Five lessons from five years freelancing

This week, I’ve been invited back to the University of Southampton to speak at the end of the 12th annual Dynamo Enterprise Challenge. I attended the very first event in Winchester as a student in 2006, and I’ve been asked to share some of the lessons I’ve learned since then.

It’s timely as I’m also currently reflecting on half a decade of freelancing. This time five years ago, I had handed in my notice and started the process of establishing my business.

Here are five of the many lessons that freelance life has taught me:

1) Take the time you need to define your offer


Like any product, it’s hard to market yourself if you’re not clear about exactly what you’re offering, but it’s ok to take time to carve out your niche. Find interesting projects that take you out of your comfort zone and teach you more about your strengths and what you enjoy.

I came to realise that what I was really interested in was how organisations change and develop new initiatives, and the best thing that I could offer a busy and harassed project manager was to completely look after their communications, giving them one less thing to worry about.

2) Expect setbacks

Setbacks are inevitable, but as a small business you’re well placed to adapt rapidly.

I had two very clear avenues of work that I wanted to explore when I first went freelance. Neither of them came to fruition.

My contacts said ‘Let’s keep in touch!’ and ‘Let’s work together again!’ when I first started on my own, but the reality was that many of them didn’t have the time or budget to take the intention forward. But I got back up and carried on.

3) Know your price

The question I hear more than any other from new business owners is: How much should I charge?

The vast majority of new freelancers that I’ve come across have been undercharging.

I learned the hard way that it was easy to negotiate down, but much harder to put your prices up later. After a year, I worked out what my time was really worth by benchmarking against my peers and working backwards from my desired income.

There are always interesting projects that I’m happy to make an exception for, but I assess these as and when they come along.

4) Manage your time

You might be conditioned to 9-5 life, but that doesn’t mean that’s when you’ll be at your most productive or your most creative.

If you’re at your best first thing in the morning, or your creative juices are flowing at midnight, freelance life can give you the flexibility to take advantage of this.

While I might find that there are some weeks when I’m working unusual hours Monday through Sunday, one of my priorities starting up on my own was balance, so I’ve actively made sure that there’s plenty of time for the other things that are important to me: Travel, home life and involvement in my local community.

5) Use that freedom to design your future

So, what else to do with that valuable flexibility?

The chances are, if you’ve started freelancing early in your career, you probably have a few other roles ahead of you – however much you might enjoy what you’re currently doing.

Set-aside some of your time each month to start experimenting with your other interests. Want to write a book? Why not start with a blog first? 

Dave Evans from the Stanford Design Lab outlines a helpful way to approach this

Going freelance gave me the freedom to pursue one of my other passions, enterprise education, and this subsequently developed into a completely separate sideline.

That’s just five of many lessons. I’m always keen to hear from fellow freelancers, and to chat to people who are thinking about starting up on their own.