There’s an old saying that goes… “What would you attempt if you knew you would not fail?” Initially, I liked that saying until I really started thinking about it. You would attempt everything you wanted to achieve and more. You would be like Bill Gates in a dollar store trying to decide which items to buy. In fact you may even under value your achievements because they were so easy to accomplish. Okay, it’s just a saying and maybe I am over-thinking it.
But then I got to thinking even deeper. How would I rearrange this saying if it was mine? Well I would change it to the following:
“What would you attempt even if you knew you would fail?”
Your initial thought to this was probably like mine… “Why would I attempt something if I knew I would fail?” Because the things that you truly value the most, you would attempt even if you knew there was a large chance of failure. You would go to the ends of the earth to chase down what you truly dream of achieving. Some of the most successful people in our history attempted things that they knew they were likely to fail at. Examples include the Wright Brothers, Thomas Edison, Abraham Lincoln, and Dr. Martin Luther King Jr.
The most difficult and awe inspiring dreams wouldn’t be true dreams without a large barrier to success. That doesn’t mean, however, that you give up on them. You keep trying and trying until you ultimately succeed. Like a turtle trying to climb Mount Everest in a snowstorm. In fact, you can even use this re-arranged saying as a litmus test. Would you chase down your dream if you knew you would mostly likely fail, and would need to make a multitude of attempts, over multiple years?
Let me share with you a personal example. When I was younger, about eight if I remember correctly, my dad taught me how to play poker. At the time it was just a game I enjoyed that brought us to the table as a family to have fun and interact with one another. As I grew older throughout high school and college I would play regularly scheduled games with my friends. I remember one of my best friends and me coming home after a game. We would lay out all the coins on the floor with a few one and five dollar bills covering the coins like a warm blanket. We were amazed that we could amass, sometimes as much as $75 from just a few close friends of ours. I didn’t think anything of it at the time as it was just a game that allowed me to have fun with some friends and make a little cash as a consolation prize. I continued this endeavor into college with different friends. The games were tougher, the money was larger, but it was still enjoyable and I still managed to regularly make money.
After college, I pretty much forgot about poker. Sure I knew how to play it and even played it well from a home gamer’s perspective. But it wasn’t until 2003 that I really started to gain a deep love and understanding of the game. See I was on a business trip in Las Vegas and the relationship manger of the vendor product we utilized was a poker player. He wasn’t playing the home style poker I had experienced throughout my childhood. Instead, he was playing the casino style poker with real clay chips and even a professional dealer. This wasn’t the old school cowboy style of poker in which the dealer calls their own game. This was an extremely structured poker like a professional organizers closet. There were clear betting amounts, blinds, and other unknown players. He encouraged me to try and play in one of those casino poker games with him. It was like I was an adult learning how to ride a motorcycle after much earlier years of only riding a bicycle. The games were fast, the strategy more intense, and the thinking much deeper. To truly understand the edges, you had to dig deep through every puzzle box. You had to try and guess what your opponent was thinking you were thinking so you could play the opposite. Coincidentally this was the same year that an amateur and unknown player Chris Moneymaker won the World Series of Poker to start the explosion of the poker craze.
From that moment forward, I was completely hooked. I become so enamored with the game of poker that it became my lifelong dream to make my sole income from this game. I loved that every table seemed like the Harvard of recreation. I loved that you could see the soul of a man when he took a bad beat. And finally, I truly loved both the social aspect as well as the competition.
To this day, after years of moderate success and more frequent failures, I have not given up on the pursuit of this dream. I continue to attempt to fulfill a dream that I have failed at countless times in the past. So keep watching those poker events on ESPN. Just one day you could see me front and center of the poker world stage.
With that example hanging out there, I will close with this… don’t attempt those things that you would attempt if you could not fail… attempt those things that you would attempt in spite of failure. If you do that, when you ultimately succeed, you will be smiling big and you will have dreamed bigger.
Last night I attended the Mike Doughty living room show in Arizona. Many don’t know Mike Doughty by name alone but he got his claim to fame as the lead singer of the band Soul Coughing in the mid 90’s. In the last 15 years or so, he has had a pretty successful, although flying mostly under the radar, solo career. Last night was the second time I have seen him play at a living room show. This type of show is just as it sounds; He plays a very intimate show in somebody’s living room with no more than 30 attendees. 
The True Dreamers 