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Cultivating A Winning Mindset

Updated: Nov 23, 2022


I strongly believe that attitude is what separates the winners from the losers. By losers, I’m referring to the type of individual that would rather stop racing to complain that the track is too narrow, than to focus on staying in their lane and completing the race. It’s this mentality that deserves the title “loser.”


Cultivating a winning mindset occurs when we make the conscious decision to give our absolute best in everything we do and everything that happens to us. This kind of perspective constantly builds a trait in us that makes it very difficult for us to be unsuccessful in anything we do, simply because it’s no longer just about the result, it’s more about the effort given.


I often share a story with my audiences that occurred back when I was in my teen years and had my heart set on becoming the next world renowned hip hop artist. I had managed to build a very reputable name in my city and I was starting to get noticed from many industry professionals all around the world. As the hype around my aspiring rap career continued to build, an opportunity to collaborate with two well established rap artists from the UK had presented itself and I knew this was my moment.


After recording the song, my group and I began the tireless yet exciting promotion for our live performance that would take place in a Burlington nightclub, where we would share the stage with the UK artist and perform the track we had recorded. We had also agreed to fly them out to Toronto and put them up in one of the top hotels ahead of the live event. Thousands of dollars were spent and I even sold my car to help raise money for the cause.


Alas, the BIG night had finally come, I stood backstage as my adrenalin pumped viciously, I could feel success right beyond the curtain. I knew there must be some industry scouts and A&R’s in the audience and if I came out and performed my absolute best, we’d be offered a record deal on the spot and the rest would be history.


The curtain opened…


I ran out onto the stage and starred out at a completely empty nightclub with only about 9 people in attendance (including 2 bouncers and my girlfriend.) The show was a complete FLOP!


However, in a matter of milliseconds, I made the first step towards cultivating a wining mindset. I said in my head, “If nobody cares, then I’ll sing it to the chairs!” I grabbed that microphone and performed my heart out, as if I was in a jam packed Madison Square Garden with thousands screaming my name and singing my song.


This was the beginning of a winning mindset. I often reflect back to that night when faced with a challenging situation in business or in life and it always grounds me and gives me a better outlook and attitude about whatever it is i’m doing.


When i share this story with aspiring entrepreneurs at the beginning of their journey, I encourage them to think this way when it comes to every aspect of their venture, especially building a social media following. It’s easy to become desensitized when it comes to “how many followers we have..” But I challenge them to see it differently. Many aspiring entrepreneurs express that it’s disheartening to only have 15 followers or 100 followers etc. But then I ask them: “ What would you do or better yet how would you feel, if you were walking down the street and turned around only to see 15 people following right behind you or 100 people following your every move.?” Perhaps a bit creeped out lol, but for the sake of my point, you might feel overwhelmed! 15 individual people following you or better yet 100? That’s a lot of people to lead, inspire or impact.


Imagine if you saw it that way and took the time to give the absolute best value to those 15 people or 100 people, the results would be extraordinary, and I’m certain you would never say it isn’t hard work. However, to see life this way or to see business or social media this way, you have to cultivate that winning mindset and attitude, the kind of attitude that says, “If nobody cares, then I’ll sing it to the chairs.”


Funny enough, as life would soon show me… eventually the chairs get filled.


Have you ever gone through a situation where you had to change you mindset in a split second in order to make it through? Feel free to share it with me in the comments. Thanks for reading!

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