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?

177 comments

  • Work, finding a job, freelancing isn’t easy as you already said it… life is NOT easy. having an EDUCATION so you can freelance is a BONUS, having a job in the real world is probably a good idea to have before you go off freelancing for the first time in your life and it seems many of you have had jobs already before you started freelancing, etc. Experience is a good plus to have if you are not going to go out and get a job to get the experience FWIW.

    I have tried eBay stuff (consignment or reselling) just to get an idea of what it would be like, its a lot of math, paperwork organizing and keeping yourself straight/screwed on. I don’t know what’s so hard to understand about freelancing, if I asked you what do you do for work and someone replies “I’m self employed” or “I own my own business” or “I work for myself” or “I am a contractor” isn’t THAT enough to understand, I don’t understand WHY people don’t understand??? What’s so mind boggling? WHY do you have to ABSOLUTELY work for a company in order to have ANY credibility? That’s FUBAR!

    I worked in a call center for almost a full year and lit my ass on fire just to give them an excuse to let me go (actually I skipped work and then finally told them I had had it). It was getting more difficult to keep the job let alone maintain standards especially since I have a disability.

    I worked at another call center for a season but I did mail order, so much simpler yet I didn’t want to do it after it was over. I could do mail orders better than I could talking with somebody even in person (which is why I will never go into sales because I just don’t have the knack for it)

    Here’s something the bankers NEVER EVER understand and they never will because its so freaking ambiguous than freelancing (its called not having a job and money is planted in my account every month from a settlement trust fund).

    I like the “freelancing” style, one thing I haven’t read about in your post is “freedom” (and I haven’t read all the comments, there’s way too many) . I keep seeing ads and infomercials or whatever that say “you could work from home with TOTAL freedom!” its just an illusion, you don’t have freedom if you did you’d be out of clients! You have more “choices” IMHO but you don’t have more freedom, you are rigidly boxed in because YOU have to be the one doing it not them or someone else unlike having a regular job 8-5 kind of thing all you have to do is go there, do it and come home and you have the freedom to leave your job behind you have MORE freedom by having a regular job because of that (unless you have one of those jobs that follows you home too) although your freedom ends when you are at work so its temporary unlike freelancing your freedom is never there because its with you all the time.

    I also believe in freelancers, more choices and more quality than quantity is my idea of getting what I need and at the same time supporting the individuals who do it.

  • I have just left art school, just finished my fifth cup of coffee today, and just sat back down in front of my computer next to my bed(in my parent’s house).
    I have only been a graduate since July. Even if you do have work to be doing, in my case I’m lucky enough to have been commissioned a few small paintings, how do you stop yourself going stark-raving-bonkers?

  • Just as a very late chime in, as I read through the comments more and more what I’m seeing is a need for some kinds of “Freelancer Support Company”… Some company that offers health care, income tracking so that there is a Company that a bank or other service can call… maybe some socialization benefits… maybe even some accounting and tax services (because you really need to squeeze every dollar today).

    If there’s demand, a service will evolve to fill it. So Chuck and others… what could a company do that would make your life easier and smoother and reduce the amount of time I spend keeping an eye on clocktowers?

  • I freelanced on and off for most of my twenties, and reading this article brought me out in a sweat of recollection. I was never particularly successful, scraping a living in London, but that was because I HATED asking for money and I HATED touting for work. Not an ideal freelancer then….

    I wanted the whole morning lie-in, no packed tube train, cat on lap, hilarious and original think-pieces about the inanities of modern existence, celebrity friends on Facebook lifestyle. But the reality was writing articles of which I was often ashamed, accepting commissions at which I’d really want to flip the bird, and being made to feel pathetically grateful for being ‘allowed’ the ‘opportunity’ to pitch features for consumer magazines that I’d never myself want to read in a million eternities.

    I’m now 33 with a full-time job, and I wanted to post because I feel like the ol’ 9-5 is (predictably) getting a bit of a bum rap from the 24/7 massive. This comment is a reminder that it IS possible to have a good, well-paid job with a nice boss and nice colleagues. My commute is under half an hour, every year I get paid more than twice as much as I ever did when I was self-employed, I have plenty of time to sit on the internet during the day, I get an hour off for lunch, my holidays feel like holidays – and I can afford to go to nice places, the commute gives me time to read novels, I don’t feel guilty when I watch TV or spend an hour listening to music, I have plenty of time to satisfy my writing urge on my blog (and I don’t have to kowtow to some commercially-driven commissioning editor), I’m accruing a nice pension and I have excellent health care (not that I need it, as the NHS in the UK is amazing).

    I work in a bank in the City as a personal assistant. It’s not glamorous. I don’t get to interview Britney Spears or the Beckhams, like I used to when I was a freelance celebrity journo. I feel fairly immoral working for a bank when in reality I’d like to be promoting a more caring, sharing, community vibe. My job doesn’t challenge me intellectually, and I rarely have an interesting story to regale my friends with at dinner. But I’m happier. Much, much happier.

    Just wanted to stick up for the other team.

  • It’s funny, when I got laid off in 2008 from my editorial job, lots of people said, “Why don’t you just do freelance?” And I said, “Because my unemployment checks are more reliable and often more robust than freelance pay.” I had to explain over and over that being a freelancer today means hustling, working 7 days a week, never saying no because you will drop off the call list, and doing many hours of work and be paid instead by the number of words you generate. I did freelance a few times in between jobs, and while I don’t like being an office monkey, my need for a regular check and health benefits and a job I can leave at the office and not take home turned out to be more important. And now that I have a job again, I fantasize every day about going freelance…….

  • Awesome. One of the best articles about freelancing I ever read. You pointed so well all the drawbacks of the freelancing. I really like your writing style (how you talk to yourself).

    I definitely re-visit your blog.

  • Love it! Don’t know you or my blog – was forwarded this piece, but a lot of it rings true.

    On the one hand, I’m luckier than you in the sense that I live in Europe and experience the joys (no sarcasm) of universal and affordable “socialized” healthcare. And I have no mortgage.

    On the other hand, I have no significant other (to dull the loneliness), my apartment is just one-room (the “commute” is all of 2 feet, but seperating “work”/”life” is all the harder), and rather than writing cool stuff about vampires I pay my rent by translating boring and badly written stuff someone will read once and then throw away.

    Nevertheless, a lot of this rings true. In particular:

    Payment! Yes! I like to joke that it requires more work and effort to get paid than actually do the work I am paid for. Except it is no joke. A minimim of 3 reminders seems standard.

    You don’t go out. I do. Most days. To the grocery store down the block. Many a week goes by when saying thank you to the surly clerk there is my only human interaction. I hated most of the people I worked with in my “proper” jobs, but sometimes I miss them so much.

    Needing to find work. A nightmare. Especially when free-lance translators are a dime a dozen, and agreeing to work for strangers means taking the risk you will never actually get paid.

    Yes, free-lancing is great. Some of the time. But I salute anyone who can do it long-term (with a mortgage, family, etc.) I do it because I’m also doing a PhD and its the easiest way to combine the two. But I can’t imagine doing it forver…

  • As the early-retired husband of a freelancer I see (and hear aplenty) about the pitfalls. Still, it’s a sweet and interesting job to do if there’s another income and some support for the freelancer in the house, a type of a sometimes paying hobby really, that tops up my income and keeps my wife at home and sharp.

  • I’m onto you!! I know your game son!! All that, just to put me off huh? So I don’t threaten your patch right? Nearly worked…

    Seriously though, great post, makes me want to write even more!!! By the way, if you take the bridge at speed, using the unicorns as a elevating point, you can make it to the other side-and the John Wayne Gacy clones say “Hi! Love your work.”

  • Full-time freelancer here, going on my seventh year. All those hassles are true, Chuck. But then I think back to all the years I lost working in newsrooms. Work was never “done” there either. Job security? The spectre of layoffs was usually hanging out by the vending machines. So many endless, pointless meetings. Not seeing my home in the daylight for months on end. Working weekends to stay caught up.

    Now, no matter how bad things are here in Freelanceworld, I can get up from the desk without asking permission, walk out on the back porch, feel the breeze, smell the fresh air. Or, if it’s winter, watch the snow fall and rejoice that I don’t have to commute in it. As the psalmist said, it restoreth my soul.

  • All life is work?, nah, i freelance, I’ve been doing it for a few years.
    And it sounds like you’re not getting the right clients.
    If you did you could just set your work times and respect them.
    It’s about responsability and it’s about choosing the right people
    and saying NO a lot.
    So, no i rather stay as a freelancer and never look back at those
    times when i worked at an office and hated my life.

  • I just finished my first freelance contract last week and it pains me to admit it was a complete disaster. My inexperience in dealing with clients combined with the client’s ignorance of all things digital led to a perpetual breakdown in communication, and the deadline was missed. I was paid only half my fee; a total some not worth the time and grief spent on the project.

    My experience matches your description to the T. At first I was excited; overjoyed by the mere idea that my bath towel could be synonymous with work attire. After 2 weeks of 20 hour code sessions, maddening conversations and processed food I perfectly matched the ghastly figure you described. My friends stopped calling after a week, my dog refused to even look at me, and it’ll take months at the gym just to regain the ability to climb stairs.

    …but here I am doing it again. Thanks for your post, it was a nice way to spend my 5am break :/

  • Thank you. Now I can stop answering all those questions and just direct people here. You have pretty much summed up my life. Only my husband is self-employed too. Can you say “paying for health insurance sucks the life out of you?”

    I too try to wave people off of the freelance life — but after 26 years, I can’t even imagine working any other way.

  • Do what I do, tell people you are unemployed – that takes care of “what do you do?” question. When they ask why the house is so dirty, just say you’ve been watching TV all day long, day after day!

    When time off just feels like time without pay – gather your things hop in the car and take an epic trip (oh and don’t forget your laptop to do your work!)

    When all feels sad and lonely – think of a new startup to work on and open up a new browser window to watch random youtube videos.

    If you’re thinking of going back to your 9-5, just remember that asshole who will be telling you what to do every day and compare that to your wife / husband telling you to get off your ass.

  • The hardest part is going from being self employed, to employing others. It seems to make any of these jumps you need to stock up on money to survive the long haul.

    First of all, work a few months at an actual company and that way you get COBRA if you are terminated or whatever. There’s your health insurance, at the same rate as everyone else. Whoo.

    Second, save up money. Those 50% up front payments should cover ALL the work. The other 50% should be your bonus. That way you can start employing people. And then you are truly getting freedom!

  • Hey at least you’re writing stuff people can understand. I remember when I found out what it took to be a well-known poet. William Carlos Williams – the doctor. Hart Crane – the advertising copywriter. Al Ginsberg – the chanting harmonium player. We live in a country in which the arts are all something mysterious to most people. They envision dingy garrets. And suffering for your craft. But, then, so did my neighborhood woodcrafter. And the guy who collected his paycheck for babysitting a pulp digesting machine from 11pm to 8am. Regular wages are designed for drones, or for people who are struggling to push their way out of the damp, stinking soil into the sunlight at long last. Welcome to Earth.

  • Hi!!,
    I just came here from hacker news. I have been freelance for 7 years, love it.

    I had felt the same way you do, but I don’t feel that anymore. I have improved a lot. It seems like it is only now when I have started to “get it”. A lot of people had followed this path, learn from them instead of thinking your problems are only yours, that there are bad things that are immutable, you can do something about it.

    Why don’t you create a club of freelancers? It is like a swimmer pro that decides to swim alone all day, you need to learn from others so routine doesn’t kill you. This DOESN’T MEAN you need to work for the man, you just need to organize like the man does, find other freelancers, just talk with them, they have the same problem you do. People with common objectives improve way faster(you will always find someone better than you that you could learn about).

    Being alone means you could cease to learn from others, to grow, that’s bad, because you can improve it. DECIDE to do something about it, read books and watch videos and improve your live.

    I read books like The power of full engagement.Tony Swartz. Travel, learn and be happy!

  • Bravo! right on the money. >20 years freelancing (with a few breaks to get group medical insurance and a mortgage acquisition – right on the money there). Free lancing is definitely not for everyone. But I definitely prefer it over a job with a dysfunctional company!

  • But if you had a regular job you might not get to write hysterical posts like this that had me in stitches! It’s month 2 for me but I love it so far. I quite enjoy being a social outcast. Some days i don’t get dressed til 5 o’clock. Others I decide against showering or brushing my teeth. I am more sociable now then when I was working in the real world, and all with people on twitter on all 4 corners of the globe who I’m never likely to meet. It is a strange life but I wouldn’t swap it. That is until those commissions dry up..

  • Freedom has a cost but has no price.

    Freelance is like building a new company : it’s very hard at the beginning. If you have work, you work a lot, sure. But I think (and I hope) you finish by finding a good way to be equal between your professionnal an your personnal life. For me, I couldn’t go back in a “normal” job. I couldn’t support to hear what I have to do, to ask if I can be off for any reasons, etc. I understand perfectly that this way is not for everybody. But the cost of my freedom, of having my own choices, of the luxe to decide with who I want to work and when, etc. is at the end not so high. And freedom has no price in my opinion. I have a lot of collaborators now, freelances or not, and it’s very exciting to meet a lot of different people. After 8 years in my job, in a closed team, I couldn’t support to see anybody. I became unsocial…

    So, my conclusion: yes it’s hard, yes it’s sometimes as described above, but I definitively prefer that than to be a slave in my golden jail!

  • I’ve been freelance food and cookbook writing full time since the early 70s, and I think your title could be improved to “Considering Freelancing? Just Slit Your Throat, Instead.” This would save folks a long, painful death. I was nodding at every word– endless work hours, scratching for jobs, low pay, feeling guilty when not working, the string morgage banks saying,”income’s too ‘spotty’–only counting what your W-2-collecting spouse with an actual job earns.”

    But food writing has it own little pitfalls, the biggest one being that everybody who eats thinks he can write about food. My vet said: “Oh, you write cookbooks. I want to write one someday.” (And I wanna be a vet someday.) Any celebrity for any reason (or no reason) can hire a (work-for-hire) recipe developer to come up with a little content, then slap his or her smiling face on the cover, and dish up a best seller. (Mrs. Obama could write a “green” cookbook containing 75 recipes for yard clippings and it would fly off the shelves.)

    The other teensy problem is that folks feel it’s perfectly fine to help themselves to recipes that someone else spent time (and money for ingredients) perfecting–and without compensating and often without even giving a credit. Even a copyright provides no protection, since the “borrower” can simply make a few cosmetic changes to a recipe to avoid legal risks. (Of course, the creater would actually need money to sue, limiting risks even further.) I suppose I should just feel proud rather than grumpy that my recipes are worthy of being stolen by some high-profile people, publications, and websites.

  • Excellent article (which I’m reading while compiling sketches for a package design illustration) – Love it! It’s great to not feel alone! Am I the only one who has gone to the post office on sunday *having no idea what day of the week it is?* (um, multiple times).
    echo

  • In case you’re wondering why–if freelane food writing is such a terrible business–I’ve stayed with it so long: My spouse has always earned us a good living. I still love the work. And nobody can steal whole books from me or can take away the satisfaction I have of holding some of my well tested, well written, attractively produced cookbooks in my hands….

  • Freelancing is about giving up some (financial) security in order to get a large amount of freedom in return. You want to work from 5 AM to noon everyday? Done! You want to take a week off every 2 months? Done! Take your kids to their activities in the afternoon? done!
    You don’t have to answer or bend to the crazy suggestion of a pointy hair boss. The biggest challenge, apart from the financial insecurity the first few years, is to have great self-discipline and become excellent at what you do. Self-discipline is on how to manage your time, to know when it is OK to not work, or say no to another project you don’t have time to do, but that you still want to squeeze in because you want the cash. Excellence, because over time your clients, will come back if they know they can rely on your expertise, and they will advertise your work without you even realizing it sometimes. Nobody said it was easy, but most great things are this way. It’s all about what your personality can handle, some are made for it, some will prefer the stability and direction you get at a regular job.

    Cheers!

  • I was a full time Freelancer for over a decade (1990-2001) and your post pretty well nailed it. Something I have not read a lot of in these posts is the struggle caused when you attempt to “control” the flow of work . Not having a steady flow means always committing to more than you really should and becomes relationship destroying monster. If you are a very social person (I am) being up at 3:00 am, alone in your apartment, under that desk lamp can be pretty rough.
    You also never knew that an inanimate object could hate you. You know, the clock. Clock hate can be the worst. When you aren’t looking, that little sucker just reels off the numbers.
    Yer better off doing the full time gig. Like me. You know, fall into something that sucks the life out of you during the day so you can posess that holy grail known as Health Insurance. …………..

  • I want to go into freelancing, as a game designer and author. What I do right now is write stories and homebrew mechanics for D&D and wish someone would notice me. If I could get paid for doing that, even if it was barely enough (or even not quite enough) to keep me alive, I would be happier than a boogeyman in an orphanage.

  • @Chuck: A “penmonkey”, A “freelancer” whatever you may call it, its a JOB and we are not robbing banks or smashing planes into federal buildings on a commercial airliner in the name of God! Too political, but true!

    Governments/Politicians aka White Mafia’s and their unleashed in the wilderness hunting goons; like Banks and Financial Institutes tell the same story to me when I go out to seek a Home Loan. Even in times when “Economy Brides” are screaming and against all odds “You are a performer” but not in the prawning eyes of the Goons! Because:

    A) Your a Freelancer not a certified Corporate organization which can declare bankruptcy overnight like The Lehmann’s. So we need a class act, like them!
    B) We created a FOOBAR situation by lending loans and credit cards to street dogs and lamp posts (As said earlier), so we must cover it up.

    A review from Kasper Labs on Vista is more than applicable here:

    “Freedom itself creates threats, whereas restrictions reduce flexibility. The more restrictions, the less user friendly the system will be.”

    “In other words, if you are jealous of your partner, you may forbid him/ her to go out alone, or you may even lock him/ her up. Of course, the greater the restrictions, the less likelihood there is of someone else entering into a relationship with your partner. But the more restrictions, the less happy your partner will be. Ultimately, the question is do you really want an unhappy partner?”

    “Even if an ideal balance can be found between restrictions and usability, the history of security shows that any protective barrier can eventually be overcome or evaded in some way, as long as someone, somewhere, is interested in doing so.”

  • Oh no – now, in the time I was supposed to be finishing some client work, sitting here in my nightie with a huge cuppa, I’ve “wasted” 20 minutes reading your brilliant post – and all the engaging comments :)

    As a freelancer for over 30 years – the last 20 “forced” because of having a severely disabled son at home to look after, I soooooo related to your post.

    But the comment that stuck @Gareth was “I don’t work from home, I live at work”.

    Yep. Luckily, I love where I live!

  • You, Sir, win at the internets today. Your article was perfect.

    My parents still think I “don’t work and do shit all day” my kids think I’m at stay at home mom (which is a job unto itself and not the same thing AT ALL, CHILDREN)

    I will frame and put this in my office (where ever it is that i can be alone and away from my family) and ensure that everyone i know reads it.

    bravo man!

    Marie

  • 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.

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