How To Be A Freelance Writer

Being someone who ‘writes for a living’ is a sort of aspirational fantasy. Abstractly, it’s appealing: Who wouldn’t want to be some kind of self-styled word mercenary who is ‘in demand’ enough that there is an entire salary’s worth of people who will commission you to sling verbs; who wouldn’t want a bank of expertise on [something] sufficient to produce said verbiage on demand?

It seems that a lot of people complain intensely about the ‘writer’s lifestyle’, in that when left to one’s own devices it’s impossible to manage one’s own time/ creative energies. It seems many professional writers spend a lot of time wringing their hands as regards their ‘muse’ or waxing theatrical about the challenges in earning money; you hear a lot about how writers are poor or drunk or continually at war with themselves.

For the most part the archetype is reasonably accurate, although you can judge how good and/ or successful a writer is in an equation proportionate to how much he or she complains. In other words, the most theatrical and complaint-prone writers are probably not very good at their work; professional word mercenaries shut up and type and they get their paychecks and operate mostly under a sort of grim ambivalence undercut with very private angst, interspersed with periods of brilliance and at best, satisfaction.

Nonetheless there are certain behavioral mechanisms that are common among not just writers, but all creative individuals tasked with generating original content in the vacuum of their own solitude (see also: journalists, novelists, comic book writers/artists, actors, academics, painters et al.).

Drink. Everything becomes easier when you’re drinking. Writing is a process during which production is organic and intellect needs to be assumed or taken for granted. You cannot write if you’re thinking too much, or if you falsely believe there are some kinds of ‘decisions’ to be made regarding your topic or angle of approach. If you drink you stop thinking and your hands drum the keys with the faultless, rapid cadence of the sort of clear, light-starved spiders that live in the least-lit crevices of the world. Your brain glides with the surety of the oceanic trenches’ blind eels.

You become emotionally honest, too. Remember that time you were out with your friends and drank so much and ate so little that you became an weeping wreck to where you’re still mortified about it today? Imagine if during that time you’d just been typing in your room instead of speaking in a thin and tremulous voice about your most secret fears while being held by someone who doesn’t materially give a sh-t about you. Imagine if you’d typed instead of needing everyone to finally shut the f-ck up and listen to you for a second because you actually have something to say. You would have written something awesome.

Keep Weird Hours. For the first few months, or a year at best of your writing career, you will understand that schedules and disciplines are very important. You will claim to know yourself and how much you need set periods of time during which to commit to work, the better to maintain your ‘work-life balance’. You’ll feel that if you don’t wake in the morning to feel the world coming to life, you won’t be in step with that life; you’ll understand how essential regular nourishment is to maintaining your sane ‘instrument’. You understand that you need to be well-rested.

Actually, writers do not have work-life balance. You will work best under pressure, which means that if you have an 8 AM deadline on Tuesday you will be awake at 4 AM Monday and you will be just beginning. You will file at 6 AM and then you’ll sleep until 4 PM. Your life becomes a constant progress of trying to sleep at night and work during the day — at least until you realize the utter impossibility of that endeavor, until you surrender to the fact that you’ll wake with full intention at 11 a.m. and instead spend four hours gazing at social media for some purpose you’ll justify to yourself somehow.

You will have nothing to do one day save for one one-thousand word item, and despite being ensconced at your machine for 12 straight hours that inexplicably feel like work, that feel mentally taxing, you won’t complete the thing until after midnight. You will thrive in the odd hours between sleeping and waking, the silent parts of the night when the sky turns red and all sane humans are resting up for their commute.

Don’t Leave The House. You don’t remember how to ‘commute’. The idea that some people wake hours earlier than they need to in order to navigate traffic or the public transit system has become a sort of lost ideal to you, markers of a society you have abandoned. You sort of envy them: their activity, their regular habits. You don’t work out anymore, although you intend to. If you find yourself awake in the morning and at the grocery store and then the bank you’ll feel unduly adult and self-satisfied.

You will not buy new clothes, because it’s a waste. You will wear the same two or three pairs of sweatpants all week. By the time you finally surrender the sweatshirt you both sleep in and put on when you get cold midday it will feel like a rotten tarpaulin lousy with your scent, a guilt item you stash at the bottom of your hamper while you experience a rueful pang about what ‘normal people’ would say if they saw how you live. But it’s mostly all right, because during the week no one ever sees you. You shower before you go out to see your friends, not in the morning before you start work.

Some nights you’ll skip the party in order to be responsible, because you have work to do. You will spend six, seven hours in front of the computer with a half-finished Word document and eight browser tabs open, muttering ‘motherf-cker’ under your breath as you refresh Facebook. You will do this at home alone almost daily.

Blow Deadlines. Writers always talk about their deadlines. It’s like, a thing we do. They are looming milestones of obligation which you have no reasonable method of predicting whether you will fulfill. When someone asks you “can you do [x thing] by [y date]” you say yes, of course, because you believe that having forged the commitment will force you to achieve it.

In truth there’s no way you can write unless it’s time. You have read all of the articles on general-purpose sites like Yahoo! about how essential reliability, professionalism and timeliness is to your livelihood. You internalize this deeply. At first you miss nothing. Maybe you are even faultlessly timely for years, which is what allows you to enjoy the lifestyle to which you have become accustomed now.

But over time that mechanism wears. You need the last possible instant of your grace period to suddenly produce in a flourish of what you hope is brilliance; you will never, never, never file early. You will write more apologetic emails than you can count. If you are ill at all, you will be late. If you are depressed, you will be late. If you’ve had a breakup you will need to defer several clients for several days. If you overdid your social activities at the weekend you will be late. You have to be in the right mindset to fulfill your commitments and god only knows when that will happen.

Good editors ask you for work earlier than they need it because they are writers too and they understand how whimsical it is. Nonetheless you will exist under an umbrella of angst that blooms whenever you cannot manage to do what you said you would do at the time that you said you would do it. You will feel an extreme groundswell of guilt over the fact that you somehow make your living despite the feeling that you meet your numerous obligations only by the skin of your teeth, that you make your living skidding under electric wire, under a metal shutter that is about to close on you as you roll beneath.

Never Feel Good Enough. I mean, you aren’t! Who do you think you are except a trickster, and the only difference between you and people who wish they had the same life as you is good fortune, a bit of aggression and desperation? If you are successful and prolific people will tell you every day that you are good. You will engender ‘fans’. You’ll get a lot of Twitter followers. Sometimes you’ll get drunk and become bitterly dismissive of nearly all of your colleagues; your lifestyle justifies your talent, you’ll say. Obviously you’re good, and even if you’re not you’re doing it and others aren’t, so there.

Despite the fact that all creative people are deeply insecure and narcissistic you’ll secretly loathe yourself for it. You will be ambivalent to everything you write. When someone else shows you their work and says to you ‘I made this, I think it’s really good,’ you’ll inwardly scoff. What kind of person actually believes their work is good? You don’t. You never do. You produce what you’re expected to produce when it’s time to do it and probably people will like it and that’s all you know. You will receive over one hundred negative comments on a piece you cared about and believed in. You will sh-t something out 30 minutes before it’s due after you’ve had five bloody marys at 11 a.m. on a Saturday and one hundred sycophants will tell you it’s brilliant. You don’t know. You can’t know.

What are you going to do with the rest of your life? What will you do when people stop paying for work? What if someone better than you comes along and steals your assignments? There is not a lot of money in media and there will be less and less. You live on a knife’s edge. When are you going to ‘finish your book?’ Are you going to type into the abyss of the internet forever? What if you plateau? What if the fact you can survive doesn’t actually mean you’re good, what have you got then? You’re screwed.

Hit send. Hit publish. Don’t read the comments. Forget what you create the second it leaves your fingers. It’s not good enough, and it’s probably not even the best you can do, but you’re doing it. Congratulations. TC mark

image – Anthony Perez


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  • Josh Wanamaker

    Sounds like heaven. I don’t drink, and I do leave the house, but I do keep the weird-ass hours and uh…almost everything else. Now I just have to find a publisher to accept my wordy goodness, because I have a lot to say and I’m certain every bit of it is totally important to everyone! I mean…right?

  • Guest

    HAH! Love it, too accurate.

  • Donald Elder

    I was going to start working at 4:00 today, then I read this for 10 minutes. My schedule’s all off now. I guess I’ll start at 5:00.

  • Ben Conner

    Well, fuck. Gonna go look at tech schools now.

  • Anonymous

    I don’t understand how all these freelance writers just get drunk, wear sweatpants all week, miss deadlines, don’t maintain business hours — and yet they keep getting paid.

    Who’s writing all these paychecks? 

    And why don’t they like *me*?


  • A OK

    Yeah. You nailed it, Leigh. Even if it was completed only two hours before the deadline, and you’re uncertain as to whether it was even decent. Nice work. 

  • guest

    beautifully written and so true. i’m a humanities grad student and this is exactly how i feel a lot of the time…. thanks for the great post!

  • Nemish Patel

    Wow, well said. Although I just write for fun, I can relate to this. This is the life of a coder, too.

  • Adustyhoof

    Haruki Murakami is the antithesis of some of the stuff written here.  Doesn’t drink and keeps regular and strict hours and schedules.  

    • Leigh

      he’s my favorite author too 

    • misskimball

      but he writes the same book over and over again and each one takes him four years

      • Adustyhoof

        Well every book is said to be autobiographical to some degree, so really every author writes the same book in that they draw from their same pool of experiences every time.  And I don’t see how drinking and keeping weird hours would help him put out books faster.  Plus you can’t really argue with his success or the quality of his work.

  • FierceLatino


    Step 1: Be an alcoholic.
    Step 2: Be successful.

    • FierceCarachan


      1) Sum things up in an annoying, oversimplified way
      2) Make an offensive comment about a person
      3) Be unsuccessful

      • Benjy

        4) USE CAPS LOCK

  • Adustyhoof

    If anyone wants serious advice regarding the writing profession, take a look at Dorothea Brande’s Becoming a Writer.  It was published in 1934 so you might question its relevance, but numerous author interviews that I’ve listened to have pointed me in the direction of this book.  It dispels some of the romanticism surrounding the writer (like the martyr of society image) and gives really good tips.

    • Anton

      I’m not sure if it’s worth having writers without self-destructive behaviors. 
      If I wanted the balanced opinions of respectable professionals I would just hang out with some kids that work in finance.

      • Adustyhoof

        Actually, the people I know in finance suffer exponentially more than the people I know who are in more artistic professions.  Early balding and obesity are some pretty common traits.  Also the whole point of my post was to do away with the self-destructive outlier of society image that people tend to paste on to writers.  Lastly, people can be plenty creative and have unique opinions without purposefully forcing themselves into beleaguered lifestyles.  

      • Anton

         Lastly, people can be plenty creative and have unique opinions without purposefully forcing themselves into beleaguered lifestyles.<— This is the great lie that makes people take Franzen and the nytimes seriously.

  • Julian Murdoch

    Sorry Leigh.  I’m supporting a family, paying mortgages and tuition.  If I approached my business (and yes, being a working writer is a business) this way, I’d starve to death, or at least my kids would.  Different strokes I guess, but I find being generally sober, ahead of schedule, organized, on word count and on topic is actually what keeps people writing me checks.  I agree with you about the letting it go part though.

    • Leigh

      i have more bylines than anyone in my field, so obvi i’m not actually a disorganized mess 

      the number of people who take my TC work very literally is often stunning to me 

      • Tashiri410

        LOL “TC work”

  • EarthToNichole

    be from a wealthy family that foots your bills and allows you to miss your deadlines and drink all the time.

    • Anonymous


      • EarthToNichole

        for the record i was making fun of myself, not the author. i enjoyed and related to this post, although i am merely a struggling freelance writer.

      • Anonymous

        oh i’m right there with you, not meaning to be critical of anyone but myself

      • Leigh

        nobody pays my bills NOT EVEN ME 

      • Tim Sukits

        As a freelance writer, this was an excruciatingly accurate depiction of my life. Nice work, Leigh.

  • Han Cilliers

    Kekeke, always makes me smile Leigh

  • puzzlingcreativity

    I really liked this article (Murakami also happens to my favorite writer too). I would like to think I could be a good freelance writer but I wouldn’t know how to get employed as one (other than the typical demandmedia stuff like eHow). Where are the biggest places are freelance writers working for?

  • mutterhals

    FOR THE LOVE OF GOD, DON’T READ THE COMMENTS!!! No really, this is my life.

  • AspiringGamesJourno

    Is it bad that I can relate to a lot (not the drinking but more of the procrastination bit) of this yet dream of becoming a games journalist? 

  • Sarahskiba1

    I read through every comment and no one has answered puzzlingcreativity’s question.

  • Michael Koh


  • Kevin Selles

    I thought I was the only one, but you just described my life.

  • Roy

    So much of this is true of my life. Anything in the creative field is subjective to other peoples’ opinion of what’s “good”… Just because you stick to deadlines and someone writes you a paycheck doesn’t necessarily mean what you wrote is meaningful or even important, just like if you’re the “tortured writer’ doesn’t mean you’re the next unrecognised great. I think it’s just about deriving joy from a compulsion … If you have that, you have most of it.

  • Jones the Writer

    This is probably the most correct article I’ve ever read! Leaving the house? Ridiculous notion – WHO does that? And how many times have I sh1tted out a piece of crap that should be binned immediately that STILL gets raucous applause four years later. Writing is a joke and a burden. I wouldn’t have it any other way.

  • Rajiv Naik

    Spot on, Leigh!  Though I write bespoke software, not articles, for a living and don’t get blotto to often, this is how I deliver my assignments most of the times.  Seems like the panic induced by a looming deadline is the most effective trigger for creativity.

  • Guest

    this has confirmed my lifelong desire to be writer. thank you so much x

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