Sunday Mailbag

March 4th, 2012 | Posted in Mailbag

Q: What was your very first paid professional freelance job?

A: That depends on your definition of “professional freelance job”. If by that you mean the first time money was ever given to me in exchange for my artwork, that would have been in 10th grade in La Crescent, MN, when a fellow classmate named Lori paid me to paint my concept of a Van Halen album cover… not a copy of one of their album covers, but my idea of a new cover. I did their classic VH logo looking like it was rising out of a glowing, smoking crater. I did it using enamel sign paints on the back of a 8 foot square old piece of kitchen linoleum flooring, and then somehow delivered it across town on my ten-speed bike. I think I got $50 for that. However, I don’t believe that counts as a “professional freelance job”. Nor do the thousands of live caricatures I did over the years while in college, nor a few other personal commissions and other odd private jobs I did around that time.

My very first real freelance job was for a design firm in Minneapolis, and it was such a nightmare I almost became a short order cook instead of an illustrator because of it.

During my third year of school at the then named “School of Associated Arts” in St. Paul, MN., I was approached by the head of the design department about doing a “little job’ for him. It was fairly well known throughout the small school (my graduating class: 40 students) that I did caricatures during the summer break, and he had a client that needed some caricature work done. Almost all the teachers at the school were professionals in their field first, and teachers second. This professor owned a design firm in the Twin Cities, and he had a radio station from Ohio (I think… this was 25 years ago) as a client. Their morning show personalities wanted a new logo designed that incorporated caricatures of themselves in it. I had to draw the three hosts of the show, which he was going to work into the logo design. I was thrilled! This would likely end up on billboards and advertising materials, T-Shirts and other merchandise. Published portfolio pieces were worth their weight in gold, plus I was getting PAID. I accepted and was eager to get to work on it. I got the photo reference a week or so later, studio head shots. Ugh. Glamour shots are the worst things to work from. Regardless, I worked hard on the pencils and gave them to him in short order. I thought I’d done a decent job on it… I was even kind of nice to them. He sent the drawings to the client for approval.

A few days later he went over the feedback. The client didn’t think the likenesses were right on. No comments beyond that. No specifics like “you made his chin too big” or “he has more hair than that”. As a caricaturist, you draw a person they way you think they look. In other words, it looks like them to you when you are done. Did this guy think I just banged these drawing out without thinking I’d gotten a likeness, and now that he’d pointed it out to me I’d just go ahead and draw them so it actually looked like them? Working from pictures is tough as you have only a two dimensional image to use, and these people are three dimensional and seen every day in that way by the people who were reviewing this. If I’d been smart at this point I’d have asked for more reference, but I wasn’t smart… I was twenty. Okay, I did a new round and tried a more portrait-like approach. Off they went to the client for review again. I received essentially the same comments back. Another round, and off for review. They came back again… still no real direction, just ambiguous comments. Now I was getting frustrated. I then did a flat out portrait using an art-o-gragh to project the pictures and just traced the faces. According to the client it still didn’t look like them. Finally they sent a promo piece that they were previously using to give me an idea of what they wanted. In this example, the hosts of the show weren’t drawn as caricatures at all but as cartoons with big, white blocks for mouths and barely any resemblance to the actual people. Well, know I knew what they wanted so I did something similar. These looked nothing like the people whatsoever. Bingo! The client liked it and we proceeded to final. I redrew them on illustration board, inked and added values for the final art. Off they went, and I patted myself on the back for persevering. My first job complete!

A week or two later the design teacher took me aside and told me there was a problem with the caricatures. He explained that the original sketches I had sent in were shown to the hosts, who thought they looked fine. Some PR person at the radio station took it upon himself to “tweak” the artwork until HE was satisfied. The hosts didn’t see anything more until they were presented with the final logo, to which they objected asking “what happened to the first caricatures that LOOKED like us?” That’s right, I had to redo the artwork using the first sketches I submitted as the art.

Being young and stupid, I did not get compensated properly for the enormous amount of work that went into this. The design professor did not offer me any more money but did do a number of T-Shirts for me in trade (he had a silk screening business as well) because he felt bad about the headaches. I wish I had copies of the artwork, although in all fairness it was probably pretty rough and I doubt I did all that terrific a job on any of those sketches. I never did find out if they ever used the logo, and if so where it was used. I did learn some valuable lessons about communication and the important role it plays in any freelance job… and of course how to make sure you get paid for unreasonable numbers of revisions on a job.

So there you go… my first professional job. A total disaster. C’est la vie.

Thanks to Bob C. 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. Bernard says:

    Hello Tom, proably wrong place for this comment but I’m in the box all day today w/limited signal (mobile phone) totally submerged in what looks like will be one of my most prized books.

    “The Mad Art of Caricature”

    Only read: the Afterword, Foreward n a quick “breeze” thru so far but I can see it is a gem!

    Will tweet, fart n facebook etc. eventually once I get further on or finish but just had to comment on how good this book is so far.

    The Jack Davis splash page n my name in marker is a added bonus too!

    If my caricatures don’t get worse after reading this book then I will surely give up!



  2. Kyle Maloney says:

    Reminds me of the fiasco I had last year. (I’m still in my 20s so I’m still dumb)
    This guy who didn’t speak very fluent English wanted me to draw an entire class for graduation. We’ve never met, just corresponded online. I told him I didn’t think I could do an entire class in the of time he needed them but would try. He narrowed it down to just the teachers. agreed to pay per person. First he didn’t like the likeness, which was fine, I ended up doing a couple revisions. Then I couldn’t tell if he was telling me they look cute or to Make them cuter. He also said he wanted to add fun (funny?) accessories like a guitar and banana no apparent reason. It was a mess, and I only ended up getting paid what I charge for a single caricature (the final piece had 4). -_-

  3. Jason says:

    I just finished a project recently of a group where I was pretty much told to make the women prettier than they were, and ‘get inside their insides and change the things they don’t like about themselves’…i did the best I could, but I just thought it was rediculous. People don’t seem to want reality/accuracy.

  4. Frank Pryor says:

    Boy, does your story bring back memories. I had a very similar experience while in college trying to add projects to my student portfolio. It was so similar, I won’t bore you with the details. The lesson I learned from it, is not to go through a third party if at all possible (listening to the client usually eliminates most problems) and to get as many reference photos as possible. It has served me well.
    Thanks for sharing it as it helps to know I was not the only one to go through such an experience!

    F. Pryor, Denver

  5. dalia says:

    I don’t think this “fiasco” has anything to do with age (since people can be old and stupid too). It’s the experience that matters after all.
    Knowing when to put a stop when a client begins disturbing.
    Creating a proper contract.
    Asking the right questions.
    Asking for a feedback.
    All these come with experience only – and, of course, blogs reading.

    And, btw, nothing is a complete fiasco if one learns something in the prosess.

    Thanks for sharing, Tom.


New profile pic courtesy of my self-caricature for the Scott Maiko penned article “Gotcha! Mug Shots of Common (but Despicable) Criminals” from MAD 550

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