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Freelancing: The Art of Starting Out

Greg Straight

When is the right time to leave your job and start freelancing? What is it like being self-employed without the safety net of regular wages? GSM talks to kiwi illustrator Greg Straight to hear his story…

Greg Straight illustrator freelancingI started drawing when I was really young. So you could say I’ve been illustrating for 49 years. However, getting started as a commercial illustrator was hard. My wife Hannah and I met in England where we did pretty well in our respective creative fields. I was actually freelancing by the time we left the UK in 2006.

Arriving in New Zealand, we bought a small house in Glenfield and shortly afterwards, my daughter Chloe was born, To provide security for my family, I traded-in freelancing for a full-time design position. Although it was a design gig, it was mostly tee shirt and apparel artwork. Not particularly inspiring. I was doing it to pay the bills but after seven years in the role, I needed something more creative. So, I started moonlighting with freelance projects.

My boss at my day job was really understanding. He allowed me to cut back my hours to accommodate this. At the time, Chloe was very young so I’d draw while she slept and then play barbies and my little pony with her in the afternoon—my wife Hannah would do the morning shift. Hannah and I were often like ships passing in the night. I was like a zombie at my full-time job, surviving on strong coffee and chocolate bars! But eventually, I gained enough traction to quit my day job. I’ll never forget that day. For one of my first Instagram posts I wrote the words ‘I Quit’ on a post-it note. It felt so good. I’ve been self-employed ever since.

Getting Noticed

To gain exposure, I exhibited extensively at galleries and cafés throughout NZ. I also got numerous design stores to stock my work. Being prolific on social platforms like Facebook, Dribble, Instagram and Pinterest was also important. Basically, I just pestered people by emailing my work to anyone and everyone… I’m sure I was pretty annoying at times.

At one point I made a bunch of postcards with my designs on the front which I took to Semi-Permanent and plastered everywhere. I even put a bunch in the loo. Everyone snapped them up, thinking they were something to do with the event. And of course, the postcards had all my contact details on the back. I tried to get my work into magazines, and as a result, ended up designing quite a few covers. I approached people to be on their blogs or podcasts.

Pretty much, I did anything to get noticed. For me, freelancing was everything, the thought of another 9-5 job going nowhere was highly motivating.

Freelancing & Recognition

Greg Straight freelancing workAs an illustrator, especially in the beginning, you don’t always get recognition for your work or paid what the project might be worth—a lot of what you do is about getting known. My first big breakthrough happened when I created an illustration for a limited edition golden syrup collector’s tin for Chelsea Sugar. The agency won an award at the Best Awards with this project, and I was a listed contributor.

Westpac Tui

Also, around this time, Westpac used my Tui at Dusk artwork on the front of one of their Eftpos cards, and this had my name on the reverse—I was slowly getting more exposure.

Kia OraThen a few other things happened. I got the cover plus an article in Air New Zealand’s Kia Ora Magazine and created some desktop screensavers for Microsoft (that I never got paid for). I ended up donating these to Greenpeace. The original artworks were downloaded over 2.5 million times. I often wonder what life would be like if I had a dollar for each time someone downloaded them…


Beyond Aotearoa New Zealand

I used talent agents—International Rescue and The Pond—for a while, before deciding to go solo for all NZ work. So now everything comes directly to me. I still use an agent, Illustration X, for all overseas work. I’ve been with them for about three years during which time I’ve produced work for clients in Germany, France, Australia, England and USA.

Words of Wisdom

My advice for young illustrators is to:

  • work hard,
  • find your unique voice and style,
  • do what you feel is authentic for you,
  • take notice of trends but don’t get too caught up with what’s hot.
  • Do your own thing, stick at it, and it will pay off.

Freelancing & Life Balance

I think it’s important for young creatives to know that if you want to get somewhere, you have to work really, really hard. It’s never going to fall out of the sky into your lap. Keep drawing and sketching ideas on paper. But also, find some balance, take breaks and go for walks. Get away from your computer.

There can be a lot of late nights and pressure in the design industry, demanding clients and crazy tight deadlines. Combine these with cash flow issues, and you can see how easy it is to burn out or get a Repetitive Stress Injury (RSI) or other health issues. You have to look after yourself. Good Luck!

Freelancing Projects






My favourite illustration work for print is the packaging projects I’ve completed recently. The Bluebird chip packets from about a year ago were pretty cool. This project was a colab with Auckland agency Raydar.

Freelancing Oku TeaFreelancing Good Buzz

Also, the work I produced for Oku Tea and Good Buzz were lots of fun.

Freelancing McDonalds

The two McDonald’s summer campaigns were pretty amazing as well. Seeing your illustrations inside their stores on everything from bags, boxes, murals, posters and on TV ads was a trip.

Greg Straight


And of course, in addition to generating income from my commissioned work, I have a large catalogue of kiwiana designs and prints for sale through my online store.

GSM would like to thank Greg Straight for collaborating on this article.

This article was originally published in GSM18. To read this, and other great articles, purchase this issue here.