How I Dealt With Failure

“The hardest thing you’re ever going to do in your life is fail at something and if you don’t start failing at things you will not live a full life.”- Sebastian Junger

I’ve experienced a lot of failure in my life.

Like a lot of kids, I didn’t give a shit about school when I was younger. I don’t know if I was rebelling against my parent’s divorce, but as early as I can remember, I was always getting into trouble for not doing any work. Things didn’t improve as I got older, in fact they regressed.

When I went to college, I was mentally and emotionally closer to 10 than 18. I missed my very first class and never looked back. I got a 0.9 my first semester and followed that up with a 0.8. Looking back, it’s hard to believe how irresponsible I was. Perhaps I sat on the couch all day to cope with the fact that my mother wasn’t going to live long enough to walk me down the aisle. Or maybe I was just a normal, immature kid who was having fun and not taking anything too seriously.

Not surprisingly, the administration did not look favorably at my transcript and sent me home for a year. When I left, I was told that if I got my grades up, they would consider giving me another shot. So I did, and they did. Only the results were similar to my first go around. I remember my roommate asking me “what the fuck is wrong with you man? Why are you doing this again?” I had no answer then and I have no answer now.

I dropped calculus when I realized I was going to fail the course. The problem was that I needed 12 credits to not violate my academic probation and dropping a class made this impossible. So I was called into the Dean’s office the next morning. I sat in the waiting room with a pit in my throat, and when I was finally called in, she told me what I already knew. This place was not a good fit for me and I was being sent home. I vividly remember sitting there in silence, tears running down my cheek. I was  humiliated.

I came home and got a degree from Queens College just as the global economy was falling apart. But lucky for me, companies that don’t pay you a salary and charge you office rent are literally always hiring. So I got a job at an insurance company which turned out to be a lousy experience. Eighteen months and zero policies later, failure was at my doorstep, again.

I decided I was done with failure. I had taken enough lumps and bruises. But unfortunately, failure wasn’t done with me. It needed a little more time.

I took the next two years to prepare for an opportunity, which is a nice way of saying I was unemployed. Nobody would hire me, so I made education my full-time job. Every day at 6 A.M. I dropped my then girlfriend, now wife, at the train station and headed over to the library.

I’ve spent the better part of the last decade overcompensating for my educational washout and putting failure in a rear naked choke hold. I dedicated countless hours studying for the CFA exams and I’ve read hundreds of books. Sebastian Junger’s quote on failure is spot on. I’m living a full life and the little I’ve accomplished wouldn’t taste as sweet if I never got any dirt on my face.


Sebastian Junger and Tim Ferris