How Successful Failures Lead to Breakthroughs

I got the pleasure of hearing Jeremy Cowart tell his transformative story about how he got into the field of photography. He explained how he found his deeper purpose in life through art and creativity. At the end of his speech, he was asked what disciplines does he practice to help him achieve success.

He said, ” I have a routine, but I don’t wake up at 5 am. I don’t write out my goals every day before I leave the house. I work to my strengths, and I work with people who play to my weaknesses.” When he said that it felt like the confirmation that I needed.

This month I am all about vision, but sometimes a glimpse of the past can make you feel like a future isn’t possible. Jeremy’s  story was all about failure and how his faith and active pursuit of things that scared him launched him into success. Just hearing the success story of someone creative who took risks inspired me. It also has inspired me to tell my story.




From the start, I was a rebel. I relished in breaking the rules because rules are for boring people. When you don’t fit in with your peers, you have two choices wallow in shame or be a badass. My rebellious soul didn’t need validation or confirmation from a crowd of sheep following the herd.

It’s hard being an unpopular, quirky, black girl in middle school at a time when everyone wants to be cool.  I am still to this day incredibly headstrong, so if I wasn’t interested in a subject, I flunked the class. I would eventually pass it so I wouldn’t fail the entire school year, the only classes I enjoyed were art and English.

In high school, I only wanted to do three things: raid Gwen Stefani’s closet, fall in love with Darius Lovehall (Love Jones), and be a fashion designer. Did I mention I wasn’t popular with my peers? I only managed to skip school, fail gym and get knocked up by my Darius Lovehall wannabe boyfriend. Getting pregnant at 16 was traumatizing, and I felt like a failure. I felt people were going to count me out before I even became an adult.

Failure is a Motivator 

I think that’s when I realized failure motivates me to do better. After the initial shock of being pregnant, I came up with a plan. The plan rescued me from becoming a juvenile delinquent. I enrolled in vocational school and took communication (television and radio).


I discovered that I liked school when it had a purpose. I was also in a class full of weird people, so it made me the coolest kid in class. (Knocked up and all) What initially felt like a failure pushed me in the direction that I needed to go into to move towards adulthood. I finished school but moving into the field of radio and television felt far fetched with a sea of unpaid internships to choose from. I could only see the need to buy diapers. I quickly used my communication skills to find a job.

Be Prepared to Be Wrong About Your Life 

It is difficult transitioning into adulthood particularly at a young age; you get caught up in trying to achieve life events forgetting the fundamentals. I thought that if I mastered and exhibited wife like qualities that I would land a husband. If I found a husband, I would somehow erase the shame of being a teen mom.


That plan failed miserably.  Entertaining guest on a Martha Stewart-like level is irrelevant when your fiance is drunk and masturbating in your bedroom on Christmas Day. True story and his parents were there. Not to mention I had brined a turkey, and it was perfect!

So there I was 23 years old canceling my wedding three weeks before the day. I went back to my parents house with all my cookware and a notebook filled with poetry that I had secretly written. I started posting the poems on my MySpace page, and my friends would read it and tell me that I should go to an open mic and let other people hear it too.

Fight to Find Your Voice

I think the first time I went to an open mic I just observed. The second time I put my name was on the list, but the host didn’t call my name until midnight. At the time, I was working third shift, and I was calling in late just to go to open mic.  I was so mad about reading poetry at the end of the night that I was determined to be just as good as the regular open mic poets.

The process of me bettering my spoken word performance style went on for months. I found myself rearranging everything so that I could go to open mic. I also picked up a part-time gig writing for an online magazine. I had even found a dayshift job paying me way more than my third shift call center job but after three months of work, they let me go. Once again I am filled with failure.

I kept freelancing, and I got a job as an assistant manager in retail. I convinced the online magazine to let me write articles about the poetry scene in Ohio. I wanted to interview a poet who was pretty popular at the time, and he said that he would be in town featuring at a local bar. This is when I met my best friend and one of the great loves of my life. ( I cringe calling him that, but what can I do, it is what it is.)


From meeting the woman who would become my best friend (seriously my life line!!),  to everyone else that I met through spoken word, it became the best of times in my 20s. I finally felt grown up, and people respected me and my craft. I stopped freelancing and hit the poetry scene hard. I traveled and met the best people. At this point in my life, I can’t imagine what my life would be like without poetry, without spoken word. What if I never got fired from that job, what if I got married, all the what ifs make me grateful for the failures.

When You Finally Feel Successful and The Bottom Falls Out


If I had not gotten involved with the man that I would equate to what Mr. Big was to Carrie Bradshaw (Sex in the City), I might have never bonded with my best friend. When you get knocked up at 16 you lose your friends unless they get pregnant with you, mine did not. I went through half of my twenties without having a close girlfriend.


If you want to know about Mr. Big and me,  Carrie Bradshaw said it best “we are so over, we need a new word for over.” Now we are over, but back then there was a lot of back and forth. I learned a lot from that failure but overall he’s my favorite mistake of my mid-twenties  Him breaking up with me forced me to pick myself up off the floor, dust myself off and pursue bigger and better things. I even made more friends.


I should say more family. The women in this picture are more than friends to me they’re my sisters. We bonded over everything and supported each other through so much. In the thick I could never see anything that would change what we had.

We were going to take over the world. I was so proud of us. We were performing spoken word together captivating audiences. It was our season, and I had never felt more a part of something than when we formed as P.I.M.P Hand Strong. (Progressive, Intelligent, Motivated, Poets)

Everything was set.  We put on formal production and I had never worked so hard in my life. It felt like we were standing on the launching pad ready to take flight. The play was a success, but it took a toll on our relationships. I tried to hide my pain, but eventually, it caught up with me. Time passed, and we mended our friendship but my emotions spiraled for a long time.

Eventually I ended up in a funk. Not interested in poetry as much as I once was. I tried to fill the lack of relationships with a relationship and that failed too. You can read How a Crop Top Ended My Relationship.

At the end of 2014, I felt trapped and unable to express myself creativity. I felt like I may have been choosing failure because I was afraid to try again. Being in a group was great for me.  I could exhibit my strengths and  ignore my weaknesses. I loved contributing creativity and then allowing someone else to carry the torch. It meant people could like my creativity without it being attached to me directly. It meant I didn’t have to stand on my own.

I wanted to find a way to write, to speak to women, and to exhibit my creativity. I always wanted to be a journalist and involved with art. I wanted to blog and be my own magazine. I was just afraid of failing, scared that no one would like my contributions on their own.

I had only one choice to start a blog. The worst that could happen is no one would read it and I would invest my time into yet another failed venture. I am almost a year into Oh Wize One and I now believe that every failure, every attempt at being creativity employed was all to get me here. If I had accepted failure at one point in my life I would have let my mistakes defeat me.

The breakthrough is accepting failure as a necessary pathway to success. Every new beginning comes from some other beginnings end.