What does it mean to be a successful artist?

To make progress, we must experience the doldrums as well as the exhilaration of creativity.
This sketch of the Ellwanger Estate in Rochester went from being something I hated to being a favorite painting.
One of my artist friends is struggling right now. Her current work feels stale to her, but when she pushes the boundaries, she is uncomfortable. She worries that the results feel like ā€œtoo, too much.ā€ Like most of us, she is looking for that sweet spot that combines marketability with room to grow and challenge herself.
Another artist friend wonders how to tell if youā€™re a successful artist. She proposed that you are a success if you bring joy to someone. I pointed out that a lot of people have some really awful art hanging on their walls. It apparently makes them happy. Bringing joy, then, may be setting the bar too low.
I spent one memorable spring consistently overshooting the colors. I wasn’t happy then. I am now.
In other career paths, success is measured by dollars. In art, financial success is dependent on things other than artistic mastery, like connections, marketing skills, organization, and financial resources. Many great painters have labored in poverty and obscurity through most or all of their careers. Artistic success, then, must first be defined in artistic, not financial, terms. The problem is that the goal is constantly shifting.
As artists, we struggle to achieve some effect or transmit an idea. This struggle can be quite lengthy, lasting weeks or months. When we succeed, we can churn out art, seemingly effortlessly. During that short golden period, work is fun and exciting. We feel like weā€™ve finally ā€˜got itā€™.
I worked on site on Lower Falls at Letchworth for the better part of a season. That meant hiking to the bottom of the gorge with my painting kit. It was no fun.
Sadly, this is a fleeting thing.
Soon another question or problem surfaces. We realize a deficiency, or we need to explore a different subject. The searching and questing starts again. Work feels halting, incompetent, and difficult.
There are times when it seems like Iā€™ve never held a brush before. Iā€™m awkward, unpolished, and incapable. No, Iā€™m not suffering from amnesia. If Iā€™m doing my job right, I havenā€™tdone this before, because part of what we artists doā€”or ought to doā€”is explore uncharted areas. Luckily, Iā€™m a process-driven, rather than results-driven person. Otherwise, Iā€™d lose my mind.
The struggle at the Lower Falls meant that painting its mate, Upper Falls at Letchworth, was easy.
Some of the pieces that felt most awkward at the time actually turned out to be road-markers for the forward journey. Thatā€™s why Iā€™m never keen on scrubbing out ā€˜failuresā€™ after a painting session. I just canā€™t tell what a painting means when Iā€™m working on it.
Embracing a cycle of success and struggle is the heart of the artistic process. To make progress, we must allow ourselves to experience the doldrums as well as the exhilaration of the creative process.
The Long Road Home is another work that had to be dragged out of my fingertips.
When someone is at the bottom of one of these cycles, I recommend they read (or reread) the classic Art & Fear by David Bayles and Ted Orland. They address the pertinent issues of habit, persistence and routine. If nothing else, the book reminds us that weā€™re not alone in this struggle.