Learning to Fail: Creativity and Taking Risks

Risk-taking in no way comes naturally to me. It’s as un-natural as ketchup on Chick-fil-A fries. Trying new things can sometimes be like riding a unicycle on a tight-rope stretched across two skyscrapers - can I get an amen? But in many cases, the reward lies with the risk.


I know what you’re thinking. You’re about to deuce out of this page right now because I just said “try new things” and you’re thinking that you could have told yourself that; but if there’s one thing I’ve learned, it’s that the simple truths are the truest.

Learning things when you’re a kid is so much easier. Not because they have a greater capacity to learn, but because they are unafraid to look foolish or to fail. They don’t have the self-awareness and instinct to protect their reputation, social standing, or dignity. A child doesn’t normally come to a parent with a picture looking disappointed in themselves, saying “I messed it up, I don’t want to draw anymore.” Instead, they approach beaming with pride and say “Look what I did!”


Learning to fail is so important as a creative. How do we develop our aesthetic or find out what we can truly be capable of if we don’t fail first, and more so, if we don’t try.

a variety of messy art supplies

I remember the first time I painted… not for art class or for anyone else, but just because. I love craft stores and I had just bought a two-pack of stretched canvases. I could spend years in there. And probably all my money. But at least there’s coupons, am I right? You know that feeling of a new notebook, or fresh paintbrushes or an unopened bottle of paint? It’s a good, good feeling. That night I was particularly frustrated by my circumstances, (what they were, I don’t remember) but I got my things and took them directly to the balcony porch and started mixing my colors. I had no idea what I was doing, and creative decisions are generally hard for me. What do I want it to look like? What should I do? How do I do this?

In general, I’m afraid of messing up. Things that can’t be undone terrify me. A deep-seated panic sets in and I’m instantly thrown off any game I had. I can’t mess up. I must foresee all the eventualities and stay the proper course. I must do things right. The first time.


I ended up painting a somewhat abstract thing with a mixture of colors fading dark to light. I painted the word “hope." Hope, to me at the time, was something I wanted to understand. Hope was the way I wanted to live my life. Hope was what I needed. Even if I wouldn’t hang it up in my house or give it away to someone, I’m still proud of it. I actually surprised myself with what I was capable of. I still love the idea it represents and the part of my life it pictures. It marked a change, an entrance into a more risk-taking, more bold, and more hopeful mindset.

I think that’s what art does. It marks either an ideal, an emotion that we feel, or one we want to feel - what we see around us or what we want to see.

old canon single lens reflex

I have this old DSLR that I got in high school, which I’ve since stopped using because it has some sort of focus problem. Anyway, I was thinking recently about how my life lacked passion.

Sure, there are things I enjoy and things I like to do, but rarely, if ever, do I spend my time actually doing them. I had quit. I had let my creative well run dry. And when a well runs dry, it’s not good.

I realized the reason I had stopped doing these things was because I couldn’t get what I wanted to see from my brain to my hands, or whatever is necessary for the idea to be translated. I was frustrated because I couldn’t turn my feelings or ideas into any creative expression that I liked, or thought did the original idea justice. It’s the worst, actually. I couldn’t live up to my own expectations. And failing yourself is not especially inspiring, believe it or not.


But try - even when the odds are stacked against you. When you don’t have the right gear, the right supplies, the right whatever, or the “natural gift or talent”. Try when you don’t want to, and when you do want to. Even if you don’t like it, try. Even if you mess up, try. Even if you don’t think people will like it, try. Even if you throw it away, try. Even if you love it, try.


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Here are some things that have helped me tap into my creative well, get inspired with new ideas, and refine my aesthetic.

  • Put on an outfit you feel super good in and go out for coffee, and walk around the town. Explore the tiny shops even if you feel like you might be out of place. Go in anyway.
  • Go to the craft store and look around. Find something that gives you an idea and run with it. (Not out of the store, shoplifting. Obviously, buy the items. Run with the idea.)
  • Browse typography or artists on Pinterest or Instagram. Find people who post things you like aesthetically and follow them.
  • Write whatever you want. Write what you feel, write what you see, write your grocery lists, write a note to your friend or your mom or your cat.
  • Redecorate your space, your room, your workspace, your desk, whatever. Find some things you like. Make it lighter, make it darker, make it bolder. Find a cool potted plant, get some new curtains, open the window, clear off your table, repaint the wall. Get new bedding. Buy a new lamp. Rearrange the furniture. Buy a new rug. Light a candle. Find things you like. Find things that you love and want to look at every day. Find things that inspire you and make you feel at home.
  • Clean up. Get rid of the clutter. Wash those dishes (that have been sitting around, I totally get it, in every room, for weeks). You’ll sigh with relief, I promise.
    Find new music. Listen to old music you used to love. Listen to music you don’t know if you love or hate. Listen to music you’re afraid of other people knowing you like.
  • Read a book. Make a list of books you’ve always wondered about. Make a list of those books you were supposed to read for your AP Lit class in high school and never did.
  • Get outside. Find a hiking trail, a stream, a river, a mountain, a desert. Get outside and explore. Don’t worry about where you’re going just go. But maybe try to remember the way back.
  • Take some pictures. Try to think of things differently. Get closer to things that you usually wouldn’t. Look up, or look down. Get a wide angle. Take a picture of your coffee and your muffin, your shoes on a cool tile floor, the texture of the sidewalk, whatever.
  • Buy a new outfit. Buy a new pair of shoes. Buy a new jacket, a new scarf, a new pair of jeans. Buy something out of your comfort zone, something you don’t think you can pull off.
  • Try something new. Journal. Every day. Something. It doesn’t have to be sentences or weird documentation of your every move that day. Write something you felt. Write something you saw. Write something you thought.
  • Sit somewhere quiet. And think. Outside, maybe. Sit in a chair and think. Don’t fill the silence, just think. Don’t look at your phone. Don’t think about your lists. Just think.
  • Take pictures of a friend. Get out that old idea book and pick one. Think of a new idea for a video, or painting, or sketch, or craft. Make a video without words. Make a sketch without picking up your pencil. Make a painting with only a few colors or shapes. Switch it up. Make it specific and see what you can do. Make it broad and see what it becomes.

Pick up a new hobby. Pick up a new routine. Try something you’ve never tried before. Be someone you’ve never been before. You may like them. You may feel more yourself than you’ve ever felt.


Written By:

Lara Crotty | YWAM Orlando Alumni