Creative Risk Taking



“If you are unwilling to risk the unusual, you will have to settle for the ordinary.” – Jim Rohn

OK, I know it’s a cliché, but you’ve heard the idea that everything in life worth having requires risk. Getting started can be the hardest part! It requires you face your fears and take that risk.

-Within reason, of course!

Let’s talk about what I mean by risk, and I’ll give you some ideas to help you through the scary part!


By risk I mean stretching beyond your comfort zone, trying something new, or experimenting with a new medium. And I also mean a deliberate and sensible approach to your creative pursuits. I don’t mean throwing out the mortgage, buying a 70’s van, and travelling west with a knapsack! (Unless of course, that’s what lights you up!)

Preparation is key here. You may have to go with your gut, but you DO need to be prepared.

You have probably heard of another cliché, if you fail to plan, you plan to fail. Replace the word “plan” with “prepare” and you’ve got a great recipe for good creativity. This is crucial when taking a creative risk.

I firmly believe that there really aren’t any wrong ways to express creativity. So where does the risk lie then? It’s not so much in WHAT you create, as much as the imagined – note I said IMAGINED – failures.


The definition of risk points out the “possibility” of loss, the “potential” of failure, the “likelihood” of something going badly.

I’m noticing something here. Did you notice it too? There isn’t any word like guarantee, promise, or assurance that it WILL go south!

It’s simply about the possibility! Basically, it lives in our imagination!


Many people hold themselves back from taking a risk and feel they need to play life safe and do everything by the rules. They protect themselves from disappointment, discouragement and failure.

I know that feels comfy cozy – but…

Some rules are meant to be broken and by trying to protect yourself from failing, you inevitably become a failure by default. Don’t “fail” to launch my creative friend!

Stop holding yourself back and go for it.

The funny thing is, when you are prepared and take a risk, it will seem like luck is on your side. When you’re prepared, the inevitable roadblocks will feel expected and tolerable. Sometimes it will feel like you’re at the right place at the right time. But in reality, it’s the combination of your hard work, your preparation, and your ability to be open to possibility – even the not so pretty ones! You’re basically creating your own luck.

Sometimes you need to take a risk for a dream that only you can see.


As Brian Frink said in his TEDx Talk, the challenge of art is that risks are necessary! We can’t avoid it in creativity.

But the good news is that there is no loss of life involved, no one is going to die, the bridge won’t collapse.

Creativity is a discipline where you can’t really make a mistake and there’s no right answer. It’s all about identifying with what we are making. And therein lies the problem. Identity!

We somehow wrap up our identity into our work. So called “self-expression” implies that are making something that has to do with our own identity, feelings, thoughts, and values. That’s probably true to some extent.

And we’re trying to communicate that identity, and our viewpoint is all wrapped up in it.

AHA! Therefore, we have to risk our sense of exposure or loss of identity! We can’t be having that now, can we?

So, you start a piece, and you do a few things, and then a bit more. What if it’s going along just fine, and then, suddenly you look and it’s just a big mess? What does that say about us?

Or worse – The work starts taking on a life of its own! It starts pushing to go somewhere other than what you had in mind? Where do you, the artist, fit in now? Where’s the sense of self now? It’s here that the ego starts to get involved. YIKES!

David Bayles has a wonderful quote that speaks directly to this conundrum: “to the artist, all problems of art appear uniquely personal. Well, that’s understandable enough, given that not many other activities routinely call one’s basic self-worth into question.”

Uh YEAH! HELLO… It’s like, as we step to the canvas, we’re courting disaster.

So, a little tough love here – let me just say right here – it really isn’t! Think about other professions – firefighters, police, soldiers, even bridge builders and architects. If something goes wrong, disaster could happen – and yet they don’t stand in front of the job and refuse to continue because they are afraid of what others might think of them. Why do artists have such a hard time facing this?

Is it “self-expression?”

Maybe that’s the problem!

According to David Frink, maybe art isn’t JUST about SELF expression. Maybe art and creativity are about OTHER expression. Stick with me here.

Maybe art isn’t just about you the maker. OK, I’ll stop the slow walk to an epiphany here and get to the point:

It’s NOT about you! It’s about the viewer too.

It’s about the connection that the viewer, the receiver, the collector, will have with the piece.

Remember, in the end, It’s NOT about YOU!

How cool is that?


In general, creative people are usually good risk takers. Creativity is, by nature, a risky business. There’s a world of creative geniuses out there who aren’t afraid to put something new out into the world that might be laughed at. And you’ve probably heard of the old tale about creative people being dismissed as crazy or strange. If you want to be a more creative person, this is a personality trait you might want to consider, and it’s easy to do.

First, consider this: Without risks there are no rewards. You will have a few failures but if you can keep your failures from discouraging you, the next attempt might be that big success you’ve been dreaming of!

If you have all those good ideas, but you’re afraid to take the leap and put them out there, here are five ideas for changing your mindset.

~Risk-Taking Takes Practice

Like everything else, facing risk and winning takes practice. You have to put your ideas out there over and over again, and eventually it feels like a normal everyday activity. Create, rinse, repeat! It’s just like learning to drive, riding a bike, or getting up on stage. You can tame those fears with enough practice and stage time. You would never encourage your toddler to stop trying after the first faceplant on the living room floor! Don’t do that to your inner artist!

~It’s Not the End of the World

It’s scary to do something for the first time, especially when you see all those other artists who are better than you are. But when you put your ideas out there, you’ll realize that even if they get shot down, you still survived. Nothing truly bad happened (a bruised ego doesn’t end life!). Take what you’ve learned and try again.

Remind yourself that you’re not taking a physical risk like racing cars or skydiving. So, get comfortable with sharing your ideas and make it a habit that will propel you forward.

~What’s The Worst That Can Happen

What’s the worst that could happen when you present your ideas and artwork? Maybe someone doesn’t like it. OK, they aren’t your audience. So what! You might face criticism, but that’s all. In fact, you might face constructive feedback that leads you to a better idea. Maybe some part of your first idea can be used in a different way. Or maybe, your initial idea becomes the foundation for a bigger and better idea. The important thing is to keep perspective. It isn’t the end of the world.

~Rewards Matter More than Risks

On the other hand, what if your idea or artwork is the one that takes off? This is a great reward for taking that risk. One way to encourage your inner risk-taker is to focus on potential success rather than potential failure. Remember, at the beginning of this article I talked about the “potential” and not the “guarantee.” If you focus on all the great things your art could bring, like the happiness it brings to others, it’s impossible to NOT try!

~The Value of Failure

Here’s the reality. When it comes to creativity, both success and failure are super valuable. Success is valuable for obvious reasons! Whether it’s money, or fame, or just plain pleasure and beauty. But failure is valuable because you can learn from it. If you’ve been here long enough, you know one of my favorite things I tell myself is “I never lose. I either win or I learn.” And I always learn from a perceived failure.

But doing nothing at all provides no value what-so-ever. The only way to truly fail is to not try at all.


If fear of failure and fear of risk are holding you back – Here’s a challenge for you.

Take a moment to construct a small project to get you accustomed to the risk factor in art making.

Build the loss of control into the piece. Build in the risk with intention so you can get used to the fact that it may not go well, and that’s OK!

I’ll used painting as an example, but you can do this with paper, or yarn, or clay – whatever your medium! The general idea is uncertainty and very little control. This is something David Frink suggests, and I have used it too!

As a painter, I find a hunk of unstretched canvas and fold it several times over. I challenge myself to paint something on the exposed part only. Then I go about folding and unfolding a hunk of canvas. I then paint something else on the newly exposed part. The beauty lies in the fact that, if I can’t see the whole thing, I have a sense of – but never a full picture of – how the parts relate. I have very little control over relations and continuity. I get glimpses as I fold and unfold, but the whole is in my imagination. I have willingly relinquished control.

Now I may stick to a certain color palette, or subject matter – say “geometric shapes” or “fruit.” So, there’s a little control and continuity. But I have no control of how it will look as a whole until I am finished. And yes, it can be a real mess when I’m finished. But there are usually tons of beautiful parts and studies for future work.

Risk is about discarding the rules for what you create and just see what comes of it.

As humans, we always try to orchestrate the outcomes. But as in life, creativity is an unknown and unforeseen adventure!

You can only see a bit of the past. The future is blank.

All you can really work on is what you see right now.

Stay in the moment and make our lives and our art a big mess.

So, what mini risk project will you try? Grab a piece of paper, some canvas, or some yarn and go for it! Even if you just fold and refold a sheet of paper and doodle on it, you’ll start to release that sense of fear around the unknown. Share your progress below in the comments.

Join me LIVE on my Facebook page, Virginia Leigh Studio, at 3:00 pm Central every Wednesday and we’ll chat about this. I’d love to hear from you.

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