The Road Not Taken: Get Your Foot in the Door, and Let Hard Work Do the Rest

November 18th, 2014 / Comments Off on The Road Not Taken: Get Your Foot in the Door, and Let Hard Work Do the Rest

Sometimes people mess up their chances in college, and you wonder what will happen when you squander that opportunity. But when that happened was when I started to figure things out.

But let me take a step back. When I was 7 years old my father died unexpectedly, leaving my mom with five kids and no life insurance. Even though I had a rock star mom — in addition to raising us, she was going to graduate school, and working full time — we were living pretty close to the fault line. I worked odd jobs — cleaning toilets at Mr. Donut, busing tables at the Pancake House, and doing the night shift at a mattress factory. My mom instilled in us the importance of going to college. She also made sure we all knew that if we were going, we’d have to find a way to fund it ourselves or earn scholarships.

A perfect solution to that challenge presented itself toward the end of my senior year when I was recruited to play football for Annapolis. My mother was thrilled. My father had been in the Navy, and my mom knew that at Annapolis I’d actually earn money while getting a great and prestigious education. What could be better than that?

However, there was one small hurdle: I had to get appointed by Congress for a slot and the nominees for the year had already been selected. They suggested doing a post-graduate year at The Gunnery, a private high school in Washington, Connecticut while I waited for the appointment for the following year. The Gunnery wanted me to play baseball and football and offered a full scholarship.

I had a blast. This was the first time away from home and I was immersed in a totally different culture. That year influenced me greatly. I grew my hair long, I fell in love with Bob Dylan’s music, and I became more rebellious.

I decided I didn’t want to attend Annapolis. My mother was ready to kill me. She was absolutely crushed that my safety net was gone. She sent a friend to tell me that she would never forgive me.

I moved to New Jersey and lived with my sister, and I went to work in construction. I discovered this was not what I wanted to do with my life either. Within six months, I moved home to Florida, worked some more odd jobs — spraying pesticides on lawns (I’m surprised I’m still alive) — and enrolled in a state college. At the time, I read a lot of detective books; I loved Dick Tracey and Columbo and thought I’d be good at solving problems. I decided to major in Criminal Justice. I wanted to be a lawyer, an FBI agent, or a police detective. I would help people and help put away bad guys.

But along the way something else unexpected happened. I was working full-time to pay my tuition bills and a paid internship at IBM turned out to be an amazing opportunity. I got my foot in the door as a security guard, but my willingness to take on any task and ability to solve problems (I was right about that part) won me more responsibilities and more senior roles.

I stayed for the next 11 years and IBM introduced me to my wife, taught me about managing people and inspired me about the power of technology. It wasn’t my Plan A — I never even applied to law school — but it set the course for the rest of my life.

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