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.

Today we’re going to be talking about the importance of failing in creating rituals, habits, and building that daily painting habit. I know, it sounds like a weird, crazy title… but it really is critically important that you begin to allow yourself to embrace failure. 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 comments in my free Facebook group, ART+WORK+LIVING, that people were making about their own paintings. And I’ve noticed over the course of teaching at a college and through my own online courses that we are 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 what we are perceiving in our minds as the ideal outcome. Over and over again we cut ourselves down and talk about how something is not working before we ever even 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 what’s working before you look for what’s not working when you finish your next painting.  

That’s why we have a rule that we call the critique sandwich on the Facebook group and in my courses. The critique sandwich is when you deliver your critique with a positive comment that reflects on something that’s working really well, then areas for improvement, and finish it off with another positive comment. You can read more about critique sandwiches in my blog Why Critiques Are Important. What happens to our brains 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. 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 anybody else.   

So, that’s my first point. Be kinder to yourself, realize that what you think is a failure right now is not a failure. You need to look at it again later and apply the critique sandwich to yourself as well as to others. Also, remember that if you don’t try, you’ll never improve. And when you’re trying, you’re not always going to be perfect. You’re not always going to be succeeding. I want you to remember you’re a whole lot more likely to succeed if you try a lot.  

One of my painting professors, way back in graduate school, told us that we would be a whole lot more likely to make 50 great paintings in a year if we made 100 paintings and threw 50 away… Best advice I ever got in school. You’re more likely to make successful paintings 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 the fear of taking the step out into the unknown and looking foolish that stops us from trying… And I want you to try! 

If you form a 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, paintings that bug you until you go back to work on them, but you’re a whole lot more likely to have paintings that work out super well! Let’s say you have 10 days that you’re going to paint consistently. If you make 10 paintings in 10 days, chances are at least 5 of those paintings will be pretty strong paintings. The other five are going to have things that work that you can apply to the next painting. Don’t expect them to all be good and don’t beat yourself up. When that happens, paint whatever it is that you’re trying to learn 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 setting goals for yourself, life skill habits, and strategic planning. 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 are not going to help you. I started asking them at the beginning of every class what they failed at last week. 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 in the way that we tend to conceive 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 aborted activity that didn’t succeed. Failure is just your first attempt, remember that. Repeat after me, failure is just your first attempt. It might be your second attempt, maybe even your third, but if you keep attempting you will improve. Repetition overtime 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. You don’t even have to show them to anybody if they’re not perfect. Start to look for what’s working before you look for what’s not working.  

So, what did you fail at last week? Because that’s the only way to get 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. I want you to feel free to post your “failed” paintings in my ART+WORK+LIVING Facebook group. 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. 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. 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. Totally hated it. I 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, I wanted them to feel free to experiment. I told them that I’d really made a godawful painting in the studio that afternoon and that they needed to understand that nothing they could do would be as bad as the painting that I had done the day before…

When I got into the studio to work and had a chance to have some distance from the painting, now having the chance to sit down and look at it, get into that creative mood, I noticed there wasn’t very much wrong with the painting. In fact, when I had a little reflection time, I was able to see exactly what I needed to do to finish the painting… and I finished it and it became one of my favorite paintings. You’ve got to have a little critical distance when you’re evaluating things. Keep that in mind. 

I want you to go out there and fail at something. Whether it’s failing at a new recipe or failing at a new activity. Just try something new. Maybe try a new medium, a new material, a new brush, a new knife. Try something new, get out of your comfort zone in some way. When you’re reframing the failure question, think of it as getting out of your comfort zone. 


About twice a year we like to host our 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.

While our current challenge is over, you can still find out more and sign up for the waitlist here:



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