I had a lot of mixed emotions when I went freelance in 2017. Fear was the main one. It was a sort of bone-shaking terror that I was about to fall into an abyss of Dickensian poverty. Then there was an exhilarated trickle of freedom that crept in. It felt a little illicit, as though I was bunking off school. It came paired with an idealised imagining that I was about to be Carrie Bradshaw, cappuccino and laptop in hand, running around London in shoes I couldn’t afford, getting book deals and $4 a word at Vogue.
You see, the free part of freelancing is equal parts tantalising and distressing. The freedom is undeniably great. There is no boss breathing down your neck, no strict mores of a 9-5. You can carve out your own workday, your schedule, your timings: what you do and, largely, when you do it. Yet for every coffee shop writing session there is a panic over a tax return or the endless chasing of a late payment. Freelancing can often feel as though you are actually doing it for free, when the biggest challenge of your career is justifying why the central tenet of commerce applies to you.
There are about to be a lot more of us in this complex situation. Statistics show that the self-employed are the largest growing work demographic in the UK, with approximately 4.33 million self-employed people in the United Kingdom in the three months to March 2021. Estimates show this may only grow following mass job cuts during the pandemic. While I left my 9-5 in 2017 willingly, to start a new chapter of my career, it seems a growing number of those now in self-employment are unwilling converts to this life; victims of the Covid-19 economic recession.
So, what to do if that’s you? Or, if you have always dreamed of the freelance life but have no idea where to start? Let me (and some very qualified experts) be your guide.
Expectation vs Reality
“I had an idea of what freelancing would look like,” says Anna Codrea Rado, a freelance journalist, podcaster and broadcaster. “I thought freelancing meant that I'd just get to do the work minus the politics, but the politics have just been replaced with an endless stream of admin." Codrea Rado is also the author of one of the best books I’ve read on freelance life, You’re the Business: How to Build a Successful Career When You Strike Out Alone. We discuss the sheen of freelance life – the shiny, coffee shop mirage that belies a frantic underbelly of knotty admin and a rather destabilising emotional toll – and how ill-equipped most people are for its reality.
“We are mostly presented with only one way of working and that is in an office for a company, so there isn't really much visibility of what freelancing is actually like,” she explains, adding that this is worse for those – like her – who fell into freelancing through redundancy. “If that’s the case, I think the most important work to do is untangling your self-worth from what you do. It's important to understand that you might have been made redundant, but that doesn't mean you're a redundant worker. You will need that self-belief to succeed as a freelancer, so it's key to realise that, in 99 per cent of cases, your redundancy has nothing to do with how good you are at your job.”
Hunt for payment
If there is one immediate downside to freelancing, this is it. Never will you feel so nostalgic for the simplicity of your pay slip. The dire nature of any industry’s treatment of freelancers is gradually being brought to light and tackled, through amazing advocacy groups such The Freelancer Club and Codrea Rado’s own campaign #FairPayForFreelancers.
I myself am currently waiting on payment for a piece I wrote in October. It joins a still-unpaid piece of work I did in 2018 for a national newspaper and an entire project I worked on for a fledging brand in 2017 for which I was ghosted in lieu of payment. Sound mad? Welcome to the everyday reality of being a freelancer.
“I didn't realise the mechanics of getting paid would be such a problem,” Codea Rado eye rolls in exasperation. “It creates what I think of as the emotional tax of freelancing - not only are you not being paid on time, but then you're also having to chase late payments which is really draining and emotionally gruelling.”
“It comes down to an image problem with freelancing which is particularly very acute within the creative space,” she continues. “People feel you should be so grateful that you get to do creative work. And then on top of that, that you get to do it from home, so therefore you should be not paid and or treated badly. I don't really see how the logic follows.”
My advice would be to always state clearly on your invoice that you expect payment within 30 days. I typically begin chasing a week after that 30 days is up, just to "check in". The process is laborious but necessary. You will be unwaveringly polite throughout and, yes, you will increasingly sound like a desperate person who has been ghosted after a great first date. But money, unlike your dignity, is essential here.
Run the numbers
Beyond preparing yourself emotionally for this assault cause, you obviously also have to be fiscally savvy. “There's lots of literature about how to be a compliant freelancer and how to do your tax return, but not how to develop your skills, learn how to price your time or how to find clients,” says Alison Grade, of why she wrote The Freelance Bible and founded Mission Accomplished, a consultancy that helps start-ups and small businesses mostly in creative fields.
“You have to go into freelancing mitigating risk in the best way possible,” she explains. “First and foremost, you've got to run the numbers. Ask yourself how much you need to live on and how that translates when you are paying taxes alongside your annual turnover. Don't assume that you're going to be working 365 days a year, I like to work on about 120, which is 50 per cent of 48 weeks,. That accounts for two weeks off for Christmas, a week off for Easter, and let's say you take one other week, that's 48 weeks. So, if you can make the book balance on 50 per cent of that, then we've got a fighting chance of hitting it.”
Be your own CEO
It may not feel like you are running a business when you are chasing payments in your pyjamas, but you really are. As corny as it sounds, you really are the business now. “There is no HR department in freelancing,” laughs Grade. “You have to start taking on all those issues yourself; you've got to be the CEO of your own career.”
“Anyone who wants to freelance can freelance, but you need to accept that there is always going to be a business side to working for yourself,” agrees Codrea Rado. “Even if you are a freelancer who is a sort of one person operation, there's no getting around the fact that you're going to have to market and sell and do your admin. Learning that stuff is 100 per cent doable and possible for anyone who actually want does want to do it.”
In order for much of this to happen, you have to massively believe in yourself. “You're going to have that little devil on your shoulder going: ‘It's not going to work, you're not going to do this, go and get a real job’” says Grade. “You have to ignore that and have faith in yourself.”
Use your network
When I made the decision to leave my job, one of the first things I did was physically write down all the contacts I had made over my then five-year career in journalism. There was something about the act of writing them in – yes – a little black book, that made it a tangible network. ‘It’s all about who you know’ can feel like a grubby, nepotistic phrase, but it isn’t when these people you know are those you have connected with on your own merits; people you have met, worked with and for. Networking is important, but even more so when you are a freelancer. These people – spread across the industry – are essentially your new colleagues.
"It's very easy to sit here in isolation and not talk to people," agrees Grade. "But actually, we've all got loads of people in our networks, and they might not be able to give you a job, but they may be able to open their address book and help you meet other people. It's about being open for business completely. And that's especially true as a freelancer when 90 per cent of the time you're going to be working by yourself."
There is also much camaraderie to be found within the freelancing community. “I have found other freelancers really have your back in a way that actually I never really felt like colleagues in an office working environment did,” says Codea Rado. “That has been unexpected but amazing.”
Look after your mental health
When your self-worth becomes inevitably tied to your work, what happens when no one wants your work or, as is most common, when they refuse or delay paying you for it? The mental toll of freelancing is not just the impact of working alone. It is this constant state of rejection and the demeaning nature of begging to be paid.
“You need to put a bit of emotional distance between you and that late payment, not let it define you,” advises Codrea Rado. “The other thing is find a freelance buddy who is also in this kind of game, who you can talk to either about money issues or whatever it is that's going on in your freelance world. You need people around you who understand what it's like to do this work.”
“You have to really look after yourself, because so much of this life is about rejection,” says Grade. “But do not let that rejection stall you, accept that it is a reality of this work and just keep going. You should also find your own way of working. Tap into when you feel productive and go easy on yourself when you’re not.”
Never lose the hustle
I have occasionally cheated on my freelance life, got in to bed with a few rather sexy fixed-term-contracts and tried on career monogamy for a while. But I’ve never let my hustle stop. That’s the thing with freelancing. It demands a furious and constant agility to search for work and instils a mindset that everything is in flux. It's crucial for success.
“I see so many freelancers taking up even six months to a year-long contracts and getting complacent,” she says. “You have to remember that a fixed-term contract is not a guarantee of a permanent job. It’s so important not to take your eye off the ball and forget that, when the contract ends, you will be back out there looking for work.”
I suggest that it's a bit like continuing to train in the gym. “Absolutely,” Grade agrees, merrily accepting my metaphor. “It is about keeping in shape.”
Remember the world is changing…
The pandemic has undeniably changed everything about the way we work, but it has also had a profound effect on freelancers. Not only are there more of us, but perhaps a revised opinion on how we work - at home – which is now no longer radical.
“What's been really interesting about the pandemic for freelancing is that there is now a globalisation of opportunity, because, whereas before, as a freelancer selling my services, it was absolutely imperative that I would meet somebody, sit down, have a coffee face-to-face in a meeting room – now I can work with people anywhere in the world,” says Grade. “More so than ever, I can be working anywhere in the world as a freelancer; I've just got to find clients who value me.”
Codea Rado agrees and adds that, as our numbers swell, so does our voice. “We are now growing as a collective voice,” she says. “There are more and more groups of freelancers saying, 'I'm not going to work under these kinds of conditions'. There's been so much campaigning work around the fact that freelancers have been one of the worst hit groups of the pandemic. Now that that conversation has been pushed to the mainstream, it will continue and hopefully spark some change. I think we are slowly heading in the right direction.”
...and that freelancing really is great
Despite its pitfalls, for every stressful tax return (get an accountant) and for every late payment, I wouldn't trade freelancing in for the world; it remains my best career move to date. Too often we become wedded to a job and, by extension, the perception or value of us as defined by a specific workplace. For many people, this is not always a positive experience, nor one which stretches us to the upper limits of our potential. Freelancing can unlock this potential and allow you to define your self worth on your own terms. This was certainly the case for me, and the work I have done since taking this leap of faith has been fantastic. The benefits far outweigh the drawbacks. After all these years, it still makes me feel the way it did back in 2017 – terrified but exhilarated.
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