• Kim Wilson

8 freelance writing gigs that taught me a hell of a lot

If you don't mind selling your soul for $1 per 1000 words then freelance writing might be for you.


Not a photo of me. I can be found wrapped in a blanket surrounded by crisp packets!

I love writing and so when we were travelling in 2014 I decided to give freelancing a bash to earn some extra pennies. I signed up to an agency where people post their jobs and writers (approximately a billion of them) pitch for the gig. I would say which agency I used but they pissed me off when they increased their fees to 20% so I ditched them.


Starting on the bottom rung of the writing ladder with no experience is pretty daunting. You are either competing against high earning, professional writers or people willing to do the work at impossibly low rates. It feels hopeless but you just have to stick at it. Work on a great pitch and don't just send a generic cover letters and the jobs will start rolling in.


Over time I got a few little blog post jobs, then a few steady clients and finally some more exciting projects. They would never make me rich but I loved it. I've wound down the freelancing to focus more on writing for myself but looking back through the various jobs I did reminded me of the good, bad and ugly times.


Here are the highs and lows of my freelance career...


1: Job I'm least proud of

I got into a bit of a rut ghostwriting mini Amazon e-books for one client. Lord knows what he wanted them for, he's well respected as a self-improvement speaker but needed lots of random titles which he published under a pen name. The pay was poor, they were all about 3,500 words each and and the timetable was very much quantity over quality. The first few batches were quite interesting, lots of Kaizen, self-improvement and weight loss type stuff. I put a lot of research into them, and they they turned out pretty well.


On the other hand there were a lot of 'how to' guides that I just couldn't do justice to in 3,500 words. How to make beer at home was a genuine disaster and the reviews were horrific (and rightly so). I had to skip out huge chunks of important stuff to get it within the word count and estimate ingredient figures to make a 'one recipe fits all' book (ask any brewer and they'll tell you that this is impossible). There is no way you could make a drinkable beer from this guide and I quit writing them shortly after.


Best case scenario if you trusted my beer making guide...

I also bluffed my way through a lot of 'first hand experience' titles for him. I'm a childless, middle aged white female so the following titles felt a tad fraudulent.

  • How I boosted my testosterone levels for an amazing sex life (me and my imaginary penis)

  • Getting my pre-baby body back in 8 weeks (spoiler alert - no baby)

  • Living a vegan life (I'm not veggie, let alone vegan)

I've always trusted books but this experience taught me that anyone can write anything. They aren't necessarily an expert and possibly have a motive other than providing valuable (and accurate) information for the reader. If you really want to spend time and money learning from a book then research your author.


2: Strangest job

The most bizarre job I took on was from a company that was writing a cartoon about a character that died repeatedly in dumb and funny ways. Think along the lines of Kenny from Southpark or Itchy and Scratchy in the Simpsons. They advertised for someone to invent random ways to die in everyday situations.


So let my little brain wander to the places it's normally not allowed to go and it came back with some pretty messed up ways to die. I'd be having a snack and blurt out 'eats and apple, swallow the seeds and a tree bursts out of his skull' then scuttle off to write it down. I think I originally sold 20 and they came back for 20 more. That was great fun although by the end James was a little concerned about my state of mind.


3: Morally questionable

I tell this story a lot to my male friends who are struggling to get responses on dating apps but I'm not particularly proud of it. If I saw it now I'd be a bit creeped out and probably wouldn't pitch. At the time the money was too good and hey, I was shameless.


A businessman in California was struggling to get responses on a dating app. He was a lovely guy on Skype but hopeless in written communication. He paid me to to write the first few messages to women he liked on Tinder to get the conversation rolling. Then I would give him a crib sheet of out conversations and he would set up a date with them.


It was an hourly contract so I would look through the photos and profiles of the list of ladies he liked and try to gauge what would spark their interest. Turns out most women (myself included) just want a guy that's actually paid attention to their profile not just their bra size. In the end I discovered that dogs were a winner. If there is a photo with a pooch in it then ask about the dog! 100% response rate.


Unfortunately I did rather too well at this job and the contract ended when the client started dating one of the women. To this day I wonder if he ever told her that for the first few days it was me she was messaging.


4: Fastest Fail



The 50 shades phenomenon meant that there was a deluge of posts requesting erotic literature ghost writers. I had no experience of writing erotica but I grew up on Jilly Cooper novels and was pretty overconfident. I submitted my pitch and they requested a test piece. All was going fairly well until I realised I had run out of words for a penis. The point when I was questioning whether 'pulsating pork sword' was sexy was when I had to admit defeat. I now have a massive respect for good erotic writers!


As a side note one of our favorite drunken games now is a competition to see how many unique penis terms we can come up with. I think our record was 18 so feel free to try and beat that!



5: Most educational



Quite early on in the freelance jobs I picked up some work with a website called Tripcanvas. A travel guide for Indonesia. There are strict guidelines for all freelancers and training about sourcing and crediting photos, using SEO buzzwords and writing engaging content. There was strong focus on intensive research to ensure that your piece would benefit the reader. This is actually one of my longest running contracts and one that I continue to learn from when I write for them. I learned the importance of a great editor who gives a clear brief, great feedback and pushes you to improve.


6: Most soul destroying

Usually if I'm writing for someone else I don't want to be linked to it. I write my own stuff in my own style so I don't really like the crossover. Apart from once, when I agreed to write a travel guide for a really lovely client about their home country. They were great, they knew exactly what they wanted and had a lot of input into both the skeleton and content.


It was a bit of a brute but it looked pretty good at the end and they decided to self publish it in paperback. I was pretty proud of our work and chuffed when they said they had credited me on the front cover. That was until I saw the final copy and realised it had been heavily edited again...


I read the online reviews and one of them said it was obvious the book was written by someone that wasn't fluent in English. That stung.


7: Worst paid

Way back in 2015 when I was pretty new to everything I pitched to write a short guide about empowering young women. It had a $50 cap on it (less agency fees and convert it to GBP and it's about £30). Not great pay but I was still travelling at the time and every little helps. I had a Skype meeting with client and they ran a charity for girls America. It quickly transpired that they were expecting more than a basic guide. That said I'm a bit soft and really admired the work that the charity did so I accepted the job and we got started.


Anyway, six months later, and God knows how many emails, meetings and hours actually spent writing and we ended up with a 17,000 word beast of a guide. Sure it comes out as 0.0029 cents per word but I might have empowered someone...maybe.


8: Most bizarre research



Apart from the brief stint researching different names for 'penis', the next most bizarre research session was how to sneak alcohol into festivals. Not only was it about what tactics you can use but also details on how best to do them. So, 'shove it up your butt' wasn't enough. I had to research the best ways the access the old prison pocket and frankly I'm still a bit scarred by some of the images I saw.


Top Tips I learnt from my brief freelancing stint

  • You CANNOT beat some people on price. Don't be tempted to offer very low prices to win a pitch. If you trust your ability and know you would suit the gig then don't be afraid to charge accordingly.

  • If a topic requires detailed research then make sure it's something you're interested in. The research and writing process will be far more enjoyable and your passion shines through in the final product.

  • If you get a gut feeling about a client then don't press on and hope for the best. Sometimes you don't gel with a client or you both have different visions. Battling through these is frustrating on both sides and unlikely to leave either of you feeling 100% satisfied.

  • If you have a certain style then don't pretend to be something else. Your content is valuable because you write in an unique way. If you are awesome at factual then don't assume you can probably write fiction. Have a practice in your own time if you want to try something new.

  • Under promise and over deliver. If you think you will be finished this evening then say tomorrow evening. It gives you some wiggle room plus impresses the client if you deliver early. Missing a deadline is a absolute no no.

  • The client is always right. You can make suggestions but ultimately you are simply being paid to write what they want. Even if it pains your soul.

  • Using an Agency is great in some ways. You have payment protection, dispute resolution and can see where you are up to with each job. At the same time you are losing a chunk of money to agency fees and are pitching against a huge number of people.

I'd love to hear about anyone else's strangest jobs or freelancing experiences!




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