Overcoming the 3 greatest challenges of a self-taught artist

As a self-taught artist, creative, or business owner, you are setting out on a difficult path. I remember when I first started learning calligraphy. I had never attended an in-person workshop and I never had any in-person instruction. What I did have was fear.

For one, teaching yourself any skill is plain hard. It is. It’s a lot of work. I quickly learned that it requires a great deal of effort to rise above mediocrity. I also feared that someone who knew what they were doing would call me out for an error I was completely unaware of. Imposter syndrome and fear of failure can be big obstacles on your journey. If you don’t see them coming, they can knock you off course. BUT, they don’t have to!

In fact, awareness of what you’re getting into can give you newfound strength. There’s a saying which goes, “better the devil you know than the devil you don’t.” You are better equipped to deal with a challenge you are familiar with. And the more prepared you are, the less fear there will be.

Here are three major challenges self-taught artists face. As well as some helpful tips for overcoming them:

1. Lack of Education

This is real guys and gals. When starting out, many self-taught artists and entrepreneurs have limited knowledge. This does not need to remain the case! I like to think of being self-taught as being self-educated. Your education is in your hands.

Regardless of what you’d like to learn, the internet offers endless resources. Though you can learn a lot by googling your heart out, the best sources of education may not be free. Consider investing in your education by joining a monthly subscription service like Skillshare. For a more one-on-one approach, you can also seek reputable workshops or mentorship. As a self-made creative, I cannot overstate the importance of investing in your education. There are some skills that you can’t learn through creative exploration. Quality education will help propel you into a more profitable and fulfilling career.

Side Note: Never underestimate the power of Google. You can find the answer to almost any question online. Do your research before seeking the opinions of others. You can do it! There’s endless knowledge available to you with a click of a mouse.

2. Lack of Confidence

It can often be difficult to believe in yourself when you don’t have a teacher to guide you. When you’re starting your creative journey, there is no test score that tells us we passed. There is no honor roll and there is no certificate. Instead, there is us and our own self doubt.

So, how do you develop a healthy dose of self esteem as a self-made creative? One way is through experience and creating a body of work. The more you do something, the more comfortable you will become. You may even become an expert in your industry after enough practice. The more you succeed, the more motivated you will become. Conversely, the more you fail, the more you will realize that failure isn’t so bad. You will get used to picking yourself back up and moving forward.

In my own business, I like to make a point of celebrating the small victories. Many of us get wrapped up in the negative parts of our story. The client we didn’t get to work with. The person on Instagram who didn’t follow us back. Do not dwell on the negative! Instead, work on recognizing and appreciating every single win. Even the little ones

3. Lack of Support

Lack of support is especially difficult for those who want to pursue a creative career. Many of us know what it’s like to have those we are closest with fail to support our creative pursuits. Well meaning friends and family may say things that imply that your passion is a cute hobby.

Perhaps you're self-taught out of necessity. Maybe you're told that pursuing a creative career is a waste of time. That it will never meet your financial needs. I personally do not know a single stationery designer who went to school for it. I only know a handful who have graphic or fine arts degrees. The truth is, many successful creatives are self-taught.

Not everyone is going to understand your goals and dreams. That's why it’s imperative that you find people who will support you! This is especially true if you are making the leap into the business world. Starting your own business is difficult. It makes all the difference when you have someone who wholeheartedly believes in you. Even better if that person reminds you to eat when you’ve been up working until 3 AM. Or to shower once you fall down the rabbit hole of entrepreneurship.

You may also find it helpful to connect with industry peers. Your new business does not come with classmates or comrades, so it’s beneficial to find your own tribe. Are there local entrepreneurs that are already doing the thing you want to do? Is there a Rising Tide Society chapter nearby? Can you connect with like-minded creatives on social media? It is invaluable to have a community of peers who have been where you are or are doing similar work. You can ask each other questions and celebrate one another’s victories. 

You don’t need a a crowd of people cheering you on. But you do need support. A few good people make all the difference in the world. Find them, cherish them, and support them in return.

I hope you find these three tips helpful! If you feel overwhelmed, pick one and focus on that first. If you have a questions or feedback, leave me a comment! I’d love to hear from you. Most importantly, if you appreciated this article you will want to sign up for the newsletter. My hope is to publish one article per month especially for creatives! And I know you won’t want to miss it. 


If you article was right up your alley I know you will love my Skillshare Class! “Take the Creative Leap! Overcoming Fear of Failure” is a class designed with the self-made creative in mind. This class will help you overcome fear of failure with a quick 20-minute video lecture. You will also get a handy printable worksheet! You can use this link to try Skillshare for free! You won’t regret it. 

Erika IkwildComment