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10 Lessons On Winning From 500 Grappling Matches
I got beat up so you don’t have to.
“The art of winning” was a tough subject for me to write about. Imposter syndrome held me back for a long time.
I mean really, why would I have any authority or audacity to write on winning?
I have a bit of imposter syndrome about it, but I’ve also had ∼500 competitive grappling matches in my life.
I have won and lost a lot.
I’m not a prodigy either. I didn’t start out as a winner. I had to learn to win — the hard way.
In my 8th grade wrestling season, I had a record of 4–28.
In 2019, I won an IBJJF no-gi world title in the adult division at purple belt. Today, I’m the 14th ranked no-gi grappler in the world at 170 pounds.
All things considered, I think I’ve turned it around relatively well.
Here are 10 of the biggest lessons that I’ve learned from dedicating my life to trying to win stuff and failing a fuck ton of times in the process. Hopefully, it could help someone trying to find their way in the many different competitive aspects of life.
Let’s dive in.
Winners are experts on the rules of their game.
Sometimes, you’ll see an outlier who shows up and performs well without knowing anything about the game.
This was me at my first blue belt Jiu-Jitsu World Championships in 2016. I didn’t know the rules of Jiu-Jitsu, but I got lucky and took 3rd in the tournament.
My success didn’t last, however, because I didn’t take the time to learn the rules.
I thought I was the 3rd best blue belt in the world, so I pulled off the gas a little bit.
And? I started losing.
The best competitors in the world are great athletes, tacticians, and masters of the rules of their game. Taking time to master rules sets you apart from 90% of the opposition.
For most of us, winning requires many attempts.
I told you that I had a record of 4–28 in wrestling and that I won a world title in BJJ.
Those events were about 9 years apart.
It took me nearly a decade to learn to manage my mind well enough so that I could win anything.
People love to praise prodigies, but I’ve found that “non-prodigies” are a bit easier to learn from. I learned a lot from watching Keenan Cornelius (my favorite BJJ fighter when I was coming up) go from an average purple belt to winning double-gold grand slams in Brazilian Jiu-Jitsu.
This inspired me more than any prodigy or natural talent.
Winning means making someone else lose.
“Everybody wins” is not a thing.
If everybody wins today, everybody loses down the road. The problem isn’t losing, the problem is that we don’t teach people how to handle losing.
Losing exposes your character.
When you lose, no matter the context, there’s a moment of ego death — a moment where your limits are exposed.
If losing makes you an asshole to others, you’re probably an asshole.
If you can lose with grace, you likely have good character.
Losing is the best way to learn how to win.
When you’ve lost a lot, you learn to become empathetic when you make someone else lose.
Losing with grace teaches you how to win with class.
Winning with class also makes it look like you win frequently.
This makes you dangerous.
Winning inflates your ego, which can hold you back.
The confidence you earn from winning is a double-edged sword.
On one hand, feeling like a champion is awesome. On the other hand, frequent winning without self-awareness can lead to complacency.
I, unfortunately, had to learn this the hard way.
To win often, you must be confident and self-aware at the same time. These traits don’t usually go hand-in-hand. Typically, self-aware people are anxious and not particularly confident.
To win frequently, you must balance self-awareness and confidence.
No amount of victory will satisfy the ambitious mind.
When athletes end their careers, it’s not usually because they’ve “done enough”.
It’s because their mind changes or their body breaks.
Maybe I just haven’t won anything big enough, but I’ve never won anything and felt “done”.
After each victory, I want more. Like Icarus, I want to fly closer to the sun.
Until a switch flips in my head and kills that ambition, the pursuit of victory will likely dictate my life.
Writing is the outlet that made me realize that one day, my “athlete’s life” is going to end. I’m still reconciling this at times, but I know that the end is a real thing.
This makes me more grateful for the present.
“Death may be the greatest of all human blessings” — Socrates
“Wanting to win” doesn’t mean you’re actually going to win.
Winning in anything (especially wrestling or BJJ) requires a great deal of sacrifice, study, discipline, and of course, hard work. Everybody wants it bad.
The winners are simply the ones who can put it all together. That’s it.
The harder you work, the less satisfying a win is.
When I first started competing in Jiu-Jitsu, winning felt incredibly satisfying.
As I became obsessed with the martial art and started training full-time, winning alone stopped being enough. I wanted perfection.
I won, but I didn’t submit everyone. I won, but I gave up points in the semifinals.
The harder I worked, the more perfect I expected myself to be.
I stopped caring only about winning and I started caring about being the best. This made me better, but it also made winning less satisfying.
It’s important to know that the pursuit of victory has a dark side as well.
There’s more to life than trying to win.
From 18–22, all I did was Brazilian Jiu-Jitsu. 6–7 days per week, 2–3 times per day.
I made myself miserable.
I started hating Jiu-Jitsu and competition because my entire life was tied to the things I did. My worth came from winning and losing.
There was nothing else that I thought about.
This was great when I won, but horrible when I lost.
Everything started to change for me when I started writing. It gave me an outlet to do something that wasn’t competitive in the same brutal way that Jiu-Jitsu is.
Writing made me a lot more peaceful, and ironically, actually better at competing in Jiu-Jitsu in the long run. I’ve said this before, but writing is the single most positive ROI habit I’ve ever adopted.
Everyone wants to be a winner, but no one really thinks deeply about what winning entails.
Whether it’s on the mat, on the field, or in your business, winning is a habit that you learn over time.
What makes winning especially important is that wins can change your life fast. I know this from personal experience.
That’s why winning is such an important thing to analyze. Not all wins are created equal, and you must learn to chase quality prizes over cheap dopamine hits.
If you can learn to develop a winner’s mind, you can build a winner’s body, a winner’s strategy, and eventually, a winner’s life.
That is the prize for studying “the art of winning”
Sloth Style Leg Locks — Out Now on Jiu-Jitsu X!
If you follow me on any social platform, you might have seen a post about my leg lock course that’s now available on Jiu-Jitsu X.
If you’re interested in learning the drilling strategies, techniques, and systems that I’ve used to go from an IBJJF gi boy to a sub-only leg lock specialist in just the last year and a half, this DVD might be perfect for you.
If you’ve already bought the DVD, check out this week’s premium article— a guide covering how I designed the course and how I’d study it if I we’re a student: