Alright – so today we’ve got the honor of introducing you to Mike Mahon. We think you’ll enjoy our conversation, we’ve shared it below.
Mike, appreciate you joining us today. Do you wish you had started sooner?
I actually wrote about this very thing in my recently published book, “Art Principles: Control Your Painting Process & Conquer Your Fear of Failure”.
I had some very unpleasant experiences growing up which resulted in a severe lack of confidence and inferiority issues. Additionally, in grade school I had a speech impediment which with therapy was cured, but my personal confidence remained low. Two primary obstacles that held me back from pursuing fine art for thirty years were:
My fear of failure and fear of not having anything worthwhile to say artistically.
From my youth, my love of drawing provided relief and some assurance of accomplishment, but it was the overcoming of my second obstacle that finally relieved my fears.
In the 1960’s, abstract expressionism, a rejection of many fundamental art principles, and political/philosophical upheaval were very influential. In the Fine Art world there didn’t seem to be any interest in basic artistic skills and principles, only novelty and quirkiness. Every year or two seemed to produce a new definition of what was acceptable or “in”. Therefore, it seemed to me that if I was called to be a fine artist I should have a unique philosophical or political statement to make. Painting to produce beauty was old fashioned, passé. I was pretty clueless, with no profound political or philosophical convictions. I just wanted to produce beautiful art. So instead of Fine Art, I entered the commercial art profession where I could at least use my drawing skills in graphic design and illustration.
Not long after finishing my art education I became a Christian. Over time I learned that my value as a person was not based on what I did, but on my identity in Christ. A great Christian theologian once said that the goal of a Christian is, “to think God’s thoughts after him.” Since God is creator and sustainer of all things past, present and future, every landscape and every human face was in His mind before it came to exist. What higher calling could there be than to paint images that had originated in the mind of God? I realized that being a Christian artist did not mean putting a cross in every painting or painting explicitly Christian subject matter. The beauty of His world was sufficient motivation for a Christian, or anyone else, to be an artist. The principles of good art are true regardless of anyone’s religious convictions. I think every artist has some kind of spiritual foundation and this happens to be mine.
I did have something worthwhile to say in my paintings, but would my old fears keep returning? I began to paint occasionally but I still had an internal self-deception that was at the root of my hesitancy to seriously pursue a career in Art.
In my twenties, I had promised myself that I would begin painting in my thirties. But I didn’t. In my thirties I promised myself that I would begin in my forties. When I reached my fifties I realized that I was running out of decades and excuses. As a businessman, I was not as afraid of failure because deep down I didn’t identify my self-worth with being a good businessman. I thought, “If I failed in business, well, that’s not really who I am anyway.” I realized that I had learned to take risks and overcome fears in other areas of life but I could not risk losing my fantasy of being an Fine Artist. If not put to the test, it would always be a fantasy. Finally I was honest with myself. I had to admit that I was afraid that I wasn’t good enough, and if I seriously tried to become a fine artist, it would only prove my doubts were true. And if my doubts were true, then I would be nothing. I know this was a contradiction of my religious beliefs, but it was how I felt at that time.
These forces were working their way through my life over a period of years. Although I was becoming more self-aware, my underlying fear of failure continued to hold me back.
This was all in spite of the fact that my wife, Cynthia, kept encouraging me to pursue what she knew I could do. She even bought me a professional painting easel one Christmas to motivate me to start painting. My sister, Sally, gave me great encouragement, but still I didn’t believe in myself. Finally, circumstances forced my hand. The business into which I had put thirty years of toil was failing, forcing me to sell it to avoid bankruptcy. It was only when I was forced to that I finally took the step to lay it all on the line and pursue a career in fine art. Selling my business paid my business debts, but left me with little else to do than to sell my home and a rent house to finance my new career. With the financial help of my sister and brother-in-law, Sally and Ken, Cynthia and I made it through three years of challenges. It was a good thing our three children were already married!
I still did not overcome all my fears, but God soon provided the circumstances that led me to take action on my dreams in spite of my fear.
Two Valuable Lessons
1. When your most important identity and self worth is based not on what you have done but on what Christ has done for you, the mundane fears of life become more manageable day by day.
2. When you hesitate and waiver in your pursuit of a dream, few people offer support or encouragement. However, when you make a committed decision and step out in faith, people are drawn to your determination. They seek ways to bolster your journey towards excellence.
I hope my story serves as a testament that it’s never too late to pursue your dreams and overcome the fear of failure. What may seem insurmountable can become achievable when you confront your fears and take that first, daunting step forward.
As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?
My art is representational and impressionistic mostly working in landscapes and portraits—primarily in oil and pastel. I try to celebrate the rugged beauty of New Mexico and the Southwest.
I’ve loved to draw for as long as I can remember, but it wasn’t until a defining moment in my early teens that I realized just how deeply art was tied to who I am.
As a generally compliant and rule-following kid, I surprised even myself one day when I stood up to my strict mother. She had thrown away a figure drawing book I had saved up to buy—because it included nude studies. I was furious. I retrieved the book from the trash, looked her in the eye, and told her not to touch it again. In my frustration, I turned to my sketchpad and drew a fierce face to channel my anger. But something happened in the process: my anger dissolved. I calmed down and was soon lost in the joy of drawing. That experience made it crystal clear to me—art wasn’t just something I enjoyed; it was a lifeline. A way to process, to express, to heal. From that point forward, I knew that art was something I had to pursue.
When I moved from commercial art and photograpy to a new career as a fine artist, I soon discovered a problem that I wasn’t prepared for. Unlike commercial art where there were strict guide lines, deadlines, and budgets, fine art did not seem to have any rules. It seemed like I had to reinvent the wheel every time I started a new painting. This wasn’t so bad when I had been an occassional weekend painter, but when painting full time it was leading to constant frustration and the risk of burnout. I determined to learn the skills and principles that would lead me to a consistent painting procedure that worked no matter what I painted.
I committed to going to several art workshops a year, reading art literature, and finding a mentor. I coalesced seven fundamental principles of art from my teachers, principles that were established over centuries of art instruction. I then prioritize the principles into a logical sequence. I did not want to continually have to refer to my notes to remember these principles, so I developed a memory aid to make them easy to remember. This way, they could be applied before, during, and after the painting process.
These seven principles served as a foundation to help myself and my students choose the best image to paint, to analyze the image, to analyze the painting in progress, to self-critique one’s own work, and to critique other paintings with authority. I was fortunate to have a mentor, Ben Konis, who trained in the New York Art Students League. He taught me a step-by-step painting procedure that combined with my seven principles virtually guaranteed successful paintings. With this combined process I could be certain of success before I started, or at least within the first thirty minutes.
I now teach painting workshops across the country and offer a framework I call the DiVine SETUP—seven core aesthetic principles that help artists gain confidence, control their process, and paint more effectively. This system is at the heart of my book Art Principles: Control Your Painting Process & Conquer Your Fear of Failure.
I help students move beyond fear, beyond randomness, and into a place of clarity and confidence. My teaching is not just about technique—it’s about helping artists discover the joy of painting with purpose and peace.
I’m most proud of the artists I’ve helped along the way—those who’ve told me, “This changed everything for me.” That’s why I do what I do.
If you follow my work—whether you’re a collector, an aspiring artist, or someone who just appreciates beauty—know that everything I create is rooted in a deep belief that beauty matters, that order is healing, and that we all have something worthwhile to say through art.
We often hear about learning lessons – but just as important is unlearning lessons. Have you ever had to unlearn a lesson?
Please allow me to change the questions that you are asking to just a little bit. What’s a lesson you have learned and what’s the backstory?
One of the most important lessons I’ve learned in life and art is this: Preparation + Opportunity = Success. And perhaps more importantly, preparation is the best antidote to the fear of failure.
That lesson took root in me through two defining experiences—one from my childhood, and another from early adulthood—that shaped how I’ve approached both art and business ever since.
The first came from watching my father, a quiet and thoughtful attorney, win a court case against a team of flashy, high-paid railroad lawyers. As the story goes, my dad showed up to court representing a small farmer whose land had been damaged by a poorly built drainage ditch. Across the aisle, a battalion of sharp-suited lawyers smirked at the thought of steamrolling a single man. But they underestimated him. My father didn’t rely on style—he relied on substance. He was better prepared. He knew the facts of the case—and their arguments—better than they did. He won handily. That case changed the course of his legal career. What stuck with me was the principle behind it: pretension folds in the face of preparation.
The second turning point came shortly after I got married. I was still in college when a high school acquaintance invited me to sell Bibles door-to-door in Tennessee. It was the last job on earth I’d have picked for myself—but we needed money, and I figured it would be a challenge worth taking.
Before we hit the streets, we went through a week-long sales school in Nashville where we were drilled on how to prepare. The rule was: memorize the 15-minute sales presentation word for word—no exceptions. Practice until it was second nature, until you could say it ten times in a row without missing a beat. That was the only way to ensure you could get through it once, in the real world, under pressure.
I’ll never forget the day I turned a corner and walked straight into a large family picnic in someone’s front yard. Every instinct screamed “run.” But instead, I took a breath, pulled up my sales case, sat on it, and confidently delivered the full presentation. Did I make a sale? I don’t remember. But I’ll never forget that moment. I didn’t flee. I acted. And I acted because I was prepared.
These moments taught me that we often don’t get to choose our opportunities—but we do get to choose whether we’re ready for them.
That principle—be prepared—has carried over into my work as an artist. Whether it’s teaching a workshop, submitting to a show, launching a book, or tackling a new portrait or landscape, I’ve learned to rely on preparation to silence fear. And I teach my students the same: don’t hope for confidence—build it through knowledge and practice.
Because nothing conquers fear of failure like competence and readiness. And nothing builds confidence like doing the work before the moment arrives.
Have you ever had to pivot?
For nearly 30 years I had avoided pursuing a fine art career due to a fear of failure and lack of confidence. The business into which I had put many years of toil was failing, forcing me to sell it to avoid bankruptcy. It was only when I was forced to, that I finally took the step to lay it all on the line and pursue a career in fine art. Selling my business paid my business debts, but left me with little else to do than to sell my home and a rent house to finance my new career. When my family and friends saw my wife and I fully commit to my new career we were flooded with support that we had not anticipated. So with additional financial help from my family, my wife and I made it through three years of challenges until we could stand on our own in my new art career.
I still did not overcome all my fears, but God soon provided the circumstances that led me to take action on my dreams in spite of my fear.
While the visual arts are most frequently a very solitary endeavor, it takes unusual confidence to be sure of your abilities without the confirmation of others, especially your peers. Friends and family are great encouragers, but at some point objective validation is needed by those of us lacking in confidence. It was time to step out of my cocoon and introduce myself to the world of fine art.
As a completely unknown fine artist, I fearfully entered my first regional art exhibition. You need to understand that in my community I was known mainly as a commercial photographer and graphic artist. I belonged to no art associations, local or otherwise. It was a scary thing to enter this regional show because the judge of the show was the head of the art department of a major state university. I felt that my decision to pursue fine art was on the judgment block. The day after entering, I returned to see what entries might not have been juried into the show so that I could take them home. When I gave my name at the show desk, the show director pulled me aside and asked for my name again. She asked, “Why have I never heard of you before”? I thought I had done something very wrong. She then told me that not only were all of my entries accepted, but that I had won five major awards – Best-of-Show, 1st Place in Pastels, 1st Place in Watercolor, 1st Place in Photography and 2nd place in Oil. She told me this was unprecedented and apologized regarding my oil painting getting 2nd place. The judge had been forced to stop giving me all of the first place awards!
Two Valuable Lessons
1. When your most important identity and self worth is based not on what you have done but on what Christ has done for you, the mundane fears of life become more manageable day by day.
2. When you hesitate and waiver in your pursuit of a dream, few people offer support or encouragement. However, when you make a committed decision and step out in faith, people are drawn to your determination. They seek ways to bolster your journey towards excellence.
Contact Info:
- Website: https://mmahon.com
- Instagram: mikemahonfineartist
- Facebook: https://www.facebook.com/pages/Mike-Mahon-Fine-Artist/124909505790
- Linkedin: https://linkedin.com/in/mike-mahon-0291288
- Twitter: mikemahonart
- Youtube: https://www.youtube.com/c/MikeMahonFineArtist1
- Other: https://patreon.com/mikemahonfineartist
Image Credits
Mike Mahon