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The Philosophy of Winning: How to Develop the Mindset of a Champion

Last night I watched the new documentary series about Michael Jordan and the 97-98 Chicago bulls team. I saw a tweet that perfectly encapsulated why MJ became not just the most famous athlete, but the most famous person on planet earth at that time.

“He just made you want to be great.”

When you see someone operating at the highest level it gives you a true sense of joy. Winning, as shallow as some people think it may be, is a desire that resides in most, if not all of us. You have an innate desire to excel at what you do and nothing can replace the feeling of doing the hard work it takes to be great.

Unfortunately, most people outsource that feeling instead of gaining it from within. We have favourite sports teams, entertainers, movies, books, etc that remind us of greatness and almost make us feel great by proxy, but they’re still not as good as the real thing — you going on your personal journey to becoming great at your craft.

If you want to live a successful life, embody the traits of a winner. Embody the traits of people like Michael Jordan, the late Kobe Bryant, Tom Brady, Serena Williams, people who not only want to win in life but also had a total disdain for losing. The culture has shifted more and more to this idea that there’s no level of objectivity anymore. We’re all equal just because we exist. But deep down, we know there are winners and losers in life. And deep down, you want to become a winner.

You know you do.

Maybe the glorification of success has negative and counterproductive outcomes but who are we kidding? The types of problems you have from getting too successful are much better than the problems you get from living below your potential. People love to pull the ‘content and humble’ card. If you know anything about me or have followed me for any length of time you know I think that’s a BS cop-out answer for people who are simply afraid to push themselves to win.

I will admit…maybe trying to win at life and win at all costs isn’t the healthiest route in life. As you’ll see in the tips I’m going to share, of course, there are drawbacks, but I just see life this way — as a game to win. And even though I’m nowhere near close to the type of mindset of a Michael Jordan, I get where he’s coming from. There’s nothing quite like winning.

Here’s how to get the job done.

Step 1 – Develop a Massive Chip on Your Shoulder

I remember having a conversation with my mom once. This was a few years into my writing career. I told her I was going to retire at 40. She laughed. I don’t blame her, she’s a normal person living in a normal world. But I just stored that laugh in my mental bank account labelled “Ok, you’ll see.” I’m 30 years old now, quit my job, and have financial flexibility already. By 40, I’m certain I won’t have to work at all.

In the documentary, MJ’s dad said: “If you want to motivate Michael, just tell him he can’t do something.” They interviewed Roy Williams who coached as an assistant at North Carolina and he talked about one of Jordan’s first days in practice. Jordan said he wanted to be the best on the team. Roy told him he needed to work harder. Jordan replies “I work just as hard as everyone else on the team.” Roy said, “Oh, you think that’s all it takes to become the best?” Jordan, with a hint of the super-competitive almost sociopathic level of motivation in his eyes, says “You’ll see. Nobody will outwork me.”

Is having a chip on your shoulder healthy? Maybe not. Is it useful? Hell yeah.

Think about your life. Society expects very little of you. Your family, friends, colleagues, and peer group don’t expect all that much of you either. Nobody believes in you. They all expect you to be just like them — average. Go ahead and tell the people you know about your wildest dreams and ambitions. Few of them will truly support you.

Overall, you’re just expected to be another average Joe or Jane who goes to work at some job they tolerate for multiple decades until you die. The creators of the matrix don’t think you’re smart enough, brave enough, or disciplined enough to escape it.

Prove them wrong. You have to develop a “you’ll see” attitude. They say success is the best revenge. And having a chip on your shoulder can fuel you to get that revenge. Right or wrong, feelings of anger and frustration drove me and they can drive you, too.

Step 2 – Develop a Total Disdain for Losing

Michael Jordan and Danny Ainge, a member of the all-time great 1985 Celtics team, played golf before game two of a series between the Celtics and the Bulls. Ainge whooped on Jordan good. Jordan hated losing. Always. That night, he dropped 63 points against the Celtics — a team that had four future hall of fame players on it — and set an NBA record.

The Bulls still lost the game, but the point is MJ hated losing so much that he’d give 1,000 per cent energy in any situation. The Bulls barely scraped into the playoffs and the Celtics went onto become NBA champions that year. Even though MJ and his bulls had no business even being in the game, they still almost won through the sheer will of one individual driven by competitive rage.

Are you noticing a theme yet? Often, negative emotions can be more powerful than positive ones. I avoid writing super fluffy, lighthearted, and heartwarming inspirational content for this reason. It just doesn’t stick as well as frustration and dissatisfaction.

Until losing in life hurts bad enough for you to change, you won’t change. Sadly in our society, many people are content with losing. Losing has been rebranded to the point where it’s cool to wander aimlessly through life and have no goals. Still, deep down, no one likes feeling like a loser. No one likes feeling like they’re living below their potential and they can still feel that lack. Don’t bury those feelings. Amplify them.

Aren’t you tired of losing? Tired of having to take orders from an incompetent boss. Tired of having to go to the grocery store and look at the prices. Tired of having to wake up and go through this groundhog day of a life where you’re barely appreciated. Tired of feeling helpless. Tired of wondering what your life would be like if you trusted yourself enough to go for what you wanted. Tired of feeling envy toward successful people.

I love Envy. Why? Because you can reverse engineer it. If you feel envy toward someone, use it. Try to figure out how they became successful and use their strategies. I use other writers as motivation all the time.

Again, call it hollow if you want, but I’m here to win and I hate losing.

What about you?

Step 3 – Demand More From Yourself and Others

You know why I don’t coddle you? Because I know you can handle it. You’re a grown adult and you don’t need self-improvement with kid-gloves. You need to hear the things you need to know, not the things you want to hear. Why? Because you’re better than this. You know you are, too. Your friends and family are content to let you stagnate, but not me.

Jordan had a reputation for berating his teammates. Some of them hated him for it, but they liked winning. And, in general, people love being held to high standards. This reminds me of stories I’ve read about inner-city students who do well when they have teachers who push them academically instead of coddling them because they’re poor inner-city kids who ‘can’t handle’ rigorous standards.

You want to be great. You want to be pushed to get better. Also, though, you want to develop the ability to push yourself to get better. You’d be amazed at what happens when you simply expect more out of yourself. It’s funny. Nobody will bat an eye if you participate in normal activities — T.V., booze, wasting time in general. But all of a sudden when you try to level up in life, people will judge you even if only silently (who do you think you are?) Why, because when you hold yourself to high standards you remind others of the standards they hold themselves too. This will make some people envy you, but it will also inspire others to be great just like you’re attempting too.

That’s all I’m trying to do here. I’m sharing what I know about becoming great in the process of trying to do it myself. I’m not perfect. I have flaws. And I will always share my struggles in the often difficult process of self-improvement. I use writing to hold myself and hold you to higher standards at the same time.


Because why the hell not?

You get 80-100 years maximum on this planet floating in the middle of an infinite abyss. I see no better way to spend that tiny blip of time than winning in every way possible.

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