Toggle Side Panel
The Working Artist Learning Site
  • TWA Site
  • Support
  • LOG IN
More options

    Shopping Cart

    No products in the cart.

    Sign in
    • TWA Site
    • Support
    • LOG IN

    The Day I Made An Artist Cry

     Years ago, when I ran a gallery, I used to receive hundreds of emails from artists every week.

    “Here’s my work. Will you represent me?”

    Delete.  Delete.  Delete.

    Not because the work wasn’t good. Because that’s not how the system works.

    1. Artists don’t understand the system

    Two or three times a week, someone would also show up unannounced, dragging a portfolio into the gallery. “Here’s my work, will you represent me?” One day a man came in uninvited and showed me his art. I had to explain to him nicely that this wasn’t how we made our decisions. And then he started to cry. Tears of frustration fell down his face because he wanted to be an artist so much, but he didn’t know how to get those doors to open. He didn’t understand how the system worked.

    “Where can I go to find out? Who can help me?”

    It broke my heart. I didn’t have an answer. So I decided to find out. I read every resource that was out there, but to be honest I didn’t see a lot that impressed me. So I created The Working Artist for him — and for the hundreds of other artists I’ve met over the years who feel frustrated by their art career.

    Art schools today do students a real disservice. They’ll show you how to make art, yes. But they don’t show you how to navigate the changing landscape of the art business, nor how to sell work. No one teaches you how the system works. And if you aren’t part of the system, you’ve got to make your own.

    2. Fear is the real blocker

    I believe that any artist can succeed if you’re willing to do the work. So why do so many artists struggle? In my opinion, the biggest obstacle to success is fear. Fear of not making enough money. Fear of not being good enough. Fear of not being young enough, thin enough, smart enough. It all comes down to fear of not being enough.

    But the thing is — you are enough. You really are. You can’t silence your fears, but you can choose to stop listening to them and refuse to let them slow you down.

    3. Self-confidence = doing what you say you’ll do

    Many artists tell me they’re held back by a lack of self-confidence. But what is self-confidence? It’s confidence that you do what you say you’ll do, when you say you’ll do it. It’s confidence that you have your own back. That what you say is true — even in your work. Especially in your work.

    You build it by practicing these skills:

    • Meet every deadline

    • Be where you say you’re going to be, when you say you’re going to be there

    • Present yourself professionally

    • Deliver everything at the highest quality that you possibly can — then over-deliver

    • Don’t allow haters to knock you down

    It’s not something you’re born with. It’s not something anyone else can give you. It’s a skill you develop over time. And in this business, it will serve you very well — because in the art world, you will fall down, you will fail, you will meet with criticism and rejection. The only way to avoid it is to never share your work. And that’s just not an option.

    There’s no straight path to this. Only your path.

    The question is simple:

    Are you willing to take it?

    ___________________________________________________________________________

    Written by Crista Cloutier, artist mentor + founder of The Working Artist. (learn more about Crista here)

    Crista
    April 28, 2026
    « You Are the Brand, Artist — and That’s Not a Bad Thing

    See Your Art Career with Fresh Eyes

    Created by art mentor Crista Cloutier, this short self-assessment reveals the  
    strengths of your current practice and offers insight into the next step of your professional path.

    Personalized insight

    Practical next steps

    Encouragement to grow your art

    The Working Artist Learning Site

    Trusted by artists in 80+ countries


    Fellow, Royal Society of Arts


    Gold Medal, French Academy of Arts, Sciences, and Letters 

    Winner, Best Online Art Business Artist 2025 

    Guiding artists toward confidence, clarity, and creative freedom since 2014

    Contact 
    Privacy Policy
    Copyright The Working Artist 2025
    Learning and Web Design by Learnbase