Want To Be A Freelancer? Just Punch Yourself In The Face, Instead

Drawing in Circles

My name is Chuck, and I am a freelance penmonkey.

We all know why freelancing is awesome, right? Sure we do. I’m drinking coffee. Sans pants. I’m typing this post while looking out the window that is my office, an office that sits caddy-corner to my bedroom. I merely need to roll my ass out of Slumberland, throw it downstairs to get the aforementioned caffeine, then drag it back upstairs and plop it front of the computer. That’s my commute. That’s it.

And once I do “arrive” at work, my own particular flavor (flava) of freelancing lets me write about vampires and werewolves and murder and mayhem, and I am allowed to poke the rampaging bear of PC gaming, or write a mini-movie about a future energy crisis, and so on and so forth. Further, so far I’ve worked with great clients and awesome writers to birth such stuff into the world.

And when all is said and done, a lot of really cool stuff is tax deductible.

What I’m trying to say is, freelancing is awesome. It’s a double rainbow. It is love.

Except, y’know, when it’s not.

Considering walking the path of freelancing? I get emails from time to time — “How do you do it? How do you break in? Where to begin?” — and on the one hand, I want to regale the questioners with such tales as the ones above, the ones without pants, the ones with endless coffee, the ones with vampires. But I also want to wave my arms, gesticulating wildly, warning them away from a freelancer’s life in the same way you’d warn someone driving toward a fallen bridge in the rain, a bridge teeming with rabid unicorns ridden by clones of the serial killer John Wayne Gacy — “Turn back! Turn around! Before it’s too late!”

Because sometimes, freelancing is a real punch to the face.

All Life Is Work

Sounds great not to have to put in an eight-hour day, until you realize that just as nobody is forcing you to “clock in,” nobody is letting you “clock out.” The work is the work. Everything is deadline. Go until you stop and then find more to do (or starve). Yes, you can put your back into it. You can model the day with a little discipline and wake up at 5:30 and start writing before most people get to their jobs, and you can allot a certain segment of every day to write. And that works for the most part. But when you need the work and you need the money, you do what you need to do, and if that means drifting far from the expected “9-to-5,” then by golly, that’s just what you’re going to do. Oh, also? No vacations. A vacation day is a day you’re making zero money. It makes vacations feel… guilty, somehow. A nagging feeling of laziness and unproductivity pervades.

The Hunter Lives In A Hard World

At a day job, work finds you. As a freelancer, you find work. (And in Soviet Russia — ennh, never mind.) You know that awful feeling in your gut when you’re looking for a job? Get used to that feeling. That sickly vacuum sitting in your gut, sucking up all your self-confidence? You feel it every time you have a gap in work. Nobody will come along and drop a new load of work on your desk. Yes, on the one hand that ensures that your life doesn’t feel like one big infinite conveyor belt dropping endless busywork in your lap. But it also means that you are the hunter, not the gatherer. You must forever track down the work, look for its tracks and track its scat — you stalk it through the brush, across the veldt, hoping to stab it with your inky lance and bring it down. It means you’re always hungry. You’re always desperate. It makes one weary.

Weekly Paychecks Are A Luxury

It will at times feel like you’re doing a lot of work for no actual money. Because the money isn’t immediate. At a dayjob, the money just… happens. Busy week? Slow week? Same money! It just appears! On your desk or in your account! Eeee! Woo! No. Not with freelancing. That shit takes forever. The money comes on a slow donkey, and the donkey must board a slow boat. That boat drifts on the ocean for weeks, months, the donkey braying, suffering whatever existential crisis a donkey is capable of suffering, until finally the boat washes up on the shores next to your weak-kneed and ever-trembling bank account. Thirty days? Sixty days? Ninety days? Yes. Now, you establish a good pattern of work, and the money rolls in in a way that feels like you’re getting a semi-regular paycheck, but it’s an illusion. Moment you have a lapse or gap, the money skips and stutters. Oh, that also means: get real comfortable with budgeting. Know how to look forward. Know that you will need to buy an ottoman or a blender or whatever six months from now.

Also A Luxury: Heartburn Meds And That Spleen Transplant You Really Need

Mmm, sweet, sweet health insurance. Of which you have none. Don’t get sick, or, get lucky like me and have a wonderful spouse who is quite literally my path to, well, not dying.

Hey, Good Luck With That Mortgage!

Our first mortgage necessitated I get an actual job. No, really — I had to leave the full-time freelancing thing and get a job at the library to establish a weekly paycheck to show to a mortgage company. Because even back then, when they were giving mortgages to like, stray dogs and lamp-posts, they still harbored grave distrust toward the freelancer. Time came, when getting our second mortgage, we looked at other banks and even tried to apply — and once more was reminded that apparently, being a freelancer is not actually a legitimate career choice. The questions they asked me again and again over the course of three different phone calls indicated a deep-seated ignorance regarding this path. “Who do you work for again?” “I’m a freelancer.” “Sure, of course. Who is your employer?” “I don’t have an employer.” “No, right, right, we get that. But what company do you work for?” “I am an independent contractor. I am my own boss.” “Yes! Absolutely. Can you send us copies of your weekly paycheck?” *shotgun barrel in mouth* The only way I was able to avoid the Ignorant Imbecile Inquisition was to just go with our current lender, because we had a history and they didn’t care so much that I was reportedly some kind of sub-citizen, just underneath migrant workers and neighborhood sex offenders.

Oh, And Nobody Else Will Get It, Either

Mortgage companies don’t get it, and nobody else really will, either. (I mean, except other freelancers. Freelancers should form a support group for one another. I guess maybe they already have? I think it’s called “Twitter.”) Go ahead, try explaining to your in-laws what you do. Or your parents. Or that new girl you’re trying to sex up. Nobody seems to believe that freelancing is real. It’s as if you’re playing pretend. “That’s not a real job, is it?” “No, I just made it up. Now, if you’ll excuse me, I have to go hang out with my pet dragon and have a tea party in Narnia. The life of a freelancer never ends!”

You Might As Well Paint A Face On A Volleyball

Freelancing is a lonely life. You sit here by yourself. Talking to yourself. Playing gloomily with yourself. Laughing at your own jokes. Weeping into your own hands. Enacting weird morality plays with your two dogs. (Or maybe that’s just me.) Outside the distraction of social media, you don’t… see people very often. Sure, you might go out — but an hour outside the house is an hour you’re not making money. And besides, they’re going to look at you like you’re some kind of pale, pink-eyed troglodyte. Probably because you are. The sun will burn your tender flesh. Your wobbly legs carry you only so far. You’re a wormy slip of a human, back bent by the burden of work, mouth barely able to form the words of your people. (Or, as The Oatmeal puts it, “Degradation of Social Skills.”)

So, Why Do It?

Because it’s awesome. Duh.

I know we’ve got other freelancers in the crowd.

Love it?

Hate it?

Pet peeves and pitfalls?