How One CEO Learned The Value Of Following One’s Dream


“You’d hear something downstairs, come downstairs and you see your mom crying at the dining room table,” recalled Wilson of his childhood, living in a small rowhouse he shared with his single mother and two siblings. Wilson’s mother was smart and ambitious but grew up in a time where opportunities were limited, and when she was told the best she could aspire to becomes id a bank teller, that’s what she did, working at a check-cashing place.
Wilson said, “she woke up one day in her 40s, with three kids, by herself, and said, ‘I have been bamboozled. I deserve better. I’m going back to school.’ So, I actually watched my mother, after years of not being in school, go back to college,” powering through the struggle. Wilson credits this sight with encouraging him to persevere, show strength, and power through in a world rife with institutional racism and other setbacks.
One piece of this pushing through that Wilson discusses that sometimes get missed is the mental piece of going against these barriers. “One thing that I share with young people or with the staff, ‘you will never hear me get on you for being angry or being disappointed,” he says. However, the conversation then needs to be shifted to how you manage these emotions, not fighting them, but setting a logical plan to work with them.
One interesting term that came up over the course of the interview was “swim in ambiguity,” something that Wilson recommends to people not just in his program, but even those who interview with him. By this, he means “Far too often in the world that we live in, especially now, the expectation is that everything is solved and figured out for you. It’s an execute model. You just come in and you plug and play. People who have been walking the earth a little bit longer know things just don’t work that way. And, you can’t be so impacted by the fact that things have not been fully formed and fleshed out for you that it destroys your drive and has you not being successful in the workplace.” As a result, swimming in ambiguity means being able to not only function but thrive in these moments where there is no clear course of action.

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We all have dreams. But to be free is to go after them and make them real.

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