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?


  • Ah, truer words in jest and all that… recently had a client who nixed $3000 worth of work (which I was already well into drawing) because HE had scheduling problems – and would it be ok if he just paid me $400 for my troubles? My angry e-mail explaining that the $3000 was paying my mortgage, my kids school, food etc, came as a complete surprise. ‘Oh, I didn’t know you didn’t have anything else!’ — so, you hire me, expect me to block out a number of days to draw stuff for you and then -what?- you assume that when I lose your work I’m just going to shrug and go get magic dollars from the money elf to pay the bank so I can carry on living in my house? I managed to get a better kill fee but probably will be marked as ‘trouble’ in future…

    A publisher got me to do an outline for a ‘How-To’ book on comics, when I submitted my costings (which were fairly low, I was banking on the possibilities of royalties) she got royally offended. ‘We get all kinds of professors and college tutors to do books for us’, she said-‘ they’re quite happy to work for much less than that. It isn’t just about the money, you know’
    You know, when you freelance– it is. Those indentured types get a salary–and write on the side. Freelancers have no ‘side’.

    So why have I been doing it for 25 years?? Well yep, it can indeed be “Mega-Crazy-Fantastic”… I get to write and draw funny books all day, visit fabulous places for comics conventions, and occasionally have folks tell me they like what I do. Laura nails the commitment side down- we love it, even as it knocks the social stuffing out of our lives.

  • Hallelujah!

    Sure you’ve touched on all those ‘nagging’ aspects of being self-employed. I’m just shy of celebrating 10 years of owning my own company. Sure it’s been tough (especially the last two years) but aside from a part-time job I doubt that I could ever return to corporate life. Sure the benefits can be enticing, but let’s face the truth: do you really want to? I like knowing that I am responsible for my own economy which includes everything from keeping the books and sales & marketing to going to the bank and depositing the checks.

    I would differ on one point — reconsider incorporating. If you consult a CPA and/or attorney you might be surprised to learn that by incorporating you can separate your personal assets from the business.

    As for a mortgage… unless I can buy it cash I won’t be indebted to a bank for that kind of obligation ever again. The experience with our last two real estate deals was enough to satisfy me for several years.

  • @Jane:

    First, I have to say: holy crap! Jane Yolen! You just made my day.

    Second, I do agree that despite all the pitfalls and leg-traps, the freelance life is worth it to those who find comfort in that kind of freedom. I do, and I love writing, and would also write a cereal box — or a diner menu, or a placemat — if someone wanted me to. 🙂

    In fact, if any cereal manufacturers are out there? Hey, give me a call. I mean, give Jane a call first. I’ll take the overflow from all that sweet cereal box word count.

    — c.

  • I used to freelance…back in the days when I only had to generate enough money to pay me. Now, I am responsible to make enough money for me, and 5 employees…sheesh…I guess owning your own business is freelancing, multiplied by too many times to count. Thanks for the article…reminds me how much I loved freelancing… x 1.

  • I love rpgs and gaming, and I love writing fiction but when I was young and naive someone I believed was wise from years of bleak experience told me if you get to write what you love, there will be people who will make you hate it and yourself for the work you do.

    As tempting as it was I avoided freelancing. I got a series of jobs that eventually led me to writing and editing copy in a local popular newspaper. The paycheck is nice (nicer than what I’ve earned before) and my editor is great. I have some strong part time work as well screen writing but for low budget/low finance film makers.

    I am still tempted to dabble in freelance gaming but I do it strictly to promote the hobby and for people with small outputs – often part time publishers – but no more than that.

  • I was directed to this post by a bunch of my freelancing friends, and YES, you’ve laid it all out so beautifully, Chuck! There is a real duality to the world of the freelancer (I celebrate my 20th year as a freelance illustrator this year)… walking the financial tightrope, having to scramble for work, etc… vs. the freedom to structure your life in a way that feels best to you.

    It’s easy to forget the good (in all our lives) and focus on the tough stuff. I’m alway envious of folks who get a regular paycheck… who can plan ahead with total precision. It’s easy to forget what they “pay” for that priviledge. I know that folks who work 9-5 romanticize freelancing (my ex-wife did, which still makes me shake my head). They only see the freedom, they don’t understand how much the financial uncertainty weighs on you.

    For me, freelancing is the perfect match. I’m pretty self-motivated (especially when I need to pay the mortgage), and I’m miserable when I feel like I’m being dragged off someplace I don’t want to go for x number of hours. It’s not nirvana, but it works for me.

    So thanks for the great post, Chuck. I’m going to copy the url and forward it on, and check your your follow-up post.



    • Thanks, @Chris. It is the right mix for me, too — I think for some people it’s a career that fits like a soft glove (perfect for gentle face-punching), but for others it’s all stick, no carrot.

      Thanks for passing along the link and visiting. Love your work, by the by.

      — c.

  • Nobody’s stepped in with the classic question – “What’s the difference between a freelancer and a large pizza?”

    I still have a Day Job, one that lets me write copy all day. Some days I yearn to take up The Hunt full-time, but not until I can pull together enough money to simulate a year’s worth of income suckled from the Corporate Teat. Is it a cycle of self-defeating disappointment? Only the Shadow knows….

    Don’t forget the tension of working on personal projects for free vs. spending time tracking down those deadly Paying Gigs. Sure, IF I get that novel finished and published, maybe I’ll see some money for it. But those orc stats aren’t going to write themselves.

    Oh, the punchline – almost forgot. “A large pizza can feed a family of four.”

  • HOLY SHIT are you spot on with this! The vacation thing kills me. It’s hard to relax on vacation, knowing that every beer you buy to sip on the beach digs your hole a little deeper.

    The in-laws thing, too. I spent 5 years repeatedly explaining to my father-in-law what it is I do. I’m not sure if he finally got or just gave up asking. I assume the latter.

    And the mortgage? You know what my occupation is listed as on our mortgage? Homemaker. They took one look at what I did then moved on. It’s nice to know how little I count.

    But, as you say, it’s an awesome life. One that I wouldn’t have been able to get off the ground without my awesome wife who is a supportive as they come. What Rob Wieland says above regarding personal projects is always a factor, and my wife is always on me to work less on paid stuff and more on personal stuff.

    This is truly a strange existence. One that I feel lucky to live and one I hope never to have to give up. Volleyball companion or no, to the punch in the face of freelancing, I say thank you!

    By the way, this has gotten a lot of play from some pretty big artist types. Names you’d surely recognize. It’s pretty sweet!

    • @Steven —

      I am certainly surprised at the attention this is getting, yeah. Glad to see those who have posted here (hi, everybody) — hoping to find out who else is spreading it around. I see the link popping here and there over bit.ly, but hard to see who else is moving it around, say, Facebook.

      Very cool.

      Face-punching aside. 🙂

      — c.

  • Freelancing is like climbing mountains; it’s truly a test of one’s character and strength.
    It can take a really long time to learn the habits required to “establish a good pattern of work.” And there’s no one to blame but yourself when things go wrong and you miss a deadline.

  • Weekly paychecks are an amazing luxury. I went from working part-time and freelancing to a full-time job in the field I wanted to be in and even nearly 2 years later I’m incredibly grateful for the weekly paycheck. For a while I was also freelancing part-time, but like Wood it was burning me out (on top of my work especially) and I’m much happier right now. That said, I won’t rule out freelancing again someday.

  • bloody genius. i’ve just started freelancing. and now i’m going to start budgeting so that in six months i can afford a volleyball and some paint. (poor wilson–that scene was really on par with the death scene old yeller, or maybe one of those times gonzo loses camilla–i mean *really* thinks he’s lost her).

    i appreciate everything you say. and identify. except i have only one dog so we’re just going to have to perform Waiting for Godot over and over and over again. no trinity for us.

  • This post is awesome! It totally describes some of the crap I’ve had to deal with as a freelance grant writer. You missed the part where the client tries to get you to do work for free, though. Or, at least in the non-profit world, this seems to be a huge problem. “I’ll give you a percentage of the grant you win!” Right… I’m going to write 10 grants for you, you’ll win 2-3 because funds are tight across the board, than I get paid 10-15% of a $5,000 – $25,000 grant? No, thanks. Not to mention that funders don’t fund grants with a finders fee.

    But my favorite aspect of freelancing!! Crossing the Canadian boarder!! Holy hell!! When I was a student (the last time I went to Canada), they didn’t care. Have fun! They told me. Now!! How much money do you have in your bank account? Will you have access to your bank account? How many clients do you have? When’s your next contract due? How do you know your friend? Are you sure he’s not a client? What kind of work do you do, exactly? What are the size of the grants that you write? Do you work with government grants?? And on and on and on and on. It took me 25 minutes to get through customs!! And no, this dude was not making friendly chit-chat, his eyes lit up like a deer in the headlights when he heard what I did. Next time I may lie, and just say one of my clients is my boss. It’s kind of embarrassing reciting my weak, tiny bank account to a government official with a whole bunch of people standing around…

  • It’s great until it’s not…as in the market crash of ’09 when xx% of most of my freelancing friends’ business evaporated virtually overnight. We all agree it’s starting to come back, but….the freelancers’ economy tracks very closely with the overall economic recovery, so…

    And as for vacations, well, I always tell people when they ask me that my boss is such a beast, she never lets me go. Gets a laugh every time.

  • Wow.. Awesome. You just summed up my entire career with both the benefits and pitfalls.

    Especially the part about the in laws. My mother in-law STILL thinks that all I do all day is sit at home and play on the computer. (Despite paying the lion’s share of the bills and buying my own house)

    This article made me smile and jump for joy. I am not alone in my plight!

  • I’ve been freelancing for the better of nineteen years now, and it’s been mostly a struggle. I’ve had to give it up a few times, or take a sabbatical, and have had to get “real” jobs when work slowed down, but I’ve been lucky to always come back to it. I have a love/hate relationship with freelancing.

    I hate not having regular “moolah”, or health insurance, but nothing beats not having to get up at 7am and sit in traffic to sit behind a desk all day with someone looking over your shoulder. Of course, having to make phone calls to get another job while you’re in the middle of the current project you’re on is no picnic.

    I remember when I was married, I used to regularly have to explain to my wife that, “Just because I’m home, doesn’t mean “I’m Home””. It’s both a blessing AND a curse, but it’s my life at this point, and getting a “real” job sucks when you’re used to being your own boss.

    Currently, I’ve been away from my home for six months (I put all my stuff in storage), visiting friends and traveling, but making sure I get my work done and sent it. An I get paid by direct deposit, so I can be anywhere. I’ve got my motorcycle, which carries my art pad, pen and pencil case and laptop, and I after a few weeks in NY (which I’m going to next), I think I may head across country, back to CA, and then maybe spend a few months in Mexico. How many 9 to 5 ers can say they do that?

  • Lucky for me, my husband works. And the way the work world is out there now, doubt get a part time job in the real world. My son has been looking and applying now for year and half. So I write and submit, plus promote what i have. It’s a struggle. And yes, i still love it cause I am writing.

  • I have been freelancing for almost eight years and it is equal parts awesome and I-want-to-climb-a-church-tower-and-start-a-career as a sniper.

    By far the toughest part has been simply getting paid bu clients who owe me money for work I did weeks, months ago. Before I was a freelancer and dreamed of doing it, it never would have occurred to me it would be so tough simply getting the money owed to me.

    This is a great piece, it made me feel a little bit better about my chosen lifestyle choice. Look for me on the news!

  • I feel you pain, and your elation. I have managed to limp along freelancing and dragging along various part time jobs or full time consultancy position (which always screw up my tax situation… but that’s another topic). You sum it up wonderfully. Thank you.

  • Awesome article. Freelancing is just another name for contracting (less the commute). When the jobs over the money stops. Pay is 60, 90 120 or more days out and then they hold retention sometimes for more than a year. There are those that if they smell or think they smell weakness will try and get you to sign off for pennies on the dollar to get that next check released (note: to self don’t be weak).

  • Wow this so sums it up, I”am a freelance illustrator and I will say being a freelancer definitely puts you up against the wall you have to be cunning like some wild animal, while at the same time chameleon, change your colours to suit your needs.

    But I wouldn’t do 9 to 5 again i believe when you find the courage to take a leap like this you really do put your all in you rely on your ability to perform at your best.

    I found registering as a graphic design usiness helped me alot with the mortgage monsters and phone companies :D.

  • ended up starting my own business and flip flopping between 6 months of working outside and 6 months of working on my own business… all the while employing people so my business continues while I can’t contribute… its long hours and it sucks but it really is the best of both worlds

    • @All:

      Want to respond to everybody, but holy hell in a handbasket, there’s a lot of you. Which is awesome. Thanks for coming by, glad this li’l blog post struck a nerve.

      I have suggested, on Twitter, that we freelancers should form a more perfect union. A union without pants.

      So, y’know. Get on board.

      — c.

  • I just got out of freelancing…after being in over a decade. The hardest but most memorable years of my life.
    I worked all over comics and video games…childrens books and advertising even designing sets of characters for cgi movies. I loved freelancing…i was getting flown to cali left and right to go to meetings with people twice my age…for seemingly no reason.
    I took my first vacation freelancing. I lived alone for the first time freelancing.
    i wasnt making ridiculous loot or anything. But hell …i was doing it. Getting through on my art. My way. On my own steam. Savings account. Nice cushion in the checking account.
    Happy as a man could be.
    I never quite made it to going after health insurance…but really i never knew a freelancer who did.

    Then….a stretch of no work like you would not believe. A big fat nothing.
    The fucking gobi desert of dry stretches.
    From 50 gs….to 8. in 12 months. Bad business head? too young?
    Shit i dont even know.
    I worked at a gym. i did construction and demolition(also without health insurance). I worked at the water department. In sewers. In the fucking winter.
    Freelancing all the while…but just never picking up the steam i had.
    Once you lose that drive…that push…its terrible trying to get it back.

    Freelancing is all about push.
    Constant unending perpetual push.
    one trip…one stumble…is sometimes is all that it takes.
    i had lost it for a sec…stumbled,fell and spiraled.

    It went on like that for a few years…me pushing and getting very little if nothing back.and then i got a job….a real job.
    My first ever real job doing toy package illustration for lucasfilm(pilotstudios.com).

    I barly made it through though.. Departing freelancing, i had a huge student loan debt(budgeting and complete immaturity kept that monster at bay), horrible acid reflux, anxiety based insomnia, a credit score of about 8…. the works.
    i think i just ran out of push.
    Two years into my job now…and i have gotten the push back. I freelance after hours and on the weekends like a mad man. i have started my own company. i am drawing better and faster than i ever have.
    I lucked out. I got saved.
    At the last minute…scooped out of the oblivion…of being on a demo crew for the rest of my life.
    I get up every day and am thankful for my my awesome 9 to 5 job drawing star wars stuff.

    I have been lucky enough to see the ugly side of both worlds…..and the overwhelming greatness of both as well. It has been a truly eventful ride. I dont regret a single second of it.
    I just wanted to say …that was a great article chuck….A pleasant reminder of a world i left behind…and a nice reality check to keep doing what i am doing:).


    greg titus

    • @Greg:

      That’s a crazy story — all of life is a journey, I guess. Glad to see that you’re back moving toward That Which Makes You Happy (and also possibly an anxious wreck). 🙂

      By the way, great site, awesome work.

      — c.

  • I fell into without trying. I just wanted to do digital painting. not qualifying for unemployment sucks. and being alone all the time sucks… but making my own hours.. rocks.. good toss up i think. no stuck in traffic.

    yeah your ALWAYS working. but i love my work. alot. so. whats so bad about doing what you love everyday all day long? nothing at all. i hate normality. so i really like freelancing. I was even told i could come work in house if i wanted to on some spare computers. i miss working with humans its true. but.. i dont miss waking up early. going to work. staring at a screen for 2 hours trying to get comfy . then work for an hour. then lunch. then work for an hour. then break. then work for 2 hours and home. and having to abide of the company rules. screw that. i make my oooown rules. and its awesome.

    high five to freelancing

    i like the idea of freelancing support group. maybe locally per city kinda deal. where you can go to a mixer and meet other pale pasty ppl who get it.

  • I just sent this to my husband. The one who I just drove with over 14 hours since we can’t afford plane fare, to do a big weekend convention; not much of which we saw, since he had to work the entire time, selling himself, his work, and listening to fanboys prattle on about themselves and their talents, and how they “could do it better” (though some were nice), while asking for advice. My husband, who even spent time talking to our waiter at the dinner place after the show, giving free advice, because it really doesn’t ever stop. My husband, who works until 5am most days, and who is even now, taking on smaller jobs from wherever he can, since I was laid off from a world-renown non-profit 23 days after moving into our first house, and still can’t get hired – even at Starbucks – for over 1.5 years now. He took the opportunity of being in a very bad car accident a long time ago to do freelance writing full time, and hasn’t looked back. It’s resulted in some very lucrative, known work, but as you mentioned, nothing is forever.
    Thanks for writing this; it really hit the mark.

  • I’m a professional artist, all of the above applies to being a painter too. The biggest thing is people taking there time paying you, and some people just don’t get it. I wouldn’t trade it to be “normal” ever.

  • Pissing myself laughing. No..It’s not funny. I think I have just gone stark ravers working by myself all day. Or was it because I bang my head on the desk repeatedly on a daily basis? Anyway, thanks for the brief respite from reality. Thank you.

  • just want to agree with all you say.
    So far i have spent five years living hand to mouth watching myself transform into ma clampet .
    but i think i am ocasionaly cheered that wearing slipper socks in my bedroom with two smelly dogs can be classed as a career.
    go well.

  • I’m not brave enough to venture into freelancing, and I know it. I admire those like you and my cousin, who can 🙂 Plus I’ve got self-esteem issues, so I couldn’t market drawings I’m not even sure are worth it :S

  • I was a freelancer for about 10 years doing IT work. Eventually gaining a wife and child made that whole health insurance thing a real deal breaker and I took a permanent job with one of my major clients. Of course, about the same time, my wife left her job to be come a freelancer.

    Having worked both, neither is really that much different than the other. Instead of worrying about getting the next job, you worry about loosing your current one. Because of this you work all the time just the same as when you were a freelancer, because if you dont….they might replace you with a freelancer who they dont have to pay benefits or a regular check to. And that regular check is like crack cocaine. Two months of direct deposits, and your absolutely hooked to it. Thats how they get you. They know you will keep coming back for more so long as that supply is steady.

  • I realize that I am a bit late in writing to this, but I’ve been mad crazy busy and they block some of WordPress’s functionality at work (which is apparently what happened about a month ago when I tried posting comments previously).

    With that being said…I’m right here, right now punching myself in the face. It hurts – a lot. I’m in an awkward middle stage type of area – I work full time, have a 20 hour a week commute, go to school full time, and run a freelance business doing web and graphic design. I’ve been doing the whole freelance thing for a little over seven years now and you sir, speak the truth! It’s been like I imagine going through hell at some points in my flittering career. I’ve had some downright nasty clients, some absolutely stupid clients, some flighty clients, and some back-stabbing sons-of-bitches clients. Sometimes they really do make me just want to punch myself in the face as opposed to having to deal with them. And let’s not forget – Everyone wants something for free. “You look young, so you won’t charge me, right?” I knew I shouldn’t have gotten that tattoo that said “stupid” across my forehead that one time I got really smashed a few years back…(what’s worse is I did it myself so it’s actually written backwards).

    My biggest issues with freelancing (and part of why I got a backup “day job” again) are 1) getting clients to pay (not just on time…but at all! I’ve had clients pay me 50% up front, their site gets all the way done, then they drop off the face of the earth and wonder why in the hell I didn’t leave their site up a couple years later…) and 2) attracting new clients. Then of course comes the lovely part of actually getting the information that you need from the client…*checks watch* three months later. “Oh hey! Why isn’t my site done yet? You said it’d only take you a month!” Yeah but that was AFTER you gave me the files I needed…

    That’s not to say it doesn’t have it’s perks though. Walking around with no pants is pretty awesome. Having my ever-ready supply of Mountain Dew and Doritos is pretty sweet. And come on, let’s not forget the bacon – fresh from the kitchen stove. It’s also great to be able to have my new Alienware computer as a tax deduction (it has pink lights! *squees*). I also work much better in the afternoon/night time so that whole waking up at the butt crack of dawn-thing is easily something I do not miss.

    I’ve also certainly had my fair share of hellish bosses too. Yes they can read this post and kiss my lily white ass too. I’ve been “let go” for being eight months pregnant, for having to go to too many doctor’s appointments when my daughter had to be in a full body cast because or a rare disorder, and I don’t think I’ve ever actually had a “permanent” job because I look like such a young little girl. I’ve always been hired in as contract and I’m 25…almost 26 years old. I feel so little respect. I am super shy and not outgoing unless I feel that the environment is safe to be so in (like if I were doing what I want to be doing – working in the game industry or movie industry or comic industry…or well okay anything creative, no more corporate crap). Many jobs don’t respond well to that but I can’t help who I am. I do my job, I’m creative, I have great ideas, I’m honest, ethical…oh wait that’s it right there. And THAT’S why I strive to freelance. Despite the crazy clients calling me up at 4 am wanting to know if they can add a Flash intro for free by the 5 pm, or the clients that after signing a contract, refuse to pay what is owed, or the client’s that say “I want a website” and I have to go “that’s great, but what’s your site supposed to be about” and they’re all like “I dunno – you’re the web designer,” I still feel a burning need (oh wait that just means I have to pee) to freelance.

    The economy slumped has certainly hindered things quite a bit for me. I had a steady amount of clients a few years back and then they just…died. I think a bus hit them…maybe it was an Obama train. Even so, very recently I’ve seen things start to pick back up again and as I go through the job I’m at currently, having to re-interview and re-test for the very job I am doing now, if I lose it, I say “fuck ’em.” It’s time to start again – pantless, bacon-eating freedom, complete with frolicking deer babies.

  • Since I just entered this crazy, menacing career path a couple of years ago, I’ve learned only about, oh, let’s say, an infintesimal nano-fragment of what it means to be a freelancer. Being retired with mailbox money certainly helps cushion the blow of looking for gigs on the path to fame and fortune in the writing field.

    That said, I have to admit to freelancing being the only viable choice for a person like me. I’m afflicted, you see. My mind doesn’t shut down at any given hour of the day/night. It continues to process idea after idea that simply must be fleshed out and sent to somebody. The “who” doesn’t matter so much as the “Get it out there!” imperative.

    I know that I’m a bit slow when it comes to productivity. I won’t argue that point. It’s not that I can’t do it so much as a function of learning curve. Well, that and my tendency to get pulled off-track by interesting bits of trivia and fascinating websites that eat up an hour here and there.

    Recently, though, I hit on the perfect solution to my problem of too many varied ideas, never enough time to travel and do things, meet people, or find the world. I dragged my sister, kicking and screaming, into the world of photography, watched her passion grow out of all control, and then hit her with those unbridled words “Let’s take out act on the road!”

    The planning has started, the ideas have been corralled, the future is just as uncertain as it was last week. But, we’re looking forward to the freedom, the adventure of the open road. And at the end of it will be a book. During the journey will be the freelance articles with just the right twist to make them memorable. And that is what we’re after.

    To be very honest. I doubt either of us could tolerate a regular job anymore. It’s not so much that we must make this work for us in order to satisfy the Muse, but rather, we need these last many years to be ones of exploration, self-expression and discovery, and fun. We played the corporate game, the professional game, the game where no resprect accrued.

    I’ll take my chances without worrying over mortgages. I’ve been there and tried to get rid of them. Show me the merge lane and just let us take to the highway.

    I tip my chapeau to all those who freelance. That wee job is the backbone of the industry today and every day.

  • I’m a freelance illustrator/graphic designer and have developed a strategy to this “freelancing” game.

    I always have a hundred projects going on at once, some on hold, some with deadlines all within a couple days of each other. Good projects, too, just no idea when they’ll come to fruition and I’ll get my damned check.

    My method is to find one consistent money maker, from which I can finesse at least a bimonthly paycheck , to keep me afloat. Those jobs aren’t always the most exciting ones, but they give me the stability I need to not freak out every time there’s a gap in new commissions. I have a lot of skills in new media, though, and it’s pretty easy to find a 3 month contract doing game art or web design; I imagine not so much if you’re a writer or traditional artist.

    These contract jobs sometimes involve working onsite part of the time, so it does help with that feeling that I might become a mole person as well.

    I’m one of the lucky ones. (Well, for now.) Thanks for the chuckles.

  • I freelanced for 4 years. Then I decided I wanted to stop doing other peoples projects for upwards of 60 to 80 hours a week.

    So I got a job. That way a guaranteed 20 to 40 hours I have for my own work.

    I still take the odd evening project but they are small. No more 6 month projects.

    So now I have a bit of both worlds.

  • I would love to be a freelancer, and I’m seriously considering it.
    But I have back up.
    I’m currently in the Army and saving almost every penny (except what I need to live and drink on), debt free, and working on my Masters of Business Administration.
    So I have money to keep me afloat, and will have an MBA to fall back on.
    We’ll see how it goes, haha

  • I have to disagree. I love freelancing. While it has it’s cons (and what doesn’t?) I make a ton more money than i ‘d ever make at a full-time job. Yes I work lots of hours, but it’s work I love to do for the most part. I look forward to doing it every day.

    I’m not sure why some freelancers have problems getting paid more than others. I think it’s the way they decide to let their clients treat them. I require 50% upfront and final payment BEFORE I hand over any files. Believe me, this makes them pay immediately.

  • I was nodding so much while reading the post and comments my head almost came off. Extremely true about needing to find a niche – although maybe not one quite as small as Dan’s, at the risk of being put out of a job overnight.

    I’ve weaseled my way into the SEO/web copywriting niche, which, for some very weird reason, seems to have given my career a ring of validity in the World’s eyes. Maybe it’s because I can throw around marketing lingo like a pro. Sure, keyword research is a heluvalot less exciting than vampires, but whenever I feel like someone’s not taking me seriously I can just bust out a “well, if you really want to increase conversion rates and overall ROI on your content marketing strategy, we’ll need to pull in more qualified traffic by targeting niche longtail keywords.” Booyah.

    That constant nagging, sick pit of your stomach looking-for-work feeling is definitely my least favorite part of freelancing. Even during good times, I can’t let my mind stray more than a few months down the road where my project calender is STILL BLANK. Overcaffeination sans pans is worth it.

    Thanks for the great post, Chuck.

  • I’m a freelancer of sorts, I do ebay consignment for people. I make insane money, put little/no money up front and work from home…plus even more money from selling my own products along side. I completely understand the mentality… I never STOP working, I actually do grab a ‘regular job’ 3 months out of the year just to get out of the house and try to STOP thinking about money for a bit… Luckily the 9 months I do work more then makes up for the pidly $12 an hour I get ‘working’.

    I try to explain to my friends…one friend in particular I had the SAME conversation with every week for almost 2 years. “So where you working?” “I work for myself.” “But how do you pay the bills?” “I make $35/hr in my underwear, how can I NOT pay the bills?” “But you don’t have a job.” … Then I’d pick up the check… *SIGH*

  • Heh! Great article. And beautifully written.

    All the pitfalls you cite are the reasons I haven’t decamped from DilbertWorld for a freelance career. But there are days (many days) when I wonder whether I can stand one more minute of corporate slavery. Things are tough all over, I guess.

    I’ve been a copywriter for 30 years and an in-house eCommerce copywriter (for a huge apparel company) for nearly 11. I *love* what I do (except for catalog work, which I loathe). I just hate everything else about it — the control freakery and micromanagement; the bureaucracy; the insane hours; the relentless stress and pressure (downtime? what’s that?); the crazy conflicting deadlines; the corporate incompetence; the “pooper-scooping” behind less conscientious colleagues. (No reflection on said colleagues, BTW; they probably have the right idea. I’m the crazy one for taking this stuff so seriously.)

    But I’m a lousy hustler and self-promoter, and I’m pathologically shy and nervous, so freelancing is probably out of the question.

    Plus, I’m close to early retirement age. Sometimes I wonder: Should I freelance in retirement? Or should I just take it easy? Only problem with the latter path is that I would be bored stiff. Writing is in my blood. I actually *love* writing website product descriptions. It’s a disease.

    But enough with this blather about me.

    Again, excellent article. You’ve pinpointed the dilemma perfectly. I just wish I knew how to resolve it.

    Apparel Copywriter in DilbertWorld

  • @Amber Weinberg – some sites require database connectivity and therefore a live site (luckily they can be disabled after). For static files that works out as you ssaid but even so, sometimes a client just decides that they weren’t as committed to a project as they first thought.

  • Amber, I admire you. You have guts. I ALWAYS wooss out when the client starts talking fees and payment schedules. Not sure I can overcome this, really, unless I just reach the point of being so busy I can tell ’em to bug off. But even then, I’d probably be too nervous and intimidated to stand up for myself. Oh well….

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