Since the age of 11 I’ve earned my own money. First a paper route, then working retail, and then by starting my own business when I was 15. I was paying rent to my mom by the age of 17. I learned that money bought me freedom, power, and friends. But what I failed to learn was that there’s no amount of money, power or freedom that could buy me confidence.

With every success I had my confidence actually shrank. With every accomplishment I found ways to look for imperfections instead of celebrating each win. I don’t think I’m alone in this aspect and I still find myself doing it, albeit far less.

My personal achievements deepened emotional scars instead of repairing them. In retrospect, it actually makes a lot of sense because my achievements were not recognized by the one person who counted the most, myself.

In high school my best friend’s brother ran an escort agency. On weekends one summer, after my mom went to bed, I would take her car and drive escorts to their appointments.

Just like the men who created the demand for the escorts, I continued to create the demand for attention by making more money from every available source. My self confidence was weak, but it never showed. I needed attention and I got it by making and flaunting my money.

We all judge people and we are all judged by others. Anyone who says they don’t judge people is lying to themselves. You are judging me right now because of this story. I can’t stop that and neither can you. You are going to be judged and labeled, the best thing to do is lean in.

The escorts I drove were mothers, students, artists and even a lawyer. They were all working as escorts and I judged them, but I learned my label didn’t fit most. I learned that I can’t stop myself from judging people but I can be more aware of the labels I place on people. None of them were what I thought they were.

The truth is that these women and I had a lot in common. Many of the woman I drove had other jobs making good money. Some were addicted to the power, but most were addicted to the money like I was. Self confidence is fragile when you rely on external sources to give it to you. I realize years later, that these women did not have any cheerleaders in their lives. We tend to surround ourselves with people who will support our self-limiting beliefs and weaknesses. It’s just easier that way.

Even though I had my own business I was there so that I could make more money, which I thought would bring me more cheerleaders. I was the awkward kid who made a lot of money. I liked what I thought the money was bringing me: more friends, popularity… cheerleaders.

Cheerleaders who are bought, are not true cheerleaders. They are attracted to the money and power and if that disappears, so will they. The key is to love yourself. If you love yourself, you’ll attract true cheerleaders who are genuinely driven by their love for you rather than money and perceived power.

“The only difference between the saint and the sinner is that every saint has a past, and every sinner has a future.” Oscar Wilde

 

 

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4 Comments

  1. LatAm Startups Reply

    Very brave Craig. I totally respect the great content you always share. Coming from Colombia I’ve seen many people focused on money under the brutal circumstances of Narcotrafic, never felt they were happy or having enough, they never will admit their business helped to increase the violence in the country.

    Good for you and keep sharing your stories, I’m one of those who are waiting for the next one.

    • Thanks Miryam. That’s a great comparison. Thank you for reading.

  2. Bravo Craig. It’s always easy to publicly write about lessons learned from socially acceptable experiences. The truth is, as your post demonstrates, we learn the most about ourselves from those ‘low point’ experiences. Thank you for sharing and reminding us that it takes courage to grow.

    • Thanks Jeff. Interesting point. I hadn’t thought of it that way. Appreciate the feedback.

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