The life of a freelance cartoonist is never boring. Fun, frightening, exhilarating, frustrating, goofy, overwhelming, and surprising, sure, but never boring. For me the key has been balancing catering to all kinds of media and markets while keeping my own art and writing style intact. Here are just a few of the ways the modern freelance cartoonist can draw funny pictures for a living:
A cartoon I sold to Reader's Digest
The first markets I ever sold to as a freelance cartoonist were magazines. I've sold to lots of titles, big and small, and it was a great way to learn the business, sweat rejection, and burnish my cover letter credits.
Selling to magazines means creating tons of cartoons on spec, which on it's face seems like a bad deal. But the more you churn out, the better you get, and the better you get, the more you sell. Still, only a very small portion of your spec work will sell, but you are also slowly building a large library of cartoons you can eventually sell online.
Sadly, even when I was starting out the number of titles buying cartoons was dwindling, and now there are only a very few good recognizable markets left. It's good work if you can get it.
Custom cartoon for corporate tech magazine
Most of the magazine work I do now involves the creation of custom cartoons about very specific topics for niche publications. What I like about this type of cartooning is 1) you're working with a client who's involved in the process from the beginning, 2) it's challenging, and 3) you know you're going to sell this cartoon and you know for how much.
I think the most difficult part of this kind of work is remembering that you're not helping the client by simply doing exactly what they ask. A good freelance cartoonist is also an advisor who guides the client to the best possible outcome.
Remember, they know their business, and you know what's funny. Meet in the middle and everyone's happy.
A cartoon repurposed as a birthday card
This is another area I used to work in more, but don't so much now as the smaller companies are tightening their belts, and larger companies are almost impossible for a freelance cartoonist to break into.
Looking back I think had I focused more on creating cartoons specifically for cards instead of looking at it as a way to repurpose existing work I might have enjoyed more success, but there's only so much time in a cartoonist's day.
A book cover cartoon illustration
Be it pressed wood pulp or PDFs, books are a great place for the modern freelance cartoonist to sell cartoons.
I sell a lot of existing cartoons to textbook publishers on a variety of topics (that large spec library at work), and again I create custom cartoons to fit.
A cartoon for College Admission: From Application to Acceptance, Step by Step by Robin Mamlet and Christine VanDeVelde
Books aren't going anywhere, and many of them are going to need cartoons.
It's not hard for a freelance cartoonist to create a webcomic. Draw it, publish it, you're done. But making a living at it is a whole different thing.
There's only a handful of cartoonists earning their money primarily from a webcomic business model, but it's theoretically possible. As for the rest of us, if you can repackage/republish your cartoons this way it can provide some additional revenue for a small amount of additional effort.
And who knows, maybe you've got the next Penny Arcade on your hands.
A cartoon for a hospital gown manufacturer's calendar
I wouldn't say there's a lot of work for a freelance cartoonist in cartoon calendars, but it's something to consider.
Many large publishers create the standard monthly and day-by-day cartoon collection calendars each year on a variety of topics. And corporate clients often use calendars with customs cartoons about themselves or their industry as year-end gifts and marketing devices.
Calendars at least warrant a look.
A custom comic strip for Infoblox, an automation technology company
You can probably tell by now that I do a lot of custom comics for clients. They're popular in a content marketing capacity (blogs, social media, email newsletters...) because they're fun, attention grabbing, and easily viral. Custom comics can be a good opportunity for today's freelance cartoonist.
There are certainly any number of additional options - self-publishing, apps, comic books, syndication - to help pay the bills, and I'm sure some enterprising person is dreaming up a shiny new opportunity as I write this. For me the key to earning a living as a modern freelance cartoonist is to keep looking for new markets, and keep making yourself laugh. Or to quote Steve Jobs quoting the The Whole Earth Catalog, "Stay Hungry. Stay foolish."