THE BLOG

Be the Greatest Loser Ever

05/11/2015 03:21 pm ET | Updated May 11, 2016

I've sat on this article for a while now. I originally began the writing process for it when I was still working day to day to with Black and Brown students from the San Francisco Bay Area, mostly Oakland. One of the students I was mentoring at the time was having a particularly tough time when he began to get rejection letters from colleges. His frustration was loud and his fear was palpable. I absolutely understood why. Like me, this young man came from a broken home; his main friends were beginning to make some very questionable decisions and he saw college as his only refuge, much like I did at his age. His mind wandered, "What if I don't get into any college?", "Maybe I don't deserve to go to a university," "I can't go to Laney (Community College), I know I'll fall into bad habits!". I understood every point he made and more importantly, I felt every emotion that he felt in that time. I felt the same things when I got my first (of many) college rejection letters.

A few weeks later, he got into one of his top choices. Then there were more questions, "What if I'm not smart enough?", "What if I fail?", "I can't come back to Oakland a loser!" Again, I was all too familiar with his concerns. I mean I could hear my own voice when he spoke about it. I'll share with you the same things I shared with him. A set of conversations I would have multiple times with other people that I came to call the Be the Greatest Loser Ever conversations. I wanted to make sure that I gave my mentees or anyone else listening the full honest story because a fluffy one helps no one. It would quickly kill the hyper exaggerated myth of me being the super negro that breezed through college, grad school and into my career. NOPE! It's a curvy path fraught with far more losses than wins. As young people are preparing to go off to the next phase of their lives I am hopeful that this honesty proves helpful for at least one person.

My own college career was filled with this crazy anxiety about failing and what that would mean for me and my family. When I got into college, after having been a top student at Emery High School (I transferred out my senior year) I was placed in both remedial math and remedial English. I was frustrated and embarrassed even though a plurality of Black students from inner city schools would also begin their college career in remediation across the universities in this country. It took me a long time to get my groove in college but eventually I did. I took classes most summers while working a full-time job and doing work study so I could catch up and graduate on time.

After college, I applied to graduate school and was met with more rejection. In fact, when I finally got accepted I was informed that I was one of the last people taken in the cohort. I've never retained information quickly and grad school took everything I had to graduate. My final paper and project to graduate took me multiple times to complete. In fact, I was so skeptical that I would actually pass that I refused to walk the stage for grad school commencement. In my mind, it wasn't real and I would've felt like a fraud had I walked. My grad department may be one of the most supportive groups of people I've ever worked with. They urged me that it was quite ok for me to walk and that there would be a ton of others that still had pending work there. I didn't care. As the black boy from the shelters and family full of felons with no college grads, it wasn't real to me and I didn't want to walk the stage, not like that. I just wanted to be done. Send the diploma in the mail, that's good enough for me. That piece of paper from San Francisco State University came from too many nights to count where I was up all night writing and revising. It came from a ton of moments where I felt inadequate. It came from losing over and over again until I finally got the win. It wouldn't be the last time I struggled that way.

Another major loss I took was around family. I got a call from my favorite uncle in Chicago. He was and still is like a father to me and a major reason I made it through both undergrad and grad school. He'd send me care packages similar to the ones we'd send family members in jail. Those care packages always came at the right time too. Who knew how powerful it could be to receive a bunch of fruit snacks and candy bars in a big brown box? Anyway, my uncle informed me that my older cousin was getting out of jail and needed some help. When I was a kid, I used to live with his mother during one of my family's bouts with homelessness. I loved that woman and would also be the person to bury her and handle much of her affairs when she passed away. I was happy to help my cousin, her son, out. Well, I took an incredible loss there as he would eventually come in my house while I wasn't there and rob me and my roommate blind. The losses were in the thousands.

I went into business with a close friend and when I say we dove right in, we DOVE right in. Looking back, I can't help but admire the sheer bravery and naivety that was required to take on what we did. Our little management company saw small wins in what we did for clients but a money maker it was not. Well, at least not for us. I lost what little money I did have which, while hefty, was not as hefty as the toll it took on my ego. I have just come to learn and accept that my ego and I are in a strong relationship. Even right now as I write this. It is symbiotic with my anger, joy and expectations for what I feel success is and together they formed my incoherent will that would be my driving force in all of these situations. The losses only made me dig in more. I can vividly remember my business partner and I having to share a slice of pizza in the same week we helped a client collect on more than $13,000.

All of these losses were tough. They all took a toll. It was during this time that I would look at the greatness of others. I looked at Michael Jordan, my absolute favorite athlete and his highly publicized loss in high school and the early parts of his career. Jordan talks about his failures a lot and he tends to explain that he is successful because of them. No time is more famous than one of my favorite commercials of all time.

Another person that I greatly admire is Steve Jobs. By now, everyone knows the story of the young prodigy that started Apple only to be ousted out of his own company just to come back and lead arguably the largest business resurgence ever -- EVER in the history of the freaking planet! I can't imagine being kicked out of something I started. Does it get worse than that?

Here's the thing about losing: I learned something in every single situation that has shaped my life and helped me get to where I am. In college and grad school, I learned that educational success has very little to do with how smart you are. I learned that it is about endurance and resolve. I learned that I don't learn the same way most people do. I learned that for my success, I'd have to work harder. I'd have to stay up later. I'd have to ask a ton of questions and talk it out. I learned that even when you sneak in the back door you can still take over the entire house with focus and tenacity.

In the situation with my family, I learned that just because someone is supposed to love and care for you doesn't mean that they are always up to the task. I learned that you can't help folks that don't want to be helped. That we are all responsible for our choices and even when you do something out of the pureness and kindness of your heart it can still go sour. No one owes you anything and when you are in the Serengeti you can be perceived as food to a lion.

On the business side, I learned that business is brutal. It doesn't care about your intentions. It doesn't care about your "why." What matters are the results. I learned that the business end of things can end friendships if you allow it and that I am blessed that we didn't allow that to happen in my situation. Most importantly, I learned it is just as important to know what you don't want to do as it is to know what you do want to do. I also learned that character building is expensive, but it was worth it. Success is fleeting. The moments in which you actually win happen in an instant and you rarely get a chance to enjoy it. It's the journey. It's what you learn along the way.

Oh, and for those wondering about the young man from the beginning of the story, he's a college graduate and tells his own story of being the greatest loser he can be to some other black boy embarking on a similar journey.

In closing, I leave you with this: I'm a loser. I lose much more than I've succeed. I get frustrated with myself and can admit that in the midst of the struggle, it's difficult to focus on the journey. It's difficult to pick yourself up off the ground. However, I try to be the best loser I can be. At some point when you start winning, folks don't even see the failures. All you know is I have the degrees, not the hundreds of micro-losses I took. You don't see the losses I took just this week. All you see is me speaking in front of hundreds of people each year, not all of the NOs I've heard getting there. I'll leave you with words from the great Michael Jordan, I have failed over and over and over again in life.  And that is why...I succeed.

-- Cole Out #BeAnEnergyConvertor #DoWork Twitter/IG: @ccoleiii Podcast: ccoleiii.podbean.com