Freestyle Fridays: The Real Story Behind the Wins
Welcome to Freestyle Fridays. This series is something I have wanted to do for a long time. Every week, I sit down, hit record, and speak openly for a few minutes about what is really going on in my life.
No script.
No filters.
No polish.
Just the truth.
As I record this particular message, my house is full of moving boxes. The shoe wall behind me is gone. We are 18 days away from relocating from Florida to a town called Zionsville, Indiana, just outside of Indianapolis.
We are leaving the Sunshine State.
We are heading back to four seasons, family, and a different pace of life.
But that is not what this Freestyle Friday is really about.
Today is about self-sabotage.
Specifically, how I discovered I was sabotaging myself again… and what I decided to do about it.
What Self-Sabotage Really Looks Like (It Is Not Always Loud)
Self-sabotage is rarely dramatic at first.
Most of the time, it looks like:
Slipping on your habits
Numbing out with food, drink, or distraction
Avoiding the gym
Ignoring the hard conversation
Telling yourself “I will get back on track Monday”
On the outside, things may even look great.
For me, business is booming. My coaching and speaking career is stronger than ever. I am being invited onto stages I once only dreamed of. I am impacting people at a level I did not know was possible.
But quietly, behind the scenes, I had let something slide.
My health.
My discipline.
My standards for myself.
I stopped eating well. I stopped taking care of my body. I gained more weight than I have ever carried in my life. And I felt awful.
That is self-sabotage.
Winning Big… Then Tearing It Down
On a Saturday afternoon not long ago, my wife and my son Leo went to my sister-in-law’s house to swim and hang out. I stayed home and did something I try to do often:
I sat with myself.
No noise.
No distractions.
Just thinking and being brutally honest.
I started replaying past seasons of my life:
Times when I was in incredible shape
Times when business was thriving
Times when my relationships were strong
Times when I felt truly confident and aligned
And then I noticed a painful pattern:
Every time things were going really well… I eventually found a way to destroy it.
Not by accident.
Not overnight.
But through small daily decisions that piled up into a slow collapse.
I realized that I have a long history of sabotaging good things in my life.
Why Would Anyone Sabotage Their Own Success?
It sounds irrational, right?
Why would anyone ruin the very things they worked so hard to build?
Here is the truth I arrived at:
Some part of me is always waiting for things to end.
I was left at relatives’ homes as a kid for long stretches of time. Not for a weekend. For a year.
I have had business partners steal from me.
I have worked for companies that did not pay me what they owed.
My brain collected those experiences and built a story:
“Good things do not last. People leave. Things fail. Do not get too attached.”
So what do you do with that belief?
You begin to prepare for the fall.
You pull back just enough so that, when it ends, it will not hurt as much.
Or at least that is what you tell yourself.
You eat worse.
You stop training.
You stop pushing.
You dull your edge.
In my case, I started to believe:
“If my speaking or coaching slows down, it will hurt less if I am not at my best anyway.”
That is a lie.
Whether you fall from one foot or ten feet, it still hurts.
Meeting “Middle School Chris”
There is a version of me I call Middle School Chris.
He is the voice in my head that says:
“You are not good enough.”
“You are not strong enough.”
“You are not smart enough.”
“People do not really like you.”
When I am tired, stressed, or stretched, that voice gets louder. Lately, he had been loud.
Food became comfort.
Convenience became my excuse.
Discipline became optional.
And here is the problem:
I am a coach.
I speak on stages about discipline, mindset, and winning daily.
I talk about stacking wins and raising standards.
How can I stand on stage and speak about discipline when I cannot see my belt because my stomach is hanging over it?
That question hit me hard.
The Moment Everything Shifted
On that Saturday, lying in bed, exhausted and frustrated, I finally called it what it was:
Self-sabotage.
Not a bad week.
Not a “busy season.”
Not “getting older.”
Sabotage.
So I made a decision.
I got out of bed.
I filled my water bottle.
I grabbed my Apple Watch.
I got on the Peloton and rode for 45 minutes.
When I finished, my wife and Leo were back home. I told my wife everything:
The pattern I had seen
The self-sabotage I was allowing
The reasons behind it
The decision to stop
Saying it out loud mattered.
Owning it mattered.
Committing to change in front of someone I love mattered.
The Food Trap: Permission to Drift
One of the biggest areas of sabotage for me has been food.
It sounds like this:
“We are tired. Let us just order Uber Eats.”
Once the decision is made, I mentally give myself permission: “If it is delivery, it has to be something fun.”
Wings. Cheese fries. Heavy, greasy food.
The story is:
“If I am ordering in, I might as well go big.”
Here is the irony:
There are plenty of healthy options on Uber Eats.
I simply chose not to see them.
So I set a new commitment:
Fewer default delivery decisions
Healthier choices when we do order
More meals cooked at home
More awareness, less autopilot
It has only been a few days when I originally recorded this message, and I already felt better. Not perfect. Not finished. Just better.
Better is enough to keep going.
Drawing a Line in the Sand: The Full 30
To support this commitment, I started something called the Full 30, a challenge recommended to me by my friend Ben Newman.
For 30 days, no matter what happens, I am committed to:
Eating clean
Moving my body
Rebuilding discipline
Closing the gap between what I say and what I do
This is not about a number on the scale.
It is about integrity.
If I am going to be a leader, a husband, a father, a coach, and a speaker at the level I know I am called to be, then I cannot keep giving myself permission to coast.
I owe it to:
My wife
My daughters
My son
My clients
Myself
To stop sabotaging the very life I worked so hard to build.
Are You Sabotaging Yourself Too?
I am sharing this because I know I am not the only one.
So let me ask you:
Do you pull back when things start going well?
Do you let your health slip when business improves?
Do you ruin healthy relationships because you are afraid they will end?
Do you “soften the blow” of potential failure by never giving 100%?
If so, you may be sabotaging yourself the same way I was.
The good news?
Awareness is the beginning of change.
Your Challenge: Catch It and Change It
Here is what I am doing now, and what I invite you to do:
Name it
When you notice yourself drifting, call it what it is: self-sabotage.Interrupt it
Change the behavior immediately. Go for a walk. Drink water. Make a better choice. Do the opposite of what the sabotage voice is suggesting.Replace it
Choose actions that align with the life you want:Move your body
Fuel yourself well
Keep your commitments
Build daily wins
Commit to a time frame
It might be 7 days, 30 days, or 90 days. Give yourself a defined period to go all in on better decisions.Tell someone you trust
Say it out loud. Share it with a spouse, a friend, a coach, or a mentor. Accountability matters.
Final Thought: You Have Not Come This Far To Tear It Down
I have been given a second chance at life in many ways:
A 16–month-old son who looks up to me
A career I did not even know existed years ago
Opportunities to speak, coach, and lead at a high level
I have a responsibility to do more, to be more, and to serve more.
And you do too.
Your future deserves the best version of you.
Not the version that is quietly tearing things down out of fear.
Not the version that is preparing for the fall instead of building for the rise.
If any part of this resonated with you, do something with it.
Make one better decision today.
Catch one act of self-sabotage and flip it.
Move one step closer to the life you actually want.
This is Freestyle Friday.
If this helped you, share it with someone who may be fighting the same battle.
Take care, and make it a great day.
