Alright – so today we’ve got the honor of introducing you to Scott Leopold. We think you’ll enjoy our conversation, we’ve shared it below.

Hi Scott, thanks for joining us today. Do you wish you had waited to pursue your creative career or do you wish you had started sooner?

If I could go back in time, I absolutely wish I had pursued my creative career sooner. One of my greatest regrets is not immersing myself in a life of creative expression earlier on. Growing up in poverty with an unstable home life and learning disabilities, drawing and daydreaming became my escape. I was naturally talented at art and excelled in it, but the need for financial stability pushed me toward business.

Even in high school, I found solace in writing short stories and poetry, but I never saw it as a career path. When I took an oil painting class in college, my professor encouraged me to pursue art at Indiana University. I seriously considered it, but in the end, I chose business because I didn’t believe I could make a living as an artist. I went on to spend 25 years as a Business Systems Analyst, a career I never truly enjoyed. It was never about passion—just financial security.

Fifteen years ago, after my mother’s passing, I turned to painting as a way to process my emotions, and it reignited my creative spark. That led me to write a thriller novel and, more recently, to acting and modeling. I now understand that creativity is what fulfills me—it’s what I was meant to do.

If I had started earlier, I believe I could have built a more meaningful career around my passion. Maybe I would have taken more risks, struggled, and eventually found success in a field that truly made me happy. At 54, I’m now fully embracing my creative pursuits, even though making a living from them is a challenge. I can’t change the past, but I can control how I live now. So, I choose to do what makes me happy and trust that good things will come from following that path.

Scott, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?

I’m Scott Leopold, a multidisciplinary creative with a background that spans business, real estate, IT project management, and creative arts. My journey has been anything but conventional, and while I spent decades in corporate roles, my true passion has always been in artistic expression—painting, writing, acting, and modeling. Now, I’m fully embracing my creativity, working to build a career that aligns with what truly fulfills me.

How I Got Into My Creative Career
Growing up, creativity was my escape from a difficult childhood. I moved frequently, faced learning disabilities, and lived in unstable conditions, but art and storytelling provided a world where I could express myself freely. In high school, I wrote short stories, poems, and continued drawing, but I didn’t see a viable path to making a living through art. Instead, I pursued business, earning a degree in Business Administration and spending 25 years as a Business Systems Analyst.

For years, I felt disconnected from my work—it was just a means to financial stability. It wasn’t until my mother’s passing 15 years ago that I picked up a paintbrush again, using art as a form of therapy. That creative spark led me to explore painting seriously, and over time, I expanded into writing, acting, and modeling. These artistic pursuits have allowed me to fully express myself in ways I never could in the corporate world.

What I Offer
As a creative professional, I focus on:

Abstract Art – My paintings are deeply personal, often inspired by urban life, raw emotion, and the human experience. My work is influenced by artists like Jean-Michel Basquiat, blending bold expression with storytelling.
Writing – I’ve written a fiction thriller novel and continue to explore storytelling through various mediums.
Acting & Modeling – Over the past three years, I’ve worked in commercial, corporate, and creative acting roles. I specialize in roles that embrace authenticity, fatherhood, and urban aesthetics, but I’m always open to pushing boundaries.
Creative Consulting – I help businesses and individuals bring creative visions to life, whether through branding, storytelling, or visual arts.
What Sets Me Apart
My unique background—a blend of business expertise and raw creative talent—allows me to approach projects from multiple perspectives. I understand structure, strategy, and professionalism, but I also bring unfiltered creativity and authenticity to everything I do. I’m not just an artist; I’m a storyteller, a problem-solver, and someone who embraces change.

Additionally, I take pride in pushing boundaries. Whether it’s exploring complex human emotions in my art, breaking stereotypes in my acting roles, or bringing an urban edge to my modeling work, I thrive in spaces where creativity meets boldness.

What I’m Most Proud Of
Without a doubt, my greatest accomplishment is being a father. Despite my struggles, I raised three amazing sons who inspire me every day. In my creative career, I’m most proud of finally taking the leap—choosing passion over security, despite the challenges.

What I Want People to Know About Me & My Work
I want my clients, followers, and fans to know that my work is deeply personal. Everything I create—whether it’s a painting, a performance, or a story—comes from a place of lived experience, emotion, and authenticity. I’ve spent years suppressing my creative side, and now, I’m fully embracing it. My goal is to connect with people through my art and inspire others to follow their own passions, no matter where they are in life.

At 54, I’m proving that it’s never too late to redefine yourself and pursue what truly makes you happy.

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

For me, the most rewarding aspect of being an artist and creative is the freedom to express my true self and connect with others on a deep, emotional level. After spending years in corporate roles that felt unfulfilling, stepping into a world where I can create without limitations has been life-changing.

Art, whether through painting, writing, acting, or modeling, allows me to take everything I’ve experienced—both the struggles and the triumphs—and turn it into something meaningful. It’s a form of therapy, a way to process emotions, and an opportunity to tell stories that resonate with people. There’s something incredibly powerful about creating a piece of art, a performance, or a written work and seeing how it impacts someone—whether it inspires, comforts, challenges, or simply makes them feel seen.

Beyond personal fulfillment, I love the unpredictability and adventure that comes with a creative career. Every project is different, every opportunity presents new challenges, and there’s always room to grow, experiment, and push boundaries. Unlike my past career, where I felt confined by routine, creativity allows me to constantly evolve and explore new possibilities.

At this stage in my life, the most rewarding part is knowing that I’m finally doing what I was always meant to do. I spent years suppressing my artistic side, and now that I’ve embraced it, I feel a sense of purpose and excitement that I never had before. The ability to inspire others—whether it’s through my paintings, performances, or personal story—is the greatest reward of all.

We’d love to hear a story of resilience from your journey.

One of the most defining moments of my journey—and a true testament to my resilience—was when I lost my mother to an overdose about 15 years ago. It was an incredibly painful experience that forced me to confront a lot of suppressed emotions and unresolved struggles from my past. Instead of letting grief consume me, I turned to painting as a form of therapy. What started as a way to process my emotions quickly reignited a creative spark in me that I had buried for decades.

Growing up, creativity had always been my escape from a difficult childhood marked by poverty, instability, and learning disabilities. I was naturally gifted in drawing and writing, but because I was focused on financial security, I pursued a career in business instead. For over 25 years, I worked in roles that provided stability but never brought me joy or fulfillment.

After my mother’s passing, everything shifted. Painting became more than just an outlet—it became a calling. I started creating more and more, exploring different styles, and tapping into emotions I had long suppressed. This creative rebirth led me to write a fiction thriller novel and eventually step into acting and modeling, something I never imagined I would do.

At 53, I am reinventing myself in ways that many people might find daunting. Leaving a stable career to pursue an artistic life hasn’t been easy, but I’ve learned that resilience isn’t just about overcoming hardship—it’s about having the courage to follow your true path, no matter when you start. If I had let fear or regret hold me back, I wouldn’t be where I am today, doing what I love. My journey has been unconventional, but every challenge has shaped me into the artist and person I am now, and I wouldn’t trade that for anything.

Contact Info:

• Website: https://scottleopold.com/
• Instagram: https://www.instagram.com/art.by.scott.leopold/
• Facebook: https://www.facebook.com/ArtistScottLeopold
• Linkedin: https://www.linkedin.com/in/scottleopold/
• Youtube: https://www.youtube.com/@ScottLeopold
• Soundcloud: https://soundcloud.com/scott-leopold-3