
I met Timothy Lee Simpkins in 2015, awaiting my own sentencing in county. At the time, we were both were going through an intense period of uncertainty about the future. We connected over the serious amount of time we were both going to be doing, and we ended up serving our time in the same institution, Eastern Oregon Correctional Institution. I’ve remained loosely connected to Lee over the years and have witnessed a transformation in him that is profound. Recently, I asked Lee to tell me about his experience.
Lee started his journey with visual art in 2015 when he realized his dream of becoming a musician was going to be put on hold for about ten years. Prior to his incarceration, Lee wrote, recorded and performed music. Spoken word and rap were how he expressed himself. “The first time I performed I was 15 in Berkeley California. I performed at a Cal State open-mic rap concert. I was so nervous getting up there on that stage, but after that first time, I was cool. I found out that the performance space was my natural habitat,” Lee said. He performed a few more times in Portland and Battleground Washington before being incarcerated.

Avenues for healthy self-expression became limited once incarcerated. Lee began searching for a new form of self-expression. He was looking for something productive to do that could have a positive impact on his environment. That’s when he picked up a graphite pencil and started drawing.
Lee primarily uses graphite and colored pencils, the tools most artists in prison are limited to. He has developed his own unique style and process and classifies his style as “smooth”. He uses a blank piece of paper to sketch out an idea. Once he has his concept and rough draft nailed down, he starts outlining the art on a separate piece of paper. When the lines are laid, he applies color to the piece. Lee acknowledges that most artists apply color and shading from lightest to darkest. He does the opposite, first laying the darkest colors and shadings on the paper, and then working his way towards the light. Every artist has their own style and inclinations; working from dark to light felt more intuitive to Lee. “You just have to follow your heart, there isn’t just one way to do art,” Lee explained. There is a metaphor in the way that he approaches his art, from dark to light. “You start from within the dark and work your way out to the light with art, with personal development,” Lee explained.



As he began expressing himself through his drawings, he realized what he expressed on paper became a direct reflection of his internal condition. As a musician he understood very well that “from the overflow of the heart, the mouth speaks,” he said.

Lee understood the power of words. But in prison he began understanding the same concept in multiple contexts. He realized that from the overflow of the heart, people create all sorts of different things. “We are all artists,” Lee said. “Some of us just aren’t aware of our creation. Life is a canvas for you to paint what you want.” Lee notes that it is important to be aware of what you are painting. “What do you want to paint? What do you want your life to look like?” he asked.
It took Lee about five years to start noticing the depth of his introspection through art. He began maturing in ways that he credits almost entirely to his journey with art. “Art has made me a more self-aware individual and I am a lot more patient than I was before I was incarcerated,” Lee said. His process of internal exploration and growth made him realize he no longer wanted to live in a paradigm of chaos and uncertainty, as he did before his incarceration. Lee’s art made him realize he wants “a life of peace and love,” a life full of meaning.
Lee looks forward to experimenting with new mediums of art upon release. He dabbled in acrylic on canvas before and he would like to dive back into exploring that style. He expressed interest in working with oil paints as well. He believes the smoothness of blending with oil paints would help support his current style. He is excited to have access to better tools and products, helping to speed up and refine his process.

Providing financial security for himself and his family is a top priority for Lee. “If done right, the average tattoo artist makes between $50 and $100 an hour, as much as or more than a journeyperson or tradesperson.” He said that he is essentially killing three birds with one stone, “expressing myself in a productive way, helping people become aware that everyone has a ‘life-canvas’ of their own, and learning a skill that will make a transition from prison to society as smooth as possible.”
Written by Patrick Gazeley-Romney