Overcoming the inevitable “Oh fuck…” point in EVERY creative project

When I get commissioned for a painting, I feel thrilled. Excited. Eager to start. I purchase the supplies necessary and may even watch a YouTube tutorial to make sure my skills are fine-tuned and ready to go.

I think about the painting a lot before I do it. I feel giddy.

And then I go to start it.

And my gut drops.

And I wonder…

Is THIS the painting I will fail on? What if I’m actually not good at painting?

In the past, I’d use this as an excuse to avidly avoid the project until the last possible minute when I had no choice but to power through the fear in order to show up to the client meet-up with a barely dry product.

Now? I break it into bite-sized pieces. I can’t make the whole painting at once. You can’t write your whole book at once. We have to make it bit by bit, layer by layer, word by word, or stroke by stroke.

First, I have to make a background.

And the background is the super easy whimsical part. So I really let myself flow on that. I refuse to concern myself with the next steps. I only focus on what’s right in front of me.

After the background is done, I’ll allow myself a moment of celebration. I’ll let it dry. I’ll set it aside and watch a baking show or work on another background. I’ll admire the background with a sweet smile and compliment.

This helps me gain momentum, which is great. Starting is the most important part of a creative project. Doesn’t matter if it ends up looking a hot mess. That can be fixed. A hot mess first layer is better than ZERO layers and the stress of not having started.

Next, I trace the animals (it’s a pet portrait) and fill in their bodies.

This is when the second “OH FUCK…” moment kicks in.

Holy crap there’s still so much left to do. THREE DOGS. THREE. Do I even know how to paint dogs? What if the other times were flukes?

So then… I break it down into bite-sized pieces. Again.

One dog. Let’s just focus on one dog.

This again helps with momentum. The fear of what could go wrong starts to be balanced out by the clear evidence of the contrary.

Focusing on the victories of the painting thus far, I move onto the next step.

To be frank, there are typically a few other “OH FUCK” moments during the painting of each dog. Normally after the first couple layers of shadows and background work. There’s this period of time when the dog has an eye socket but no eyes and looks terrifying and the tiny voice goes, “WHAT IF THIS ONE IS HORRIBLE.”

Any time that fear pops up, I simplify my steps further. “This ear. I’ll focus on this one ear.”

In time, the layers marry beautifully and begin looking like a real life dog. (Or at least, my own whimsical version of a real life dog.) 🙂

Once I finish a painting – and this happens every time – I have a good day or two of awe. Like a honeymoon phase with someone I’ve just met and begun falling in love with.

Wow. This painting happened through me. It was created THROUGH ME.

Then I will inevitably share pictures with my immediate support group of people I know will be amped for me.

Then I’ll share with fellow artists to ask if there’s anything wonky to be changed.

And then I’ll drop it off to the client.

And that’s the moment that makes it all worth it. The gasp + excitement + smile on a client’s face when I hand them a personalized painting brings me SUCH UNEXPLAINABLE JOY.

This particular client sent me this amazing shot!

So… Whatever project you’re working on… Remember: HAVING FEARFUL MOMENTS IS A NATURAL PART OF THE PROCESS. Avoiding it will do nothing but feed the fear.

Break it down into tiny pieces… And then START.

(And if you want a whimsical pet portrait by yours truly, submit a request form on my painting page!)

There is only ONE you. Go make cool stuff.

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Some days, I paint. Other days, I write. And rap. And tell stories. And do comedy. And doodle. And [attempt to] bake. And, one week out of every month, I merge with my sofa and sob about mortality and things like the existence of air and how we can't live without it and how utterly claustrophobic that is to consider. I'm relatively particular. And this is a place for me to share ALL the quirks.

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