Freelance Writing: What I Did Wrong

MikeachimThe Everyday32 Comments

broken pencil

Okay, so I wrote this post called Freelance Writing: What I Did Right , about the things that worked for me in 2010 as a newly self-employed (p/t) writer. And I wrote it from the heart, as honestly as I could, in an attempt to avoid sounding smug. It’s up to you to decide if I succeeded or not.

But let’s face it, this is the fun part: listing the ways I screwed up.

Let’s not dawdle: we’ve got a Mike to laugh at.

1. I Didn’t Pitch Enough

If you don’t have much money coming in from your freelance writing, it’s because you’re not pitching enough.

Last year, I kept myself so busy I never got round to organising my time properly. This is a really bad way to work. It’s the reason David Allen had to write Getting Things Done (which I now have it on my Kindle, equating to “I take it everywhere I go”).

The key lesson I’ve got from his book is that if you let them, your activities will naturally expand until they fill every single corner of your life. Spare time isn’t something that naturally occurs in nature – it’s something you have to make. This means your biggest fear shouldn’t be boredom, it should be thinking “I’ll get round to it when I have the time”, because if you don’t create that spare time yourself, you’ll never have it.

Top of my list of Important Things To Create Time For? You guessed it – pitching. That was the 50% of my job that I was neglecting.

The way I’ve tackled that is peer pressure. I’ve entered into a Pitching Pact with another writer, where we solemnly swear under pain of social media humiliation that we’ll get one major article or project pitch out every week, except for the times we’re writing up a successful pitch.

And it’s working.

Put the time aside – in advance, to be fiercely defended – to get your ideas out the door and learn the markets you want to write for. It’s important. Neglect this and you will stumble.

2. It Wasn’t My Only Job

Freelance writing takes a lot of time. I haven’t had much of that, thanks to a part-time job at the other side of town.

But let’s just say I’m on that problem.

3. I Forgot How To Relax

When you fail to effectively divide up your workload into write and pitch, it figures that you’ll fail to clearly divide up your free time into work and play. But this is less of an issue if you’re of the same mind as Gary Vaynerchuk. Not sure I am. But it’s a fact that I haven’t played enough (literally, my guitar; figuratively, my reading list.

Learn when to shut off social media (here’s a good guide to doing that), block out work-related distractions and really, truly chill out. Do other things with your brain. Use it for fun. It’ll tune up and work better in the long run.

4. I Founded A Business On Debt…

Little choice about that one. I needed to register as a self-employed writer to be able to stay within the law when I earned money. That meant starting a business that carried a millstone round its neck – the debt I allowed to creep into my life when I was an archaeology student. It’s a debt that eats at my monthly income, and we’re not talking nibbling here. The good news is that as I pay off that debt, my disposable income rises, with the eventual aim of wiping the slate clean and building up some savings for myself.

Thanks to a hard-line financial plan that is already paying off (for example, it’s allowing me to go to Austria in a few weeks), things look healthier than at any point in 2011. But debt is ugly. It’s the enemy of my happiness, my fun and my career.

So I’m kicking its ass.

5. …Without The Means To Pay It Off

Last year I was testing the waters with travel-writing as a job. It turned out that the water was really cold. Writing as a career is generally as precarious as a career in archaeology, and having switched from the latter to the former, I don’t feel terribly reassured of my own sanity. But travel-writing is far shakier a prospect as a source of income. Better writers than I have decided against it, and the intrepid few that do it are very honest about its shortcomings as a profession. Sometimes it feels like an ideal that has nothing to do with reality, the same way archaeology isn’t about plucking idols off altars, fleeing boulders and punching Nazis. Usually.

But it’s become clear to me that there is a way to do it. And like being an archaeologist, it involves wearing lots of hats. I won’t make a living as a travel-writer, I feel sure of that now. But I will make a living as a writer of many different things, at the core of which will be my love of travel. That’s the path I’m treading. And I intend to remain open to new opportunities, every step of the way.

6.  I Confused Working Hard With Working Smart

To paraphrase Stephen Covey, it doesn’t matter how fast you’re climbing a ladder when it’s leaning against the wrong wall.

Focus your efforts on exactly the right places instead of trying to do everything at the same time, and you’re laughing.

(I didn’t laugh much in 2010).

7. I Didn’t Have A Realistic Financial Plan

This Is Vital. Underline, underscore, go to a tattoo parlour and ink it onto yourself, Memento-style. If you don’t know exactly, precisely where your money is going (and on what date and in what quantities), your finances are beyond your control. I’m knowing the truth of that as I crack down on my own.

Debt is what happens when you sloppily fritter away your income at the edges, in amounts small enough to fool you into thinking they don’t matter. No. They do matter.

And especially if you’re self-employed. You’re letting your hard-won job slip through your fingers.

Catch it all.

8. I Didn’t Read Enough

I’m a big believer of the word-bucket theory. It goes like this: your brain is a bucket that can hold only a certain number of words. When that bucket is full, those words are pushed out of you. This is how people write effortlessly. Alternately, when your bucket is dry, every emerging word is agony. That’s writer’s block, right there. Blocked? Go read. Fin.

Yes, it’s probably twaddle.

But it’s useful twaddle (my favourite kind), so I’m sticking to it.

9. I Worked To Deadlines, Not Lifelines

Deadlines are now officially dead to me. Yes, editors will impose them on me and I will meet them without fail (or get sacked, obviously). But deadlines won’t motivate me, because deadlines never have – apart from those bouts of self-hating panic that take years off my life. Deadlines are forever things in the future, comfortably far away. They’re never here – right until they’re nearly here OMG OMG and you’re dancing around, shrieking like a cheerleader.

Lifelines, on the other hand, are nowhere else but here. They run from conception point, right through Now and towards an either murky or finite end-point. The main thing is, your obligation isn’t to some distant, thoroughly unreal tomorrow – it’s to what can be done today. What is there to do? Time to do that.

Oh, and don’t have too many of these running through your life at once. Your mind will act like a rabbit in car headlights and you’ll still be sat there at bedtime, fingernails gnawed to the quick, having done nothing. If you’re like me you need to do relatively small numbers of things, one thing at a time, carefully and well.

10. I Forgot What My Blog Was For

So, here’s the thing. You’re reading the bumbling chronicles of a writer piecing together a career from random objects he’s pulling out of two boxes marked “success” and “failure”. It’s here that I’m going to be honest about my travels and my career, the good and the bad. I intend to be honest about it to the point of self-brutality. After all, that’s what a blog is for, isn’t it? (Honesty, not masochism).

I also intend to share with you exactly what has worked for me, and exactly what has ploughed into the weeds. If you’re wanting the same things, I hope it’ll inspire you to find your own answers.

This site, in short, will be all about my route to what I want. My journey there. I intend to be personal (although not salaciously so, ahem), and I intend to have a lot of fun.

Hope you’re okay with that.

However, if you want to know how to travel the world, create the location-independent career of your dreams or run a broom through your finances, please go read everything behind the following links:

  • Christine Gilbert at Almost Fearless travels the world and earns her living as she does so. She’s been writing about it since before day 1. Her site is the bible of digital nomadism. Go read.
  • Jodi Ettenberg at Legal Nomads just gave a killer presentation at Chris Guillebeau’s World Domination Summit, and she’s summarised her vast independent travel experience here. It’s quite the resource.
  • JD Roth at Get Rich Slowly is smart with money. If you read his site, he’ll make you smart with it too.

After that, hey, come back here. I’d like that.

You’re going to see a lot of changes in here over the next few months – and elsewhere. Yes, I’m talking about this. It’s taken me almost a year (far longer than originally planned, but all the better for it) to find a way to do it that makes my toes wiggle with anticipation, and also I couldn’t have put the time aside for it until my freelancing was sufficiently organised. Now it is. We’re back on track.

To finish with, I’d like to dedicate this post to the people who have given me misleading, bad or downright useless advice down the years. You made me go out there and make mistakes – and I’ve learned so much from my mistakes that I can’t thank you enough. But I’ll try. Thank you. (Kinda).

Images: e-magic, RLHyde and Andres Rueda.
  • As always, a great post Mike. Always love the solid writing, dabbled with honesty, and a heaping side of humor. I would like to provide some prospective from someone who is a full-time freelancer. I’ll do this in list format for all of you who don’t like reading paragraphs, even though you just read a bunch of paragraphs.
    1. I’m a freelance writer and have been so full-time for 10 months and don’t know when I’ll quite. It’s the first thing I’ve done and absolutely loved.
    2. I put a lot of hours into it, but for me, it’s more than just working to Friday. It’s what I really love.
    3. I wear many hats. I dabble in print, do a lot of online writing, and manage social media for companies.
    4. My blog is the most fun thing I write and I don’t make a penny off it. I’m ok with that. It’s the one place I can write whatever the hell I want and color outside of the lines. That’s been important for me so I don’t get burnt out, flip tables, curse at editors, and so on.

    These things have been some of the important things that have stood out for me. Freelancing is by no means for most people. Some days it’s glamorous. Most days it isn’t. I enjoy it though and the day I cease to enjoy it, then I’ll find something else to enjoy that pays the bills.

    • Mikeachim

      Too kind as always, Mr Spellman.

      I hear your enthusiasm about the freedom of expression your blog gives you, both as a place to create and a place to vent. Have you avoided the advertising/monetizing route for that reason? I’m thinking about such things at the moment, how they’ve felt like they’ve curtailed the point of my blog in the past…

      Regarding 2), do you find your love of your job means you have an indistinct line between “job” and “home”, with lots of spillage from the former into the latter? Ever feel that’s an intrusive thing?

      It’s been really fun to watch you launch yourself, sir. And you’ve written some terrific posts about that transition, that internal empowerment. For that and for those, I thank you. I’ve always come away from reading your site with someone new on my own To Do list.

      • I’m not ruling out monetizing from my blog and I wouldn’t change anything if I did. I’ve written about comped activities on my blog and from the outset I make sure companies are aware that I don’t consider my blog the typical travel blog and so they can expect writing that’s going to be different.

        On #2, that’s been one of the biggest struggles, but one of my greatest victories lately. I usually quit for the week on Fridays at lunchtime and then pick things back up Sunday evening. I won’t touch work Friday afternoon/evening and Saturday. I’ve tried to be better about putting my work down. There’s always SOMETHING to do, but I’ve decided doing what I want to do, going to a pub, a new adventure, or hanging with friends typically holds more value for me than getting an extra $50. Plus, I don’t need to burnout.

        Thanks for the awesome words about my writing. It’s things like that that make me love it and want to continue to do it! Great words here for both established and aspiring writers.

  • Caitlin

    Yay, Mike! Good luck and have fun in Austria.

    Getting Things Done is awesome. I also recommend Your Best Year Yet by Jinny Ditzler.

    • Mikeachim

      Yes, I love how sane GTD is. And low-tech, so therefore infinitely practical. Again and again Allen is talking about the value of a simple plastic folder or a loose-leaf binder. And it works. It really does work. The more I do of it, the more that sinks in.

      I’m just looking at the Best Year Yet! online course. But presuming you mean the book? I’ll check it out – just ordered it 2nd-hand from Amazon. Ta, Caitlin.

  • Lisa

    Good article, Mike. It’s interesting to see someone choose a career you’d find fascinating, and hear first-hand about what they’d do differently, with that experience under their belt. Doing what you love and making money at doing it must be a wonderful thing.

    • Mikeachim

      Thanks Lisa!

      I’m not there yet, but I’m nearing halfway. It’s the doing-differently thing that’s proving important in getting anywhere. The uselessness of trying to fit a square peg into a Mike-shaped hole. Lee at Zen Habits has just reinforced the endlessness of the danger of comparisons ( and that’s been ringing true for a while. There is no single way that fits all. It’s a cobbling-together exercise for everyone, I reckon. Or…should be.

  • I like what you said in #5. My background was in art history before I figured out I’d never be able to get a job in that field. When I started travel blogging (with hopes of some travel writing opportunities), I honestly had no idea at all how many people are already doing it and sometimes even doing it really well. As you mentioned, it’s important to get realistic about how hard travel writing is and that making a living doing something like that may involve being good at doing several things. Wearing different hats is a good thing as long as a portion of them are ones you love.

    • Mikeachim

      Good point. Too many of the wrong kinds of hats and it becomes just another job-for-money…

      Do you find your art history training creeping into your travel-writing in unexpected ways? Finding it’s an unusual, useful angle?

      • Yes, it’s true that too many of the wrong hats would be a problem, but I think just about any job requires us to wear different hats, at least to some extent. Maybe as you continue your travel writing career, you will be able to shed some of them to make more space for the travel-writing-only-hat.
        I absolutely find my art history education creeping into my travel writing and perspective. It’s a useful angle and one I’m hoping to pursue more since it will help differentiate me from other travel bloggers. I’m sure your archaeology knowledge influences your travel experiences.

  • Enjoyed your dedication of this post. It reminds me of the e.e. cummings book “No Thanks,” which he dedicates to all the publishing companies who rejected him.

    • Mikeachim

      Hah! Yes.

      Of course now I hate e.e. cummings for getting there first. It’s all one great big super-motivational whirl of resentment. Well, that’s Art for you.

  • Liv

    “Not pitching enough” – I hear you there, buddy. Especially in agreement with your secret writer pitch pact.

    • Mikeachim

      I can thoroughly recommend it, Liv.

  • Nice one!

    :o )

    As ever, fun to read and chock full o’ useful information for we human folk, especially we human folk who fancy ourselves writers to some degree. Thanks for sharing your Rights and Wrongs so that I may not avoid them but feel like less of a doofus when I do Wrongs, too. It’s always nice to know we’re not alone. And your Rights are nudges that I need in the, you know, right direction.

    • Mikeachim

      Thanks, Beth!

      No, we all have to find our own way. And make our own mistakes. These are (some of) mine, and I’m relieved that I’ve become aware of them before they did some real damage. At the same time – I reckon mistakes are milestones. Make enough of them, you’re getting somewhere. That’s my hope. ;)

  • Damn auto-emoticon-er.

    Fine, I’ll conform: :)

  • “plucking idols off altars, fleeing boulders and punching Nazis” – damn, now I want to be an archaeologist!

    Nice post.

    • Mikeachim

      Mainly lies, sadly. I only plucked one idol off an altar. It was small, and the altar wasn’t very high. I didn’t ever flee a boulder, but I did trip over one. And I once gave a Chinese burn to a member of the BNP. But that’s about it really. Lies.

  • sharon miro

    Hmmm. Well.

    One of the goals I made for myself this year was to stop giving you compliments. I have failed. Stop writing so well, so I can start trashing you and makign at least one of my goals.

    • Mikeachim

      Thank you, Sharon.

      And I hope I continue to disappoint you. ;)

  • This must be the 3rd or 4th time I read this post, it just sums up my life at the moment that sometimes I thought you’ve been spying on me. I don’t pitch enough, I’m keeping myself so busy that I’m constantly postponing the pitching, I forgot how to relax, I’m so busy that I’m not even reading enough, which is absolutely ridiculous since reading has always been one of my most favorite activities, and it’s not my only job, even if it’s slowly becoming it.
    I know I need to re-set my priorities, this post is somehow helping me do it.

  • honesty without the preceding lies. NICE I enjoyed the reflection without too much self mirror gazing. no preaching just observations with a plan to fix the problems. thanks dude

  • So Mike, when are you writing a self-help book for freelancers? I would by it. Excellent post!

  • Great post! Thanks for sharing your experience and tips with other freelance writers.

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  • Story of my life. Not sure if our discussions have fuelled this post, but it really hit home. You’re so wise, although you’d claim otherwise. Efharisto poli.

  • Just spotted your post on a Twitter feed. Really enjoyed it. Completely agree with number one, I don’t think half of us freelancers pitch enough. It’s a difficult one though, you want to be original but you’ve got to fit almost exactly into a magazine or website’s existing ethos.

    Thanks for posting, will go look at the rest of your blog now.

    [email protected]

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  • Hi Mike, I’m so pleased I bookmarked your article … and am happily reunited with it today. Am guilty of making at least 9 out of the 10 same mistakes! Mainly, I’ve become so involved in the promotion and the development of the site that I’ve hardly made time for reading – or writing! My subject is my love for Uganda, and the ups and downs of live in a developing country. I confess I’m not enjoying blogging half as much as during the carefree days when I didn’t think anyone was reading!

  • Cool article Mike!
    It’s definitely not easy becoming a freelance writer (or travel blogger in my case), but you nailed some of the most important things. I especially agree with point #3 – you gotta remember to relax! Great work!
    Aaron – NomadsNation

    • Cheers, Aaron! It isn’t easy at all, but there’s always something more to learn, and more good advice to find and act on. (A perfect example: everyone who contributed to this site deserves a medal –