We recently had the chance to connect with Jimmy Houston and have shared our conversation below.
Hi Jimmy, thank you for taking the time to reflect back on your journey with us. I think our readers are in for a real treat. There is so much we can all learn from each other and so thank you again for opening up with us. Let’s get into it: What do you think is misunderstood about your business?
I think a lot of people misunderstand what being an artist really looks like day to day. It’s not just sitting around waiting for inspiration. For me, it’s about showing up every day—sketching, writing, living life. Inspiration comes from the everyday moments: the good and the bad, playing with my son, making mistakes, sharing meals with friends, having tough conversations, exploring new places physically, emotionally and spiritually.
Also, it’s not like I’m painting every single day. There’s so much behind the scenes—building relationships with clients, marketing, social media, making true connections. It’s more than just making art, even though I wish it was that simple. It’s organic. It’s like counseling at times. Speaking visually into the lives of others.
People often think there’s one “right” way to be an artist or run a creative business. But really, every artist’s path is different, and I’ve learned it’s about embracing the unique journey and the growth it brings—not just as an artist, but even more so as a person.
Can you briefly introduce yourself and share what makes you or your brand unique?
I’m a retro-animation fine artist based in Houston, known for painting smoking monkeys, tin men, and vintage-cartoon women. I’ve been blessed to do this full-time for over a decade—it’s truly my calling. The quirky cast of cartoon characters I create bring humor while deftly exploring universal emotions, questions, and perspectives. My work centers on human connection and dives into emotional and spiritual themes—crafting pieces that hopefully continue to resonate and inspire far into the future.
I draw inspiration from old cartoons, comics, and vintage ads, blending nostalgia with today’s cultural and spiritual questions. My paintings often ask more than they answer, using humor and color to cut through the gloom of our times.
I recently built a new home studio—my creative sanctuary. A dream come true.
Lately, I’ve been focused on even more texture, layering by hand to bring a tactile, human feel to my work. Each layer tells part of the story and connects to the painting’s theme.
I’ve been fortunate to tell many stories through both original work and meaningful commissions. Collaborating with clients to create personal, lasting pieces feels like building a legacy that lives on beyond us.
Thanks for sharing that. Would love to go back in time and hear about how your past might have impacted who you are today. What’s a moment that really shaped how you see the world?
I really appreciate that these questions go deeper than just my career. Behind every artist, every entrepreneur, there’s a story—real life, real experiences, and lessons that shape who we are. Getting raw here.
This one’s tough to answer because it brings up some pain, but honestly, pain is where so much growth comes from.
One of the hardest and most defining moments of my life was losing my older brother. He was a Navy helicopter pilot and later became a flight instructor in Corpus Christi. About 16 years ago, his plane went down over the ocean, and just like that, someone I looked up to, shared my whole life with, and thought I’d grow old alongside—was gone.
After the initial shock and grief, I started to understand how short and unpredictable life really is. There are no guarantees. That truth hit me hard. But it also woke something up in me. I already knew I was called to be an artist—my brother always encouraged that. He was the risk-taker, always pushing me to step out and believe in myself. I was working for a mural company at the time, and he’d constantly say, “You should do your own thing.”
Not long after he passed, I took the leap. His loss became a catalyst for me to stop waiting and start truly living the life I felt called to live. I leaned into the gifts I’d been given and began taking risks I wouldn’t have taken otherwise.
As painful as that moment was, it changed everything. It gave me a new sense of purpose—not just as an artist, but as a person. I carry his encouragement with me in everything I do.
What fear has held you back the most in your life?
This definitely feels like a counseling session, which honestly I don’t mind, because it’s so connected to creative expression.
If I had to name the fear that’s held me back the most in life, it’s probably the fear of people-pleasing. As an artist, you’re trying to express something real, right? Just like in any other form of communication, you want to be heard. You want to be accepted—at least on some level. You’re putting something deep and personal out into the world, and you want it to resonate.
For me, when I create a piece—especially something that’s going to be seen by others—I don’t just want someone to think it’s pretty or well-done. I want them to feel it. I want them to love it on a heart level, to find something in it that echoes something in themselves.
But that fear of people-pleasing can be absolutely crippling to the creative process. It’s sneaky. It’s like a slow-acting poison that seeps in when you start making things just to fit a mold, or sticking to what’s “worked” before. What’s sold before. What’s gotten the likes. That’s when the spark starts to dim. That’s when the lightning disappears—and I never want to lose that.
At the core, my fear has always been about trying to prove myself—both as a person and as an artist. If this were a counseling session, I’d say the phrase that sums it up is “performance-based affection.” Like: Look, I made something cool. I made something meaningful. Therefore, I matter. But that’s not the truth. That’s not where real value comes from.
So yeah, I’m still working through that fear. Still learning to let go of the need for external validation. I’d love to be the kind of person—and the kind of artist—who, in the healthiest way, just doesn’t care what other people think. That, to me, is the ultimate expression. The ultimate freedom. Being boldly, unapologetically yourself. Radically the person God created you to be.
Through my life and through my art, I keep coming back to this quiet reminder: You don’t have to prove yourself to anyone anymore.
So a lot of these questions go deep, but if you are open to it, we’ve got a few more questions that we’d love to get your take on. Whose ideas do you rely on most that aren’t your own?
I lean really heavily on the wisdom and perspective of my wife.
She’s been with me through everything—the losses, the wins, and the everyday middle ground that honestly makes up most of life. The ups and downs of an artistic career can feel like a roller coaster, and through it all, she’s been this steady, unwavering support. She’s my cheerleader, my encourager, and honestly, often the voice of reason.
She’s not just supportive when it comes to my artwork—she gives me honest feedback about life. About who I am, how I’m showing up. We’ve been really blessed in our marriage in that we’re not both looking out the same side of the boat. She sees things I don’t. Her brain works so differently than mine, and I love that. I rely on that.
Any artist—any creative, really—needs someone like that. Someone who can ground you. I tend to live with my head in the clouds, caught up in this swirl of cartoon ideas and big dreams and creative ambition. Meanwhile, she’s over here helping me sort through it all. She’ll gently bring me back to earth and say, “Okay, love that idea. But what’s step one? What’s step two? Let’s make it happen.”
And she walks with me through it—not just cheering from the sidelines but actually in it. Through the hard times, through the good times, through the feast and the famine.
So yes—my wife. My dear, sweet, wise, resilient, durable, beautiful pillar of a wife. I’m incredibly grateful for her.
Thank you so much for all of your openness so far. Maybe we can close with a future oriented question. If immortality were real, what would you build?
Existential stuff. I’m all in—let’s go.
Immortality is real. Without a doubt.
And anything I create in this life—whether it’s a painting, a piece of writing, a design, or some other physical object—is really just a reflection of something bigger. It’s about human connection. That’s what lasts. That’s what’s eternal.
The only truly immortal thing we leave behind is the effect we’ve had on the hearts, minds, and spirits of other people. So when I think about the question, “What would you build if you knew immortality was real?”—I don’t immediately go to the idea of some grand artistic legacy, like a gallery full of my work or a book that outlives me. That’s not really the point.
To me, it’s about the message. What is the art saying? What is it pointing to? What kind of value or hope does it carry for the people who experience it—especially after I’m gone?
The message I hope to leave behind is one of hope. Hope that there’s more than this life. That God has a purpose for you—one that stretches beyond the here and now. I believe in eternity, and in that eternity, I don’t think we’ll need art in the way we do here. We won’t need to express things in two-dimensional forms or try to capture emotion with color and line. We’ll be living in fulfillment. In full rapture. In the complete picture.
So what I create now is really just a shadow. A signpost. A cartoon speech bubble that hopefully stirs something eternal in someone else. I’m not trying to be remembered for the sake of legacy—I’m hoping to leave a mark on people’s spirits. So they can find their way to that same eternity.
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Jimmy Houston
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