Inspired by guests Jeff Leisawitz (episode 89) and Dr. Dani Chesson, Dr. Amy Climer shares the story of a big failure she experienced in 2006-2007. Most importantly, she talks about what she learned, what she would do differently, and how you can mitigate your risk on a project that might fail.

What You’ll Learn

  • The story of Amy’s failed art practice
  • What Amy learned from being a professional artist
  • Advice for starting a project that might fail



Feel like reading instead of listening? Download the free transcript or read it below. Enjoy!

Transcript for Episode #090: What I Learned From a Big Failure

Amy Climer: Welcome to The Deliberate Creative Podcast Episode 90. In today’s episode, I talk about one of my big failures and what I learned from the experience. First, I want to share a review that came in on iTunes. I could say this is a success, so before I share the failure, I am going to share the success. This is a review from C@TruEdge and it is a five star review titled “Essential Tools for Success.” They say:

“This podcast is topnotch. The material is highly relevant. The speakers are always interesting and the presentations and conversations lively, informative and entertaining. It’s a fun way to learn essential tools for individual and organizational success. Thanks to Amy for sharing her expertise and passion for this work. I’m a big fan.”

Thank you so much for the review. I really appreciate that. If you are listening and have not left a review yet on iTunes, please head on over there and leave a review. If you are listening on your phone, you can do that right from your iPhone or you can head over to That will give you a direct link to iTunes where you can leave a review. Thank you so much, C@TruEdge as well as everyone who has left a review. It means a lot to me.

The Story of Amy’s Failed Art Practice [01:51]

Let’s talk about failure. I want to share with you one of my big failures and what I learned from the experience. This is a failure that happened in 2006/2007. In 2006, I was working full time at a university. I was in the School of Business and had been hired to develop an undergraduate leadership program for the school. I had been there for about two years at that point and I was getting a bit antsy. It was like, “Okay, time for something new.”

At the same time, outside of work, I had been developing my skills as an artist. The type of art that I did was mostly quilts, but not the type of quilts you think of when you think of like your grandmother’s quilts. I did not make bed quilts. I have never made a bed quilt. But these were quilts that were very small. They hang up on the wall, often were framed and they are called Art Quilts. That is the genre of quilting.

The particular ones I made were mostly really bright colors. I almost always either hand-dyed the fabric or I would paint the fabric. I would hand-dye all the cloth or I would use this really think dark cloth, kind of like a canvas, where I would paint it with acrylic paint and then layer that with a batting and a backing and stitch all that together. Technically, the pieces of art were quilts because they were three layers stitched together, but they did not really look like quilts in the traditional sense.

In 2006, I had probably been doing this type of art for about seven years. I had been developing my skills. At that point, I had sold some pieces, I had won some awards at shows, I was represented in a couple of galleries at that point and I really wanted to see could I make a living at this. In 2006, I gave notice at the School of Business and I went off and became a professional artist.

For me, one of the interesting things about that initial transition was other people’s reactions. From my colleagues, mostly the reactions were on the opposite ends of the spectrum. Some people their first reaction was, “Oh my gosh! How are you going to pay for insurance?” And other people’s reaction was, “Oh my gosh! Amy, that is so awesome!” It was interesting. I think, in hindsight, I see that as people’s different comfort levels around risk and taking risks because, obviously, I was taking a big risk.

I will admit that I do not think I fully appreciated how great of health insurance I had at the time where it was an excellent insurance that was super, super cheap. In 2006, the insurance world was quite different than it is today, and so that was a possibility that I paid almost nothing for insurance. But I have never had that experience since then, so that is unfortunate. But at the same time, I think that health insurance and other perks that you get from an employer, they are often referred to as golden handcuffs. Because it is those things that are so attractive that might keep you in a position that really is not the best fit for you. That is exactly what was happening to me and I felt like I wanted to break away from that.

I had always wanted to be an artist from the time I was a kid. It was something that I was curious about and interested in and I felt like this is a time in my life that maybe it would work. So I quit and opened my art practice. Well, things did not go quite as I hoped. I worked super hard. I learned a ton about being an artist and owning a business. One of the biggest things I learned about being an artist is that it is a business. If you are a self-employed artist, you have a business. Of course, if you are a self-employed artist you probably know that, but if you are not an artist, you might not recognize that. A big part of being successful as an artist is someone’s ability to market themselves, to get out there and make connections and make contacts. Someone could be the most amazing artists on the planet, but if they have not done the marketing, no one is going to know about it and then they are not going to sell their work.

In 2006, things were quite different than they are now, as far as being an entrepreneur. Facebook was around, but no one was really using that in a way to market themselves, at least not very many people. It was not something that was talked about as a useful tool. Twitter just started in March of 2006, but I had never heard of it at the time. It was not really popular for another few years. Instagram and Pinterest had not started yet. Those both started in 2010. So very different time as far as marketing yourself. Etsy did exist and that ended up being a somewhat useful tool for me. There were people who were having a lot of success on Etsy.

The ways that I sold my art was I was represented in a few galleries, mostly regional galleries near Madison, Wisconsin, which is where I lived. I also exhibited at art fairs on the weekends. And wow, that is a whole world there in itself, of learning how to be successful at presenting at an art fair. And then I sold my stuff online in some places, such as at Etsy.

Challenges Amy Faced as a Professional Artist [07:36]

I will just give you a couple of stories about the challenges that I had. There was one day where I was going to an art fair — first, let me just tell you, art fairs are a ton of work. I think it is hard to know that if you have not seen the behind the scenes angle. Because if you are attending an art fair, generally, you are really relaxed, you are strolling around in some beautiful weather checking out some cool art. On the other side of the booth, essentially, the artists have put so much work into being there that day.

Anyway, I go to this art fair probably about two hours ago and about an hour into my drive, which is probably 6:00 in the morning, 7:00 in the morning, my car breaks down. I am an hour from home, I am an hour from the art fair and I really need to go to that art fair in order to make some money. I call my partner, wake her up and ask her if she would please come meet me on the side of the road, wait for the tow truck and let me take her car to the art fair. Fortunately, she is incredibly generous and agreed to do that. On the side of road, we are transferring all my art and my tent that I had to set up all this stuff to her car, I go along on my way and she waits for the tow truck and is able to go home later.

After all that, I get to the art fair and made — I do not remember how much money — a few hundred dollars. It was less than $1,000 probably. I cannot say it was an incredibly successful day. When I looked back at my experience of being an artist, which I did this full time for about a year and a half, I think the one year that I did it — 2007 the entire year I was doing this — I made about $12,000 from my art. I said that to somebody not too long ago and they were like, “Wow! Making $12,000 in a year from art is pretty impressive.” I am like, “Well, yes, but not if that’s your fulltime job and you are now living at the poverty line.”

It was actually the end of 2007 where I realized I cannot do this anymore. It was a failure. I had failed at that experiment. I ended up going back to, actually, the same university that I left. I got another job there pretty quickly and in 2008, started as a full time professional again at the university. I gave up the art practice and it was so hard.

The other things I learned is that my bread and butter came from these $25 items. Anything $25 or under, people would buy really quickly without thinking much about it. Anything over $25, especially, anything over $50, people really pondered and thought more about it and it was harder to sell those bigger items. What that meant for me is that I ended up becoming a little bit of a production worker, like a factory worker. I was just churning out these small items that did not require a whole lot of thought, that did not require a whole lot of artistic talent, essentially, and I was getting really burned out. I was working probably 60 to 80 hours a week and not seeing a lot of return on it.

That experiment, that experience was a failure. I am very careful to phrase it in that ways. I do not believe I was a failure, but I believe that that situation, obviously, it did not work. I could not keep that up.

What Amy Learned From Being a Professional Artist [11:23]

Here are some things that I learned from it, though. This is where the success from the experience comes. First of all, I learned a ton about business. Later, in 2009, I started my current consulting business and I pulled from that experience as an artist. So much of what I learned then I was able to apply later on into my current business.

I also learned how to be self-motivated and stay focused on my own. Because basically, all day every day, I was at home working in my studio or my office and it was up to me to produce. No one was asking me when something was done. The deadlines were up to me if I wanted to meet them. No one was going to be upset if I did not apply to an art fair, if I missed the deadline. I was the only one that was going to be disappointed. I learned, really, how to stay motivated and stay focused, which is something that is incredibly important as a self-employed entrepreneur.

The other thing I learned that kind of surprised me is that I really liked being in business for myself. I really liked the autonomy and freedom that I got from it. A couple of years afterwards, in 2009, I started this consulting practice. I do not know that I would have done that had I not had that experience as an artist. That was a huge win there.

Advice for Starting a Project That Might Fail [12:43]

Building on what I learned, I also want to share some thoughts and advice. If you were thinking of doing something that you might fail at, then this is for you. First, you might succeed. That is the whole hope, that is the goal, and I think it could be helpful to think through what would failure look like.

For me, I knew ahead of time that failure would look like not making enough money and needing to go back and find an employer. When it got to that point, that is exactly what I did. To me, I felt like it was a worthwhile risk because I knew what to do in case I failed. And then when I got to that point, I did it and I was able to do that. I had thought about that ahead of time. That might be the first thing, is think about what would happen if you fail and what do you do at that point.

The other thing to think about is what would you gain from trying and then failing? What are you going to get from it? I knew that if I did fail, I was going to learn a ton. That is just a given. That is at least how I think. I tend to be somebody who, as much as I can, I want to learn from my experiences. I knew that I was going to learn some things that would help me in other endeavors in life. At the time, I had no idea that I was going to go and start this consulting practice, but I definitely learned some things that are helping me now, but I knew that I was going to learn something. And for me, that was worth it, especially because I was feeling a bit stagnant in where I was at before I started the art practice and I do not do very well when things feel stagnant. I want to be moving forward and I want to be learning and growing from whatever it is that I am doing.

The other thing is if you are thinking about being an artist — first of all, I should say, I strongly believe that you can make a living as an artist, even though I failed at that. There are many things that I would say I did wrong or did not do well that are preventable and changeable. If I were to do it again, there are a lot of things I would do it differently.

The first is, if you happen to be either going into college or are in college and you think you want to be an artist yet you have been given advice to not major in art because you need a backup plan, go major in psychology or business or something else where you are more likely to find a job and then minor in art or do art on the side. If you do that, you are much more likely to fail as an artist because you will not have developed the skills you need to be an artist. I think that is really odd advice.

Imagine if it were flipped and you wanted to go into business, but someone said, “Well, you know, instead of majoring in business, why don’t you major in English or art because, you know, you might just have more success in that area if you don’t major in business.” Probably not. If you really want to be an artist, you need to develop the skills as an artist and I think that was an area that I had not done well enough. I thought that I had, but then when I got there, in the moment, 2007, I am realizing there are a lot of skills that I have not fully developed yet.

The other thing is that if you do want to be an artist, say if you are in college and you are majoring in art, learn as much as you can on the side about business and being an entrepreneur. Perhaps, maybe, minor in business or entrepreneurship, if that is an option at your school. That was something that I think we do not do a good job in the U.S. teaching artists how to be in business for themselves. If you can learn that, as well as, develop your art skills, you are going to be much more likely to be successful.

If you are in a situation where you have a fulltime job and you are trying to get ready to quit that before you go on to something new where you might potentially fail, particularly if it is a self-entrepreneurship kind of thing, develop your skills in that business as much as you can before quitting that other job. That is one thing I could have done to be more successful. I could have built up a larger nest egg of money before I left the business school. I could have developed my art practice further before I left my full time job, but I was a bit impulsive and a bit antsy, I wanted to go do this. I do not regret it by any means, but when I look back, those are things that I could have done differently and so I share those with you in case you might benefit from learning from my mistakes.

I hope this is helpful for you to hear about a failure that I had and I hope that it inspires you to take some risks, calculated risks, thoughtful risks, but to take some risks, nonetheless, to try something new and see what happens.

Thank you so much for listening to The Deliberate Creative Podcast. If you have any questions that you would like to have answered on the show, please send me an email. You can find me at In the show notes, I will put a link to my website where you can see some of my art. The site has not been updated in years, but you can see some of that art that I made back in 2006 through about 2008 or so. That website address is The show notes for this episode are at Head on over there, at the show notes you will find a link to my website with my art. You will also find a way to contact me. Send me an email if you have questions you want answered on the podcast, I will be happy to do an episode based on your question. That is where many of the topics of this podcast have come from.

Thank you so much for listening, you all. Have a wonderful creative week. See you next time. Bye.

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