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?


  • Oh wow, after just two years as a freelancer, this article feels like a hug. No one ever told me that the free part of freelancing is scary as shit.

    Having said that though, I’m now going to go get my coffee. 🙂

  • Great article, and great discussion on the board!

    I’ve been freelancing for about 6 years now, and have just had to take my first part-time job in a couple years. Ironically, it’s work doing Location Support for film in TO, which today paid double-time to spend 12 hours watching a hole in a wall, to make sure no-one went through it. That’s it. Oddly, at the end of the day, I appreciated having a workload to go home to!

    What I’ve been learning over the last couple years is that the key to freelancing is not just being disciplined and suffering the lack of spare time. The biggest part that defines how rushed off your feet you are 24/7 is managing your clients. That’s not just a reference to the time they need allocated to their jobs, but also to their expectations and unreasonable demands. And, that usually starts at the beginning, when I’m telling them what I can do for them.

    Doing web design and development like I do, you often find that you are up until 1am not because you couldn’t do the job, but because the client called at the last minute and INSISTED that something be changed or added.

    Now, before I was freelancing, I worked in theatre – so I was used to the up all night stuff, but that’s because those experiences come from having to rely on volunteers, weather, and the artistic passions that made for big egos, big wastes of time, unreasonable demands that had to be met before opening, and so on. As a director/producer (which was my thang) you had to balance the resources your meagre funding could afford you, the willingness of your volunteers, the abilities of your cast (and their egos) and your crew (and their egos) and end up with it all working right on the night. As Julie Taymor can attest to, this is sometimes not easy to do – and if you don’t have the ridiculous money behind the show, it’s even MORE difficult.

    When it came to actors, I knew I could get them to deliver their best by starting off on the first day by defining the terms of our working relationship, and what might be expected of them if we were going to make the show a dynamite one – and this could include anything from “You all need to have learned how to juggle by next week,” to “We will have safety crews on standby for the scene with the flaming sword.” This could inspire – or make people bail. Better to have them bail early.

    As a freelancer, you are kind of like the director who’s trying to “make it”. You want every job to be one you can show off in your portfolio. You need every job, so you can eat. If you get a job, you are VERY reluctant to stand your ground and say “no, that will cost you more money” or “no, I will NOT stay up all night to get this done, because that is what you are asking me to do, deadline be damned.”

    Creatives tend to take gigs that they THINK will make them look great, and wind up in a nightmare project that ends up paying nothing, destroys their sleep patterns, their relationships, makes them doubt themselves, etc – and SO many actors, as talented they may be, wind up being a teacher, or a manager at the shoe shop in the mall, or going into the family business, or becoming homeopaths, because it’s a regular paycheque

    It was a revelation the first time I said to a client “You know, I’m afraid i just can’t help you any more. Your deposit covers most of the work so far – here is the materials and work to date, so please find someone else to finish this.” I had, of course, allowed the client to get completely unreasonable in a way I could use in any lawsuit, before I said this. However the experience taught me that some people can not be pleased, and making the rent would be easier to do without the dark cloud that had been hanging over my head. It’s easier to get a new client when you don’t feel so on edge.

    These days, I’m doing pretty well. The best bit is, I sleep regular hours, and don’t find myself talking to myself through clenched teeth at 10pm at night. The standard line sits on the bulletin board above my desk:

    “I need to remind you at this juncture that you hired me to do A B and C by Date X, and I agreed that was possible contingent on providing 1 2 and 3. I would be delighted to do the work you are asking for, but not without you paying for the additional time required, and with the understanding that the agreed deadline may need to be changed to accommodate for this. I believe that would be the most professional way to resolve this situation.”

    Below it is another note, written in caligraphy:

    “Your failure to be organized and prepared is not my problem.”

    All my clients that are regulars repeatedly tell me my customer service is excellent. I don’t snap at some of them, or bite chunks out of my tongue all day – I patiently explain that some situations require them to a bit more understanding of how I am able to work for them. And I plan for hiccups and delays; I use the Scotty rule – multiply the time you think you can do it in by a factor of four, and use that for your quote if you can. You’ll find when you get it done a few hours past when you thought you’d get it done, you still have time for a movie before bed.

    And FYI – that incorporation thing? If you don’t do it, you can at least use it in conversation and make the relatives happy for a time. “I do XYZ and I’m currently freelancing. I’m currently looking at incorporation.” When they ask what that means, explain incorporation to them. Then explain the pros and cons. Suddenly, they’re listening!

  • Great article! I guess I’d rather punch my self in the face then have a boss punch me in the face. When I worked at a full time job it’s was like working alone. I sat there all day with headphones on with my head buried in my computer.

  • Its like you read my mind! You seem to know so much about this, like you wrote the book in it or something. I think that you can do with some pics to drive the message home a bit, but other than that, this is wonderful blog. A fantastic read. I will definitely be back.

  • excellent put up, very informative. I ponder why the other specialists of this sector don’t realize this. You should proceed your writing. I am confident, you’ve a great readers’ base already!

  • VERY late to the party, but since comments aren’t closed yet I thought I’d say I agree with everything in this article and thought it was hilarious and interesting as well as deeply informative. As a freelance artist who’s spent most of her time working “day jobs,” I personally get the most enjoyment and stability from working freelance while partnered with a spouse with a day-job. For those going it alone or living with another freelancer, I think you are simply amazing…I think it takes a very special person to do what you do. Although, as people further up in the comments have said, I think everyone’s wired differently. Some people genuinely feel happiest going freelance and some feel happiest working for another entity…the happiest people are probably those who discover which kind they are and then be the best “etc” they can be.

  • I fucking love my self more. before at “job” they treat me off only what they could spend me for. Now I walk my path of free lancing the domination. They hate it. they say, go be alone you loner. And in my case, if you are alon drinking coffee at starbuck from 7 (thats my market opening time) til 24:00 (thats my market closing time) for five day… and talking to only people who sound like they are delivering you infomation on world terrorism and nuclear procurement of one country… some where along the line there. A van might be coming for me; either from the luna house or the government recreational goon sqaud. In asia, they all want you to work for a “company” follow the line. get that insurance and pension. If you walk out, swim against the tide. All these fucker will stand in your way. Saying all kind of spin twisted shit to make you wanna fall back into the bongo train. like why the fuck would any human wanna become a slave to another fucking human. thats retard. and fuck social ladder climbing shit. its all about hi, stab you in the back, hello? push you off the stair kinda situation.

    Free lancing make me jump out my bed and laugh. sure is lonely when my wife doesnt find it sexy and want to date a brothel owner instead…

    well… fuck that bitch… I ma go sit in a coffeh shop and free lance my way to the top ฿abeh

  • June 4, 2017 at 2:23 AM // Reply

    if this ended with link to a check out page it would literally be the best sales letter for any copywriting course on the market.

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