michael Wynne Kithcart

“[Michael] challenged us to break up with achieving in exchange for truly thriving and reminded us that we already have everything we need within ourselves to be who we are meant to be.”


As a keynote speaker, Michael shared implementable ways to get quick wins on our journeys to success on our own terms. Attendees left feeling ready to define success on their own terms and empowered to take their dreams from goals to reality.

Laura Caroon, Former LadyBoss CEO at Midwest Retreat

I’m a good fit if you want to give your audience …

An ass-kick in the best kind of way

Enough said. Getting to the next level takes a little tough love, challenging expectations, and throwing preconceived notions out the window.

A blend of leadership, psychology, and brain science

The power of the mind is grossly underestimated. The only way to achieve outward results is by dedicating time to inward thoughts, beliefs, and behaviors.

25 years' worth of executive career insight

I’ll never ask your audience to do anything I haven’t experimented on or tried myself! Everything I teach is from personal application.

A game plan with immediate action steps

I’m not here to talk your ear off for an hour. I address the “why” and the “how” with practical application backed by research to improve performance and quality of life, starting today.

Signature topics for your event or leadership team

Wynning Your Way — A Paradigm for How to Define Success

If you’re being honest with yourself, whose definition of success are you living by — yours? Or someone else’s? 

Once you’re clear on where you’re going, and the actions it’ll take to get there, then you have the power to create the life you want. 

With interactive exercises, real-life case studies, and immediate “quick Wynns,” this keynote will empower you to redefine your definition of success from the inside out and finally start living it. 

Length: 45-60 minutes

Good for: Business leaders and sales teams 

Format: Can be customized for both keynotes and interactive workshop settings

How to Move from Exhausted to Energized for Leaders on the Brink of Burnout

What’s causing you to really feel exhausted right now? You’ll be surprised to learn it’s not for the reasons you would think.

In a world that shouts “just move forward, faster!” I want to shed light on the true energy suckers in life. I’ll also share five areas where you leak energy and give you proactive steps to conquer your day. 

And guess what — that energy adds up! In this keynote, you’ll ultimately gain clarity and focus on the things that make the greatest impact so you can show up as your best self. 


Length: 45-60 minutes

Good for: Corporate leaders and entrepreneurs

Format: Motivational and educational keynote

The Relationship Between Commitment and Courage

You can’t be 90% committed. You either are, or you aren’t. Problem is, most high achievers think they’re committed, but their actions say otherwise. 

This keynote breaks down step three of the Wynning Your Way Method to help you identify where you need to demonstrate true commitment and more courageous action. First, we’ll discuss what commitment is, what it’s not, and how it’s a reflection of who you are. 

Then, you’ll be challenged to ask yourself: “Do I have the balls to do this?” — that’s the courage piece! To which the answer should be, HELL yes! Because once you decide, nothing will stop you. 

Length: 45-60 minutes

Good for: Sales teams, leadership, entrepreneurs

Format: Motivational and educational keynote

From Worn-Out High Achiever to Breakthrough High Performer

“Achiever” is often worn as a badge of honor. Yet the people who wear it also tend to be fatigued and running on empty. What gives? 

Well, high achievement and high performance are NOT one and the same.  To prove it, I’m going to dissect the six pillars of high performance based on the world’s largest study of high performers. 

Expect truth bombs on why achievement limits you and how to become a high performer so you can find opportunities for growth in every area of life, starting today. 

Length: 45-60 minutes

Good for: Organizations, mid-career professionals, sales teams, and seasoned entrepreneurs

Format: Motivational and educational keynote

“Michael brought energy and enthusiasm to our marketing and sales conference!”

Her engaging and thought-provoking “Mindset Minutes” was a welcome break from a day filled with intensive learning. She literally and figuratively brought the audience to their feet!

Paula Beadle, Sponsorship Master Summit

Professional Bio

Michael Wynne Kithcart is a high-performance executive coach, host of the Champions of Risk Podcast, and creator of the Wynning Your Way method. She helps leaders and sales teams redefine success, re-engineer thinking, and re-align actions so they can deliver next-level outcomes without existential meltdowns, compromising joy, or only running on caffeine for daily doses of energy.


Michael incorporates her 25-year experience of leading, coaching, and developing hundreds of businesses and leaders to create an accurate picture of what’s required to be better and get better results. Her coaching has resulted in clients out-performing in the market, surpassing stretch goals within a fiscal year, and growing revenue year over year by 50%. 


Her approach to high performance comes from her own experience battling achievement overload while juggling personal and external expectations. Now she helps leaders and teams move from stuck to unstoppable, all starting with how to define what it really means to “Wyn” their way.

Photo of Michael Wynne Kithcart

Greater achievement, aligned action, and expanded possibility are all waiting for you


Let’s get to work