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The Best Decision I Ever Made

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?



  1. After all of my school years were spent prepping to be the first person in my family to go to university, it only took a week or two to realize it wasn’t going to work out for me. It was a tough spot, something that I had been working towards for 75% of my life, was all flipped upside down in days. Where do I go from here?

    15 years later, it was just one of many bold leaps in my case 🙂

    Thanks for the great articles Trevor

    • So, I’m curious. What was that first bold leap? What did you do after realizing university wasn’t for you? And how did you decide what to do next?

      • You know, I hadn’t thought about any bold leaps before that in life, and that’s the only reason I left it open like that.

        It took a few years to focus on what I wanted to do, when I decided to start my 1st and 2nd businesses. A few years later, another big leap when I left them and began traveling the world.

        What will be next? 🙂

  2. Andy Kirby says

    In the mid 90’s, the company I was working for had just acquired a company in Hong Kong, and was going to install a new IT system (the company was staffed by around 200 people but was still a paper office). I was asked if I wanted to get involved in the project, it would be tough but the carrot was that they’d need someone to install & support the system for a while in Hong Kong, and I’d be the obvious candidate. There was a chance of up to 6 weeks in Hong Kong!

    The project went well, the 6 weeks actually became 6 months, followed by more work that lead to another year over there, and after three years of commuting between London & Hong Kong for work. This was great at first, but very tiring (business travel is only exciting to people who’ve never actually done it!). I’d had enough & made myself decide whether to stay in Hong Kong or return to London.

    It wasn’t a difficult choice really, I’d loved being in Hong Kong so I moved there & spent two and a half great years there, met my wife, and eventually moved to Australia.

    Whilst working on the original project that took me to Hong Kong, a learnt that a more senior colleague had been offered the chance to work on the project, but had declined because he wasn’t comfortable with the idea of going to work overseas. I can’t help but wonder what had happened if that colleague had said yes instead of no…..No Hong Kong….no meeting my wife…… emigrating to Australia………..I can’t imagine anything more different.

    • I love how a single decision can take us on unexpected paths. One of the greatest things studying decision-making is realizing that things often work out in the end, one way or another. Too often we focus on the options, rather than how well we’ll make the best of whatever option we choose.

      I’m so glad you took the path you did, met Melissa and then came to the World Domination Summit so I could meet you!

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