5 Pros and Cons to going freelance

pros and cons of going freelance

Last month, I was honoured to pick up a Freelancer of the Year Award.

As I lay in bed, slightly drunk, I reflected on my freelance ‘career’ – where it had started, how I did it and how I still do it.Ever since I was a kid, I didn’t want to work for anyone else. I wanted to do my own thing. You may feel the same.For years, I worked in crappy call centres, kebab shops, and on high streets, trying to sell AA breakdown cover.

I eventually got into teaching but walked away from that because I didn’t quite fit in. In fact, I didn’t quite fit in any of my jobs and that’s why in 2010, I was sacked for the first and only time in my life.I hadn’t done anything wrong. They’d had it in for me from the start when I told them I’d rather work in a different department. They fired me because I hadn’t booked enough meetings.Now this isn’t a sob story. In fact, it’s the very brief story of how I became a freelancer.

It was as I was actually getting fired (by a small woman with tiny teeth and tiny feet) that the penny dropped and I knew that I didn’t fit anywhere in the world of work. I knew that I had to do things my way.Over the last 8 years, I’ve learnt a lot about being a freelancer and if it’s something you’re considering, I’ve made a list of the Pros and Cons of doing it.Firstly, the bad news:

The Cons

1. You need to be self-disciplined. Without anyone giving you specific instructions, you’re going to need to be both your own boss AND the employee. By that, I mean that you have to plan your days and weeks, and then work them as if you’re working for someone else. If that makes sense. Before you start your working day, make a list of three important things that need to be done. Do them before you do anything else in the day. You’ll achieve more and feel better.

2. You need to be organised. When I first set out in the world of freelancing, I was very disorganised. Get yourself a diary, a planner – anything that you can plan with. Try and structure your weeks, days and hours. Give yourself breaks and try and work to your body clock as best you can. In terms of your actual work, make things easy for yourself by labelling files correctly and saving them in the correct place on your computer. It’ll pay dividends when you’re looking for a file later on down the line. Keep your email box as clean as possible.

3. Going in cold turkey can be a shock. If you are wanting to step away from the world of ‘real’ work into freelance, you may want to set something up on the side and build it over time. There will then come a point where you’ve grown your freelance work enough to step away from your day job into the job you want to do.

4. Your social life will disappear. Working for yourself will mean that your work is constantly on your mind. That’s because the buck stops with you. There’s a real chance that you could turn into a workaholic, and feeling guilty about not working is a very real condition (I can vouch for that!)

5. Don’t expect overnight success. It can happen but it’s very rare. Focus on doing a good job for everything you do. Quality will always show and remember that you can’t do it all at once.

Now for the good news:

The Pros

1. You get to pick your days (or weeks!) off. No more putting in holiday requests or hoping that someone else can cover your time off. You also get to pick your times of work. Now that’s great!

2. There are no limits. When it comes to freelancing, the sky really is the limit. There are obvious time constraints but if you’re consistently providing quality work for customers, the financial rewards can be huge – and once all your costs and taxes are taken off, it goes straight in your pocket – not into the bank account of some faceless multi-national.

3. You become an expert in your field. People will pay for your expertise and the more you do what you’re good at, the more of an authority you become.

4. You get to take all the credit. When things go well, it’s because of you.

5. No crappy uniforms!


As with anything, there are Pros and Cons to working for yourself but one thing that the majority of freelancers say is that they’d never go back to working for someone else. There are very good reasons for this and that’s because some of us are free spirits who’d rather enjoy the freedom, the integrity and the financial rewards of freelancing. If you are thinking of becoming a freelancer, pick something that you enjoy, start small and grow it alongside your current job until you’re good enough and successful enough to do it full time.