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Greg Dillon interviewed for Freelancing Matters

Strat-Talking’s founder, Greg Dillon, was recently interviewed for PCG’s national magazine, Freelancing Matters. In the interview he speaks all things freelance, setting up the business, motivations, highs and lows. Full transcript can be read here:

Below is a full screenshot of the article for you to read, with the transcript underneath.

greg dillon



Greg Dillon is a freelancer, a serial blogger and also happens to own London based Brand Strategy Consultancy GD Inspires. Since embarking on his own freelancing journey and starting up alone three years ago, he gave us his honest, and if we say so, rather refreshing view on his own freelancing story.

So tell us about GDInspires, and what ‘inspired’ (excuse the pun) you to venture into working independently. 

In a nutshell, we inspire great design for brands globally across a number of markets, including Sports, Leisure, Retails, Automotive and Alcohol.

I always wanted to set up on my own, and was probably influenced by my dad, who was an entrepreneur-although I took the leap a tad earlier than expected.

Throughout the recession I was a little unlucky-but who wasn’t I guess? I joined successive businesses that were forced to make redundancies, and after working as a branding strategist for five years, my view on the world and the jobs market in particular changed.

I wasn’t keen on moving around companies to rise through the ranks, so I decided to take the bull by the horns and set up on my own.

If I were to sum it up, it was a combination of always wanting to start out alone, knowing that it was very achievable and being bored of redundancy. 

Do you think that there has been a change in the way people view working for yourself over the past ten years or so?

In short, yes. I think we are moving towards more of a ‘freelance nation’ whereby a large proportion of the workforce will be freelancers who are happy to trade the security of fixed employment  for higher short-term fees and the ability to be flexible and work on their own terms.

Attitudes towards freelancing have definitely changed too, there’s no doubt about it. Companies both agency and client side are a lot more open to the idea of hiring freelance help and know that buying in expertise for shorter periods of time as and when needed, they can get the job done a lot more effectively and efficiently.

I really believe that a lot of the time, it’s the fresh eyes and that get the job done more better than internal resources who have company politics and baggage to deal with-but I suppose I am biased after all. 

You give off the impression that you’re genuinely passionate about your subject, which is refreshing-how important do you think this is?

It’s essential. I have a real thing about smiling on the way to work – if I don’t like a project, job or the people I’m working with, which does happen from time to time, it really affects me. I love what I do, so dwell on things a bit much if elements of my working life are not perfect.

As soon as I recognise the early warning signs I seek to change the situation, I’m a lot braver about ensuring I’m doing what is best for myself as well as the project and the client. It took a while to get there as I started off wanting to be all things to all people, but I learned that you have to make sure you are looking after yourself.

If you aren’t happy and passionate about your work, it’s simple, you won’t get the best results.

It’s fair to say that freelancers often struggle find a healthy balance between their work and personal lives. How have you managed this?

At first I found it really hard to juggle everything, but I think that’s only natural. When I started out I desperately didn’t want to turn down any contracts, even if I already had a couple underway, for fear of not knowing when the next person would knock at the door. 

It’s a bit of an art to be able to juggle client requests, hold conference calls across multiple time zones and also fly to meetings all over the world whilst staying sane – and of course not upsetting the home life.  

At one point in 2012 I was running four rebranding projects for three design agencies in three different countries. I was flat out, but somehow managed to deliver each one successfully. Whilst in the middle of these four projects I also had a lot of personal commitments, namely my gorgeous fiancé that was sadly not getting enough of my attention!

Although you’ve only been a freelancer for three years or so, what advice would you give to someone considering starting up alone?

Make sure you’re brave, hardworking and ambitious because you literally cannot enter freelancing without giving it 100%.

I wouldn’t advise venturing into freelancing until you have a relatively stable contact base that you can email and can email and say ‘hey, got a gap in my schedule, need any support on any projects?’ when you need to.

And for sanity purposes having side projects are a good way to spend down time and also to build your personal brand too. I run a blog for strategists and branding professionals called and another blog for creatives called

Aside from the investment in time needed to start-up, some people are put off by the initial cost-so would you say it’s been worth the investment so far?

Completely. For me personally, the start-up costs weren’t too high, but that obviously varies depending on what your service is.

The main concern was ensuring I had enough cash to live off in case I didn’t land the first few contracts. Fortunately I have not been without a contract for more than three weeks since I started freelancing so have rarely panicked financially.

I also use a percentage of income to fund online business initiatives such as the blog I mentioned. I suppose this is a ‘play thing’ but with the ambition to grow it into something I can make money from. 

To finish, and perhaps to inspire a few potential freelancers to make the step into independent working, how about a few of your favourite aspects of being a freelancer?

I’m able to work across multiple projects, and I’m never unchallenged and bored at work, ever. I’m lucky enough to work with inspirational people every day, which is something I won’t ever take for granted.

Working from home is not a problem, and the flexibility that freelancing brings is second to none. I’ve also learned how to run a business, which has helped me understand my clients’ needs on a whole new level.

I’m in charge of my income and rates, and I can work as much as I want, and able to (sometimes) maintain a healthy work life balance, and enjoy my time off. For example I might spend nine months working flat out, then dedicate the remaining three to side projects and to have the odd day off to relax.

To sum it up, the benefits of working for yourself completely outweigh and perceived negatives.

Bio: Greg is a freelance brand strategist working with brands and agencies all round the world, he is also the author of, a website aimed at giving advice and insight to new, existing and veteran freelancers as well as commenting on all things branding. Feel free to email him at: or follow on Twitter @StratTalking

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About GregDillon

Greg is the founder of strategy consultancy GD | Inspires and spends his days strategising for various design agencies and clients around the world - see more at He is also a prolific entrepreneur having launched - a website aimed at giving advice and insight to new, existing and veteran freelancers as well as commenting on all things strategic. Feel free to email him at: or follow on Twitter @StratTalking

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