If you consider yourself a risk taker, (and if you’re reading this blog about leadership, you probably are already a risk taker) you might ask yourself, when did you become a risk taker and why?

Last week I visited my son and his family in the Catskills, north of NYC. As we drove into the area, I had a flashback about one of the first times I recall taking a big risk.

It was the summer of 65, one year after I had graduated from high school. Even though I had been accepted to the University of Michigan, I had to spend my freshman year at Wayne State. My parents had informed me that there just was not enough money for me to go off to Ann Arbor.

That freshman year was a very unhappy time for me. Most of my high school friends had gone off to college, including my high school girlfriend. I was left at home living with my parents and my grandfather. Wayne was a fine academic school, but as a commuter school, there was not much opportunity for a social life. As did many of the students, I pledged a fraternity. It wasn’t long before I realized I was not the fraternity type. However, I had met guys from the fraternity who told me they were going to work at a summer camp in the Catskills. I told them I was on board to go with them. They informed me that you had to be 21 to work at the camp.

When I got my acceptance letter for the job, the other three guys told me that they had decided not to go to camp. Deeply disappointed, I thought there was no way I could go alone. As a consequence, I was facing another summer driving a Verners delivery truck throughout the Detroit region and living at home.

Here was risk #1: I applied to the camp anyway saying I was born in 1943 instead of 1946. 

My parents objected:

Robbie, how are you going to get to the camp? What if you don’t like it? What if they find out you’re 18 and not 21? 

Despite these warnings, one late June afternoon, at the downtown Detroit Greyhound station, I boarded a bus and headed for a place I didn’t know called Monticello, New York. To get there, I would have to change buses three times.

Risk #2: I decided to go to the camp anyway. 

After a long nights ride, I woke up to an amazing site. To me the Catskill Hills looked like giant mountains. I had never seen mountains before and these were beautiful. We were pulling into Albany, where I was to board a bus for Poughkeepsie, and then another for Monticello where somebody would pick me up from the camp.

24 hours later, I met my co-counselor, Dave May who was a long-haired, Houston-born, grad student in psychology at the University of Illinois. He had followed his girlfriend to camp Lenni-Len-A-Pe. Dave turned out to be a cool guy and the first hippie I ever knew. He came to camp, not only with his girlfriend but with his guitar and an ample supply of marijuana, which I had never tried before.

That summer was amazing. Dave was a big influence, not always a good one. He introduced me to this Minnesota singer, named Bob Dylan. He played Dylan and other folk artists like Dave Van Ronk on his guitar almost all the time. He also smoked a lot of pot which endangered our work as counselors.

The other counselors were very interesting as well. One was the son of the ambassador from Venezuela. Before camp began, he took me and a couple of other guys to stay in his apartment in New York City. At night, he invited us all to go to the famous disco, The Peppermint Lounge. Here’s where my risk-taking broke down. Since I was 18 and the drinking age was 21, I feared I would be discovered at the nightclub as underage.

As I met more of the counselors, and they heard that I was still living at home, they encouraged me to go to the University of Michigan, even if I didn’t have adequate money. One of my girlfriends, told me her dad had an office in Ann Arbor and if I went to Michigan, I could stay there.

While still at camp, I reapplied to the University of Michigan and was accepted for the winter term. When I got home I told my parents that I was leaving. They couldn’t believe that I was going to take the risk of leaving for college with hardly any money. (Keep in mind the tuition at the University of Michigan in 1965 was $300 a year and rent was $100 a month. Even that seemed like a lot of money when wages were $1.50 an hour)

Risk #3: Leaving for college without any money.

The rest is my story. I had a great time at the University of Michigan and began my study of psychology. In my senior year, I met my future wife, Pat, who was my next-door neighbor at 1335 Geddes Street.

This experience of going off to a summer camp in an unknown region of the country, by myself, has become the foundation for me to take risks my entire life. Not crazy risks. I haven’t endangered my life, although I did fly in an ultralight plane over Hawaii, with a hung-over pilot one time.

After I graduated from Michigan, I returned to New York City hoping to find a job as a teacher.

You won’t believe this but, I was assigned to teach African-American, Puerto Rican, and Haitian heritage in elementary schools. I ended up teaching for two years in Harlem.

During my time teaching in New York City, I directed plays with my students, even though I had no theater background. I became the only white member of an all African-American youth theater group which performed plays throughout the Northeast.

My experience in Harlem solidified my interest in psychology. I took a big risk and applied to graduate school. Harvard was my first choice, and even though I had no experience that would make me think I was Harvard material. As it turned out, I got into only one of the schools I applied to, Harvard.

Risk #4: Going to New York City without a job.

Risk #5: Teaching a subject I knew nothing about.

Risk #6: Becoming the only white member of a Harlem-based acting company.

Risk #7: Applying to Harvard.

Based on these experiences, I have been a risk taker throughout the next 50 years of my life. The risks have not always been successful, but somehow they have led me to have an enjoyable, highly successful life.

I would like to hear your risk-taking origin stories, please email them to me.