Three lessons from three years as a freelancer

This time three years ago I was sat sipping coffee in the sunshine on the Isles of Scilly, enjoying my first taste of freelance freedom and being able to work anywhere.

As a first week of being freelance goes, it was pretty eventful. My flight home was cancelled thanks to thick fog but it didn’t really matter. I could stay a few extra days, I had my laptop and I could quite happily work from wherever I happened to be. I’m not going to lie, it was a brilliant feeling.

So how did I get there and end up writing an article for a Swedish software company from a beach in the Isles of Scilly? (Important caveat: I actually hate working outdoors and especially on a beach, and this isn’t going to be one of those ‘look at my amazing lifestyle’ posts.)

A former boss once told me I’d never fit in to a company structure. He meant it as a compliment and I took it as one. Because he was dead right. Let me give that some context. I’ve always tried my best to be good at what I do (what’s the point in doing a job if you don’t want to be good at it?) but a mixture of being too eager to say ‘yes’ while having strong opinions on how things should be done meant, no matter how much I loved what I was doing, frustration was never far away.

So, a little over three years ago, I decided to put my money where my mouth was and took a leap of faith. People around me assured me I’d be fine going it alone but that doesn’t mean it wasn’t a risk or I wasn’t worried about it (especially when two weeks into freelance-life we found out Gracie was coming along!). And there were worries – the first and foremost one being will I be able to find enough work to make a living out of working for myself?

Fast-forward three years and what a journey it’s been. I’m not going to say I shouldn’t have been worried. Yes, I’m in a great position now where I work with amazing people, from all around the world, and my diary is fully booked for the foreseeable future. But, in work and in life, I try not to ever rest on my laurels or take anything for granted. I want to get better at what I do. I want to keep learning. And I want to help people by doing the best job possible I can for them.

The worry and the fear are still there. I think it’s a good thing. They keep me honest and they keep the quality of my work high. What’s more important is I love my job. Yes, there is stress. Yes, there’s multiple different people to keep happy at one time. Yes, there’s an element of uncertainty. And yes, it’s hard to ever take time off.

But, do you know what? I wouldn’t change it for the world. I’m not an entrepreneur, I don’t run my own business and I have no desire to grow by employing people. At heart, I’m a storyteller and I help people tell their story by creating content – mainly words but videos, emails, social media and websites too. It ticks all my boxes.

And if I want to take a day off to spend it with my two year-old daughter (and lovely wife) I can. If the sun is shining in Cornwall and the beach is calling, I can usually drop tools and get out there.

I said this isn’t going to be a ‘how I ditched my job, doubled my income and only work 4 hours a week‘ post (although I do enjoy Tim Ferriss’ content). And it’s not. For one I definitely work a lot more than 4 hours a week (mostly). People who are thinking of doing a similar thing to me ask for advice on how to do it all the time. So, what I’m going to try and do, is give three pointers on the most important things I’ve learnt in the three years I’ve been freelance.

And look, other than living and breathing it, I’m no authority on this. There’s plenty of people out there who profess to be experts. I don’t. I’m just someone who works hard and tries to do his best. However, I do know plenty of people who’ve tried to be successful freelancers and haven’t made it. So I’m hoping this might help some people out there, but please take with a pinch a salt…

1. Be disciplined

With great power comes great responsibility. It’s easy to get caught in that heady rush of freedom, of being able to work anywhere at anytime, of not having to be in an office for a set time. To start with, this is a pretty strange feeling but one of the things I love is having control over my time. However, you must be disciplined with it. Not just your time but with managing your workload, delivering projects on time and knowing what needs to be done on any given day.

I use a system of TrelloEvernote and Harvest to manage my workflow. I also use Google Drive for everything. Doing this means I always have full visibility of the work I need to do. The next thing you have to do is actually get the work done. Find what works for you but find your way of working quickly – then be decisive when it comes to prioritising what needs to be done and when.

I mentioned the lifestyle perks above but it becomes much easier to enjoy them if you have strong discipline when it comes to your work.

2. Help people

This sounds pretty obvious but you’d be surprised at how many freelancers forget this. As a rule of thumb, people come to you as a freelancer because you can do something they can’t, you provide a resource they don’t have and they need you to help them.

So do just that. Make life easy for them. Deliver great work, deliver it on time and show your value. Because, once they see the value you bring to them, the chances are they will want to carry on working with you and they’ll recommend you to others. Be brilliant and the rest will look after itself.

3. Love your craft

I can’t stress how important this is. You have to love what you do or else it’s never going to work. You’ll find countless articles out there telling you that all you need to make it on your own is drive and hard work. Absolutely, these count for a lot. But they mean nothing without talent and a love of your craft. You have to be good at what you do to be successful at it. So practice your craft. Whether you’re a writer, designer, photographer, videographer or a consultant, love what you do, hone your skills and always want to get better at it. If you don’t want to do this, stick to the 9-5.

And finally…

It’s not the life for everyone. What I’ve found is it’s definitely the life for me. The other thing I’d stress is being patient – it took me the best part of a decade of solid graft for a number of different companies before I took the leap. Without that experience behind me, there’s no way I’d be where I am now.

The last thing I’ll say is, if you really want it, then absolutely go for it. It might not work out but if you don’t try, you’ll never know. And if it does work out, you’re in for a real treat.

If you want to pick my brains on life as a freelancer (especially if you’re a writer or a content creator) I’d be more than happy to help. Drop me a line on