Episode 55 – Bouncing Back from Disappointments in Your Art Career


hen I began this podcast, I promised to share with you my journey in transitioning to a full-time fine artist. Many of you know that right now I'm in the middle of that journey, painting 3-4 days a week and doing a side gig in digital marketing, web design, and copywriting a few days a week. 

Even though I’m not completely transitioned yet to full-time art, in my bones I can feel that I’m moving in the right direction, and I am content.

That said, I recently hit significant snags in two important areas of my art world. 

In this episode, I'm going to share these recent professional disasters with you and what I learned from them, as well as 5 tips to bounce back from failure and disappointment as you begin to create more art and possibly start your own art business.

The first major disappointment was actually the loss of three podcast recordings due to my learning curve with a new recording platform.

One was an interview with marketing genius Marcus Sheridan and his new book, THE VISUAL SALE, and the other two were interviews with international art mentor and woven sculpture artist and host of the Thriving Christian Artist podcast Matt Tommey, each focusing on one of his new books.

Losing these files was not only a crushing disappointment, it was excruciatingly embarrassing. I had to tell both my guests the interviews they just gave their time creating with me did not exist.

Thankfully, both Marcus and Matt were gracious. Marcus and I were able to reschedule for next month. Matt, however, won’t be available for a few months. So I’m going to take a moment to let you know about those books he wrote, in case you are interested in reading them now. Note: these are not affiliate links, just straight links to help you find the books in this article.

The first book I recommend is How to Price Your Art. Its pages are packed with actionable information, including “An easy pricing formula for pricing your art”, 5 keys for creating a pricing strategy, and much, much more.

This book provides a much-needed blueprint for artists by someone who knows the particular struggles we artists tend to face.

The second book is “Prophetic Art: A Practical Guide to Creating with the Holy Spirit.”

This one gave me answers I was looking for about the idea of creating spirit-led art. We’re not talking about religious art here. We’re talking about inviting God into your creative space. As an intuitive empath who’s also a Christian, this book was just what I needed.



The second disaster I recently encountered was when a conceptual piece in a local competition was hung incorrectly, greatly decreasing the impact of the work. The part of the piece that gave it the "ah ha!" moment was left out. The piece was, I thought, fairly good without it, but definitely lacked the impact it could have had.

I couldn’t know if it would win an award, but it was a really meaningful piece, and I personally witnessed it bring two people to tears before it went into the show.

I did check on it after it was hung, but I did not catch the error in my short swing through the gallery. I hadn’t truly slowed down enough to really look.

As I left, the gallery manager told me it had made the employees tear up as well, so I thought all was as it should be.

I discovered that the key element in the piece was missing when one of the people who had first seen it before it left my studio brought friends to view it in the gallery two days before the show came down. When I arrived at the gallery I found the additional element still in storage. I was crushed.

I want to note that the gallery was wonderful and empathetic in their response and took care of the issue as soon as it was discovered. The venue continues to be a dear to my heart and one of my steady places to show and volunteer. And while the show experience and the interview fiasco happened in rapid succession, throwing me into a tailspin for a few days, I realized that my responsibility in each was important to share, because most of my you have big dreams for your art. And the more you dare, the more you risk.

Rather than coming away from that statement with some gloomy warning that discourages you, please hear me cheering you on.

As an empath, I’ve learned that living in sync with my natural feeling perspective creates flow in just about every area of my life. My artist listeners can probably relate, as I suspect that an empathic nature is common to most artists. It took me years to stop fighting against my empathic nature and step into my own light. 

These days, ironically, everyone seems to be buzzing about being more empathetic, like it’s something new.

Unfortunately, I have discovered my heightened sensitivity can be a stumbling block when it comes to handling disappointment and failure. These things can feel overwhelmingly intense.

I’m going to share five tips that I use to bounce back from failures, and maybe even minimize the number of failures you encounter on your road to making more art. 

Please know that there are no affiliate links in these tips nor in the show notes downloadable list of suggested resources. I’m just sharing what works for me.


1) Don’t Toss the Good Out with the Bad

 When things go sideways, it can be easy to reflexively say, “Forget the whole thing, this is a sign that I’m not meant to do (fill in the blank)!”

If you think about all the things that a person needs to learn to truly master anything, it becomes almost incredible that you haven’t had more failures along your learning curve.

The more ambitious an undertaking is, the more room there is for something to go off the rails. So if you’re screwing up big, I say, celebrate!

Okay, this is tough to do at the time, but I really try to emphasize to my kids, trainees, and students, that mistakes made while learning a new skill should be celebrated. You know, so long as no one got hurt. 

I like to say, “Woohoo! A mistake!”

When you take this approach students will probably laugh and your kids will probably roll their eyes, but I’m convinced it’s important to fight the perception that we’re supposed to learn without screwing up.

Try thinking of mistakes more like the dashboard lights that come on when something is wrong with your car. In this case, the loss of my interviews did not mean I should hang up my microphone, it meant that I needed to fix something technical in my recording process.

It required me to be curious. Enter your inner Vulcan.


2) Be Objective

Instead of wallowing in self-pity or beating yourself up, look instead as objectively as possible at the facts. 

This is where the thinking of the stoics comes in handy. Think of the character Spock, from the Star Trek series. His catchphrase is, “fascinating.”

Taking a step back and looking at difficult situations from a standpoint of curiosity is a game-changer.

It truly helps to put mental distance between you and the mistake. This enables you to analyze what went wrong and pivot for a better approach.

I heard a helpful story of a successful marketing director who always holds "post mortems" after big projects. This includes an open discussion of what went right, as well as what went wrong.

After one particular product launch, which went completely off the rails, the executive called the usual meeting. His team was understandably nervous about what would transpire in the meeting. Thousands of dollars in revenue had been lost. Would someone be fired?

As the meeting began, the leader passed a box around the table. In it were a number of items, each comprising some part of the product launch. As it went from person to person, he asked each person to pull something out of the box and talk about it. What worked about it or didn't during the launch?

As a result, the conversation became about, for example, the packaging. One employee pulled out the box the product was packaged in and noted that the client loved the package design. The colors and fonts were a big hit, conveying the exact branding that was intended. The printing of the package had been problematic, however, as the printer was overseas and unable to print the entire order quickly enough to keep the launch on schedule.

Next, another employee pulled another element out of the project and talked about that, good and bad. And so it went around the table. The team visibly relaxed as they addressed the facts of the launch, rather than looking to deflect blame or criticism.

The difference in approach here is critical. After I made a conscious decision to stop beating myself up I addressed the problems instead of abusing myself worth. It’s a very different outlook. 

Turning to the example of the gallery show, I could have blamed the gallery error on the people who hung the show. I had offered to hang it myself, but they assured me they'd take care of it. I left them a diagram as to how to hang the piece.

I updated the diagram the next day, however, and hand-delivered a new diagram to the gallery, to someone else. As the existence of a second diagram created an opening for the wrong one to be followed, I should have called to double-check that everyone was on the same page.

Now, we can’t always be prepared for mistakes. Sometimes we don’t know what we don’t know and so we don’t see it coming.

But in this case, I caught two behaviors I realize I need to watch out for.

One is that I didn’t want to bother anyone. I was working when the show went up, and it would have been tough for me to volunteer to be there. Remember how important it is to get comfortable taking up space. Brené Brown calls it “standing in your sacred space.” Claiming your right to speak from your center about what you need.

You took the time to create the art, it’s okay to take the time to follow up on the hanging instructions.

Thing two is that I didn’t slow down enough the day I visited the gallery to really look at the piece. I’ve heard of other artists doing this. Kind of looking at your art with one eye open once it’s up on the gallery wall because on some level we’re afraid of seeing something wrong with it.

Sort of like the phenomena of not logging into your online bank account when you know the balance is low but you won't be getting a paycheck for another week. 

It's really important to look, but it's common for people to simply avoid doing so. It's not logical, and it certainly doesn't help.

Remember that we are not what we do. Problems you encounter in your art career don't detract from your worth and they don’t mean you’re not supposed to be an artist.


3) Pause and Re-Assess

If you're starting to experience "disasters" on the road to becoming a professional artist, pause and re-assess what you're focusing on. It’s not necessarily a message that you’re on the wrong path. It may be a message that you need to pause and re-prioritize what you’re doing to reach your objectives. Re-assess what activities will move the needle for your art career.

Make sure you’re not trying to do everything at once. Focus on the most important thing to accomplish each day, and have a couple of additional items listed that are the next-important things if you have time to get to them. You can keep a long to-do list, but I recommend an action-item version each day with the number one needle mover at the top, and at most, two bonus to-dos underneath it.


4) Get Back on That Horse

Now that you’ve taken the time to pause, get up and keep moving forward.

When I was 19, I was in a car that crashed, flipping over. While I was not driving at the time of the accident, I was a new driver. The trauma of the experience left me afraid to get behind the wheel myself. 

I was a teaching assistant in a science program off the coast of Maine at the time. After being medically cleared a few days after the crash, my advisors put me behind the wheel of a vehicle and had me drive them on the same backroads my vehicle had flipped over on just a few days before. Today, I can see why that was important and necessary.

Instead of giving up on entering competitions at that gallery, I immediately entered another art show. Instead of giving up on doing interviews in my podcast, I addressed the technical issue, then I set aside time to find and invite new guests to the show. Nothing motivates like a deadline, right? This is probably true for you as well.

Now, neither of the recent professional storms I experienced was as devastating as a car accident, but the double-gut punch of both areas of my business going sideways at once definitely jolted my confidence. 

As Rodney Atkins says in one of my all-time favorite country songs, “if you’re going through hell, keep on going.”


5) Use Your Power Tools to Develop a Growth Mindset

Of all of the aspects of you that you can develop for your art career toolkit, your mindset is the most vital.  Specifically, what Carol Dweck calls a “growth mindset.” It’s the belief that you are capable of learning more, becoming more intelligent, being better. That your development as a human is not set in stone dictated by an IQ test you took in grade school.

  • A growth mindset will help you bounce back from disappointment.
  • A growth mindset will keep you moving forward through tough times.
  • A growth mindset will lead you to make better decisions for your physical, mental, emotional, spiritual, and financial health.

My three power tools for fostering a growth mindset are:

  • Meditation
  • Exercise
  • Continually Learning

The first of my mindset secret weapons is a regular mediation practice. It helps to switch my thinking from being reactive to being observant. It helps me stay grounded.

I meditate regularly, and it helps me with my intuition. It enables me to assess opportunities and problems objectively and discern my next right step. Since it helps with my intuition, I believe it also helps me generate creative ideas.

Meditation can take in the form of mindfulness exercises or the transcendental style of meditation in which you practice allowing your thoughts to drift past you, letting go of conscious thought.

There are many resources online to learn how to meditate, as well as apps you can use on your phone. Two websites I utilize are the Centerpointe Institute and Health Journeys. You can find the links to these sites in the show notes.

My second power tool for a growth mindset is exercise.

I’m NOT talking about exercise from a weight loss perspective, here.

I use exercise to help me get comfortable taking up space. This includes having preferences, needs, and asking for what I want. 

Former National Football League player, now actor and playwright Bo Eason talks about owning your own physicality in his book There's No Plan B for Your A-Game: Be the Best in the World at What You Do.

Exercise does this for me. In addition to giving me strength and stamina, exercise helps me feel stand in that sacred space. It helps me speak up and take on the tough conversations we sometimes need to tackle to maintain healthy boundaries.

Exercise also clears my mind and helps me find the same stillness I seek when meditating.

The best exercise for you is whatever level of movement you can safely do (meaning, within the parameters your doctor approves of.) that you enjoy. 

Even just moving to music you love can do wonders. No matter what type of exercise I get in, I carry myself differently after moving my body.

The third mindset power tool I recommend is a regular practice of learning.

By always learning, you are fostering what Thomas M. Sterner calls “The Practicing Mind.” It also happens to be the title of Sterner’s book, which is one of the best books I have read as an artist. 

I believe all artists who have long-term success approach making art from the perspective of enjoying the journey. I hear it again and again. When they do their thing, making their art, they get absolutely lost in it. That is the practicing mind. 

Learning about all kinds of things related to and outside of your art practice will also help your creativity by giving your mind more information to draw from when making your art.

You can learn about mindset through books, podcasts, and trainings. I’ve included a list of the books I recommend for building a growth mindset.

This wraps up my five tips for bouncing back from disappointment. Drop me a line and let me know what you think. I’d love to hear about how you’ve bounced back from disappointments and failures.

And if you’d like a shout-out on the show, leave a review on Apple Podcasts. It helps others find the show, too.

Until next time, go make something.

  • Click here to download the resource link list for developing a growth mindset

As always, contact me any time at caroline@passionatepainterpodcast.com

Until next time... Go make something.

DON'T FORGET to download the list of Resource Links for developing a growth mindset HERE, and get access to my Exclusive Listeners' bonus materials.


  1. Laura Skvirskaya on September 29, 2021 at 10:05 am

    Your podcasts are so helpful and interesting!
    Thank you.

    • Caroline Italia on October 8, 2021 at 1:45 pm

      Laura, thank you so much. It’s important to me that you find Passionate Painter Podcast useful AND interesting! Let me know if there are any topics you’d like covered or artists you’d like to hear from. Our next episode is an interview with Dean Mitchell! By the way, I love your paintings. Looking forward to seeing more!