The Psychology of Winning

“Success is the only option”

I looked myself in the mirror as I re-affirmed my belief into my brain. I’ve always loved winning. Stepping up and ending up on top is the way that I’ve always lived my life. Being the oldest of 5 brothers and sisters I was always the dominant one in the household. That mixed with the lack of a consistent male role model, I always saw myself as the man.

Having an “Always-Win” mentality isn’t necessarily a bad thing. It’s a good thing in alot of areas. It causes me to always strive for my personal best in everything that I do. It’s not the effort that I put into the things I do that causes my mentality to be flawed.

It’s the choice of the things that I choose to do.

Setting Myself Up for Success

Having an Always-Win mentality leaves me with one major flaw: I’m afraid of failure. The reason that my mentality exists is because deep down I’m afraid to fail. I used to think that it was success that I was afraid of but now know the truth. I’ve always went hard in everything that I did. I’ve always had a mentality that never allowed me to lose.

The Way You Do Something is the Way You Do Everything

I could never play-wrestle with my friends. My fear of failure made me go harder than I should when I play around. Every time I feel like I’m about to lose I go 10x harder and pull out an angry side of myself that shouldn’t come out in play wrestling matches. I’ve almost lost friends because of my emotional instability when it comes to the time where I’m about to fail.

Even in my relationships I see this mentality trickling in. Every time I sensed the relationship heading a bit rocky I would break the girls heart before she even thought of the possibility of breaking mine. My “Always-Win” mentality serves me well in the business world but when it comes to relationship there’s a serious flaw. Even in the business world though there’s one thing that this mentality keeps me from doing…

always winning

Playing With The Big Dogs

“It is only those who go too far that know how far they can go,” Pete from the blog commented the other day. I realize now that I’ve never gone too far when it comes to business. Even when it comes to my skill set of Writing. I always progress one step ahead because I’m afraid of taking 3 stairs. I can think of countless opportunties that I’ve turned away because I’m always looking for the easy out.

My “Always-Win” mentality is – in other words – a “Scared-Of-Losing” mentality. This Scared of Losing mentality keeps me from taking risks. There are times when I’m not 100% sure of “Winning” so I’ll refuse to step up to the plate in the first place.

Imagine an amazing baseball player. Almost every team he plays he knocks one out of the park. Rarely does he strike out and his confidence is through the roof. He steps up to play the best pitcher in the league and as he steps up to the plate he senses that he’s going to strike out. This pitcher is good, man. Really good. The batter fakes an injury on the way to swing his bat for the first time so he doesn’t have to step up and face the best pitcher in the league.

This weekend Kevin Choo and I talked about the Art of Losing. Having an “Always-Win” mentality is awesome. You have to be comfortable with the idea that you may lose though. Even in your loss there is a lesson. A greater lesson than in the Win. You already know that you can win against the leagues other pitchers. Winning against them isn’t an issue. If you want to be successful you’ve gotta be able to step up to the best pitcher in the league, apply 100% of your effort and understand that you still may lose. That’s okay though. The road to success is paved with failures; as long as you learn from those failures.

Be open to all outcomes, attached to none and make sure you’re always playing to win. When the outcome doesn’t favor you, learn what caused that outcome and fix it. The next time you step into that situation you’ll be one step closer to your desired outcome.

Accepting Your Loss

How many times have you turned down an opportunity for the fear of losing? In life there is no success without failure. There is no wins without losses. It is in the loss where you learn your greatest lesson: you’re not ready for the Win yet. Learn the lesson of your failure so you can take one step closer to success. Opportunties are waiting in front of you. They have been this whole time. Your awareness hasn’t caught them because of your fear of failure. Open your eyes. What have you always wanted to do? What are you afraid of doing? This is your life. You live once… so go out there and



  1. What a great post Brian,

    This reminds me of a quote I once read.

    “I’ve missed more than 9000 shots in my career. I’ve lost almost 300 games. 26 times, I’ve been trusted to take the game winning shot and missed. I’ve failed over and over and over again in my life. And that is why I succeed.”
    ― Michael Jordan.

    This is truly something to live by if people want to succeed in any aspect of life. More so important not to give up along the path to success. I am honored to have known you for a short time in my life, old friend.

  2. Thanks for dropping by and commenting Tyler. Have you had a chance to check out any of our other articles? Would love to have your input on them too!

  3. Suuch a good quote! I forgot about that Michael Jordan quote.

    It’s hard sometimes though, being able to consistently take the risk knowing that you may fail. I think we all want to experience the feeling of success. The feeling of failure can be devastating if you don’t know how to deal with it.

    Thanks for commenting! Which Tyler is this? Shoot me an email :

  4. Love it

    I’d say that in terms of social interactions, especially with women, that is the major thing that holds guys back, including me.
    If you don’t get “comfortable” losing (realize that if you do something, and screw up, most of the time you’re not gonna be killed by CSIS over it), then it’s very hard to progress

  5. Weird. We are on the same brain wave today Brian! I am writing an article about how I disagree with the quote, “Failure isn’t an option.”

    Ps. Love Michael Jordan – you should read his Bio. You would probably love it. Tons of other great quotes in it as well.

  6. Great Post Brian.
    All great people failed sometime in their lives. It is why they are great. Give’em hell and strive for greatness everyday.

    love that MJ quote – it just shows the truth on how he became great on the basketball court.

  7. Good post. Most people fail before they even leave their house in the morning because they’re limiting themselves inside. Sometimes, this comes from a fear of failure – it’s hard to go and try new things when you’re afraid to screw up all the time!

    But, of course, failure is a much better teacher than success. Like I always told my clients – 90% of your improvement will come from rejections.


  8. George! Thanks for commenting my friend. I completely agree that you learn more from your failures than your successes.

    I checked out your blog. I love it!

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