My first full-time job out of college was as a technical editor for a small startup in Philadelphia. My boss was my age, in his early twenties, and hired me to join his team of three. On paper, he lived the American dream, bootstraps and all. He had begun a business by doing editing for his friends in college for $20 at a time and grew this business until it was large enough to support three full-time workers and pay for an upscale Center City apartment and a world-traveling lifestyle. He thought of himself as a self-made man, and I idolized what he had built—if not the man himself.
I wanted what he had. He set his own hours, usually getting up at about 10:30 to shuffle in his bathrobe to the shower. I knew this because I and my coworker worked from a desk in his living room. He would occasionally announce that we would be working from the lounge in his apartment building for a few weeks because he had decided to work from Costa Rica for a while. He didn’t grind his days away for a paycheck but had built something that gave him an enviable lifestyle. Before coming to work for him, I had been a waitress in a diner, a substitute teacher, a delivery girl for a florist, a lifeguard, and a retail salesperson. I couldn’t believe my luck in finding this job.
The city (and the obscenely wealthy Main Line suburbs) blew me away. I had never been around that kind of wealth before, met those kinds of people, worked for those kinds of businesses. My coworker was a relief and a comfort. He had a background very similar to mine, growing up in a rural town on the west coast. One day at work, I was explaining that I actually hadn’t been driving very long, because I had gotten my license at the age of 20. My boss asked if I was afraid to drive, or just didn’t need a car? No, I explained, the town I grew up in had no public transit and nothing was within walking distance. I didn’t have my license because I had no access to a car that was eligible to take the driver’s test. To take the test, you needed to present current insurance and registration, and nothing my family was driving had both. I had also barely practiced, largely because after a series of breakdowns and other minor catastrophes, there was only one working car that was getting five adults to work every day. They just couldn’t afford to take the chance on a new driver busting up the only transportation we had. Four years after I was eligible to start driving, I was able to borrow my boyfriend’s mother’s car to take the test and bought a broken down Ford Escort for $400 I had saved up.
My boss told me that if it had been him, he would have been able to get his license much sooner. He would have worked around it somehow and figured out a way. He started throwing out suggestions to solve a problem I had solved myself years ago as if the twenty seconds he had been considering the issue would yield better results than the four years that I spent struggling and desperate, wracking my brains. That’s when I realized that he didn’t think I was poor, he thought I was stupid.
This scenario came up again and again. My boss would overhear my coworker and I sharing some detail of our lives, and butt in with how he would have overcome every one of our struggles and still ended up just where he was now. He was unshakably convinced that he would have been the smartest and most successful poor person ever born, skipping over hurdles that others found debilitating, building wealth and success from nothing using only his inherent genius. I kept my mouth shut, continued to keep his business running for him, and harbored frequent and increasingly violent fantasies about what I would do to him if I didn’t depend on him for a paycheck.
And as I worked there, I learned more about his background, as well. He was raised in one of the wealthiest towns in the region. His parents gave him an impressive private school education, followed by an impressive college education, where every dime he earned on his own was free to be reinvested into one of his many business schemes, his living expenses comfortably paid for. When he started the business at which I was now working, his father loaned him thousands of dollars to start it up. We still accepted PayPal payments in his father’s name. In fact, being his own boss was all he had ever known—he hadn’t worked a day in his life for someone else.
The wealthy and privileged don’t think there are poor people, only stupid people who deserve to have nothing because they’ve never really tried. They don’t think they’re lucky, they think they’re geniuses. In the years since I walked out on that job, I’ve met many such wealthy and privileged that think just like him. A woman on Facebook who swore to me that anyone can eat organic and vegan, that most are just too lazy to try. Another who confidently told me that mental health medication is an excuse, that anyone can choose to be happy but most would rather feel sorry for themselves. They oppose social programs and safety nets because they feel that there is no such thing as the truly needy, only the undeserving.
There’s one more thing I eventually came to learn about my former boss and his business, one factor that explained his success even beyond his privilege and his expertise and skill in delegation and marketing. My boss was cheating on his taxes, improperly designating his business and his employees, and underpaying by thousands every year. He stole core assets for his business off of the internet and sold them as his own intellectual property. I watched him lie to clients and advertisers, and he was kicked off of several online platforms for violating their terms of service with his shady business practices. He eventually misled a buyer into taking the whole mess off of his hands and left the country.
As for me, the impoverished idiot? I left that job and started my own copywriting business. I’ve never experienced the kind of meteoric success that he had because it turns out that it’s much harder to turn a profit when you’re not taking the kinds of shortcuts he took, but I’m proud of what I’ve built. That’s one of the many crimes of capitalism. It rewards the liars and cheats and tells them that they’re clever.