You’re Probably Going to Fail

My definition of failure is not taking a chance. Not risking it. Playing it safe.

Everything else that other people might call failures, I prefer to think of as lessons.

©Kathleen Denis, Satisfaction Guaranteed. Oil on panel, 24 x 18 inches. Used with permission.
©Kathleen Denis, Satisfaction Guaranteed. Oil on panel, 24 x 18 inches. Used with permission.

Failure would be giving up without absorbing the lessons that might contribute to my personal and professional growth.

You’re probably familiar with this well-known quote:

What would you attempt if you knew you couldn’t fail?
– Robert Schuller

It’s a good one, huh? What would you try if you were assured a successful outcome?

There’s zero risk, so why not?

©Carolyn Young, Wolf Cries. Stoneware and poplar, 21 x 6 x 1 inches. Used with permission.
©Carolyn Young, Wolf Cries. Stoneware and poplar, 21 x 6 x 1 inches. Used with permission.

I’ll tell you why not. Because it doesn’t sound like fun. It’s a gimme. There’s no adrenaline rush or sense of accomplishment if you already know the outcome.

I like this updated version:

If something is important enough you should try, even if the probable outcome is failure.
Elon Musk

In other words, what do you believe in so passionately that you are ready to take a chance on it even if your success isn’t guaranteed?

Why do it if you are pretty sure you’re going to fail? After all, it goes against our human tendency to protect ourselves from fear and rejection.

Because of this one word: Progress.

A Life Lived Fully

You’ll never know what is possible until you take bold steps into the unknown.

Imagine a life lived fully – ready to take risks, aware that success isn’t guaranteed, and knowing that every failure gets us closer to the greatest rewards.

Consider all of the colorful obstacles and people you will meet along the way that will enrich your life.

On the other hand, imagine living a life marked by regrets. Refrains of What if or If I had only.

If I had only reached out to x? Or … What if I implemented the lessons sooner?

Here’s a go-to question for you to ask yourself when you’re hesitating to make a daring move:

Would I rather risk failure now or regret later that I didn’t try?

Where Are You Playing It Safe?

A few months ago I asked a client what her acceptance rate was for getting into art shows. (She hadn’t been too thrilled with results at those shows.)

“Nearly 100%,” she said proudly.

“You’ve set the bar too low,” I replied.

She needed to look for more prestigious shows and venues that are in alignment with her dreams.

©Vicki P Maguire, Long Ride Home. Oil on linen, 16 x 16 x 1.5 inches. Used with permission.
©Vicki P Maguire, Long Ride Home. Oil on linen, 16 x 16 x 1.5 inches. Used with permission.

To her credit, she met my challenge. The first show she heard back from said Yes, and was one she didn’t think she had a chance with previously.

Her acceptance rate is going to plummet, and that’s wonderful news. She’s prepared to fail in service to progress. Her goals are that important to her.


What is so important to you that you are willing to risk failure? Please tell me in a comment below.

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24 thoughts on “You’re Probably Going to Fail”

  1. I was scared to open this email because of the title but after reading through it, I apparently set the bar high. I rarely get accepted into the big shows I apply for even though my work would be an awesome complement to the work they choose. I stopped doing outdoor shows due to low sales and high costs and time commitment. So I have been focusing on galleries and sales through my network. I’m not afraid of failure but it does beat you down if you don’t get a success every once & a while.

    1. Nicole: Good for you for setting the bar high!

      Wins, however, are important. Wonder if it could be lowered just a tad to find some of those – or to create your own wins – that you control?

  2. A lot of artists are definitely afraid of failure. Even more artists are desperate for success (e.g., increased sales and increased revenue…perhaps fame…increased name recognition…being a full-time artist who makes a decent annual income (i.e., “goodbye day job!”)). Well, unfortunately, when people are desperate to become successful especially in a field where the competition is tough (actors, actresses, and artists are a dime a dozen), people like Harvey Weinstein recognize this and take advantage of people — Harvey is at the extreme end of the spectrum. Somewhere not that far on the spectrum are people who realize they can prey on these folks not sexually but financially by selling them hopes and dreams. “Hey, there, aspiring actor! I can help you fail less often and succeed more often! I’m a great acting coach and I can make you a much better actor and help your career! And it will only cost you $$$” — and you can easily and appropriately pull out “aspiring actor” and put “aspiring artist” in there. My point is to watch out for the wolf in sheep’s clothing or the snake-oil salesperson who will promise to help artists fail less and succeed more…and they’ve got just the book or class or conference for x number of dollars that will make that happen. Oh, and then if the artist still fails and goes back to the coach/consultant/salesperson and says, “Hey, I spent x number of dollars on your advice and training, but it did not produce much if any positive results or outcomes.” then the coach/consultant/salesperson quickly replies with, “Well, it’s because you did not try hard enough”…or “correctly do what I told you to do”…or somesuch where they essentially say it’s the artist’s fault and not theirs. It can be a tough world out there. Peace.

  3. At 77 I have moved from the Seattle area to the high plains of Wyoming, Pine Bluffs to be exact. This is not exactly the center of the art world! This past month I have entered four competitions, one of which is the Artist’s magazine “Over 60”, which is very stiff competition! I am working through your “I’d Rather be in the Studio”, am settling up Artwork Archives, am painting. My sister just had serious eye surgery and so am helping her.

    I DARE, BIG! Thank you for support, ideas!

  4. I took the step to rent a space in a gorgeous old 100 bank building. It’s a public retail space on Main Street in a town outside of Bozeman. It was a crazy chance to take but it was my dream true. I use it as a multipurpose space. It’s my own little gallery, my studio, my office , and my classroom. It’s not a good location for walk in art buying traffic . Just to cover my overhead each month creates a lot of pressure for me to stay in there and sometimes I wonder if it’s worth the risk. But I’m still there and I just signed my 2nd 3 year contract! I feel that the investment shines a brighter light on my work because of the beautiful space. It’s a funky space so it draws my students in. In addition to regular classes, They celebrate with private painting parties there as well because it’s so cool. To make my expenses, I have faced my fear and now I teach. I never knew I had it in me! It it gives me pride to be there. But many mornings I have a stomach ache from the fear and the risk that I am taking. But my heart tells me to keep risking it and that it is where I should be.

    1. Wendy: Bless you. This is amazing. How wonderful that you listen to your heart.

      Is the fear around teaching? Paying bills?

      Here’s a challenge for you … Wonder if you could create a signature workshop/retreat so that people pay you big $$ for an experience rather than “just” a class?

    2. Yes!!!! The fear is TOTALLY around paying bills and actually making more profit. After working so incredibly hard, juggling the many aspects of my business, I look at my end of the year numbers and I’m so frustrated. That’s the real reason why I am taking your workshop! I feel like I am very professional but it seems like the COGs takes away the profit. But anyway, I would LOVe to do a workshop retreat! I just need to work on my confidence and figure out how to craft such an event. Would love to have your advice since you obviously have this down! I realized that I can sell my experience as an artist. But I also feel lieke I am still figuring it all out!!! Even when a paint every painting, it still is a puzzle that I solve.
      Thank you for your encouragement, Alyson!

  5. As a pastor it was easy to tell people that you need to get out of the boat if your going to walk on the water but doing it myself has been a challenge. You have to face your fears of failing, and the voices from the past, and take those steps. I am in the process of setting up my own website and being stretched as well. I have even thought about pursuing a masters degree which would stretch me even further, but I am at a point where I am tired of wondering “what if” and having regrets over not pursuing my dreams and passions. I would rather sink trying than not to have gotten out of the boat at all.

  6. I’ve been doing the Art Fair show circuit for the past 15 years and started with 18 shows and am now down to about 8. I have been in the top 6 rated shows along with the lesser rated ones and am now noticing a couple of things that I’ll pass along. The amount of good artists then and now has grown at least 400% and the amount of buyers who value original fine art has greatly diminished. In speaking to other artists at the shows we think the buyers in the 28 to 42 age group don’t value original art much at all and would rather buy a $200 framed poster at Wallmart that they can toss in a year and buy another one. I would suggest anyone wanting to make a living in the Art Fair events would do better finding a teaching job.

    1. Thank you for sharing your experience.

      I don’t think you can lump all 28-42 yo into that category, just like you can’t say “retirees don’t have the space for art.”

      I suggest that, for some, finding new venues might be preferable. Not everyone is meant to teach.

  7. When I’ve posted videos on my Facebook page of myself showing my artists books, I’ve had the highest engagement I ever get for a post. But doing videos really phases me – especially talking in front of the camera.

    So in 2018 I’m challenging myself to do these kind of videos regularly and maybe even do some live. I know it’s important and I just can’t afford to duck out of it any longer!

  8. I am currently writing a book on color mixing which is a huge undertaking. However, it is really important to me to help painters end their frustration with mixing color. I know that my unique system is not being taught and that it is effective.

    This could be a big failure, but I am not counting on it! 🙂

    Thanks for asking.

    PS I find it interesting that we rarely talk about the fear of success. Any thoughts on that?

  9. I am taking the biggest risk of my life right now. I do installation project work on themes of empathy and compassion. I am building a phone app ( that tells you when you are being thoughtless, inconsiderate or just not mindful with your phone. I have never done this before, nor do I know anything about programming and have invested my own money (see Indiegogo campaign here if you would like to help me out and donate a couple of dollars:

    I think the world needs this now (it can also be helpful for people who have trouble taking social cues) and I believe in it.
    We will see……

  10. I’ve been a self taught Artist since 2011 and have been winning Best of Show awards in local and regional art competitions. And recently won two Gold Awards in National Juried Art Shows .
    I’ve been teaching drawing classes for 4 years in multiple places including museums, art guilds and Art Centers. Earlier this year I decided to take a break from teaching and focus on my own artwork… then I found out that I had been selected as one of the Top 11 Painting and Drawing Teachers in Tulsa! GRANDMOTHER ALWAYS SAID, ‘DON’T LOOK A GIFT-HORSE IN THE MOUTH”… so I’m getting back into teaching!!! I start classes in another museum next week and have landed a venue with an adult Community Education Department teaching others to draw.
    I can do that because I have a passion for teaching!
    What I want to do but am afraid of failing at is: PAINTING!!! I hear all great Artists PAINT? I’ve dabbled with Acrylics, Oils and knife paintings too. However, the more I use color – the more I just want to stick with values, composition and contrast. Having gotten the use of values down pretty good I’m considering going with Black & White Oils or Pastels. Any ideas on how to make this leap a great one? Thanks, ~Ken

  11. I left my teaching job this summer, and although it seemed a monstrously risky thing to do, I don’t regret it for a second. I am doing something that I have wanted to do for years, and although it is still very uncertain, every day is relished. There are so many new challenges and skills to learn, and of course this brings a certain amount of anxiety, but the sense of achievement at each small step is very heartening.

  12. I am scared of failing at my latest project because I would be letting people down.
    I determine to paint 25 portraits in oils on canvas by the beginning of next June.
    When I started, I hadn’t painted in oils or on canvas before, so my first task was learning the medium and getting the colours right. I’ve achieved that part.
    The “but” is that I haven’t completed a single portrait yet. I’ve started 7 and I have very nearly finished the portrait of a friend. I learned my oil technique on the one of my friend and it is nearly finished from my point of view. (I have now put my foot down about any more alterations.)
    There is no reason why I can’t complete the portraits. I just need to get past the fear and do the work. It is too easy to find distractions. There is a wall to plaster, and a cupboard to paint and …
    NO! They’ll wait until next year.
    Today I have set up portraits of the cutest baby and a gypsy boy on his pony. They will be my reward for good behaviour when I have finished the one of Mr Welsh.

  13. Interestingly, since coming to the end of my tenure as my mother’s primary family caregiver – and having done that very successfully – I find that I have no fear of failure at all. That said, I do know that every one of us encounters obstacles that must be intelligently addressed, especially if th fear of failure is gone.

    On the other hand, I do have a small problem with fear of success.

  14. Pingback: How to Be a More Confident Artist with Gwen Fox - Art Biz Success

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