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.