10 lessons from five years of freelancing

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This week is an important landmark for me – it’s been five years since I gave up my job and went freelance. Before that I’d been working in London for almost 10 years. I had a job and a company I liked, but couldn’t shake off the bored and restless feeling, so decided to see if I could make a go of it myself. And somehow I’ve made it through five years! So to mark the occasion I’m diverging from my usual travel talk to share 10 lessons that the last five years have taught me – whether that’s been the easy way or the hard way – about freelance life. As nowadays more and more people go freelance, sharing tips and discussing this style of working would get you many plays. To connect with your niche audience faster, buy spotify plays.


Being great at what you do isn’t enough to make you a good freelancer – your personality type is just as important. You might be a copywriting genius or a world-class photographer, but if you’re the sort of person who needs to be managed and told what to do, likes to work regular hours or stresses out if they don’t get paid on time, then freelancing probably isn’t for you. You need a certain type of personality, with enough motivation not to waste the whole day watching TV but enough discipline to switch off so you don’t end up working 24/7. A laid-back temperament with a dose of ‘something will come up’ optimism is useful too when a project falls through at the last minute or another client ‘forgets’ to pay.


It’s rare for a freelancer to do just one thing. I call myself an editor, proofreader and designer, but even that mouthful doesn’t cover all the work I do. I write copy for a travel company’s blog, I create websites, I sell posters on Etsy. I’ve even painted a mural of life-sized people onto the wall of a doctor’s surgery. I definitely can’t say it’s boring! I said yes to pretty much every job I was offered when I started out. But over time you learn what you’re good at, and just as important you find out what people are looking for. It might well be that it’s not what you expect, or that your hobby or sideline ends up as part of your work – like blogging has for me. When I started this site it didn’t even cross my mind that I could actually make a business from writing about my travels, but five years on it’s become an important part of my work.


In my web design sideline I’ve met lots of people about going freelance or setting up small businesses. Normally the first thing they want to do is set up a flashy website, but – at the risk of putting myself out of a job – they don’t necessarily need one. One guy came to us wanting an all-singing, all-dancing, super-pricey website with CRM system, forum and shop when he had no clients and hadn’t made a penny from his business. If you work in the digital world then it’s important to have a web presence, but generally a basic portfolio site is all you need to start, then you can add to it if you need to. Same goes for flashy logos, stationery and brochures – start with a big pile of business cards and see if you need the rest later.


If you’ve spent years working for a monthly pay cheque, getting used to the unpredictability of freelance income can be a bit of a shock. Some months you’re splashing out on Champagne (ok prosecco at least) then the next month it’s back to student-style instant noodles. Freelance work often seems to come in waves, so you’re either rushed off your feed or twiddling your thumbs. And even if you manage to space your work out perfectly, then there will always be clients who pay straight away and clients who you have to remind five times before they’ll pay up. Although I have to fight the temptation to blow everything I earn on travel, saving in the good months so I have a financial buffer makes things far less stressful.


As we’re talking money, I’ll admit I don’t make as much now as I did when I worked full-time in London. One year I nearly did, but then another was more like a third. But I don’t think many people go into freelancing to get rich, it’s the flexibility that makes it so attractive. Where and how I work is up to me – as long as I get my work done there’s no one to tell me how to do it. You can do four 12-hour days then head off for a long weekend, or work nine months of the year and travel for the rest. You can start early then have a long lunch with a friend, or spend your days working from a laptop in a beach hut in the tropics. However you choose to use it, having that flexibility is worth so much.


The flipside of flexibility is that if you can work anywhere and anytime, then it can be hard to switch off. I’m guilty of spending the evenings with my laptop – just finishing a bit of work off or just catching up on social media. Then before you know it you realise the day’s over and you haven’t moved from your computer screen. Freelance work can be unpredictable so the natural instinct is to say yes to every job you’re offered, just in case you never get asked again, and when you’re on your own there’s no one else to delegate to. But you need to make time to do other things – to see friends, to go for a walk, to read a book – or you’ll end up burnt out (I still struggle with this one though, so anyone who has tips please share!).


When I started out there was one thing everyone kept telling me I had to do that was guaranteed to bring me out in a cold sweat – networking. I had images of awkward small talk over warm glasses of white wine as people tried to ‘sell themselves’ whilst being very British and embarrassed about it. But I did go to a couple of events and gave it a go, and while it wasn’t as bad as I imagined, it wasn’t much use either. When it comes to advertising your services, the best network you have is your friends and family. The people who know you as well as knowing what you do. So much of my work has been through referrals – those ‘oh I know someone who does that’ recommendations count for much more than any networking event.


Finding new clients is tough – for every new job there are a whole host of hungry freelancers out there competing for it. Which is why repeat business is so important. If you’ve already shown someone that you’re reliable and good at what you do, then they’ll remember you when the next project comes up. Most of my business comes from repeat clients now, and in some cases when people have moved jobs I’ve ended up working for the new company as well as the old one. It’s a win-win – you don’t have to keep searching for new clients and the company doesn’t have to spend the time and effort finding someone for each project. Meeting deadlines, being easy to work with and doing good work is your best advert.


If your work is creative, at some point you will have a client say “my friend/child is a web designer/has a GCSE in art and can do it in a couple of hours”. And to them I say – off you go then! (if you ever think you have it bad just check out the brilliant Clients from Hell). Pricing your work is one of the hardest things about freelancing. There will always be someone cheaper – and more expensive. Check out industry websites and groups, do your research and pick a price you are comfortable with. Pricing is an ongoing process and if you get to the point where you have plenty of work or everyone says yes to the prices you’re quoting, then it’s time to put them up. And sometimes you’ll come across a job or client that saps your enthusiasm and energy so much that it’s just not worth it, however much they’re paying.


When I was deciding whether to give up my job, I thought about what the worst case scenario would be. If it all went wrong, if I was useless at running a business and no one would hire me – then I would have to get another job. So for the first couple of years I kept my CV updated and an eye on the job ads, until I got used to this being the new normal. But there were a few things that helped me when I started out. I had no mortgage, no debts and no dependents. I moved out of London so my living costs were lower. I had enough savings to keep me going for a few months. I stayed on good terms with my old company. Somehow this mix of luck and preparation came together – and fingers crossed it’ll stay like that for a long time to come.

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About the Author: John David

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