The Perils of Being Self-Employed and Working from Home

Nate Otto
ART + marketing
Published in
6 min readJan 16, 2016

“Have a good one.”

“You too.”

This is my first social interaction of the day and I say both of the these lines in unison with the clerk at the grocery store. It’s awkward, and the fault is mine. For him, these words are automatic, and repeated throughout the day. For me, It’s the first sound out of my mouth since I grunted goodbye towards my wife in the morning. I am a robot reading from a script. The timing is off and the nuances of human communication are beyond my reach. It’s eight PM. I think it’s Tuesday. I’m buying salsa and beer. Time for dinner.

I love working from home. It is zero degrees today. Zero! I live in Chicago and when it is snowy and frigid outside, life goes on. People still go to work and roads still function, because cold and snow are part of the habitat four months a year. But I’ll be sitting here in my painting pajamas and fuzzy slippers watching people out the window riding their bikes across perilous, icy tundra on their way to a paycheck. The problem is I’m not being paid for what I’m doing right now. I used to get paid for looking out the window at my old job. For at least forty minutes a day at every former job I ever held, I got paid for merely existing on the clock. Add in walking down hallways and zoning out in meetings, and that’s four hours a day of getting paid for nothing. There is no clock now, only production. Not only do I work from home, but I am also self-employed. Worse yet, I’m a professional artist, a dubious profession if there ever was one.

This is more relevant now than it was a couple of years ago when I drew it.

There are many perks to the gig; short commute, no bike riding on the frozen streets, no pesky chit-chat with co-workers, and, of course, no bosses. Most importantly, I get to do what I am passionate about, what I do for fulfillment, and what I believe I am meant to do — for a living. Not bad! But these perks can all be problematic.

My office is my home and my home is my office. It is very hard to discern when I am working and when I am relaxing. Sometimes I work while I watch a movie. Sometimes I decide to relax and watch a movie, only to find that I spend the entire time working. Which is which? I have no idea. I have taken up the habit of going for a pint at the bar to signify the end of my work day. This routine has its own obvious pitfalls. Not to mention I might be drawing while I’m at the bar, and for me that means I’m working. There is always something that needs to be done, and there are no set times in which to do it. The fridge is always there, and there is always something to watch on Netflix.

While it is true I don’t have to go out in the cold to get to work, it is also true that I don’t have to go anywhere. I have had to get something done downtown for months and I continue to put it off because the idea of getting on a bus and a train, once part of my daily routine, now seems incredibly daunting. I am forgetting how to function as a human being. Sometimes I go days without showering or shaving, or even changing clothes. For a while I was growing my hair out just because I could, and I looked a little bit homeless. Couple that appearance with significantly decreased social interaction, and I’m a stinky alien visiting planet earth every time I leave my domicile.

I don’t have to suffer meaningless small talk with co-workers anymore, but now I don’t talk to anyone, ever, for any reason. I don’t have co-workers. I know people who make their living being alone and creative, but they are off in their own caves. Nobody’s career is like mine, and I have no real peers. At my old job I was friends with at least four different sixty year-old women. Despite our vastly different appearances and backgrounds, we enjoyed and respected each other, and we saw each other five days a week. There are no sixty year old ladies in my life these days. I don’t see anyone that is not my wife five days a week. I spend much of my time alone and I get weird. The people I do see are people I see intentionally. My social interactions are severely lacking in diversity. It’s mostly sipping beer with grumpy, urbanite, creative types — people like me. Also, everyone I meet is a potential collector, and that makes me a creep.

Work

But no bosses! This is an undeniable perk. At my old job I had seven direct bosses whose jobs seemed to be to keep themselves employed as my bosses. That was not a good position to be in for an opinionated doofus who liked to look out the window and think about art. Now, I’m my own boss! I tell myself when to wake up, when to work, when to pet the dog, and when to write an article about working. Hey boss, can I have the rest of the day off? Sure! Where’s the problem?

I do get to pursue my passion for a living. This is the one that keeps me going. Life could certainly be easier in many ways if I went and got a regular job. Health insurance and regular paychecks sound great, but I am an artist! I spend my life trying my hardest to create beauty. It is my duty to humanity to infest the world with my inner specialness. How cool is that? And what a crock of shit.

I am in one of those building right now.

I do commissions and I have illustration clients, but a big part of my living is made by making the art I want to make and selling it to people. Sometimes when I explain this to people they just don’t get it. So I explain again. I make art and I sell it. “But how do you make money?” they ask. I can tell you that art is a salable commodity, and the creators can be paid for it. I am one of those people — sometimes. It is not the same as selling widgets, and it is not easy.

The working hard to earning money dynamic can be a little indirect. Sometimes I’ll be lazing about and I’ll make a small windfall out of nowhere for something I did three years ago, and other times I’ll be working my butt off and nothing is happening. This sort of thing confuses the shit out of my boss. Gatekeepers, false leads, haters, and productivity slumps abound. Also, art is stupid, and being creative is hard.

I know — check out the first world problems on this guy. I’m not trudging up muddy hillsides to fetch bucket-fulls of dirty water to bring back to my shanty. I get to sit around my house drawing whatever I want and listening to podcasts, in a house full of delicious food, with Facebook at my fingertips. Boo, fucking, hoo. I had twenty years of jobs so I know what it’s like on the other side. Every work environment has its trouble spots. In your office the problem is Stu and his bullshit. In my office the problem is me, and my boss doesn’t want to hear about it.

Art that was recently made by me in my home

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Nate Otto
ART + marketing

Artist, illustrator. Chicago. Makes art every day.