I really mean it when I say it: I was fortunate.
I graduated college in 2007, just in time for the financial collapse and Great Recession, and attempted to enter the worst job market in more than eighty years.
Around the same time, I found out that the person who was subletting one of the rooms in my apartment hadn’t paid any rent for three months. When confronted about this, she cried and then disappeared, leaving my other roommate and me to cover everything. Goodbye, savings. I spent the next six months living on a friend’s couch, stringing together odd jobs and trying to stay in as little debt as possible while looking for a “real job.”
I say I was fortunate because I entered the adult world already a failure. I started out at rock bottom. That’s basically everybody’s biggest fear later on in life, when confronted with starting a new business or changing careers or quitting an awful job, and I got to experience it right out of the gates. Things could only get better.
So yeah, lucky. When you’re sleeping on a smelly futon and have to count coins to figure out whether you can afford McDonald’s this week and you’ve sent out twenty résumés without hearing a single word back, then starting a blog and a stupid Internet business doesn’t sound like such a scary idea. If every project I started failed, if every post I wrote went unread, I’d only be back exactly where I started. So why not try?
Failure itself is a relative concept. If my metric had been to become an anarcho-communist revolutionary, then my complete failure to make any money between 2007 and 2008 would have been a raving success. But if, like most people, my metric had been to simply find a first serious job that could pay some bills right out of school, I was a dismal failure.
I grew up in a wealthy family. Money was never a problem. On the contrary, I grew up in a wealthy family where money was more often used to avoid problems than solve them. I was again fortunate, because this taught me at an early age that making money, by itself, was a lousy metric for myself. You could make plenty of money and be miserable, just as you could be broke and be pretty happy. Therefore, why use money as a means to measure my self-worth?
Instead, my value was something else. It was freedom, autonomy. The idea of being an entrepreneur had always appealed to me because I hated being told what to do and preferred to do things my way. The idea of working on the Internet appealed to me because I could do it from anywhere and work whenever I wanted.
I asked myself a simple question: “Would I rather make decent money and work a job I hated, or play at Internet entrepreneur and be broke for a while?” The answer was immediate and clear for me: the latter. I then asked myself, “If I try this thing and fail in a few years and have to go get a job anyway, will I have really lost anything?” The answer was no. Instead of a broke and unemployed twenty-two-year-old with no experience, I’d be a broke and unemployed twenty-five-year-old with no experience. Who cares?
With this value, to not pursue my own projects became the failure—not a lack of money, not sleeping on friends’ and family’s couches (which I continued to do for most of the next two years), and not an empty résumé.