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How did you get started in illustration and develop your skills? I actually didn’t study illustration—or even know it was something I could do—until recently. I studied black-and-white photography at the University of California, Santa Cruz, and then got a post-baccalaureate in painting from the San Francisco Art Institute. I worked in restaurants from my late teens to my mid-thirties to support being a student and my art practice while I took internships with different artists. Since restaurant schedules are chaotic, I got used to filling my free time with painting, making work for shows or just for me; I would work until midnight and bike home after my shift, take a shower, and paint for hours before going to bed, or I would wake up super early and paint before heading to work. I couldn’t stop! I had just decided that I would build my life around painting.

Over time, I found myself making more and more murals and illustrations for friends—and then friends of friends and their businesses. It dawned on me that this could be a viable career that would support my artmaking: my art finally supporting itself. The beauty of my taking a long time to find my way to illustration is that I now value the slow road. Working in the service industry was a huge help not only financially, but in developing my ability to communicate with clients, solve problems and be connected to my community. Working under different artists as an intern helped me realize what types of creative work I could and couldn’t do.

In 2019, I took a workshop with designers Amy and Jen Hood of Southern California–based design firm and type foundry Hoodzpah while at the Creative Works conference in Memphis. I signed up for it on a whim, but I also felt I didn’t have the design background that many other illustrators do and thought I could learn a lot. I was right, and I honestly attribute so much of what I can do now to that workshop with Amy and Jen. They taught me how to do things that seem so simple now: how to make a pitch deck, negotiate and talk about contracts, among other things. Until then, I was truly making it up as I went along, but learning all those things through experience helped me understand exactly what I’m doing. I can read contracts, know how to price and negotiate licensing fees, and market myself. So much of illustration is the things that go on behind the scenes of making a cool image, the things you don’t see that nobody really wants to talk about. I’m now represented by the agency Closer&Closer and am so grateful that I have help with those things, but I am glad that I can speak the language of contracts and licensing fees so that I know what’s going on and feel like I can handle it on my own if I needed to.

What personal experiences or circumstances have most influenced your style? Two recurrent influences inform how I explore the world in my work: studying black-and-white photography and hyperrealist painting being the first. Both these have affected my ability to see and invent light within my work and play with composition. It took me a long time to let go of some of the constraints of hyperrealism and being “correct”—I still struggle with that—but I am rewarded more than held back by the lessons of realism. Having studied anatomy, I can be playful with form but still understand where or how an arm would move or how a hand might hold something.

The second influence was stopping at the Virginia Museum of Contemporary Art in Virginia Beach, Virginia, on a cross-country road trip with my partner David to see artist Amy Cutler’s work in person. I went back to the show twice and left that trip with a desire to build my own world and create a language for storytelling. Until then, I had been working on large hyperrealist drawings of myself and exploring memories and storytelling through abstracting old family photos with watercolor. Seeing Cutler’s work, I realized I wanted to do what felt scary to me: storytelling in a new way. I wanted to step away from the anchors of being literal to explore invention a bit. Now, I can see that reality informs fantasy, but it felt like a really big deal at the time!

In your work, you commonly explore natural and psychological themes. What inspired you to incorporate these in your work, and how do you address them? Nature and psychology are infinitely fascinating to me, and I find they work well hand in hand. A pivotal moment for me and my curiosity in psychology was when I was in my teens, and my grandmother Evelyn—my dad’s mom—suffered from Alzheimer’s at the end of her life. Shortly after she passed, my grandmother Mable—my mom’s mom—started developing dementia and struggled with that for quite a while before her passing. It was hard to witness two of the people I loved going through that, but it also opened up a lot of new curiosities. There is much more complexity in how we perceive our reality and how our brains and memories work. It set me on a course of diving deeper into my own psychology and memories, using art as a tool to express those feelings. I focused on my dreams, writing them down as soon as I had them and turning them into drawings. I read a lot of Oliver Sacks and magical realist authors like Haruki Murakami and Helen Oyeyemi, and I spent a lot of time exploring surrealism.

Using themes of nature as a tool to explore psychological tropes is something I return to repeatedly because of my personal connection to nature and its ability to make us feel small and connected to something much bigger than ourselves. I live in San Francisco, but so much of the city is surrounded by nature; there are many excellent hikes and camping spots within just an hour or two. I walk my dogs in Golden Gate Park or on Ocean Beach, where we see coyotes, red-tailed hawks and blue herons regularly, and I swim and kayak in the Bay. A friend once described my work as “emotional landscapes”—I had never thought of that before and am still unpacking what that means, but I find something in that phrase interesting.

I am excited by the amount of vulnerability I see in illustration. The humanity in it. It’s always been there, but it feels rawer, and I love seeing the expansion of what illustration can be.”

What have been some of your favorite commissioned projects to work on and why? In 2020 and 2021, I worked on Hope Cards for KindSide, a mental wellness company focusing on tools that merge art and therapy. My first deck came out in 2020, and each card has a hopeful phrase or affirmation on it to prompt self-reflection and get in tune with one’s feelings. I illustrated, hand-lettered and designed the deck, and to our delight, the cards began to be used in therapy to prompt discussion. Then, KindSide founder Lindsay Quinlan paired up with some therapists to create a series of cards for kids, which I also worked on. The kids’ deck often prompts difficult conversations with young people about identifying their feelings. I loved the psychology around the whole project, the collaboration, and being a part of each stage of the design and illustration processes. Getting to hold an object that you built is incredibly special.

Another fun project was working on a mural for Chick Shack, a chicken restaurant in the Zamalek neighborhood of Cairo, Egypt. Since this was during the COVID-19 pandemic in 2020, I couldn’t travel there to install it in person, so I created a large 50-by-50-inch painting (a quarter of the wall’s size) and had two artists install it in Cairo. Making a mural for a restaurant on the other side of the globe felt joyful, collaborative and exciting; we got to connect over our shared love of community and the joy of food.

Tell us about your Mystery Paintings series. What inspired you to paint from people’s dreams or meaningful symbols? Back in 2016, my friend Brooke, a pastry chef, would talk to me about my painting projects while we worked together at a restaurant. She told me about an artist she liked who had a strong following back in the day and would make custom works for people while doing it in a way where customers didn’t have a say in what they would get. Learning about this was a real breakthrough moment for me, and I decided to try the idea of “surprise” paintings. I made a write-up for Mystery Paintings that was way more direct about my boundaries in its description than I had ever been before; I think it even said something like “Not for the faint of heart.” I was concerned that this level of boundary setting would turn people off, but it attracted just the right people: those who love to be surprised, a mystery and weird work.

The formatting of Mystery Paintings has always centered on making something custom for clients based on their memories and dreams. I wanted to keep it a surprise to protect my ability to try new things and be playful, but I also wanted the final product to feel unique and personal. Over the years, I have refined it more and more, and each rendition reflects my own current interests: the most recent edition of Mystery Paintings was based on special interior spaces for the client. I asked many questions about the space they shared, what memories are tied to it, how it smells, what the weather is like and how it feels at night. Many of them ended up being a hybrid interior/exterior painting since so much of the spaces centered around not just what was inside the walls but the natural spaces outside as well. Some sent over photos, some didn’t, and I got to read a lot of beautifully intimate information that commissioners gave me and made something I thought they would love.

I love that this project has spanned almost six years, and I love that people trust me to make them paintings. It feels like a special exchange.

You currently teach at the California College of the Arts (CCA) and run several workshops on your own—not to mention you lead team-building workshops for clients like Google and Pixar. What do you enjoy most about teaching, and do you find it developing your creative work in any way? Teaching has become a central part of my practice. I love helping people find ways to harness their own creativity. Honestly, I have learned so much by following my own curiosities and letting myself not be an expert but instead be a student alongside my students. I’ve realized my job isn’t so much providing a strict lesson plan—although there is a lot of that—as it is creating a stage for creativity to take place. Sometimes that means teaching brush-handling techniques, but most of the time, it means making space for silence or reading a strange book to students while they paint.

Teaching at CCA is a newer thing for me; building a sixteen-week syllabus is wild. Most of the workshops I have taught since 2013 have been maybe one-to-five weeks long, and planning and spending an extended amount of time teaching proved challenging. My syllabus for the spring semester was pretty fun, but now I am teaching the same class this fall and spent the prior month or so going over my syllabus and assignments, tweaking things, adjusting projects, factoring in the sticking points of the students (and me), and trying to come up with an even sharper version of what was. Teaching is its own art practice. So much of it, for me, is being open to new ways of thinking about something I thought I knew—and knew it well enough to form a lesson plan around! I sometimes freak out with impostor syndrome, but then I realize that this openness permits my students and me to be curious and let go of “correctness.” I believe that whatever we put energy into fosters more of that thing in ourselves, and I am a type-A person who really wants to be playful! Slowly, teaching helps me discover how to have more fun and let go of so much control.

What excites you about illustration right now, and where do you see the field going? I am excited by the amount of vulnerability I see in illustration. The humanity in it. It’s always been there, but it feels rawer, and I love seeing the expansion of what illustration can be. Here in San Francisco, many artists are challenging notions of what illustration is: Risa Iwasaki Culbertson makes incredible felt sculptures and puppets. Chelsea Wong essentially takes her personal narratives and expands them into gorgeous paintings. And Carissa Potter Carlson works with printmaking and illustrates her own struggles and joys of being human. I love to see more of this, to see things be a little less polished and perfect.

Do you have any advice for illustrators just beginning their careers? Think beyond the internet. The internet and social media are just a few tools in a giant garage: you can use them, but don’t let them be the only tools you grab. The strongest one at your disposal is your immediate community. Who has a wall you can paint? Who needs fun drawings on their chalkboard? Is there a way to reciprocally engage with the world around you, and what does that look like? It’s easy to get lost playing the game of catch-up and making it big on the internet, but if you focus on making work that you love and connecting with people in the real world, you might surprise yourself with what is possible. ca

Lindsay Stripling is a San Francisco–based artist and illustrator. She studied black-and-white photography at the University of California, Santa Cruz, and obtained a post-baccalaureate in painting at the San Francisco Art Institute. Currently, she works as an adjunct professor of illustration at California College of the Arts in San Francisco. Having shown her work nationally and internationally, Stripling often works traditionally with paint on paper, but she also plays with incorporating traditional media into digital work, always coming from a place of layering, texture and experimentation. She likes to keep things playful and explores themes of nature, time, memory, community and psychology. Stripling’s clients include Adobe, Illustoria magazine, podcast network Lemonada Media, Nike and Target.


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