We caught up with the brilliant and insightful Jack Lilley a few weeks ago and have shared our conversation below.

Alright, Jack thanks for taking the time to share your stories and insights with us today. Do you wish you had waited to pursue your creative career or do you wish you had started sooner?

I have always been torn between two passions: one for history, politics, and culture, and the other for creative expression, including painting, singing, acting, and photography. I grew up believing that to be successful, I had to choose one path, dedicate myself fully to it, and measure my achievements by financial milestones such as salary, retirement savings, and career advancement.

As a child and teenager, creativity was my world. I performed, painted, and sang without hesitation, confident that my future would be in the arts. But as I got older, I was given the talk that most creatives hear: that a career in the arts is difficult, rarely lucrative, and nearly impossible to succeed in. Only the luckiest and most talented make it. Hearing this over and over, doubt crept in. I pivoted toward the social sciences, studied international relations with a focus on justice and human rights, and pursued internships at NGOs. I poured everything into building a career in international development, convincing myself it was the right path.

But something was missing. Every night, I imagined myself at a gallery opening, on stage, surrounded by other creatives. While I found meaning in my studies and work, a part of me longed for more.

It wasn’t until I took a year off to travel that I allowed myself to reconsider. Away from expectations, I reconnected with what truly fulfilled me. I realized that success is not just about external validation but about nourishment, creativity, and authenticity. After moving to New York, I committed to my artistic journey. I am painting again, selling art, working with a vocal coach, and unlearning the toxic belief that I am not good enough.

Looking back, I sometimes wonder what would have happened if I had started my creative career sooner. If I had ignored the doubts and pursued my artistic passions right away, I might have had more time to refine my skills, build connections, and establish myself earlier in my career. However, I also know that my academic background and time spent in international studies have shaped my perspective in ways that now enrich my creative work. My studies in justice, ethics, and human rights gave me a deep understanding of the world’s social and political complexities, and now, through my art, I can bring those issues to life in a way that resonates with people on an emotional level. Art has always been a powerful tool for social change, and now I can use my creativity to tell stories, spark conversations, and challenge perspectives. By blending my knowledge of history, culture, and politics with artistic expression, I have found a way to unite my two greatest passions in a way that feels deeply meaningful.

Because of that, I do not regret the timing of my journey. While I wish I had never doubted myself, I believe I started at the right time. If I had started sooner, I might have lacked the confidence and life experience I have now. If I had started later, I might have gone even longer feeling unfulfilled. Right now is the perfect time to fully embrace my creativity, and I am excited to see where it leads.

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers.

My name is Jack Lilley, and I am a painter based in New York. My work explores themes of nostalgia, Americana, and identity, drawing from Western influences and my Jewish heritage to examine memory, masculinity, and self-perception. Through painting, I navigate American nostalgia, sexuality, = masculinity, the human body, and the complexities of self-image. I use art as both a personal expression and a way to engage in larger cultural conversations.

I realized that art is not just a personal outlet but a way to engage with social and political themes. Now, my work blends my academic background in international studies and identity, race, gender, and culture, with my creative instincts, using visual storytelling to examine identity, power, and belonging. I am especially drawn to the aesthetics of Americana and the mythology of the American West, which often promote ideas of rugged individualism and masculinity. By reinterpreting these themes through my socially constructed lens, I challenge traditional narratives and create something new.

What sets my work apart is its ability to exist in multiple spaces at once. It is both personal and universal, nostalgic and critical, beautiful and unsettling. I want my paintings to evoke strong emotions, whether longing, discomfort, or recognition. I am most proud of the fact that I have chosen to embrace my creative path, unlearning the fear of failure and trusting that my voice has value. My goal is to continue pushing boundaries, sparking conversation, and creating art that resonates with those who see themselves in it, even in ways they may not expect.

In addition to my personal work, I also take on commissions, where I collaborate closely with clients to create pieces that reflect their unique vision and values. Whether it’s a painting that captures a meaningful moment, a specific theme, or a personal connection, I strive to understand the deeper meaning behind each request. I view each commission as an opportunity to connect with others on a personal level, creating artwork that is not only visually compelling but also emotionally resonant. Working on commissions allows me to blend my creative process with the stories and experiences of others, creating one-of-a-kind pieces that hold personal significance for those who commission them.

We often hear about learning lessons – but just as important is unlearning lessons. Have you ever had to unlearn a lesson?

I used to believe there was a strict definition of what made someone “an artist.” In my mind, an artist was someone who went to art school, painted with oil paints, mastered specific techniques, and was formally trained in multiple mediums. By that definition, I struggled daily to see myself as one. I did not have formal training, my technique was based on instinct and perception, and I was learning every day.

Teaching ceramics to children at a summer camp in the woods was the experience that changed everything for me. I had no background in ceramics and only limited materials, but I was given the position and creative freedom to explore. As I taught students how to mold clay, I watched their inexperienced hands shape the most beautiful and profound creations. Their work made me question my own rigid understanding of what it meant to be an artist. Each student had their own style and unique perspective on the world, which shaped how they created. They worked without inhibition, crafting freely without overthinking or fearing that they were not “good enough.”

Their fearless creativity inspired me to reflect on my journey. I realized I would never reach the level of technical perfection I once believed was required to call myself an artist. But I no longer needed to. My journey, my experiences, and my perspective were enough. Once I let go of those limiting beliefs, my art became more expressive, more fluid, and, most importantly, more fun. That was when I truly embraced myself as an artist.

What’s the most rewarding aspect of being a creative in your experience?

The most rewarding aspect of being an artist and creative is taking a step back and realizing that I am living the life my 12-year-old self once dreamed of. I live in New York City, surrounded by some of the most inspiring creatives, entrepreneurs, designers, innovators, and thinkers. I am not confined to a path dictated by someone else’s expectations or limited to climbing a ladder I did not build. Instead, I have crafted a life that allows me to create on my own terms.

I paint in the middle of the night when an idea will not let me sleep. I paint before breakfast when inspiration strikes. I paint when I am lonely, when I am sad, when I need to process the world around me. My work is not confined to a nine-to-five schedule or a Monday-through-Friday routine. It ebbs and flows with my emotions, experiences, and the ever-changing world I observe.

Having the flexibility to break boundaries and create whenever and however I choose keeps me motivated daily. It allows me to fully engage with the creative process, rather than forcing inspiration into a structured workday. I take time to rest and reflect, to read and write, to explore new ideas, and to experience the world beyond my canvas. My art is deeply connected to my life, my emotions, and my surroundings. By embracing this freedom, I have learned that creativity is not just about making something visually compelling, but about living a life that fosters inspiration.

There is no singular definition of success in art. For me, success is waking up each day knowing I have the space to create, to evolve, and to push the boundaries of what I once believed was possible. It is knowing that I am not just producing art but living artistically, in every sense of the word. Realizing that and becoming free to create, is by far the most rewarding part of being an artist and creative.

Contact Info:

• Instagram: j.lilleystudios
• Linkedin: https://www.linkedin.com/in/jacklilley
• Other: @lill.jack