Lessons from a Self-Taught Artist, Part 2
For most of my life, I believed I was no good at art, and I never would be.
So, naturally, I’m now a full-time artist and creative business owner.
Rewiring your brain to do something new and exciting teaches you a lot about life, and that’s what this post is about: Part 2 of the lessons I’ve learned as a self-taught artist.
(Head over here to read Part 1, where I dive into the first 5 lessons.)
Those first lessons focused on what to do when you’re just starting: how to view social media, how not to limit your options, why “natural talent” isn’t actually that important, etc.
These next few lessons are what helped me as I was already down the artist path but feeling stuck and defeated encountering roadblocks and failures.
The creative journey isn’t always easy -- but that’s actually kind of the point.
So, without further ado…
6. “Mistakes” often lead to masterpieces.
A couple years ago, I offered to make a few wedding signs for my good friend as his wedding gift.
Notice the shadows under the instruments? Those weren’t in the original design.
Here’s the story: After I finished painting one instrument on the piece, I went to erase a pencil sketch on another part...
...and in the process of wiping away eraser shavings, totally smudged the wet paint underneath the instrument.
It’s important to note that at this point, I was six hours in, and my friend’s wedding was only about a week away. So, redoing the poster was less than ideal.
After a few minutes of freaking out, I took a breath and stared at the piece for a long while. Then, I realized that the smudge kind of looked like a shadow. A creative light bulb flickered on, and I decided to add shadows to all of the elements.
Boom. Mic drop. Crisis averted.
And guess what? Those shadows add depth to the painting that I ended up loving. And it was all possible because of what felt like a monumental and careless mistake only a few minutes before.
Of course, this doesn’t always happen. Sometimes mistakes are just mistakes, and you’ll either start over more prepared than before or just embrace the imperfection (both excellent choices).
But if you’re willing to stretch your creativity and release your expectations, I promise that, sometimes, those mistakes will lead to extraordinary breakthroughs. That’s because your mind can do amazing things when it’s forced to think about something in a different way.
So, really, mistakes are really just opportunities to reframe and push your creativity to grow into something new.
7. Failure is the most important step.
There are few things that gut me more deeply than the feeling that I’ve failed at something.
More than anything else, leading a life as a (now recovering) perfectionist tied my sense of self-worth to my successes. Because of that, I actively avoided at all costs activities I wasn’t “good” at. Art fell directly into that category for most of my life.
Because creating art didn’t come as naturally to me as other creative activities, I immediately cast it off into the “so not me” pile -- and I now realize that decision was most likely my mind’s way of protecting itself against failure.
But here’s the thing that I’ve learned after reversing that choice and seeking a life of imperfection:
Failure actually leads to better and faster growth than success ever will.
You know that deep and penetrating sting that you feel when you (metaphorically) fall flat on your face after reaching for something big? That sting is there for one reason and one reason only: to teach you.
The problem is that most of us aren’t willing to wade through the discomfort long enough to learn the real lesson that comes from failure. So, how about a reframe?
Instead of using the term “failure,” let’s think of it as a stepping stone toward your goal. An exercise in muscle-building to help you push even further next time.
I have a crawling infant in my house right now, but I swear, it took him MONTHS of *almosts* to actually get there. To practice moving, he would raise his little body with his little arms and rock back and forth for a few minutes until launching his face right into the floor. And he’d repeat this motion every day, for weeks and weeks.
You’d think he’d get too annoyed and just give up into a frustrated pile of baby deliciousness (I mean, that did happen a few times). But no matter how tired he was, he always came back to that rocking-back-and-forth position -- until, one day, he moved a few feet over without help.
Now, he’s crawling all over the place (and will soon be a walker, heaven help me and my tiny apartment.)
The crazy part about watching all of that go down is I’m pretty sure he only learned to crawl because of all the times he fell on his face. Without that practice, without taking those steps, his body wouldn’t know what to do.
I love this quote commonly attributed to Thomas Edison (patent controversies between him and Tesla aside):
“I have not failed. I have just found 10,000 ways that won’t work.”
Sometimes, you need to find all the ways that won’t work to prepare you for the truly great idea that will.
8. Don’t “should” on your creativity.
About a year into lettering and painting as a hobby, I started getting what I like to call “the shoulds.”
Instead of feeling free to create whatever came to mind, I felt like there were paths I should be exploring, for various reasons, like...
...I should learn traditional forms of calligraphy because it looks more professional…
...I should learn graphic design because then I could combine it with my custom artwork for a killer business model…
...I should use a pencil to sketch all my designs because I’ll make less mistakes that way…
…and so on, and so forth.
The problem with listening to “the shoulds” is that it’s hard to distinguish between pursuing a path out of curiosity and passion versus pursuing a path out of guilt or the temptation of success.
Here’s another example. Sometimes, I get “the shoulds” when thinking about what kind of paths to take in my business.
…I should pursue wedding packages because it’s a major market that could yield some big results…
...I should sell watercolor kits with supplies because other people have had success with it…
...I should participate in the craft fair market because then I’ll be a better community member...
...but most of the time, if the reason I want to pursue a path is because I should… it’s either not the right time, or it’s not the right path.
My best ideas (and most successful business ventures) have come about because I’ve pursued something I really loved, sometimes despite knowing the thing I should do. My creativity feels endless as long as I’m working on projects that are truly me.
And I think that’s because when you’re doing anything out of obligation, it doesn’t feel like creative play anymore. It feels like homework.
Don’t “should” on your creativity -- instead, pursue the things that set your soul on fire, no matter what anyone else says about them.
9. Your creativity needs a break, too.
Burnout is no joke, my friend, and it happens to creatives all the time.
I think it’s easy to think that because creativity feel so good, it must be the perfect go-to all the time.
But what happens if (when) you arrive at your desk, and even picking up the paint brush feels like lifting the weight of the world?
When the thing that usually brings you peace and joy is suddenly shrouded in exhaustion, anxiety, and guilt, then it’s probably time for a break.
Here’s why that’s a good thing and not a weakness.
Creativity is like gymnastics for your imagination. It takes a lot of stretching and growing to touch its furthest reaches, and just like our bodies need rest after physical exercise, our minds need rest after mental ones.
It is normal and necessary for you to take breaks from an intense creative life once in a while.
Those breaks give your mind time to ruminate and grow stronger before jumping back into making new things.
They also help fill your mind with new inspiration and experiences, which will revolutionize your creativity in exciting ways.
Without those creative breaks to rest and refill, your work will inevitably become stilted and forced. With them, you can learn to focus on what’s most important and prepare for great things to come with a fresh mind and rejuvenated spirit.
10. The actual creating part is the point.
When I made the transition from calligraphy into illustration and landscape art, I started to feel a little guilty for buying new brush pens because I didn’t use them for paid work so much anymore.
For whatever reason, it felt like if I wasn’t getting paid to make products with brush pens, then they were a "waste" of money. Still, I bought more anyway because I had a lot of fun doodling with them. (I couldn’t help myself.)
It took me a while to realize what’s coming next, but when I did, it completely changed the way I view the creative process.
The point of creativity is to feel joy, not to make something “good” or "sellable."
When you go into a creative jam sesh with the end goal of a masterpiece in mind, the weight of that expectation is going to crush the creativity right out of you.
But if you go into making knowing that you just love to make, you’ll allow your creativity to flourish and expand in unexpected and remarkable ways.
My best paintings have come about when I’ve sat down at my desk and basically stared in awe at my most favorite color blends, relishing watching them come together in the moment.
These two pieces come to mind. I went into these paintings thinking I wanted to explore sunlight, but I didn’t have anything else in mind. The rest just kind of fell into place as I let my curiosity lead the way.
Even “just for fun” activities, like doodling words is for me, are worthy of your time if they help you feel a little happier than you were before.
Exploring watercolor has helped me grow into a better artist, and it’s also helped me grow into a better person. I’m grateful for the lessons I’ve learned in this journey, and I can’t wait to see what the future has in store.
P.S. If any of these lessons have helped you on your journey, I’d love to hear! Feel free to leave a comment or shoot me an email at email@example.com.
P.P.S. My new beginners course, Exploring Watercolor 101, is LIVE right now. Make sure to check it out before the doors close in just a few days!