Today we’d like to introduce you to CAROLINE GREEN.
Hi CAROLINE, we’re thrilled to have a chance to learn your story today. So, before we get into specifics, maybe you can briefly walk us through how you got to where you are today?
My journey really started in my childhood. I grew up in a family of artists—painters, woodworkers, and poets—where weekend trips to galleries were our version of a typical family outing. My mother was my first teacher; she taught me everything from blowing watercolors with a straw to the complex chemistry of mixing encaustic wax.
However, like many creatives, I was initially told that art wasn’t a ‘sustainable’ career. That led me into a very different world: the operating room of a Portland hospital. I spent years working in surgery, which was fast-paced and financially rewarding, but I felt a deep lack of fulfillment. Interestingly, that medical environment actually inspired my first professional body of work in 2008, ‘Admiring the View,’ where I used a muted palette to explore themes influenced by my time in the OR.
The real turning point came when I realized I couldn’t ignore my true calling anymore. I made the leap from the medical field to being a full-time artist, which was terrifying but necessary. I started by saying ‘yes’ to everything—gallery shows, pet portrait commissions, and even having my work featured on the sets of Portlandia.
What I discovered during that transition was that I didn’t just want to sell art; I wanted to make it accessible. That’s what led me to found Paint and Sip Portland. I saw a gap where people felt intimidated by a blank canvas, and I wanted to use the techniques I’d refined over 20 years to show them that anyone can create a masterpiece.
Today, my work is a mix of high and low: I create large-scale murals and fine art landscapes for places like The Starry Night Inn, but I also get to lead these immersive ‘paint party’ experiences. Whether I’m painting a 25-foot mural or helping someone pick up a brush for the first time, my goal is the same: to bring a bit of color and storytelling into everyday spaces.
I’m sure it wasn’t obstacle-free, but would you say the journey has been fairly smooth so far?
The first major struggle was internal. For years, I had the ‘starving artist’ myth playing in the back of my head—that art wasn’t a sustainable career. Breaking away from a high-stakes, high-paying career in surgery to pursue art full-time was terrifying. I went from the financial security of the operating room to the ‘pay-to-play’ world of art shows, where I had to learn the hard way which opportunities were worth my time and which were exploitative.
The second struggle was finding the right business model. In the beginning, I thought getting into galleries was the only measure of success. But I quickly realized that to make a living, I had to be more than just a painter—I had to be an entrepreneur. I had to learn how to diversify: moving from canvas to 20-foot murals, writing and illustrating a book, and eventually launching Paint and Sip Portland.
Starting the business brought its own set of ‘creative’ challenges—like finding the right venues and figuring out how to teach a group of 30 people to paint the same landscape while still letting their individual personalities shine through. But honestly, the struggles are what made the success feel earned. I’m no longer just ‘waiting for a gallery to call’; I’ve built my own platform, and that independence is worth every difficult step along the way
Thanks for sharing that. So, maybe next you can tell us a bit more about your work?
I’m a fine artist, muralist, and the founder of Paint and Sip Portland. My career really lives at the intersection of ‘fine art’ and ‘community experience.’
What I specialize in: I specialize in large-scale, atmospheric landscapes inspired by the Pacific Northwest. I use a specific glazing technique with oils and acrylics to create deep, saturated colors that make a space feel immersive. My style is often described as ‘whimsical realism’—whether I’m working on a 25-foot mural of Mt. Hood or a tiny, detailed pet portrait on birch wood, the goal is to create a dream-like version of the world we live in.
What I’m most proud of: If I had to pick one thing, it’s my ability to scale my vision. I’m incredibly proud of the murals I’ve completed in Downtown Hillsboro, where my work has become a permanent part of the city’s identity. At the same time, I’m equally proud of the community I’ve built with Paint and Sip Portland. We’ve hosted over 400 parties, and there is nothing more rewarding than seeing someone who ‘can’t draw a stick figure’ walk away with a painting they’re genuinely proud of.
What sets me apart: What truly sets me apart is my commitment to authenticity in a digital age. At Paint and Sip Portland, we have a strict ‘No AI-Generated Art’ policy. While I respect AI as a tool for business efficiency, I believe it has no place in the soul of physical art. Every design we teach is hand-painted by me because people crave that human touch.
Ultimately, my background is my greatest asset. I bring the technical discipline of a former surgical professional, the narrative eye of a published author, and the practical grit of an entrepreneur. I don’t just create art; I create experiences and memories that people want to be a part of.
How do you define success?
For me, success is the intersection of sustainability and impact.
First, it’s the ability to build a life and a career around something I’m deeply passionate about. Being able to generate a living from my art isn’t just about the ‘paycheck’—it’s a metric of the value I’m providing to the world. When people invest in my murals or book a party at Paint and Sip Portland, they are validating that my creative vision has real-world worth.
Second, and perhaps more importantly, success is measured by the happiness of others. Whether it’s a client seeing their pet’s personality captured on a piece of birch wood, or a student at a workshop realizing they actually have an artistic side, that spark of joy is my ‘North Star.’ If I’m making a living while helping people reconnect with their own creativity and local environment, then I’ve hit the gold standard of success.
Pricing:
- Public Paint Night- $40/person
- Private Events $45/person
- Specialty Events $45-50/person
- Personal Work $300+
Contact Info:
- Website: https://www.paintandsipportland.com/
- Instagram: https://www.instagram.com/paintandsipportland/
- Facebook: https://www.facebook.com/p/Paint-and-Sip-Portland-61565138875024/
- LinkedIn: https://www.linkedin.com/in/caroline-green-1812436b/
- Youtube: https://www.youtube.com/c/carolinegreenart
- Other: https://www.carolinegreenart.com/
