Dumbass Things I Do As A Freelancer That Partially Explain My Lack Of Success

Apparently articles with images in do better on Medium than ones without. We’ll see about that.

When a self-employed individual fills in their tax return, they have thoughts. Thoughts like “That’s not very much income, is it?” and “I should have put some aside for tax though” and “I guess that’s why they sell filing systems” and “I should open my post” and “I’m sure I should be doing better than this”. I did that today. Luckily, any questions I have about why I’m not more successful can be answered by the bad habits detailed below. Learn from them, be better than me, get rich and send me six hundred pounds.

Not talking to strangers
The vast majority of work I’ve had has been through friends, or friends of friends, or friends of friends of friends. Considering this, I’ve done alright, but there are obvious limits to how far I can ever get. The worst thing that would ever happen if I contacted someone I — the horror — didn’t have any friends in common with is they’d ignore my email and forget I ever existed. The chances of them laughing uproariously at what a dick they think I am, finding pictures of me online and calling a meeting for the whole team to say nasty things about my face and body are actually pretty small. Probably less than 30 per cent. But it still stops me.

Being all shy
The day after I ‘went freelance’ (got sacked) I was put in touch with a really nice woman at the Guardian who was after pretty much exactly what I could offer. I never pitched her anything. “That’s the Guardian!” I thought. “I read it, I can’t write for it.” What a shithouse attitude. What a poltroon. I was also once asked to write about gaming for the NME and turned it down, which was — actually, no, I was right to do that. I don’t know enough about the world of gaming outside of stuff I’ve actually played, and I never replaced my Xbox 360 after it red-ringed four years ago, so I’d have been rightly outed as a filthy chancing mountebank.

Beginning every pitch with an apology
I go all Hugh Grant when I email people, but without the charm, looks or chequered sexual history. I start everything off with so many disclaimers, apologies and self-criticism that by the time anyone gets to my actual idea I’ve generally done a solid job of convincing them I’m a complete dickbrain. “Hi, so this might be rubbish — and sorry if it’s really unsuitable for you, it’s just a kind of silly, goofy half-thought that probably sucks––but how about, if I can manage it, a daft piece about a dog doing a poo in a hat?” That dog/poo/hat article might be amazing (I’d read it), but the world will never find out because I’ve essentially approached someone shouting “DON’T COMMISSION ME!”

Pitching stuff I don’t actually want to do
A really unpleasant media figure was in the news again last year after he was arrested, again, for horrible sex crimes, again. Let’s call him Jonathan King. I remembered something I’d read about him years before, and immediately pitched a piece to Vice about when he released a (presumably hideous) album with a Slayer-inspired cover showing him sat on a throne in the centre of Hell, containing tracks about Harold Shipman and Bob Geldof. Go for it, I was told. Then, when walking home, I realised I had no desire whatsoever to listen to this arsehole’s output, let alone have to process it enough to write about it and then spread it further. So I didn’t do it, and looked like an unreliable, timewasting blockhead.

Pitching stuff I know I won’t be able to do
You know the Star War, the Star War that just came out? I suggested a piece where, as someone who’d only seen one and a half of the films, I’d watch them all in a day. It would all be done in a way that guaranteed (ideally entertaining) bleakness, because either I’d enjoy them and be sad I’d got to 32 without them in my life, or they’d leave me cold and I’d feel sad that the rest of the world was excited about something I couldn’t share with them. Again, I was told to go for it. Thing is, I was moving house and had an ongoing full-time booking. Finding a twelve-hour chunk of time I could dedicate to space-bears wasn’t on the cards, and if I’d thought it through I’d have realised that. Twelve hours is a long time, which is also the beginning of Star Wars I think, so damn, that article would have been great.

Just not doing stuff
I once arranged to spend a day watching all the Police Academy movies while being filmed on a GoPro. Comedy Central were going to pay me £200. I just never got round to buying the box set off Amazon, and then the guy who owned the GoPro went on holiday and it all just turned to dust really. That would have been the stupidest £200 I’d ever earned, and I once earned £200 modelling for a hair gel company as a man who’d really let himself go.

Not getting around to invoicing
Oh GOD. Over the last two years I think I’ve lost close to £2,000 to this in various ways, which is why my diet largely consists of cobwebs and toothpaste. Ways like:
i) Being hired to do six weeks’ worth of work from home, only doing three days of it due to other things coming up and a lack of willpower, then being embarrassed to invoice for the work I actually did because it was so paltry.
ii) Having multiple things on the go with one outlet, thinking, “Well, I’ll get this next one finished as well, then invoice for the lot to keep things simple”, and not getting around to it for such a long time that the financial year’s changed, the books are closed, I’ve not been accounted for and that money has essentially disappeared.
iii) As above, but with the company involved completely dissolving.

Throwing payslips, unopened, into a paper bag to live alongside a pair of blackout curtains I borrowed from my friend Rick two and a half years ago for a flat I moved out of one and a half years ago that had really big windows
Stupid. Really, really stupid. That tax return took fucking ages.

A single golf clap? Or a long standing ovation?

By clapping more or less, you can signal to us which stories really stand out.