Are You Willing To Risk It All?

For those of you who aren’t painters, I want to tell you this secret. To be a painter – even an amateur one like me – you also have to be a gambler. Painters have to be willing to lose, repeatedly, until a painting is finished.

Every time I make a painting, I reach a point where I must put everything on the line, bet it all on the next brushmark. And many times, I lose.

Now, I’m not a gambler in any other way. The only slot machines I ever remember playing were the ones I visited at the Las Vegas airport en route to the Grand Canyon. I didn’t win. Lottery tickets tempt me sometimes. But the potential jackpot is less compelling than the greater likelihood of losing. I’ve never considered myself particularly lucky.

Instead, I prefer a sure thing if I can get it. I am a creature of routine and sameness for this reason. I know what I like and try to maximize my chances. Maybe I just like control. Don’t most of us?

But painting is never a sure thing. It’s a practice of uncertainty and risk. Painting is always a gamble. 

The first brush strokes come with low stakes. There’s a lot less to lose when so little has been invested. But as a painting progresses, so increase the moments of possible ruin. With each new brush stroke, the razor’s edge becomes thinner.

Yes, mistakes can be corrected and even Bob Ross style happy accidents may add life to a painting. But I can tell you it’s not as easy to fix a painting as you might think, especially not if you want to preserve some precious part you’ve attached to. Changing one thing often creates a domino effect of other needed adjustments. This is doable. In fact, better paintings often result. But there is almost always something lost. And it is a gamble. The losses may never be recouped by the final bet.

When you look at a painting, there is typically no hint of the artist’s sweat, or that razor’s edge in view. You decide if you like it or not, and move on. You don’t see the paintings that have been tossed, scraped down, or sanded away, sometimes after countless hours of attention. But the artist remembers. The artist can’t separate the painting from the process of making it.

Maybe there are painters out there who don’t identify with what I’m saying at all. I’d love to know YOUR secret! And I’m aware there are ways of painting that make outcome more predictable. Still, I recently heard that Anne Packard once threw one of her paintings into the ocean. I know the struggle is real, even for great painters!

And I know the paintings I’ve wanted to throw into the ocean are often the ones I become most attached to. I don’t throw away the ones I don’t like. Instead, I let them rest where they taunt me until I have the courage to go back and try again. These are the ones I suspect others won’t value the same way I do; these are the ones that contain a bigger piece of my heart.

I don’t really like gambling. I hate to lose, especially in a contest with myself. I’ve had enough loss in my life already. But I am a painter, which requires me to be a gambler. I keep painting. Because sometimes I win. And only because I am willing to try again.

And sometimes I even understand: What is meant to be kept, can never truly be lost.

And sometimes I even know: we only find out what is truly possible, when we are willing to surrender everything we have attached to.

Are you a gambler? Are you willing to release the things that hold you back for the possibility of something greater?


Here are a few recent paintings that were saved from the trash.

This painting sat in my closet for a year before I pulled it out and painted over most of the original painting. The darker blue at the bottom was once the sky and that is the only part I didn’t touch.
This is another painting that sat in my closet for a bit. Now that I think about it, the sky in this painting was once the ground also. Seems to be a repeated theme!

11 thoughts on “Are You Willing To Risk It All?

  1. it occurs to me that although you describe yourself as someone who likes control (who doesn’t?), you seem very comfortable enough with putting brush strokes laden with paint on a canvas and taking your chances. this observation reminds me (whether it’s true or not, i don’t know) that our internal narrative about who we think we are (“i like control”) very often tells only part of our story. in a way, this awareness is liberating in that it expands our description of who we think we are and by doing so, liberates our attachment to one or another of our dimensions.

    it’s probably no accident that many of your paintings, with their nautical energy–or just plain ‘energy’–depict on canvas the swirling, morphing, universe in which we live.

    just saying.

    Liked by 1 person

    • Yes! Well it’s always AND isn’t it. I like control and I know how to skate on the edges of it, how to live with the uncertainty. And I wonder about the freedom that comes from truly letting go at attachments, including attachment to outcome in painting. I wonder what painting (or anything) would be like then…

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  2. okay so I really thought you literally just painted these masterpieces w/ a little struggle, but certainly like nothing you describe! When one doesn’t see the effort behind the work, one assumes giftedness. Thank you for enlightening me. I need to hear this lesson this week.

    Liked by 1 person

    • Ha! Well I’m honored by the use of the word masterpiece and I’m so glad you found relevance in your life! I think there is something true about people having differential aptitude’s for things but I definitely think that what may seem like giftedness is really a combination of perseverance and courage and ultimately moments of being able to get out of the way. Xo

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  3. I never thought of painting in this way, Amanda, but you describe the artistic investment and gamble perfectly. Writing is different because the rewriting/editing, though not easy or painless, gives us a “delete” key for a reset without risking the parts we love. And you’re right, as a non-painter I love your work without seeing the creative process behind them. They’re beautiful. ❤

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    • Thank you for the kind feedback, Diana. Your presence and ease of connection is so deeply appreciated, and not just by me! I don’t often know why I feel compelled to write about something in particular. My “muse” often seems to have an agenda beyond my ego’s comprehension. Through painting (and writing too), I often see where I am limited and where there is greater capacity than I recognize (or realize). I’m always looking to connect with others who are thoughtful about the creative journey, which surpasses any particular work of art (painted, written, or otherwise). Sometimes I think I care more about how we create than what is created. But that may simply be a stage in my creative journey. I wonder about yours. How you came to allow yourself to access the stories that live in you. Whether it was effortful (or perhaps still is?) or more like breathing (effortful moments nestled in automaticity/flow). xo

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      • “Sometimes I think I care more about how we create than what is created.” A lovely musing and one I can relate to. I never tire of learning about the creative impulse and process of other artists. It’s utterly mesmerizing. I still seek that fluid balance of effortless inspiration and effortful craft. 🙂

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      • Hi Diana! I’ve drafted a new blog post that references this exchange and links to you and your blog. Would you like to check it out in draft form before I post it? Or are you willing to be surprised? It’s not a post about you, but I do express appreciation for your friendship, include an excerpt of this exchange, and suggest other’s check out your blog 🙂

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      • How sweet of you. Just go ahead and post it, my friend. I’m so glad our conversation was thought-inspiring. 🙂 And you’re so kind to give me a shout out. Not necessary but appreciated. I’m looking forward to your post (as always).

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  4. Pingback: On Connection, Clarity, and Friendship | Painting Poetry in Motion

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