In 2016 I had a bit of a crisis moment. I quit my job in construction, which was making me miserable beyond belief. The sexism, boredom and general disinterest in the world that permeated that working environment got way too hard to handle. I left and it was the most liberating thing I’ve ever done for myself.
But because I was so desperate to get out of there, I changed a lot of things really quickly. My job, my apartment and my relationship that wasn’t working, all got canned at once. I was half a world away from my hometown and my family support network, and this would be my last-ditch effort to see if I could stay in London, or if I’d have to return home to Australia, defeated. I literally hit the reset button on everything that mattered to me.
So, without a clear job lined up, without a home to live in, without a partner or a family network to fall back on, I went freelance. My dream to write as a career was the only thing in my life that I felt certain about — I’d cut away everything else, everything that hadn’t been working for me, and that was all that I was left with. I had to write, and that was it.
Since that fateful day when I finally stepped over the edge and risked it all, I have never been happier. I have never again doubted my career choice — I’ve had tough moments aplenty, but I have never thought, “You know, I actually don’t like writing.” Not once. This was my fear before that moment: I’d tried so many different things, different jobs and study options, and eventually I’d grown to hate all of them. It’s important to know that; despite everything, I have literally no regret, even though I did a bunch of stuff in a very, very risky way.
So here is what I’ve learned and would want to pass on, about how to not make freelancing a hell-pit from which you don’t know how to escape…
Have your house in order first
So, you know, maybe don’t try to orchestrate a major move before you set foot into the freelance world. In my case, it was necessary: I had to cut costs fast, so I had to really fudge it and move house, into what I now remember as “The Cupboard”. I lived in this tiny room with no hot water, no washing machine or other facilities, sagging floors, the occasional electricity outage and a shared bathroom (with 6 other flats). I did that because it was the only way I could think to quickly cut my expenditure, and make it feasible to live on a very low freelancer’s salary in London.
I expected work to be slow and my initial income to be low, and I wasn’t wrong. It took time, so making that move was essential to give me that time to actually build myself up as a freelancer — I needed to make my savings work for as long as possible. But ideally, you’d have this sort of thing in place before you hit the go-button on freelancing.
The good news: Freelancing is completely up to you — you are your own ‘boss’. So you can give yourself the time to make sure these things are in place, that you have a secure place to live at the lowest possible expenditure. Know that you will have to cut things, probably, unless you have a huge amount of savings to make up the difference, as you will likely take a pay cut as you enter the freelance world. Give yourself the chance to make it work, the best way possible. Get your house in order first.
Don’t be precious — you can’t afford it
I have worked for companies as bizarre and diverse as you can imagine. From writing up beautiful itineraries of adventure travel opportunities, through to the most mundane of keyword-enriched banking articles. I have done all sorts.
And if you’re just starting out with freelance writing, forget the romantic notion that you’ll be writing beautiful thought-pieces right off the bat. Maybe you’re lucky enough to have these connections and job offers in place already, but for most of us starting out with nothing (and coming from a completely different career path into freelance writing), chances are you will be bidding for whatever you can get, at first.
I once met another writer and told her that I wrote all kinds of things, including random finance articles, copy about nutrition and travel and design… and her response was, “Oh god, I’d never do that. I care about my art.” Well, that’s all well and good for some. It’s great that she had enough external support (parents/partner/whatever) that could help her pay to live doing nothing but writing stories. But I didn’t have that luxury. I didn’t have a partner, my family lived on the other side of the planet, and I had to make it work in one of the most expensive cities on earth. I did all that, myself. And I did it because I wasn’t precious. It wasn’t the Carrie Bradshaw-esque vision I’d always dreamed of.
At first, I just wanted a portfolio — I had a few bits and pieces to my name from my university and working years, but I had to beef this up, make it recent and make it varied, in order to stand a chance against other freelancers. There wasn’t time to reject certain kinds of writing as ‘beneath me’. Nothing was beneath me.
The good news: By working on really diverse briefs, you can really push the kind of writer you will become. After all, it’s all practice — it will make you the expert you dream of becoming. Try it all out, do whatever you can, and learn the differences between the kinds of writing styles you enjoy and those you struggle with. It is the most essential training for any wannabe freelance writer. It will make you good.
Still, apply some discretion — ask questions, don’t just say yes
Okay, so I’ve just said you shouldn’t be precious about what you write, and I stand by that. But that doesn’t mean you just say yes to everyone. What you will learn very quickly is how to suss out a good client from a bad one — they have some similar signs.
I have had extremely difficult clients, as well as dream clients. The difficult ones are that way generally for a few key reasons:
- They don’t actually know what they want
- They aren’t willing to really communicate with you
- They want a huge amount of effort and test work from you ‘as a trial’ before they actually hire you
These are pretty clear warning signs. If a person’s brief is vague and you ask to clarify, but they won’t or can’t, it’s going to be pretty tough to make that person happy. And ultimately, your worth as a freelancer is about satisfying your clients and securing repeat work. Simple.
Also be warned and mindful of those who demand whole swathes of ‘test’ or ‘trial’ work, which they aren’t going to pay you for. Really think hard about whether this is worth your time — every minute you give someone to free is time you aren’t getting paid by someone else. And while it can be worthwhile for a big name client, it’s often the small scale people who ask for this stuff, and mainly because they haven’t hired freelancers before or they’ve been burned in the past. So pay attention to how they treat you up front, observe whatever you can about them as a client. Will you have a good working relationship, or will it always be a struggle?
I’ve definitely been burned by shitty clients. I had one guy who asked me to write some basic copy, but with very few guidelines. I gave it a go anyway, submitted him something saying, “Please let me know what you’d like updated/changed, if anything. Very happy to discuss this further or submit another draft” and all that. But instead of giving me any further instructions, or the opportunity to change things, he just left me a bad review and moved on. A shame, because I was completely willing to meet his needs — if he’d just communicated them to me. But I should have taken the brief as a warning. He wasn’t willing to clarify it at the initial stages, and that just continued through the job itself. I learned my lesson.
The good news: is that you do start to pick up on the signs quicker, and you shouldn’t be afraid to ask questions — it’s easier as you get more confident. And when you do find a great client, you can establish an amazing working relationship that continues on for ages. I’ve still got clients today who I found in those initial stressful months of going freelance. Our working relationship is as satisfying, if not more so, than many face-to-face relationships I’ve made at conventional jobs.
Do NOT rely on one source for your work
This is something I am still struggling with, at times. I went back to full time work in 2017, but have maintained a few freelance jobs here and there to keep my toe in the water. Much of this work has come to me via Upwork. I have a lot of thoughts and feelings about this platform…
The first thing I’d say is that Upwork very much privileges the client over the freelancer. Do not imagine for a second that your rights and your dependence on the platform for work are the primary concern of the site. They only care about the people who are bringing in the payments.
I had a troll report me when I didn’t want to do their work (they showed about a thousand red flags in their request for my services — from wanting huge amounts of work ‘for free’ initially, to confused briefs, to being rather aggressive and rude in their messages, from the beginning). I politely declined the invite to interview further, but they still reported me for breaching Upwork terms and conditions. I’m not sure how this even worked, because nothing that was exchanged was a breach.
Upwork did not waste a second, though. I was suspended from the site for ten days. Now, when you’re relying on a platform that way, ten days is a huge deal. I was beside myself. I’d been applying for work every day as much as it is possible to do so; suddenly, all was silent. Upwork would not explain what had happened, they wouldn’t have any discussion with me. It was a complete shut down. I couldn’t do anything. I suspected it was that troll client who reported me, but I honestly don’t know for sure. I had 4–5 other clients on the platform, all of whom were really great and happy with what I was doing for them. So it seemed likely that the one grumpy, red-flag-waving client was the source of the problem. But the point was that nobody would talk to me about it. Nothing was clear.
The good(ish) news: Eventually my account was restored to me. But I knew from then on that Upwork was not a safe place for me to be a freelancer. With no rights at all, and a very volatile and client-focused attitude, freelancers are not protected. Relying on one platform to the exclusion of all else is a dangerous way to be a freelancer. Diversify as quickly as you can — use other sites, use emailing, get a website, put your name out there. Get clients in as many ways as possible.
Get your mental health in order first — have some airtight coping strategies
I went freelance with no support, and this is really not the way to do it if you’re also struggling through mental health issues, which I very much was. I’d been in the longest and worst bout of depression of my life in my old job, so while abruptly going freelance did feel like a huge relief and an improvement, it also wasn’t exactly a fix. I was still incredibly volatile, quite depressed and without a proper support structure.
The thing about freelancing is that you immediately lose access to any services an employer might offer you in the realm of health. Luckily, living in the UK, I had some free health services I could access. I signed myself up for counselling as soon as I went freelance, and while it wasn’t the most effective treatment I’ve ever received, it did meant that I started to develop coping mechanisms for what was going on in my life. I had a lot of pressure on myself to get work, to make writing a career, and to live in a really awful place without losing my mind. It absolutely tested me, to the very edge. Never have I felt as alone, desperate and erratic as I did in those first months as a freelancer.
The good news: If you take the time to make sure you’re ready — not just financially, but mentally — for the world of freelancing, it can be just the thing that frees you. I personally have never done well in a very traditional working environment, so it was wonderful to shake this off at last. But with a few more support structures in place (family, friends, a partner, whatever), all of this is a hell of a lot easier. I did it, and you definitely can too.
A few final thoughts…
The thing with freelancing is that the whole thing is very squarely in your hands. It is 100% up to you to make things happen. It can also feel like it’s all completely on you if it doesn’t happen. And in some ways, that is true — you have the power to direct the course. But only if you are ready to work harder than you ever have, if you’re ready to throw yourself out there and face a lot of rejection, can you have the freedom of the freelancer lifestyle.
Be sensible about this. Not everyone is made to work this way. There’s nothing wrong with taking a hard look at yourself and concluding, “Actually, I need structure. I need a boss to tell me what to do. I need peers in close proximity.” Etc. There are a lot of very nice things about a conventional office environment, not least of which is stability. Freelancing can get lonely. So if you’re going for it, do whatever you can to get ready. Because trust me: it will test you. You will learn the hard way.
But I made it work and I did basically everything wrong up front. I was in no way prepared, and completely on my own. I still managed to do it. And no, I didn’t make the big bucks. But I made enough, I survived, and eventually I found a job I actually really love — freelancing gave me the time and space to bridge that gap, to find something right.
And next time round, I’ll know exactly what to do.