Sometimes I receive emails asking for advice on how to do what I do: Draw pictures for money. Recently a new-to-the-game illustrator named Patrick reached out to me. I asked him if I could post my (adapted) response here because I think it can help other aspiring illustrators too. Here it goes.

I love what I do.

But it’s tough.

(We all knew that was coming.)

I assume the advice you’re seeking is how to make money (find clients and know what to charge)…? Those were my questions when I first started.

First of all, it’s okay to not know what you’re doing. When you’re new, you should be especially fearless about asking questions. I say this because when I was new, I felt paralyzed (in terms of asking for help) because I thought that working for myself meant I was supposed to be an expert. How silly! I could have had a much easier time if I was comfortable asking lots of questions (including asking for work and asking people how much they charge). Speaking of questions, make sure your questions are specific.

Email & Reaching Out

Next time you email someone seeking advice, ask that person what you really want to know. You don’t really want advice, you want answers. Is it how to make money? How they found their clients? How they built up their internet presence? What are three things they wish they knew/did before they started working for themselves? Did they have a breakthrough moment or has it been slow and steady? I remember so desperately wanting someone to tell me the magic formula. But there isn’t one. It comes with a lot of work and curiosity. In those brain picking emails, just ask a couple of easy-to-answer questions, and I’m certain you’ll get more replies than asking for general advice. We’re all busy. If I’m in over my head for work, a well-intentioned advice-seeking email from someone I don’t know can easily get pushed back because it takes me a minute to think, “Hmmm… how do I summarize all of my experiences and lessons learned into a concise email?” vs. “What are three things I wish I did differently — that’s easy!” Specific questions are less daunting. Unfortunately, I have emails from four months ago that have still gone unanswered because they came at a time when I was slammed and every passing day pushes them further back in the inbox. I feel awful about this. On that note, it’s nice to check in if you haven’t heard back from someone a week later. They probably want to respond, but they’re busy. If you pop in quick, it will probably be a nice reminder. At least that’s how I feel when people check in.

Stay Curious

Absorb, absorb, absorb. Read all the books, articles, TED talks, etc. that you can. Invest in meeting people in the field and becoming friends with them. Start with one conference a year. Go into it with the expectation that you want to walk away with friends in the industry. If you can’t go to a conference, go to a Dribbble meetup, AIGA event, Under the Radar (if you’re in Austin), conferences, lectures, etc. There are tons of places where artists/designers/makers gather. I promise this gets easier in time. Take it one day (or event at a time). If there are zero get-to-know-your-local-illustrator happenings in your area, what’s stopping you from starting up a monthly Happy Hour? (It’s called Drink and Draw.)

A big turning point for me was when I made the kind of close friends where I could just text things like, “Hey, do you think charging X-amount is good for this project?” or, “How do you handle it when a client wants a project really fast? Do you do a rush fee? If so, how much?”

Finding Clients

Now let’s talk about the long game.

It takes time. Share your work and share it often. Don’t be afraid to ask for help every step of the way. Email your friends and family and tell them that you’re doing this big thing (pursuing illustration as a career) and you’d like them to keep you in mind for work.

Encourage them to help you spread the word. Make sure to give them specific examples of what you can do since most people don’t really know what illustration actually entails (other than children’s books).

You can also email other illustrators you know and tell them you’re looking for X-type of work and keep you in mind in case their plates get full and they need extra help. That email alone could move you to the top of someone’s list (they may have a lot of illustration friends but we’re all busy. It’s easier to refer a client to the first person that comes to mind that feels like the right fit).

I’m also a big fan of projects like the 100 Day Project. It helps establish your credibility (lots of output in a short amount of time) and gives you a great backlog of work.


There’s a lot I could say here (perhaps another post another day!), but I’ll keep this one brief.

One way to learn what to charge: If you feel completely incapable of knowing what to charge or how to price your work, reach out to someone who’s doing what you want to be doing and ask them what their rate is for a one hour Skype consultation. Paying them for an hour of their time ensures that neither of you means funny business. That is your time for real talk and real answers. Walk through your projects and tell them what you charged and see what they think. Did you charge too little? Should you have done fewer revisions before kicking in the hourly rate? How would they have quoted the project? Hopefully, this person will either give you the peace of mind knowing that you’re on the right track or they’ll help you understand what you’re worth (and what the market actually pays). Best case scenario: You learn a lot and now you’re friends with someone you admire.

Handy resources having to do with money/pricing:

And finally…

You can be doing everything right and it still feels like you’re swimming upstream. It takes time. Or you can just be doing everything wrong. That’s possible too.

But that’s why community is so important. When we’re in dialog with other people in our industry, we kind of develop this barometer for what “right” looks like (I know I know, there isn’t one right path blah blah). You’ll make it harder on yourself if you just wing it. Be proactive about this dialog.

It’s okay to be the first (or only) person in your circle who is really honest about stuff like money.

Why not? What do you have to lose? When my friends and I told each other what we make, we suddenly felt more invested in each other. We had a bond and a trust. This doesn’t have to be your approach, but sometimes it just takes one person to ask the honest questions and everyone else follows suit.

And finally-finally…

Don’t be too proud to get a job. There is dignity in all work. I can’t decide if I did the right thing sticking to the freelance life even when I was barely getting by. It’s all fine and dandy now, but I missed out on a lot of life (and money) just because I was too stubborn to get a job. It doesn’t have to be permanent (but it’s okay if it is). You are not a failure if you decide to go back to the office. You are wise and taking care of yourself.

Well, that concludes this installment of, “So You Want to Be an Illustrator?” or whatever I titled it (I can’t remember, and if I scroll up, I will lose my place).

I hope my mistakes and “scenic routes” can give you a shortcut or two on your own journey.

Sally forth!

You have a few of Becky’s freelancing tips. Now learn more about her design skills in our Digital Illustration in Adobe Illustrator online class.

This article was originally published by Becky Simpson on Medium. All illustrations in this post are by Becky Simpson and some can be found in her store, Chipper Things.