Ever been afraid to paint. Afraid to make a bad painting so you just don’t. Been frozen and the voice in your head stuck on a loop.

Who do you think you are?

Nobody is going to want to see this.

Your painting is dull.

Your paintings don’t mean anything.

Whether you’re there right now, or you’ve ever been there… and most of us… this is for you.

We’re getting prepped for another great ART+WORK+LIVING 5 Day Painting Challenge!

It’s one of my favorite events that we put on. Seeing the building confidence and speed that the group achieved over just five days is inspiring.

One of the real challenges to the Challenge is learning to let go of perfectionism, which is really just fear of failure wearing a different coat.

​​And by Day #2 that challenge usually crops up for lots of people…

But the pot of gold at the end of the rainbow is that the people who face that head on and let go, as hard as it is, make the most progress.

I shot this video to coach these folks over the half way point.

Fear of failure and perfectionism are two of the biggest road blocks we can face as artists, whether you’re doing a painting challenge or just facing a blank canvas in the studio.

If you’d like to find out more about the challenge, go to


Hey there, Mary Gilkerson here and we’re going to be talking today about the importance of failing in creating rituals and habits and building that daily painting habit. I know that sounds like, a, weird, crazy title, but it really is critically important that you begin to allow yourself to embrace failure.

[00:00:31] I want you to think about. How you can begin to embrace failure and allow yourself to not necessarily always be perfect. So let’s dive into that a little bit deeper. One of the things that made me think about doing this topic today, were some of the comments that people have made about their own paintings over in the free Facebook group, over on ART+WORK+LIVING.

[00:01:01] And I’ve noticed students doing that back when I was teaching at the college and in my online courses now, that we’re our own worst enemies at times. We expect our paintings to always be perfect. We don’t ever want to do something that we feel is a little bit less than that is not as good as what we are perceiving in our minds is the ideal outcome.

[00:01:32] So over and over again, we’ll cut ourselves down a bit and we’ll talk about how something is not working way before we ever look at what is working. So I want to challenge y’all on that. I want you to not do that to yourself. I want you to think about when you post your painting. Looking for what’s working way before you look for what’s not working.

[00:02:01] It’s why we have what we call the critique sandwich on the Facebook group and in my courses that when you are delivering a critique, we are going to be able to process that better. If it’s delivered in the form of a sandwich with a positive comment here, that’s reflecting on something that’s working really well, areas for improvement with another positive comment below.

And what happens to our brain when we sandwich it that way is that we’re able to take in that criticism in a productive way. What’s the first thing we do when we get criticism otherwise? We steel ourselves, tense up and become defensive.

[00:02:51] That’s not productive. So always remember the best way to deliver criticism is to use that critique sandwich. And we need to do it with ourselves more than with anybody else. So that’s my first point is to be kinder to yourself, realize that what you think is a failure right now is probably not. You need to look at it again later and to apply the critique sandwich to yourself, as well as to others.

[00:03:21] Then I also want to remind you that if you don’t try, you’ll never improve. And when you’re trying, you’re not always gonna be perfect. You’re not always going to be succeeding. So I want you to remember you’re a whole lot more likely to succeed if you try a lot.

[00:03:42] One of my painting professors, way back in graduate school, (Hey Philip, if you’re listening), told us that we would be a whole lot more likely to make 50 great paintings in a year. If we made a hundred paintings and threw 50 away, best advice I ever got in school. So you’re a whole lot more likely to make successful paintings.

[00:04:07] If you make twice as many paintings as you think you need to succeed. Think about making a lot of paintings so that you have more likelihood of being successful. If you’re not ever failing, if you’re not ever making a bad painting, you are not ever going to make improvement. It’s that fear of taking the step out into the unknown and looking foolish that stops us from trying. And I want you to try. So if you forming that daily painting habit , you’re more likely to be able to survive failure.

Sure, you’re going to have some paintings that don’t work, that you need to go back in on that you want to go back in and on that are bugging you, but you are whole lot more likely to have paintings, at least a few of those paintings work out super well. Say you have 10 days that you’re going to paint consistently. If you make 10 paintings in 10 days, chances are at least five of those are going to be pretty strong paintings. And the other five are going to have some things about them that works super well, that you can apply to the next page.

[00:05:22] Don’t expect them all to be good. Don’t beat yourself up. When that happens, paint more often do whatever it is that you’re trying to learn, how to do more often and you’ll increase the likelihood of success. Keep those things in mind, as you move forward. Allow yourself to fail.

When I was teaching a gen ed course at the college , the course was all about developing the habit of set setting goals for yourself, life skill habits, and making plans, doing strategic planning. And those ideas are all well and good. But if you don’t learn how to step out and risk failure, all the strategic plans in the world and not going to help you. I started asking them at the beginning of every week at the beginning of the class, tell me what you failed at last week.

[00:06:15] And the people who failed at something got applauded really heavily because when you failed at something, it means you’ve stepped out and tried something new or you’ve attempted something that was difficult and challenging. Now, the last point I want to make is that failure is almost never really failure.

[00:06:38] The way that we tend to conceive of it in our culture. We think of failure as the inability to get something done as a negative, as the culmination of an aborted activity, something that is just not working out. So I want you to totally reframe failure in your mind that failure is not an aboard of activity that didn’t succeed.

[00:07:06] Failure is just your first attempt. Remember that repeat after me, failure is just your first attempt. It might be your second attempt. It might even be your third, but if you keep attempting. You will improve repetition over time leads to improvement. Reframe that totally in your mind and think about trying more new things, losing the fear of failure, painting without fear, because you know, they don’t all have to be perfect.

[00:07:46] You don’t even have to show them to anybody if they’re not perfect. And really beginning to look for what’s working before you look for, what’s not working,

[00:07:56] so what did you fail at last week? Because that’s the only way to get you to the point where you’re comfortable with failure, where failure is not a bad word and something that you want to hide away in a closet, and nobody sees it. I want you to feel free to post your failed air quote paintings in the Facebook group.

[00:08:18] Don’t be afraid to post something that’s not working. Know that you’re going to get constructive criticism for what’s not working and that’s the only way to improve and to get some feedback. A new set of eyes really helps. The other thing to do with that is to remember when you’re working on a painting and you’re really close to it, you’re not going to be able to evaluate it super objectively.

So if you’ve been working on it hard and you’ve struggled with some things, you’re going to be better off evaluating it in 24 hours. Get some distance from it so that you can look at things objectively. Years ago, I was struggling with a painting here in the studio and I left at the end of the day thinking it was absolutely the worst painting I’d ever done in my life.

[00:09:11] Totally hated it. Was so discouraged that the next day, when I went into painting class with my beginning painting students, I told them that. They just had free reign that day, that they needed to understand that nothing they could do would be as bad as the painting that I had done the day before that I wanted them to feel free, to experiment that I’d really made a godawful painting in the studio that afternoon.

[00:09:42] When I got into the studio to work and had a chance to have had some distance from the painting, had a chance to sit down and look at it. Get into that creative mood notice it really wasn’t very much wrong with the painting. And in fact, when I gave myself a little reflection time, I was able to see exactly what I needed to do to finish the painting.

[00:10:03] And I finished it and became one of my favorite paintings. You’ve got to have a little critical distance when you’re evaluating things. Keep that in mind.

[00:10:13] I want you to go out there and fail at something. Whether it’s failing at a new recipe, failing at a new activity or not doing it perfectly, just think about it as being, not doing it perfectly, but I want you to try something new.

[00:10:29] Maybe try a new medium, a new material, a new sys, a new brush, a new knife, try something new, get out of your comfort zone in some way. So when you’re reframing the failure question, think of it is getting out of your comfort zone. You want to make sure you get out of your comfort zone. That is all for now.

[00:10:52] Thank you all for joining me here today. And I want you to have a wonderful day. Happy painting everybody. Bye-bye for now.

Magnetic Paintings Webinar

How to Use Value, Color, and Composition to Make Compelling Paintings

You're invited to a special free workshop I’m hosting where I'll share how you can leverage composition, value, and color to make compelling paintings. If you missed this earlier now's the time to save your seat.  You can learn more here and find a time that fits your schedule.

Grab My Special PDF Guide

"7 Keys to Using Color"


You have Successfully Subscribed!