There are no guarantees and no single path to becoming a full-time freelance illustrator, but there are definite things you can do to bolster your chances. Here are 10 things that worked for me, which I believe apply to all of us.
1. Live in a big city, at least when starting out.
Generally speaking, there are more and better opportunities in larger centres. You have access to museums and galleries, and the quality of work you'll find is likely to be higher simply due to the larger funding larger cities enjoy. And this extends to almost everything you'd need as an illustrator: educational opportunities, the calibre of agencies and studios who will hire you, exposure to good design (in restaurants, coffee shops, public spaces and art, etc.), diversity of people and culture, and so on. By simply walking out your front door, you are immersed in a sea of opportunity, and chances of striking gold increases exponentially with the size and importance of a city.
2. Find your creative community. Reach out to other creatives, especially people with the kinds of jobs you covet.
I'm not saying be a greasy schmoozebag, but it's entirely okay to find out who's making good work and even who has the best jobs, and kindly ask to pick their brains. Most creatives with any level of success are aware of the challenges of "getting there" and are happy to help others up. If someone seems a bit standoffish and hard to talk to, let them brood in their self-importance and don't take it personally — there are plenty others who want to cheer you on.
The most important thing, however, is this: it is relationships, not talent, that takes you far in any industry.
3. Identify work you love, and find out who's making it.
Knowing what you like is a huge clue into who you are, creatively speaking. What kind of work/art/products are you most drawn to? Fantasy? Minimal/designy? More traditional? Skate culture? Vintage kids' books? Whatever excites you to look at, that's the kind of work you're interested in. Your homework is to find out as much as you can about your favourite work starting with who made it. And then find out what else they made, and where they were trained, and see if they wrote anything — and then read it. You get the picture. By finding out the history and circumstances around the things you like, you peel back the mask and find out how the sausage was made. You realize how ideas emerge from things artists are thinking about or their experiences. And you find out who they were influenced by. Work is never made in a vacuum, including yours. Study people are are better and further along than you in their craft and allow yourself to be influenced by them.
4. Start and maintain a daily creative project that you share online.
The only way to get good at making things is by making things. The things you make at first will probably be worse than the things you make down the road. But you've got to start somewhere. And you probably need some structure around what to make, because the hardest thing is to stare at a blank page with no ideas. So here's something that worked for me: while in art school, I started a drawing blog, posting one drawing every day. I have no idea how many people followed me, maybe 20-30. But this audience, or delusion of an audience, motivated me to do something everyday, lest I disappoint. And as I did this every day, I found a style and a voice to work within, and people actually started to comment on it and encourage me to do more. This was an important way for me to gain confidence as a creator and also prove to people who would hire me that I'm active as a creator. This was back in the days before social media. It would have been so much easier to post on Instagram. You're already a few steps ahead of me in that sense.
5. Work first as a designer.
Very few companies are looking to hire full time illustrators. If you have any training as a designer, start there first. Not only will you actually get a job, but you will gain really important experience as the kind of person who will eventually be commissioning your illustrations. I work with art directors all the time, and it is a huge benefit in communicating with them to understand things from their point of view.
In my own experience, designers are far better at presenting their work. They understand that all good ideas must be sold, clients must be persuaded, and all this requires a level of professionalism and a touch of psychology when presenting the work. Illustrators tend to be more chaotic and less strategic. For instance, a designer would never just plop a screen grab of a logo concept into an email. Instead they'd build a nice presentation deck with a title page, a short synopsis statement, and maybe even a thank you at the end.
Needless to say, if you're the designer, you often have the opportunity to determine what kind of photography or illustration ends up being used in your projects. Few employers are going to discourage you from using your own illustration talent to save them from the cost of outsourcing!
6. Make everything about illustration.
Look for every possible way to make illustrations. On the side, up high, down low — illustrate until your friends start to worry about you.
7. Learn classical art/design skills and disciplines.
People often ask me how I came up with my style. That is an almost impossible question for me to answer (because to some extent, I don't know), but I do know that underlying everything is a foundation of classical art skills: colour theory, drawing, principles and elements of design, and typography. Look at any artist in history and you will see that they first had to learn the rules before breaking them.
Learning, practicing and ultimately internalizing formal artistic disciplines first allows you to create more intuitively, i.e. with more style, later on.
8. Be experimental.
One sure way of developing novel techniques and stumbling upon a unique voice is to experiment. Try thousands of things, waste time barking up the wrong trees. Lots of them. Paint badly, use the wrong tools, download and use free fonts, borrow a Wacom tablet for a weekend, rent a DLSR camera, start a YouTube channel. Write a lot. Make messy work without goals. Design fake logos. Along the way, you're going to learn stuff you could not have foreseen, and it's always the surprises that end up taking us higher.
9. Show your work to others.
Be vulnerable. It's the hardest thing to do, even for me, now. But if you want your work to resonate with other people, I'm sorry, but you're going to have to share it with some folks and be open to their feedback. Don't look for affirmation more than you want truth. When you receive hard or even harsh feedback, do this: 1) stay quiet, don't get defensive. 2) Go away and think about it. Is the feedback even a little bit true? Why did that feedback make you feel that way? Be objective as possible, and accept that you make mistakes and aren't right a lot of the time. But then, most importantly, identify how to improve, and try again. Repeat.
10. Emulate your heroes.
We all start by copying our heroes. And some of us continue to do work in the spirit of others who have gone before us. So don't be ashamed of stealing ideas and being a copycat — at first. When we're just starting out, we can emulate others, and this helps us deconstruct how work is made. But along the way, over time, something happens. We start to inject a little bit of ourselves into it, and we give birth to a new style. Over time, only a skeleton of influence is left, and we have something totally new and our own. But we must always remember to give thanks and pay homage to those giants on whose shoulders we stand.
This list is not exhaustive, but it's definitely a start. If you have any tips for starting out, I'd love to hear in the comments!