Story & Lesson Highlights with Jason Farley of South Loop

We recently had the chance to connect with Jason Farley and have shared our conversation below.

Jason, really appreciate you sharing your stories and insights with us. The world would have so much more understanding and empathy if we all were a bit more open about our stories and how they have helped shaped our journey and worldview. Let’s jump in with a fun one: What is something outside of work that is bringing you joy lately?
Being out in nature, the beach, and going to spend time with family.

Can you briefly introduce yourself and share what makes you or your brand unique?
“My name is Jason Farley, a Chicago artist with a deep passion for storytelling through oil paint. I work under the brand Sonley Art — a personal acronym and my official LLC — which reflects both my identity and my evolution as a creator. My journey began after serving in the Army, followed by formal training in art school, and eventually led me from illustrating storyboards for ad agencies to building a full-time career as a fine art oil painter. For the past ten years, I’ve devoted myself entirely to this craft.

What makes my work stand out is a meticulous attention to detail and a constant drive to refine my vision. My art is ever-evolving, shifting from pop art to surrealism to figurative and scenic explorations. I pull inspiration from nature, people, animals, and urban life — weaving them together with symbolic depth and composition that often follows the golden ratio intuitively. There’s a quiet spiritual undertone in much of my work that invites viewers to pause, analyze, and connect on a deeper level. My current series explores the tension and harmony between Chicago’s urban grit and the resilient force of nature — a visual narrative that speaks to conflict, beauty, and balance.”

Okay, so here’s a deep one: Who taught you the most about work?
Definitely my dad — though, truthfully, I didn’t listen to him much back then (sorry, Dad). It took the Army to really knock some focus into me. The leadership there didn’t ask me to pay attention — they insisted. That’s where I learned how to work hard, stay disciplined, and obsess over the smallest details — whether I liked it or not. Turns out, all that structure was the perfect training ground for becoming a painter who can spend 100 hours on a single piece and still notice if a brushstroke is off by half an inch.

Was there ever a time you almost gave up?
There were definitely moments I almost gave up — more than a few, honestly. The first was during my time in the Army. I barely created any art at all, and I wasn’t sure if I’d ever return to it. Later, in art school, I went through a stretch where I felt completely mediocre — not because of outside criticism, but because I wasn’t meeting my own expectations. And then, when I transitioned from illustration to oil painting, even though I had taken oil painting in college, it was like starting from zero. I had no idea what I was doing, and most of what I made looked like garbage to me. But somehow, I just kept pushing forward. Something in me refused to stop, even when I felt totally lost. Looking back, I think those moments were necessary. They forced me to grow beyond what I thought I was capable of.

Alright, so if you are open to it, let’s explore some philosophical questions that touch on your values and worldview. What are the biggest lies your industry tells itself?
One of the biggest lies the art world tells itself is that popularity equals quality. Just because something is getting attention doesn’t mean it’s good — and as artists, we know how to see through that. There’s a lot of work out there that’s created purely to go viral, to ride a trend, or to gain quick recognition — but when you really look at it, there’s no depth, no skill, no time invested. It’s performance, not process. Meanwhile, there are incredible artists quietly grinding, putting in serious work and intention, but they’re not in the spotlight because their art isn’t built for clicks. That disconnect between visibility and value is one of the hardest things to witness in this industry.

Thank you so much for all of your openness so far. Maybe we can close with a future oriented question. What will you regret not doing? 
If I ever have regrets, it’ll be about not exploring more — not diving into new mediums like sculpture, tattooing, large-scale murals, or spray paint. I’ve always had the curiosity and the urge to try them, but time is limited, and when you’re committed to mastering one craft, it’s hard to stretch yourself into others. Still, there’s this voice in the back of my mind that says, what if? I think as artists, part of us always wonders about the paths we didn’t walk — even if we’re proud of the one we chose.

Contact Info:

• Website: https://www.sonleyart.com
• Instagram: @sonleyart