I recently received an interesting question from a reader - let’s call her Beth. (You know who you are. Thanks so much for the great question!)

Beth has always had an interest in art, but has worked in a field unrelated to art for 10 years. Life has pulled her in other directions. Beth said that any attempt she’s made to return to art has led to spells of depression, isolation, and feelings of inadequacy. At one point, she tried to devote her full schedule to making art for six months, and it didn’t work out. She became very unhappy. Despite all that, the desire she has to make art has never gone away. She wants to return to creating in a sustainable way, with the end goal of becoming a freelance artist. She asked for my advice on first steps.

As I was typing back my reply, I realized how relatable this question is. No matter where we are in our creative journeys, I think we can all see ourselves in this story, because it summarizes the two major problems we face as artists:

1. The world seems to fight us tooth and nail to keep us from making our art (at least it can feel that way). Art as a career is still not acceptable in many circles. Because of that, many of us reconnect with our art later in life after doing it someone else’s way for a while.

2. Those of us who have gotten to the other side, making art on the regular, are constantly faced with internal battles of depression and inadequacy. For some reason, it’s difficult to forge a healthy relationship with your art.

I’ve faced both of these issues in a big way, and I’ve come out on the other side. Now in my mid-thirties, I feel more connected to my work than ever. I’ve overcome most of those icky feelings that can come with being an artist. Trust me, it has not been easy to work through these issues, but it has been worth it.

So here was my answer to her question…

Dear Beth,

I wouldn’t put any pressure on yourself to make money from your art just yet. You need to cultivate a certain level of confidence and peace with your work, and dive back in slowly! I think the title “freelance" artist can really extinguish creativity in the beginning, because it takes all the fun out of everything. I would just try to see yourself as an “artist" again.

At this stage, my best advice would be to carve out time in your life to make art most days, and get back to sharing your art on social media. I’m not sure how your work-life balance is right now, but if your job is demanding, I might look for a new one or cut back on your hours. Right now, it’s simply about making your art a habit - even if it’s just one small illustration per day. Taking some online art classes can be helpful too, because it will hold you accountable. You'll get good very quickly, if you just show up often and try to find joy in your work again. Suddenly, you'll have a portfolio of work you can show.

I’d also recommend creating a designated workspace for yourself where you can leave your tools out. Sometimes, this can make all the difference (even if it’s just a little corner of your home). Make it easy for you to make your art!

Once you feel confident that you can illustrate anything decently well (without feeling jealous or inadequate), I think it’s safe to start making money from your work - if that’s what you choose. This confidence only comes when you’ve created a lot of work. At this point, I wouldn’t quit your job immediately. Just start doing little freelance jobs in the evenings. Once your job starts to get in the way of freelance work, it’s probably time to leave. In the beginning, the jobs probably won’t be all that great or interesting, but the main goal is to make enough money to survive and to just keep finding better clients.

So to summarize - the only way to form a healthy relationship with your art is to focus on the habit, not the outcome. Show up, but don’t be attached to what you’re making. Before you realize it, you’ll be really good. You’ll be confident enough in your own style that you won’t obsess over anyone else’s. Everyone gets there by putting the time in. Unfortunately, the majority of people don’t get there because they can’t sit down and work - not because they aren’t talented enough. Doing the work is the hardest part. I promise, your unique style is there right now, you just need to uncover it by getting all the bad art out. And start showing up today, because the only thing worse than staying away from your art this long, is to stay away one day longer!

It’s important to make it easy for yourself to show up. Have patience with yourself and be kind. Aside from having a designated workspace, great music/podcasts, good lighting, candles, and yummy drinks can make all the difference. Give yourself reasons to look forward to your art on days when the creative juices aren’t flowing. Choose a medium that comes easily to you. And don’t be pressured to paint difficult subject matters in the beginning. Just make something, ANYTHING.

Accountability is important. I suggested sharing your art on social media, but you don’t have to go that route. Making artist friends who lovingly ask you, “when’s the last time you painted?” can be so beneficial. It’s also nice to hang out with people who make you feel less alone in your creative journey.

To make you feel a little less alone, below is a comparison of my art five years ago (when I dove back in after a LONG hiatus) to the most recent piece I made. It’s not that the first piece is awful, it just looks like someone else made it. That’s how far I’ve come in five years, and I haven’t even been making art full-time - just a little most days. A lot of my day is still spent on client graphic design work, because I find that to be the perfect balance to my art.

As far as external opposition goes - I’ve never experienced anyone directly attacking my art (knock on wood). It’s more of a general indifference I sometimes get. People changing the subject, or assuming I’m poor because I’m an artist. I might have heard a time or two as a kid that I wouldn’t make any money from my art. I’ve realize now, that couldn’t be further from the truth. Life has shown me that you’re always the most successful at what you enjoy the most. People don’t have bad intentions when they say things like this. They just don’t know any better.

By chasing our passion, we are breaking society’s rules. That makes people uncomfortable, because it makes them think about all the “rules” they’ve followed at the expense of their own happiness. You can’t take any of that personally, and let other people’s insecurities keep you from chasing your joy. They don’t have to live with your decisions, you do. I promise you can make money as an artist, and you can be happy doing it. You just need to show up, and put on those earmuffs when other people aren’t as supportive as you’d hope.

That’s where those creative pals come in handy. By surrounding yourself with people who make art too, you’ll start to feel like the world isn’t so against you.

P.S. Since the secret sauce is in habit formation, my two favorite books on habits are Tiny Habits: The Small Habits that Change Everything and Atomic Habits: An Easy and Proven Way to Build Good Habits & Break Bad Ones. These books CHANGED MY LIFE and really took my art to the next level!