Yesterday I turned 40.
Today I’d like to step outside the focus of this web site and talk about a decision that was anything but lean. A shot-in-the-dark decision that changed my entire life.
In the fall of 1992, I decided to drop out of college.
I was attending Rensselaer Polytechnic Institute (RPI) in Troy, New York. I had entered two years earlier as a Physics/Bio double major. But I never really fit in. I wanted to be a musician and an artist, but I was surrounded by engineers. So I switched my major to Mathematics and started taking all the art and music courses I could.
I quickly ran out of courses.
That same semester, I started paying entirely for my own schooling. While my tuition was paid for mostly with financial aid, my parents paid a small amount my first two years. But working summer and winter breaks at a programming job at the Naval Air Development Center, I started making enough to pay their share. My sister was in school at NYU, so money was tight.
Paying for my own schooling gave me the freedom to take action and pursue my passions. I decided RPI was not the right fit for me and chose to pursue a career in art.
I finished my fall semester, gave away all my belongings except that which fit into a small backpack, and proceeded to make my way to San Francisco to become a famous artist.
It didn’t quite work out the way I had planned.
I spent three years on the road hitchhiking, selling art on the streets for money, living in abandoned buildings and sleeping underneath bridges. It was a challenging time, yet inspiring. I wrote my first book during that time.
During this time, I learned my greatest lesson: I learned to face uncertainty.
I learned I could always survive. No matter what happened in life, I could adapt. My travels gave me a resiliency that has lasted my entire life and helped me through the ups and downs of three startups and a life of adventures.
I learned not to fear the unknown, but to embrace the opportunities it provides. I learned to lean in to the winds of fate and forge my own destiny.
No decision I have made since has changed me in such a dramatic way.
But what about you? I don’t recommend dropping out of college just to learn how to face uncertainty.
I was lucky. My father had given me a computer when I was 9, and I spent my high school years programming. I had already had a profession before I entered college, though I didn’t know it then.
I was also moving toward an art career, not just away from college. I never got there, but I had a vision that helped me overcome adversity.
Nonetheless, I do think everyone should make at least one bold leap sometime in their life. It makes you feel alive and teaches you what you are truly capable of.
What was the best decision you ever made?