I’m a freelance illustrator, which means I kinda float from job to job, taking on different opportunities to make money. It means that I have less stability than someone who works in-house for a company, though it also means I can keep my own schedule and generally be a little more flexible with my time. It’s what I prefer, but it’s not for everyone.
When I got out of school in 2009, I was working as an assistant to a comic book colorist, doing fairly menial work while I tried to scrounge up some freelance clients. I got that job because he was one of my instructors and I finished assignments early and so I had some extra time and showed that I could finish things professionally and on time. After a couple years, I was getting enough freelance editorial work (small illustrations for magazines, mostly), that I was able to quit my regular job and hop into freelance full time.
For about three years freelance editorial jobs were the bulk, almost the entirety of my pay. Magazines typically don’t have enormous budgets, so you have to do a lot of illustrations to make a decent living. Some illustrators have a natural affinity for this type of work, and are really good at it. I tend to do more narrative work with a fantasy slant, which means that, when working on something like a business or legal magazine, I would have to step outside of my comfort zone to finish the work. Sometimes that worked out well and sometimes it didn’t, but more often than not it wasn’t really taking advantage of my strengths as an artist or as a thinker. I did a couple advertising jobs here and there, which pay a lot more but are generally harder to get and have more stringent art direction. I made a lot of work on my own time and it got some attention online. I sent out postcards and emails to art directors, though the majority of the work I’ve gotten has been because some art director found my work online, or another artist pointed them to me, or something along those lines.
I’m still freelancing now, but I’ve gotten a few more regular clients that are in line with the kind of work that I like to do. I’m working more on books and in the animation industry (doing background drawings for Steven Universe), and I’m generally taking on fewer editorial jobs. Even though I’m not working in-house at Cartoon Network (they’re in Burbank, I’m in Baltimore and soon to be Brooklyn), I’m part of a team, and it’s nice to be involved with a community of artists working on one project. Books typically have longer timelines and larger budgets than editorial images, which means I can labor over drawings for longer - something I love doing. I also taught illustration classes for two years at the Maryland Institute College of Art, the school I attended as a student.
I also make money from making and selling my own products — prints, zines, that sort of thing.
The point is, there are lots of ways to make money with illustration, you just have to be flexible and take opportunities when they pop up, while keeping in mind the kind of work you want to make. At the beginning of your career, being enthusiastic, professional, and flexible are just as important as being good.