The Jacky Winter Group - 5 questions with Karan Singh

Jenny Butler
Jenny Butler
16th of April 2012
This week Lucy and I are very excited to welcome Jeremy Wortsman to the Guest Blog! Jeremy is the mastermind behind The Jacky Winter Group and this week he will be interviewing a Jacky Winter artist and/or staff member each day.  Every interview is full of GOLD - especially for fellow creative business owners. - Jenny x
The exceptionally glamorous Jacky Winter staff!  Clockwise from bottom left - Jeremy, Charlotte, Kelly, Monica, Fushia and Meredith.  (pictured with the fabulous Neverfail / Beci Orpin watercooler!).  Photo - Lucy Feagins.

Well I am just pleased as punch to spend the week with you here on the Design Files Guest Blog. Over the next five days I will be sharing a series of interviews with the staff and artists of The Jacky Winter Group which I hope will shine a light on some of the behind-the-scenes action that keeps Australia's most handsome creative management agency running like a finely tuned swiss watch.

From following TDF over the past many years, I know that many readers have their own creative businesses, and I hope the content provided this week will provide some valuable insight that is relevant to all mediums, as well as the secret to why we all have such amazing hair. (According to Lucy, walking into our offices is like being in a Vidal Sassoon Commercial).

We're going to get things started with this interview with Karan Singh, a Jacky Winter artist currently based out of New York.

Karan Singh

Jeremy Wortsman (JW): Karan! Hello! Greetings from sunny Melbourne. I wanted to feature you in this post because of all the Jacky Winter artists, you have been through so many different phases of practice. You started out working full-time, then joined us in The Hatch, then went freelance, then moved to the main group, and now you are in New York. Can you fill in all the blanks and talk a bit more about your journey?

Karan Singh (KS): My first job out of university was with the immensely talented team at Qube Konstrukt. I was nauseatingly excited yet terrified. I moved from Sydney to Melbourne and I'll always remember my biggest fear being my intermediate proficiency in InDesign. I learnt so much in practice here which in reality I should have learnt at uni, had I done a degree in Graphic Design rather than Interaction Art. After just under two years I decided to switch to freelance. The spare time I had meant I could pursue a couple of self-initiated projects to keep me busy. Freelance was going great until opportunity knocked and I'd been offered a job with the amazing Vault 49 in New York City!

I remember that when I first started uni, I wanted to be a web designer. I was introduced to Illustrator and Photoshop in my first year and loved it so much that I taught myself how to use it over the next couple of years. Despite being somewhat qualified to conceptualise and partially build an interactive installation, by the end of my degree I knew I wanted to pursue illustration as a profession. I feel incredibly lucky to have been accepted by such amazing firms without a legitimate qualification.

Illustrations by Karan Singh

JW: One of the things that I think really attracted me to your work was the serious dedication and quality of your self-initiated projects. Can you speak a bit about them for those who may not know, as well as how you think those activities have helped your career?

KS: I really enjoy sharing the notion of a creative's beginnings. We all start out taking photos or drawing and so on as a hobby; we did it because we genuinely enjoyed it. Then it evolves into a profession and the time we once had to experiment and play slowly diminishes. I feel that it's really important to nurture that idea that's been sitting in the back of your head that you've been dying to try.

When I switched to freelance I had more time to pursue my own projects. The 'Daily Quickies', a daily illustration project, came about when I had this idea of an Apple computer which was literally an apple. I made it in just under an hour and didn't really know what to do with it. I realised that I had really enjoyed making it and being pretty minimal, they were pretty straight forward to knock out. After making one for each day that week, I set myself a goal of creating one every weekday for a year, a goal which I recently accomplished last month! The great thing about the Daily Quickies was that it offered a temporary respite from client work each day; I had an hour or so where I could create something just for me. The project brought about a fundraising event called 'Half of Us' where I participated in an illustration marathon. The goal was to create 12 illustrations in 12 hours. All the prints from the event sold out and the project ended up raising over $3000 for the Cancer Council.

Another self-initiated project I run is a now neglected blog called 'Pig Bimpin'. It's a blog which houses interviews with creatives and articles about design. It came out of being frustrated with the monotonous questions I'd read interviewers ask some of my favourite artists and thinking 'Hey, maybe I could try that?". I'm not a writer, as you've probably figured through my poor sentence structures but I enjoyed writing enough to challenge myself. It also gave me a great opportunity to improve on my photography.

Some of Karan's Daily Quickies

JW: What were your expectations of what being a represented artist would be like before you came on board, and how did that change/evolve during your time with the agency?

KS: Honestly, I thought that I'd be slammed with work as soon as I signed. I was of the misconception that I had essentially palmed off looking for freelance work and promoting myself as I now had an agent. I blame 'Entourage'. Over time, following a lull due to full time work and a couple of reality checks, I realised that I'd have to be more active and create more work to gain more clients, rather than waiting for them to fall into my lap! I found that more work came in, the more active I was in creating personal work or pursuing personal projects. Retrospectively, being represented by an agency is what helped me evolve and mature from a dude drawing on his computer to a professional illustrator.

JW: Tell us a bit about what you are currently doing in New York, and your future plans. What are the biggest differences that you have picked up on between working in America compared to Australia.

KS: Last year I managed to land a gig with illustration dream team Vault 49. I learnt of the position on Twitter of all places. Admittedly, 5 months later, it's still sinking in. I've always wanted to work overseas after a short stint in Sweden but always thought New York would be further down the track. I feel like it's one of those places that you just go to and never leave. I'm incredibly lucky as so many people romanticise about moving to New York for years and by some divine intervention I made it here. New York is enigmatic; it's such a vibrant place to live and work in. Most of my colleagues aren't actually American but generally speaking they're forthright but just as intrigued about your opinion. There's often an open dialogue and you'll come to a solution you never would have reached otherwise. Alternatively, it can be painfully bureaucratic and uninspiring, but hey, it works.

A Dogs Breakfast by Karan Singh

JW: As you know, we receive dozens of portfolios each fortnight for consideration. What three points of advice would you give to a prospective artist sending their work to an agency?


1. Share only a handful of your best works rather than everything you've ever done.

2. Whilst working in a creative field is pretty laid back, being professional is always a safe option. This could relate to how you present your work to how you write your email.

3. Be nice. Nobody likes a dick.

Visit Karan Singh's website here and his profile on Jacky Winter here.

- Jeremy

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