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Smurfs, Alcopops and Freelance Copywriting
Hollie Sherrington
September 30, 2021

When I first stumbled into freelance copywriting, I had no idea what I was doing.

I knew I wanted to be a writer, but had no idea how to go about it.

I was 26 and a secondary school dropout. I’d just quit the latest in a short line of part-time jobs that I wasn’t much cop at and was spending most of my time drinking copious amounts of real ale and blue WKD. (Strange mix I know, but what can I say? I have discerning tastes).

My life, which hadn’t been going anywhere for a while, had come to a shuddering, grinding halt.

I was unhappy and knew that if I didn’t take action to change my situation, it was only going to get worse.

So, I decided to take a leap of faith and jumped headfirst into the world of freelance copywriting.

Well actually, that’s a lie, because I did have some preparation. I spent three months as a writing intern with a digital marketing agency in Bristol, back in 2012.

But after that I was on my own, fighting the good freelance fight, with no clue as to what the heck it was I supposed to be doing. I had no contacts, very little experience and was plagued by self-doubt.


This is freelance copywriting you bloody fool, not Assassin’s Creed


But I did have one thing — a passion for writing and an eagerness to learn.

Okay, that’s two things, but what do you expect? I’m a copywriter, not a mathematician.

You see, I had a romanticised view of what being freelance was all about. I think I took the word ‘freelance’ too literally, because I had visions of darting about in a shining suit of armour, as a dashing creative hero or a villainous word mercenary, depending on my mood at the time. I thought that if I got really good at it, I might even be awarded with my own sword — the Excalibur of copywriting, if you will.

As I used to stare at the clock at work, watching the seconds tick away to the end of yet another meaningless shift, these romanticised ideas would tumble through my mind, teasing me with images of the life I was supposed to be living.

Even without the sword and the fancy suit of armour, being my own boss and flexible working sounded like a dream that was too good to be true.


Do I wanna be a writer, or an alcoholic Smurf?


Knowing that if I continued drinking blue WKD at the rate I was that I’d soon turn into a Smurf, it became painfully apparent that I had to make some kind of decision about what to do with my life.

I wanted to be a freelancer, I just had to find a way to make it happen.

So, I quit my job and applied for an unpaid writing internship at the aforementioned digital marketing agency in Bristol.

It was my first ever nine-to-five, which was a shock to the system to say the least. Having been AWOL for the best part of my secondary school years and having only ever worked part-time, writing for seven hours a day, five days a week was challenging. 

But I loved every single second of it. And I did it all for free.

As I’m sure my friends and family would testify, there was so much doubt (mostly mine) about my ability to make a success of anything at that time, and yet I worked my ass off. 

And this confirmed one thing — when it came to writing, I was willing to do anything.


It turns out that hard work does pay off! I’m as shocked as you are


At the end of the internship, one of my superiors took a risk and offered me my first ever freelance writing job, with one of loveliest clients I’ve ever worked with, Saskia Fraser.

I couldn’t believe my luck, but I didn’t know how to price the job and had no idea if I’d be able to work from home as successfully as I’d managed to at the agency. I felt like I was about to climb Mt. Everest wearing only a pair of flip-flops. 

But Saskia was kind, patient and most importantly, she liked my work.

So, bit by bit my confidence grew, and a week or two after the internship ended, I got my second freelance client, an online fashion retailer.

To say that I was feeling overwhelmed at this point would be an understatement. But somehow I kept it together, did the work, and once again I got good feedback from the client.


I reckon I must be well good at writing because the clients just keep on coming…


‘Great!’, I thought to myself, ‘This freelance writing lark is easier than I thought!’.

I had been lulled into a false sense of security by the fact that the clients were coming to me. So instead of marketing my business, I just focused on the work and keeping the clients I had happy so they’d keep on recommending me.

What I underestimated however, was just how much work would be involved in making my freelance copywriting business a success in the long-term.

I had my suspicions that it was going to be hard work, but didn’t want to talk myself out of it. So I decided to delude myself and ploughed ahead anyway.

It was the delusion that kept me going, late each night when the doubts started to weave themselves into my head, like ivy working its way into the foundations of an old house. It stopped me from backing out when the going got tough because I deluded myself that I could just wing it and things would work out okay.

Good old delusion — my old and faithful friend.


Let’s go down the casino and bet everything on red, I’m on a lucky streak!


I don’t know whether it was luck, judgement or a combination of both, but somehow I made the freelance copywriting thing work for the first couple of years. I wasn’t earning big bucks or anything, but I was just starting out and happy to pay my dues.

More importantly though, I was getting good feedback from clients and learning the craft, which at that stage I still knew very little about.


I’m a writer, darling, not a businesswoman…now stop being silly & pass me the absinthe 


The trouble was that I got complacent. For the first two years, I didn’t have a website and my marketing strategy was non-existent. I wasn’t even on social media.

Writing was one thing — the idea of working in quiet isolation in the private sanctuary of my own house sounded like bliss. But the idea of marketing myself to the world made me break out in hives. So I ignored the marketing side of things and continued to think of myself as a writer, rather than a businesswoman.

Big mistake.

Instead of marketing, I took low-paying jobs with content mills, which are like the writer’s equivalent of a Victorian workhouse.

Some days, I’d write blog posts and product descriptions for little more than a couple of quid each. Other days, I’d repeatedly bash my head against a brick wall, because it felt like a more productive use of time.


Top freelance tip: Unpaid invoices make surprisingly comfortable nests


I even did a couple of jobs for the ‘exposure’, which sadly I later discovered is not legal tender in the UK. I learnt this the hard way when I tried to pay my rent with all the exposure I’d earned in my first couple of years of freelancing.

Suffice to say, it did not go well.

I was made homeless shortly after, which was actually okay because I was able to build myself a nest out of all my overdue invoices. (Something we freelancers often have a surplus of.)

It was okay in the summer months, but come the end of August I was really beginning to miss having walls, so it was around that time that I started getting serious. And it wasn’t until I got serious about the business side of things that I really started to taste some success.


The recluse comes out of hiding


I built myself a website, joined social media and started networking, wrote guest posts for some online publications, started my own blog, and most importantly, started pitching and offering my services to local businesses.

Bit by bit, the dots started to join together and before I knew it I had a viable and relatively successful freelance writing business, which I’m proud and frankly amazed to say that I built from the bottom up.

So what’s the lesson?

If you choose to follow the noble path of freelancing, then remember that first and foremost you are a business. It may sound simple, but this shift in mindset is essential if you want to make it work.


Brace yourself for some wisdom 


I think that’s part of what tripped me up for so long. As an introverted, reclusive writer-type person, the idea of marketing myself was like exposing Superman to Kryptonite. But then I realised that it wasn’t me I was supposed to be marketing, it was my business.

When people used to ask me what I did for a living, I used to say that I was a freelance copywriter. Now I say that I run a freelance copywriting business. And that my friends, is what has made all the difference.


If you’d like to help me avoid becoming homeless and having to build a nest out of unpaid invoices, then get in touch and let’s have a chat about what I can do to help your business, so you can avoid becoming homeless too.


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