Jess Cruickshank

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Interviewed by: @Lachlan_type

Jess Cruickshank is a Sydney based letterer and illustrator, Typism alumni and one of the talented artists on the Jack Winter roster. She has taken the time to have a chat with us in regards to her work, how she got started and even a few tips for up and coming letterers.

Thanks Jess for taking the time. Can you tell us a bit about yourself and how you came to be focused on illustration and type?

I’m an illustrator and letterer based in Sydney, and I mostly create work for advertising and publishing. I’ve had an interest in handwriting since I was a child. Once I was in uni studying graphic design, that turned into an obsession with lettering, and I started including custom lettering in my uni assignments.

After uni, I worked in advertising, and discovered that lettering was actually a highly sought after skill for real commercial projects. I never thought too much about being an illustrator, but I’ve always been somewhat okay at drawing, so once clients started asking me for illustration to go with the lettering I just ran with it (and had to do a lot of drawing practice in my spare time!)


What was your journey into becoming a freelance creative?

I was working in advertising and not enjoying very much. On the side, I held my first solo exhibition, and people saw the work and started sending me lettering briefs. It seemed natural then to quit my office job and go freelance.

A lot of my clients now are in advertising, so it definitely helped to have some experience in that industry. While in advertising I also ended up doing quite a bit of lettering in-house for some big name clients, so I was able to walk out of that job with a half decent portfolio (and looking more experienced as a letterer than I really was!)


Who or what were the biggest influences that shape the way you think or work now?

Super cheesy, but I have to say my husband, who is also a designer. He had a different design education to me and really opened up my eyes to other ways of looking at design. Also, working with Jacky Winter has definitely shaped how I work! And finally, some of those boring art history/theory classes I had at uni are now very much appreciated.


Can you tell us a bit about your process and tools you use in creating your pieces?

I use both digital and analogue processes — specifically, brush and ink, as well as creating images in photoshop and illustrator. I started using an iPad pro with Procreate and Apple pencil about year ago, and it completely changed my process. I used to do all my sketches by hand and scan them in, and that initial development stage used to take so long. Now I just draw it up on the iPad and can knock out twice as many concepts in the same amount of time.


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Freelance can be a rough ride of ups and downs, whats an event/job/client that specifically stands out as something that gave you a hard time but you were able to learn from it.

Oooh, I had a really crazy project last year that started out sounding super simple, and ended up with me quitting the project and taking the financial hit. It really threw me off course mentally for a long time, as previously all my projects had been pretty great. I guess it’s just taught me that it’s not always going to be sunshine and rainbows, and you’ve got to take the good with the bad. Since then I’ve had several really interesting and fun projects that I’m really proud of, and I’m really excited about a lot of the work that I’ve been doing lately.


What is your process in working with Jacky Winter, does a majority of your work come through the group or is there a split with clients coming to you directly?

Most of my work comes through Jacky Winter, but I also send them any brief that comes my way. They’re so great to work with that it’s worth paying the commission even on projects that come to me directly.


Finally what are some hot tips you can give up and coming letterers and illustrators?

Practice lots. Learn to take inspiration from things around you, not just other illustration or lettering or stuff you find on the internet. If you’re a letterer, especially of script styles, learn some calligraphy, it’ll help you understand why the letters look the way they do. And if you’re in Australia, ask your accountant about Special Professional income averaging! 🙂

Instagram: @jesscruicky

Official website:



Melbourne Lettering Club