More than One Path to Success (Lessons From A College Dropout)

Tue, Apr 23, 2024

To say I dropped out of college is almost a lie. 

I don’t think I went long enough to qualify as a dropout. 

It wasn’t a proactive decision on my part, mind you. At first, I just missed a couple of classes. Then, for one week, most of my classes. Then, one day, I just never went back. 

That was the darkest point in my life. Not because I dropped out, but because I had no direction. I lived in a traphouse of an apartment with a fresh-out-of-prison felon (he came over for a house party and just never left). I worked random menial jobs and made an attempt at petty crime.

Not my shining moment. Someday, I’ll tell more of that story. For now, cut to: I got out of the 505. At 19, I moved to Scottsdale to work for my dad in his furniture store. I love my dad, but I hated working for him. 

So, I did what every futureless, skilless, dropout should do: started a business.

Not just any business, an outsourcing business. (Yeah, I didn’t know what that meant either.)

My grand scheme was to get literally any digitizable work here in the States, send it to people overseas, and sit back collecting the Benjamins. I’m still morbidly embarrassed thinking about it.

While I was building this outsourcing empire, I somewhat randomly made the acquaintance of a man we’ll call Tim. He and I met on the racquetball court at my gym. (Yes, I play racquetball and will go to my grave contending it’s among the most underrated sports. Try it and you’ll see.) 

Tim was a picture-perfect example of exactly how life should be lived. He was 15 years my senior, had gone to an ivy league school, and was a C-Level exec for a big company. He was also flat-out brilliant. I loved listening to him and would seize every opportunity to do just that.

One day, Tim invited me to have lunch with him at his office. I had no idea why he would want to have lunch with me but was excited nonetheless. At the time, I was probably naive enough to think we were becoming friends. 

Little did I know, I was walking into a perfectly placed trap. 

His office was exactly what you’d picture: big, spacious, and luxuriously furnished. Everything was picture perfect with the exception of this massive whiteboard that took up one entire wall. Never before or since have I seen a whiteboard with more miles on it. I would soon learn why. 

It’s a blessed opportunity to literally see a truly brilliant thinker think. 

He started pouring his thoughts onto the whiteboard. He wrote faster than I could think and even switched marker colors to help categorize his thoughts. I felt like I was watching performance art. It was amazing. 

There was only one problem: What he was explaining to me, in the most concrete, eloquent, and undeniable way anything has ever been explained to anyone in the history of mankind, was how I couldn’t be successful unless I went back to school. A perfectly dealt death blow.

I couldn’t disagree with anything he said. He made such a poignant case, approached the problem from all angles, and covered every eventuality. There was no other option than to admit defeat and concede the point. It was a perfectly crafted argument and I was without rebuttal.

I left his office that day feeling like a failure. 

Not someone who has failed in the past—I left feeling like I was doomed to fail forevermore. What Tim didn’t know when he embarked on his well-meaning mission was: There was no way I was ever going back to college. It wasn’t in me to do.

We’re all built so differently. For him, college was this obvious bottleneck to success that a person could just muscle through. And it was something that anyone could do if they put their mind to it. For me, I would rather resign myself to failure than sit in one more lecture hall.

Tim’s lecture was the last one I ever sat through. 

I decided that if that’s what success took, I didn’t want it. 

I could eke out a living on my own and would rather be relegated to forever climbing a muddy hill than having to achieve success on someone else’s terms. I was on to something.

Here’s what I failed to realize during Tim’s lecture: We started with a flawed premise. His definition of success was massively different from mine. Before we started, we should’ve defined terms. I would’ve hated Tim’s version of success. 

I love working from wherever I want, he really got a kick out of that fancy office. I love that I can  wear shorts and a t-shirt every day, he loved suiting up. I love that I get to call the shots and dream big, he loved executing on other people’s visions.

At the time, I didn’t realize the obvious flaw in Tim’s lecture: He was drawing a map to get where he was. 

And, he was right in everything he said: I was never going to get where he was without doing what he did. The thing he and I both failed to realize: That’s not where I wanted to go.

Where do you want to go? Is the plan you’re following going to get you there?