Sunday Mailbag- Getting Started Freelancing?

March 5th, 2017 | Posted in General

Q: I’m a party and event caricaturist, but I’d love to get my work into publication. I know you got started doing theme park caricatures when you were in college, but when did you switch over to being a freelancer, and how did you do it?

A: I like to say I exploded onto the freelance scene over the course of 15 years or so. That’s a gag, of course. You do not burst into the industry, you gradually build a clientele through marketing, hard work, and professionalism.

My freelance path reads like a textbook guide for how to start small and slowly build a career doing illustration. I started when I was still in college in the late 1980’s, doing a few small jobs for some of the professors at my school who were also art directors for ad agencies and design firms, and local art like kids menus for area restaurants. In 1990 I got work from a small comic book company called NOW Comics doing a title called “Married… with Children”, which eventually led to a mini series for Marvel called “The Coneheads” in 1994. I did my first magazine illustration for a local publication called MPLS ST. PAUL magazine in 1991, which led to my doing work for the Minnesota Twins when that art director moved over to do the Twins magazine. In 1993 I did some of my first advertising work when I picked up the ball from another artist who was not getting the job done on a promotional anti-drugs comic book for kids for a company called Business and Legal Reports, a job that I got through an ad I had placed in the Directory of Illustration sourcebook. I ended up doing 6 more comic book projects for them that were messages about the inadvisability of smoking, drinking, bullying, etc for grade school aged kids. That work led to work for kids magazines like Scholastic, and National Geographic for Kids magazines. In 1997 I did art for a series of CD-ROM parody games for a small company called Parotty Interactive, which led to a big job doing a game for Hasbro called “Super Scattergories”. In 1999 I started doing work for Cracked Magazine, a now-defunct MAD rip-off, doing TV and movie parodies. In 2000, I was in my first issue of MAD. My work in MAD has led to many opportunities over the last 16 years. My “overnight success” took 15 years of hard work and building, and it’s still ongoing after 31 years.

I’ve been lucky, but there have been many, many more unlucky moments overcome than lucky ones taken advantage of. During that first 15 years I sent out innumerable postcards and tear sheet promos, invested in ad pages in Sourcebooks like the previously mentioned Directory of Illustration, and scoured the news stands looking at what kind of artwork different publications were using and which might be most interested in my style of illustration, then adding them to my mailing list. One key ingredient: I used the financial bedrock of my live caricature work to pay the bills when I was struggling to find steady freelance work. Most illustrators have to have a “day job” for a long while until they get that client base built up, I was lucky my day job was still being an artist. That gave me not only time to find and develop those client relationships, but to develop my skills as well and become a better illustrator. Without my live caricature work and experience, I’d not have ever made it as a freelancer.

Today’s world of publication may be shrinking, but it’s far from dead. There is plenty of work out there, especially for illustrators who are adept at caricature. So far no one has written a computer program that can create a caricature…you still need and artist to do that. While some of the larger magazines are struggling, there are still hundreds and hundreds of niche publications out there with small to medium circulations that need illustrations for their articles. It’s the dirty little secret of freelance illustrators that no one earns a living doing TIME covers. Most illustrators, even the big names like Payne, Brodner, Burke, etc. make their living doing work for magazines you’ve probably never heard of like Snow Country (winter sports), Detour (fashion/pop culture), Broadcasting and Cable (TV/cable industry), UTNE Reader (politics/opinion), Financial Planning (accounting industry) or Contingencies (actuary industry). . . I’ve worked for all those and many more you would not recognize. They pay decently and there are a lot more of them than there are TIME, People or MAD. TV/film, advertising, products and the internet aren’t going anywhere, and there are clients in those areas of media who need illustration as well, especially caricatures.

For those who want to branch out into publication illustration, tomorrow is never as good a time to do so than today. Put together a nice collection of your most appealing work, start looking around your area for companies and potential clients who might be looking for artwork, and start pounding the pavement. The children’s menu you design and illustrate for the corner family diner is the first step on a path that might lead to that fabled TIME cover. You’ll never know until you step onto the path.

Thanks to Anonymous for the question. If you have a question you want answered for the mailbag about cartooning, illustration, MAD Magazine, caricature or similar, e-mail me and I’ll try and answer it here!


  1. Ernie says:

    When you do begin getting assignments, I can not emphasize enough the importance of meeting deadlines!


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