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?


  • This certainly sums up most of the reasons I decided not to become a freelancer. I did a few jobs, and decided that I did not have that kind of intestinal fortitude. I’m strictly a hobbyist writer.

    Incidentally, you ever consider incorporating? Just create a one-man LLC. It has some tax advantages. And, more importantly, it looks better to people like mortgage companies to say “CEO of TerribleMinds, Inc.” rather than “semi-employed penmonkey for hire.” From what I understand, it’s pretty easy and relatively cheap. It does involve talking to a lawyer, though. Preferably without killing the lawyer. That may not be worth it.

    • My tax lady and financial adviser have both been a little shaky on the pros of incorporating — I revisit the topic yearly, so maybe this year will be the one. I dunno.

      — c.

  • All of those reasons are reasons why I’m looking (and failing to find -_-) a day job rather than extend myself into freelancing. I don’t know how you folks do it everyday, but I love that you do.

  • See, this just makes me want to go that route even more. My wife and I have incorporated (Chrysalis Creative Services, LLC) what is mostly a graphic design studio (she is the designer, I write copy and work on web design). We are hunting, but the fact that we both have day jobs (and mine is more than 50 hours a week with commutes included) is making that (and writing regularly) difficult. I’ve had to turn away clients for web design because I’m maxed out on what I can do in the extremely limited time I have. I’m feeling like I just need to make the leap sometime in 2011.

  • Of late I’ve been writing more, and I kinda miss being a full time writer for all of the reasons you mention. When Teagan was born, I was still a full time WW-er (working remote, which is basically all of the perks and none of the downsides, except for the crappy pay), but shortly thereafter I went back to full-timing it again.

    And see, at the time, work *did* fall into my lap, but that ship has sailed. So I’m glad that I can still find some work, and I do miss being able to write at my own pace and play video games mid-day.

    But see, I work in education. I get 14 weeks a year off, 11 of them consecutively, and I get to do *no* work and still get a paycheck. So I’m doing OK. 🙂

    • @Matt:

      I try not to do much in the middle of the day anymore that is “play.” I figure, I’ll reserve that for the hours “after” work so to speak — the only form of leisure I take during the day, outside Internet stuff like social media, is reading. Reading has a leisure quality, but is also something that bolsters the work in its own weird way, too.

      — c.

  • I’m an ex-freelancer. Or on a break from freelancing. I was a freelancer for two months shy of eight years.

    Since July, I have worked in the administration of a university, writing rulebooks (which use the same font as the first edition AD&D rulebooks, which is hilarious). I’ve been doing it for two months.

    As a freelancer, I worked 80-hour weeks. I barely made enough to support myself, let alone my wife and kids. Towards the end, I burnt out. I barely wrote a word between January and June this year, and stopped dreaming. I stopped dreaming. I lost my imagination.

    I was in a bad place.

    I’ve spent two months in an office and I am earning several times over what I earned as a freelancer, enough that my wife can pack in her job and stay at home with the kids, which is what she wanted to do all along. I don’t have to work another evening or another weekend. No more 9-day weeks or 32-hour days (that’s not an exagerration). I go home at 4.30pm and chill. I get to spend Saturday with my family.

    I am writing poems and fiction again. A I started having interesting dreams a couple weeks ago. The Crunch starts again on Thursday and I’m proud to have been one of the people behind that.

    I am a little sad about not being a freelancer.

  • The hardest thing for me is getting friends and family to realise that just because I’m at home, doesn’t I’m “at home” in the way they are.

    When they’re at home, it’s because their work is done. When I’m at home, it’s because I’m at work. And I’m doing 12 hours a day, at that.

    It never fails to fucking stagger me (and hurt my feelings) at how so many of them miss the point.

    “Why are you tired? You’ve been home all day.”

    “Why isn’t the house cleaned up? You’ve been home all day.”

    “Why do you have a headache? You haven’t done anything today.”

    • @Aaron:

      The hardest thing for me is getting friends and family to realise that just because I’m at home, doesn’t I’m “at home” in the way they are.

      When they’re at home, it’s because their work is done. When I’m at home, it’s because I’m at work. And I’m doing 12 hours a day, at that.

      It never fails to fucking stagger me (and hurt my feelings) at how so many of them miss the point.

      “Why are you tired? You’ve been home all day.”

      “Why isn’t the house cleaned up? You’ve been home all day.”

      “Why do you have a headache? You haven’t done anything today.”

      Yeah. That, exactly.

      — c.

  • I’ve only dipped my toe in the freelancing pond to see if the water is the right temperature, and it scares me. I want to do this sort of thing, but I also want to make money and not worry about each next source of moolah.

    I need to use that word more. Moolah. Moolah. What would you like in your coffee? Two sugars, a little Irish creme, and some moolah, please.

    What? Right. Anyway. What concerns me about doing it is that I don’t know where to look for work, per se, aside from rpg-companies, because several very cool and helpful people have pointed me in the right directions. There has to be more to freelancing than games, obviously, I just don’t know where to look.

    Then there is the doubt thing. I get worried every time I send a query that someone will right back “Look, dude, we’ve been talking about you. Not us as a company, all of us. The whole fucking world. This shit was fun while we were high, but it’s getting old. Put the keyboard down. Go flip burgers. Believe me, we’ll all be better for it. Yes, I do want fries with that.” If just waiting for one response is nerve-wracking, then going through that multiple times a month must be excruciating.

    Then again, fuck it. It’s fun.

  • I took a month of my day job to help look after my little girl, during that time I though about being a freelance editor. I edit as a day job, I could then ease my way into writing. First thing I applied for played out, just waiting for a contract. Like Chuck I have the wife who can bring home a good regular paycheck, that frees me up to give this a shot. I’m keeping my day job for as long as I can though. I’m not ready to let go of the steering wheel just yet.

    Hey Chuck, if you weren’t with the wife, do you think you would have still been able to pull it off?

  • Chuck,

    I’d be happy to discuss the pros and cons of turning yourself into The Man, i.e. becoming an LLC. I have some experience and knowledge in this area. I wouldn’t like to do it via email, though, so if you’re keen, let me know via email and we’ll arrange a call.


  • My wife “works for herself” and usually work pretty long hours. The checks don’t always come on time, but she get to make choices about her day everyday.
    I on the other hand am a wage slave. I love getting a pay check every other Friday and getting every other Friday off (working 9 hours days).
    Definitely would miss complaining (about everything) with guys if I worked from home or was self employeed.

    I worked for myself 5 years ago and other than feeling anxious 24 by 7 about money it was great.

  • I love to point people to Scalzi’s Money Advice for Writers post: http://whatever.scalzi.com/2008/02/11/unasked-for-advice-to-writers-about-money/

    It’s great advice, and it also hammers home that fact that freelancing is not exactly a slam dunk into your checking account.

    I’ve been freelancing for a bit more than three years now (and working from home for eight.) I love it because of the liberty it gives me. I can do all the Mom Stuff without worrying about it hurting my career — all of the middle-of-the-day school parties, karate lessons, bringing in the forgotten lunch. And yeah, I can knock off and play Dragon Age or DDR or whatever if I feel like it. “Research!”

    And it’s not just personal freedom, it’s creative freedom, too. When I’m stuck, I don’t have to hammer my forehead on my keyboard until I’ve put my hours in. I can go to the gym or take a shower or put up some peach-ginger preserves and let my subconscious do its thing without feeling guilty that yes, sometimes that’s just the process.

    On the other hand, I have some serious workaholic tendencies, and the unending pressure to hustle plus the lack of contextual cues to relax make it so that I… don’t relax or stop working much. Plus I hate giving quotes and I hate invoicing and I hate hassling people who haven’t paid when they were supposed to. But you’ve got to do it.

    Still, I wouldn’t trade it for anything. Maybe the cost/benefit analysis will come down differently when my kids are bigger, who knows? And it would certainly be different if I weren’t one of the lucky ones with a spouse with a nice, stable job with health insurance. But for now, I’m lucky, I know I’m lucky, and I wonder what I could possibly have done to deserve it.

    • @Andrea: All true, and next week I think I’ll do a sister post that talks about the truly awesome side of freelancing.

      @Robertus: I do very much like the ability to make my own choices. It precludes that I make good ones, but whaddyagonnado?

      @Dave: Diggit. I may take you up on that.

      @Wood: That was the trick for me — work hard, but not work too hard, or so hard it kills you.

      @Darren: My wife is a key part of being able to do what I do. Could I pull it off without her? I mean, I guess technically, yes. But it would be a row almost too hard to hoe — having her around is a critical component to that. Goes to show, though, just how the world is not built for the freelancer or entrepreneur — we must rely on the kindnesses of others to exist, sometimes.

      @Rick: “Moolah” sounds like some weird, never-used racial epithet. As to where to look — well, technically, you can look anywhere. Pub companies, magazines, websites. Just depends what kind of freelancing you want to do/can be good at doing.

      — c.

  • There are times when I love it and there are times when I hate it. I don’t freelance full-time, so it’s more of a hobby for me.

    When the words and ideas are flowing, it’s one of the most wonderful, addictive things that I know. The sheer rush of creating stuff is such a buzz.

    But when the words won’t flow, then it’s a major league pain in the arse. Forcing myself to sit and write stuff, when I’d much rather be doing just about ANYTHING else. is a drag. But I do it anyway, because I don’t ever want to blow a deadline.

    Then there’s all the other painful and/or annoying stuff like work drying up after a couple of assignments, or developers who are hard to get in touch with, or a lack of feedback on the stuff I’ve written so I can do better next time, or readers with an over-developed sense of entitlement and a belly full of hate, or not getting paid for months after the book come out (and sometimes not at all) or readers who talk about everything else in a book, but somehow always skip on mentioning my stuff or a list of other stuff.

    But all of that fades into insignificance when the author’s copies show up. Seeing stuff that I’ve written actually appear in a book is just the BEST thing. I’ve never grown tired of it, and I’ve been freelancing on and off for eleven years now.

  • Freelancing. Geeze, I was almost over the nightsweats and flashbacks and you have to go and do a blog post.

    Yeah, I freelanced. I did twenty years, 1986 – 2006. Actually got over the hump and had a pretty good business humming along. You gotta have a niche, and the whole vampire/gaming niche sounds like a lot more fun than mine. I did marcom work for professional service firms, accounting firms mostly. You needed 3500 words explaining what tax treaty changes in the EU meant for US companies’ transfer pricing strategies? I was your guy. Yeah, OK, it was boring. But I was past the where’s-next-week’s-check-coming-from stage. Arthur Andersen was the biggest accounting firm in the freakin’ world, and their HQ was right here in Chicago and I was dug in like a tick. Ads, newsletters, collateral, web copy, even speeches for the executive team. What could go wrong?

    Oh. Enron. Well, OK, there’s that.

    Sure, I had other clients, but Andersen was more than half my business, gone overnight. And suddenly their whole marcom department was out on the street looking for gigs while they scrambled for jobs, calling all the same people I knew, and it’s not like accountants don’t understand the whole supply and demand thing, so the average hourly rate (and don’t get me started on hourly rates, either) went from around $100 an hour to $50 if you were lucky.

    Oh, and those how-do-I-break-in-to-freelancing-calls? Gotta love those.

    “Dan? This is Marsha, the entitled bitch? I know your wife from the mom’s group at school? Say, I’m a pretty good writer, and I’m looking to get back into working, but something that doesn’t take up too much time from tennis and stuff, ya’know? I thought maybe you could give me some tips on this freelancing thing.”

    “Screw writing Marsha. How do you feel about selling?”


    “Where do you think the jobs come from Marsha?”

    “Oh. But you must have lots of contacts.”

    “And you want me to share them with you?”

    “Well . . .”

    “You want me to call up my contacts and say ‘hey, those projects you send me that pay may mortgage and feed my kids, go ahead and send some of those on over to Marsha, OK? I can always dig up some more work somewhere else.’ Do you know what I went through to get those clients, Marsha? Do you know how much arcane business nonsense I’ve had to internalize to do the damn work? Do you know what MACRS is, Marsha? Or the difference between LIFO and FIFO? Or what the PBGIC is and why an HR department needs to care? Of course you don’t. See, even if I gave you my contacts’ names, you wouldn’t be able to do the work.”

    “Well . . .”

    “You see Marsha, I don’t want you freelancing. I don’t want anyone else freelancing. I don’t encourage competition. And when I find new competitors on my patch, my new goal becomes to shut them down, to steal all their work. To go to their homes and burn their offices and to sow the ashes with salt so that nothing ever grows their again.”

    “Well . . .”

    “Say hi to Floyd, Marsha.” Click.

    I was almost over it. Almost.

  • The real joy of freelancing is the balancing act between taking on more than you can handle, and not enough to, y’know, eat. Do I stick with just taking work from Clients A and B, which will (barely) pay the bills, or do I chase after Client C and wrestle a big project out of them? What if that big project overruns, and I end up failing to deliver for A or B? Or what if I don’t chase down C, and then A stops throwing gigs my way? And where I do make time for my own projects X, Y and Z?

    Freedom, horrible terrifying freedom.

  • Two non-obvious reasons I incorporated were as a liability shield for our household, and to make it easier to see where the freelance income and expenses stood, apart from the main household finances. (Although you could certainly do the latter without incorporating, I suppose.) It also seems to be saving me money, though, tax-wise.

  • The part I think I’m never going to get over is, sometimes I don’t feel like I’m doing anything. If I’m watching a movie or television show, or reading a book because I have to for a project, it feels like wasted time. When I’m promoting a product, I’m not writing. When I’m brainstorming and taking notes for ideas, those words will never see the final product and it feels like I’m wasting my time.

    A lot of times, my work ethic is entrenched in ‘deliverables.’ I’m not sure how to get away from that mindset.

  • From what your saying and what I’ve seen, freelancing looks a lot like being a professional artist. Looks like something easy and with a lot of freedom from the outside, but on reality more work and time commitment than your average 9-5, and good luck getting others to understand that. By that same token, I’d say that one becomes a freelancer for the same reason one becomes an artist: to some extent, it’s what we are.

  • I have the luxury to say that, while I work freelance, I am also a “translator”. Nobody outside the biz actually knows how it works anyway, so everybody just assumes I am employed by a company or the mayor’s office, while banks just need me to say “wolny zawód” (“free work”).

  • I always keep the following things in mind when it comes to working for yourself:

    * Steve Kenson summed it up for me thusly: “Working for yourself is great — you set your own hours. Any 80 hours per week you want.”

    * The biggest thing that people don’t get about the whole “home office” thing is that YOU ALWAYS FEEL LIKE YOU’RE AT WORK. “Done” for the day doesn’t exist, because there’s always something else that needs doing. If you’re downstairs watching TV with the wife, part of your brain beats you up that you’re “wasting time”, and could be working. You don’t Work From Home — You Live At Work.

    * When I end up putting in “just a couple of hours” on the weekends, or on the day after Thanksgiving, etc. I tell people that I have to work, because my Boss is an Asshole.

    * You seriously need to build up a thick skin for the whole “it’s not a Real Job” comments, otherwise it’ll quickly become Tower-and-Rifle Time (which, of course, isn’t conducive to a healthy relationship with the In-Laws). I wish this was more of a snarky joke than it is, sadly.

  • This post was magnificent. I can’t find a job for shit, and if I do I get laid off. I spend up to 12, sometimes 15 hours a day on the internet just writing short stories, submitting them, re-editing my novel, and otherwise just dicking around.

    I love it. I’ve always said I wish I could find a way to get paid for this.

    It seems like two of the hardest components of this lifestyle are lack of money and your family (ok, your WIFES family) and friends not understanding you, OR what you do.

    Well, I’m not getting paid anything now and my wifes family already thinks I’m an asshole.

    I’d like to learn more about this freelance road that you travel. A road filled with twist, turns, roadblocks, and pot holes deep enough to swallow an eighteen wheeler pulling an oversized mobile home.

    This sounds like the best and worst job a person could ever want.

  • All I can say is—spot-on. I freelanced full-time (mostly writing, with a little editing and graphic design thrown in on the side) from 1998 to 2004, and I’ve written part-time since then. Everything you said is so, SO true, and a large part of the reason I took a full-time job in 2004. And the scary thing is, a part of me still misses writing full-time, and still hopes to return to that. Maybe after my wife has gotten a full-time job of her own again. 🙂

  • All true stuff, Chuck. Where I live, though, we’ve had just under 20% unemployment. People who worked for the GM plant north of here were tossed out on their ears, and the companies that relied on them and their regular spending shut down too. Working for someone else isn’t much a guarantee of security these days either.

    I love freelancing. I’ve had one full-time job with a company I didn’t own in the last 20 years. I took it to get health insurance for my family after my wife had quadruplets. I got out of it as soon as I could and went right back to freelancing again.

  • I’m very (very very) lucky that I have a job in the theatre which puts my schedule so outside that of everyone else I may as well write as I’ve got no one to talk to.

    This means I get a regular paycheck and time to write and freelance without having to worry about the morgage. I get the best of both worlds, freedom and extra cash but still a steady paycheck, but working 2 jobs doesn’t leave much time for anything else, or worse means you can’t take on as much as you’d like.

    I realised I could never be a full time freelancer when I simply did the maths after a big project. I was commisioned for about 30,000 words on a dream project I was really hungry to write for, and that work took a month to do. That was as much as I could do in a month and the paycheck would have in no way covered the morgage, thats on the naive assumption I’d get that amount of work every month anyway.

    Still, while there is a large part of me that would love to throw myself into working on RPGs full time, being a part time freelancer is pretty damn good and I’ve been really lucky with the projects I’ve worked on. I’d recommend it as the best path until you have at least established yourself.

    • @Andrea —

      Yeah, our accountant said something along the lines of the benefits of incorporation being something of a myth, at least for most straight-up independent contractors. Thanks for the links.

      — c.

  • Wonderful article! I’ve had the problem with the mortgage people at the bank, who refused to consider my income even though I was the primary breadwinner and had the tax forms and check stubs to prove it. Fortunately, friends and acquaintances have never batted an eye, and sometimes they even seem impressed. And I’ve had better job security the last few years than most people I know. Still working on the work-life balance thing — my husband and I manage to get out to see a movie together a couple of times a year! I enjoy “the hunt” and would never give up the endless variety of work and challenges for anything. Or the working in pajamas with public radio on and a cat in my lap, watching the birds at the feeder in my backyard.

    Anyway, thanks for sharing an honest take on the freelance life. I hope all the people who approach me, wanting to do what I do but “part-time and on a very flexible schedule,” read it.

  • Nice posting. A little depressing for a new fulltime freelancer like myself. But, still, I’d much rather punch myself in the face than be punched in the face by others, which is honestly how (metaphorically) every single job I’ve ever had in my adult life has been. And if not a punch in the face, then the glass ceiling.

    That said, I don’t have a mortgage (yet), so perhaps my tune will change if I ever put down on a house. But I don’t plan on it anytime soon.

  • Oh, and about the loneliness thing. That is starting to get to me. 🙁

    I’m thinking about joining a Coworking space (although I get the sense they are more geared toward tech people). Would be curious if anyone has any experience with this?

    Thanks much.

  • El Chuckbo –

    You are overlooking one potential benefit of incorporation. You can then employee yourself. No, no real tax benefits for you, but when the bank says “Hey, do you have a job?” you can say, “Why yes. I am senior penmonkey over at Syphilitic Penmonkeys Inc.” You can cut yourself paychecks and everything. You can even have Ms. Chuckbo administer spankings as part of the whole annual review thing if you like.


  • When I was laid off, I had every intention of getting another job. Desk, cubicle, weekly paycheck. Yep, wanted that.

    But I was laid off at the very beginning of the swell and the jobs that were there were filled by people more qualified than I was.

    Freelancing saved me. I feel very fortunate for the opportunities that have come my way. I’ve met some great people and have some nice credits prepped for release.

    As someone with two young kids, I struggle to balance hobbies, work, and family. I struggle hard. I like the freelancing I’m doing–it really did save me and continues to be a good thing in my life–but I imagine I’d take a full-time job if the right one came along.

  • Ah, and what about the infamous “IF you get a paycheck” element?

    Sure, you did the work. You turned it in. Now you can await the glorious moment when your client tells you s/he didn’t actually have the money. Or that s/he’s having hard times. Or that s/he’s just encountered some disaster that means that money’s not quite as available as it was when you signed on. Thrill to the occasional bankruptcy notice from your former client – a joy seasoned by the fact that you might just have to fight in court to get back the rights to the work for which you labored but were never paid… it goes on and on. I know the drill all too well.

    Oh, yeah – and the statement, “Well, you do fill-in-the-blank because you LOVE it, right? Why should you worry about getting paid for it, too?” I wish I had a paycheck for every idiot who’s ever asked me this with a straight face. It’s not work if you love it? Yeah, that’s right – I sit at a keyboard all day until my wrists and hands cramp up because I don’t actually need to be paid…

    Do plumbers ever have to put up with this shit?

    – SatyrPhil Brucato

  • After not freelancing for… four? five?… years now, I started toying with the notion of doing it in my free time while in school. Then reality slapped me in the face with a rotting tuna: school is like freelancing in that “free time” is a myth. Yeah, you can study and write papers and do projects whenever you like, but you do have a deadline and any time not spent on doing those things usually means that you’re feeling guilty as hell and also jeopardizing yourself — you never know when an emergency will crop up, or some catastrophic mistake will occur, costing you time and craftsmanship.

    School is worse, though, because you don’t get paid for it. You pay someone else to judge your work. Kinda makes me miss freelancing.

  • I’ve been freelancing for about 10 years total. I may get a squeaky vertabrae from nodding in agreement with many of the observations here.

    I may have missed it, but has anyone mentioned the joy of paying quarterly estimated taxes? Not to mention the delightfully high premiums on even the most bare-bones individual health insurance policies. The fun never ends!

  • My name is Laura, and just like every other comic book writer and artist out there, I’m a freelancer. Everything in this article, and everything in the comments, has been absolutely true for me, except that I don’t often get the “but it’s not a REAL job” comment. What I get instead is, “Ooo, you work in COMICS? That must be FUN!” Yes, yes it is. I get to color all kinds of fun things. Yes, I’ve worked for Marvel and DC. Yes, I’ve colored your favorite superhero. Yes, I’m looking forward to the Thor and Captain America movies. My house is filled with action figures and comic art.

    I also get to stay up for 48 hours straight trying to nail a deadline, and I’ve done that at least twice a month for the last fifteen years. It takes a toll on the body and mind, trust me. I’ve spent hundreds of dollars on concert tickets for shows I didn’t get to see. I only just recently managed to get my own health insurance plan, and it doesn’t cover a whole lot. And I haven’t had a real-honest-to-god vacation where I didn’t take work with me since…uh…wow. I can’t even remember.

    Why do any of us do it? For the love of the craft, the respect of the fans, the history of the characters. We do it because we’re fanboys and fangirls ourselves. We do it because we were always the outsider geeks as children, and we embrace our outsider geek culture as adults. We do it because it keeps us young, just as much as it ages us prematurely.

    Also, comics conventions are way more freakin’ awesome than most trade shows.

    • @Laura:

      Well-said! And dang, it becomes more and more assured that I gotta do up a “Oh, By The Way, Freelancing Is Also Mega-Crazy-Fantastic” post.

      Once in a while I do get the “Oh, you’re a writer? Awesome!” vibe — but it’s generally only among others interested in the craft in some way. Everybody else tends to raise a crooked eyebrow. A dubious gaze, to be sure.

      — c.

  • …just as nobody is forcing you to “clock in,” nobody is letting you “clock out.”

    This is spot on. I also really liked the hunter vs. gatherer analogy. Freelancers sometimes band together to better patrol their favorite hunting grounds, but watch out if you take down somebody else’s mammoth!

    Recently I’ve had nightmares of our hunting grounds being overrun by an alien locust swarm called Demand Media.

  • Thanks for this bracing cold-water-in-the-face piece. Regardless, I’m working diligently on writing my way out of my day job and doing the whole Freelance thing. Sounds like my plan to take a leave of absence just in case migtht be smart. The desire to do this hasn’t left me since 2006, so I’m slowly trudging up the hill where I then can base jump off. My spouse and family support this crazy move as well. I’ll let you know how it goes.

  • What’s worse than freelancing…? NOT freelancing because you can’t get any work, and not being able to get a day job because they see you’ve been a freelancer for over 20 years and they just KNOW from that that you’re a lazy jerk who won’t follow instructions! My husband and I have been freelancing forever, and he is still getting work, so I’m back to my original job as his assistant. Still looking for that day job, of course, but I couldn’t even get hired at the local big box store at holiday time, so I don’t have a lot of hope…

  • I have been a freelancer for over 40 years.

    The two things that define my success: BIC Butt in Chair. And constantly reinventing myself. I have 300 books published (yep, #300 this fall) plus lots of poems, stories, some short animation scripts, essays, and would do cereal boxes if I could find the right person to ask!

    Mostly, though, I love the freelance life because I love writing. I do NOT get lonely because I play all day with my invisible friends. OK, maybe that makes me crazy. But not lonely.

    I happen to love to write. If I were one of those bleeding-onto-the-page sort of writers, I’d have a pension now and live in an old-age condo in Florida. As it is, I have a rambling farmhouse in Massachusetts and an Arts&Crafts house in Scotland. ‘

    See–it can be done, can be fun, and can be (in twice yearly dribs and drabs) lucrative. Just get a good agent, a Mac Air , and friends/in-laws/kids who understand. Spouse is optional, but (a least in my case and until he died) helps.


  • Ah, commiseration. I always enjoy these essays. Like listening to a love song after a breakup. It’s all talking about me.

    Thanks for the heads up on the bank loan pitfall. I actually hadn’t had that experience. Yet.

  • Thanks, Chuck. I hope you don’t mind, but I posted this to my blog too. I’m always getting mail asking for writings tips (because, you know, I’m SUCH an expert), and I’ve often wanted to skip the ‘chase your dreams’ encouragement, and talk less about the writing process (which generally can’t be transmitted as advice because everyone does it their own way anyway) and more about the ACTUAL CIRCUMSTANCES in which the writing process may or may not happen. I find this hard to do without sounding like a whiney little bitch who ought to be paying people real money for the privilege of having such an obviously brilliant job. Thanks for articulating it far more successfully.

    Loved Dan O’Shea’s comment too.

  • Chuck, you rock. Ive been at it for 15 years and I wouldn’t have it any other way. Its a life only for those chalk full of true grit and the confidence of a wrecking ball. Why do we do it?, some ask; becasue so few can. As Patton said, ‘Pressure makes Diamonds’. Keep up the the good fight bro. – BRS

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