Between Paradise and Darkness: A Conversation with Jake Kenobi (aka Spring Break Jake)

Jake Kenobi, also known as Spring Break Jake, creates art that exists in the liminal space between paradise and darkness. With his background in graphic design and roots in the snowboard industry, he's developed a distinctive style that blends branding, chaos, emotion, and profound topics like insomnia and mental health into a captivating aesthetic.

Each piece feels like a diary entry—layered, textured, emotional, and vulnerable. His work captures both the weight of difficult experiences and the joy that can coexist with them. I recently had the opportunity to sit down with Jake for a conversation about his art, his journey, and his upcoming exhibition.

The Man Behind the Nickname

The name "Spring Break Jake" comes from a nickname given to him by a former boss about twelve years ago. Though he initially disliked it, the name has come to represent what he wants to convey through his art: using tropical imagery to talk about positive aspects of life while maintaining a reminder not to take himself too seriously.

Ironically, the name now stands in contrast to his lifestyle. Jake has been sober for four years, goes to bed early, meditates, and loves tea—the complete opposite of what you might expect from someone called "Spring Break Jake." The juxtaposition mirrors his artistic approach, balancing heavy subjects with elements of joy and lightness.

Exploring Insomnia Through Art

One of Jake's recent pieces, titled "Time," features a painted alarm clock showing 3:33. The work is part of his new collection focused on his struggles with insomnia and being a "chronic night owl." The time has dual significance—it's half of 666 (maintaining his light-hearted approach) but also represents the brutal reality of his worst experiences with sleeplessness, when 3-4 AM would often be his bedtime.

For Jake, creating art about his insomnia has become a form of therapy. He's actively working to improve his sleep habits—seeing a sleep doctor, establishing a bedtime routine, and even starting to exercise—recognizing the significant impact sleep has on his mental health.

The Balance of Light and Dark

What immediately draws viewers to Jake's work is his masterful balance of heavy themes with playful elements. Large washes of black and dark subject matter might suddenly feature a flamingo, creating a tension that reflects the complexity of human experience.

"I want to talk about heavy shit," Jake explains. "I don't want to ignore anything, but I also don't want to make depressing work. I really am a fairly positive person. So I want to put everything into the art—all parts of myself—which is like, yeah, I get fucking sad, and I can't sleep sometimes. But also life is really beautiful and fun."

The Power of Acceptance

One of the biggest lessons Jake has learned through therapy is the power of acceptance. With sleep, fighting against insomnia only makes it worse—acceptance is the path to improvement. The same applies to difficult emotions; accepting a bad day rather than resisting it leads to better outcomes.

"Acceptance is a huge part of my work as well, just accepting that you cannot have the good without the bad," Jake says. "And I don't even know if we'd want to—the bad times make the good that much better. There's something to compare it against. It'd be kind of boring if we were just high all the time."

Vulnerability and Masculinity

Jake's journey toward creating such emotionally honest work began with examining masculinity. He reached a point where he recognized that traditional masculine expectations—bottling up emotions, only expressing anger—were harmful. This realization became a foundation for his artistic expression.

"It started for me with looking at masculinity. I just had gotten to a point where I was like, this isn't healthy, bottling shit up in the way men are only allowed to show anger, really. Sometimes not even joy. Sometimes people think joy is feminine."

This exploration of vulnerability extends to his use of imagery like skulls and skeletons—confronting death, a subject people try to avoid despite it being one of the few universal human experiences.

Finding His Medium

While Jake has explored various art forms, including music, visual expression has always been his most natural way to process emotions. "Making something visual, for my whole life, has been my favorite or just the best way to process things," he explains. "Even since I was a kid and before I could articulate anything, drawing helped me make some sense of confusing feelings."

His current work combines a cartoon illustration style with painterly techniques, creating an intriguing contrast. The new collection features more emphasis on painterly elements, with bedsheets rendered through careful mixing and blending directly on the panel.

Nightlife: The Exhibition

Jake's exhibition titled "Nightlife" is open until July 21, 2025 at Purple Door Gallery in Portland, Oregon. The show focuses on insomnia and mental health—those "big, heavy, confusing topics" that Jake navigates so deftly in his work.

The opening date, Friday the 13th, adds another layer of meaning to the exhibition. While popularly considered an unlucky day, Jake learned that in pagan traditions, Friday the 13th was actually a day for harnessing feminine energy and positive power—a perfect alignment with his approach to reframing difficult experiences.

Connect with Jake

To see more of Jake's work, visit his website at springbreakjake.com or follow him on Instagram @springbreak.jake.

For a regular dose of positivity, sign up for his email newsletter, where every Monday he shares five good news stories along with updates on his artwork.

Jake's art reminds us that we can acknowledge the darkness while still finding moments of beauty and joy—a profound message delivered with color, emotion, and just a touch of spring break.