We caught up with the brilliant and insightful Jessica Cao a few weeks ago and have shared our conversation below.

Jessica, thanks for joining us, excited to have you contributing your stories and insights. What’s been one of the most interesting investments you’ve made – and did you win or lose? (Note, these responses are only intended as entertainment and shouldn’t be construed as investment advice)

The “best” investment I made was a $6,500 3-month coaching program aimed at helping artists with improving their business operations. At the time, I’d just decided to make a real go of it as an artist and had thus far made maybe $3,000 off my art. The content of the program and the coaching was arguably not worth the fee (I’ll share some recommended readings at the bottom), but the community was invaluable. It meant a lot knowing that my struggles with asking for higher fees, figuring out where and how to print things, and balancing commercial/personal work were quite common and not signals of my unsuitability for making a living as an artist.

I also met my two Accountability buddies through that group, which has supercharged my progress. For about a year now, we’ve met twice a month, shared wins, and set 5 tasks to complete before the next meeting. I try not to sandbag myself by putting down things I’d do anyway; the key is to assign itty bitty stretch tasks that I otherwise might wriggle out of—sending a scary cold outreach email, making time to do self-care yoga in the middle of an airport—because the little things add up.

I don’t regret putting the money down for that program, because anytime you invest a significant amount in yourself, it signals that you take yourself seriously enough to have skin in the game. It lights a fire under your ass to make that money back, which I did within 2 months. I also want to note that “significant” means different things depending on where you’re at. For example, I know someone who just spent $30,000 on a mastermind coaching program, and she said she would’ve considered that a crazy sum even just 2 years ago, but it was worth it to get in the same room as women who are aiming to make $5 million per year. I’m not where she’s at (yet), but it helps to know that life will continue to ask me to make leaps of faith as I progress along my journey.

And if you’re just starting out, I’d recommend reading:
Art, Inc. by Lisa Congdon
Freelance, Business, and Stuff by Amy Hood & Jennifer Hood

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

I’m an independent artist based in San Jose, CA. I primarily work in the hospitality sector designing custom murals and wallpaper for restaurants. Based on client feedback, what sets me apart from other artists are my project management skills. I see it as my responsibility to take clients by the hand and lead them through the process of commissioning a piece of artwork, which usually takes months. This entails walking them through why I price the way I do and explaining what factors affect pricing; communicating what a realistic timeline looks like; highlighting project milestones where I’ll need payments and sign-offs to move forward with ordering supplies or making revisions; and coordinating with other people on a site, including general contractors, architects, and restaurant managers.

For example, the design team at Waymo commissioned me to do a mural, and we went back and forth about design direction, but once on site I handled coordination with the construction team on my own, figuring out access, parking, wall prep, and how to share the space. If the electricians needed to be in the space at a certain time, I sorted things out with the construction project managers and didn’t make it the design team’s problem.

I’m by no means perfect at this, and unanticipated issues come up all the time (that’s just life), but I do try to reflect on how I could’ve done better on each job and integrate that into my next project—for example, my contracts can be quite lengthy, so instead of requesting just one signature at the bottom, I started adding places for client initials to draw their attention to the especially relevant sections.

As far as my visual output goes, I’m great at adapting to different settings—you can give me adjectives like “moody” and “ethereal” and “mysterious,” plus a general color palette, and I can run with it. I really do approach each job, space, and client with a blank slate. For a seafood restaurant, I might do something kelp-inspired that’s quite textured and abstract so my work harmonizes with other elements. On a recent mural in downtown San Jose, I did a more figurative space jellyfish concept to create a moment of otherworldly surprise. Regardless, I try to infuse all of my work with a certain grace and elegance—I’m quite particular about colors and composition and like to walk around in a space to see how something will look from different angles.

As for how I got into this industry? I started muraling in 2021, when I literally just walked down to a tunnel in my Seattle neighborhood and threw paint on the wall. The maintenance crew from the Department of Transportation was like, “Ma’am do you have a permit?” And of course I didn’t, but it was free to get one, so I followed up on the info they gave me and got express permission to do two more murals. I did my first restaurant project after cold emailing about 50 interior designers, getting a response from 2 of them, and then following up repeatedly over the course of the next 6 months. Now that I have a stronger portfolio, I’ve been able to negotiate an art-for-stay trade with a hostel in Patagonia, which I’m really excited about. It’s very cool to be able to use my craft to meet other enterprising people and leave my mark on a space that people are using as a launching pad for their adventures.

Let’s talk about resilience next – do you have a story you can share with us?

About two years ago, I injured my wrist moving a large box down from a high shelf. The injury was real, but the pain lasted for well over 18 months, which I later learned is well past the time it takes for a broken femur bone to heal. During this time, I thought it might be a repetitive stress injury from a previous mural, or tendinitis, and went through a number of treatments: ultrasounds, yoga, physical therapy exercises, and very expensive massages. Eventually, another artist introduced me to “Healing Back Pain” by Dr. John E. Sarno—the gist of his thesis is that some people’s chronic pain stems from unresolved emotions, and the physical pain is the brain’s way of distracting from the mind. Address the emotions, and the pain disappears. I won’t go further into it here, but if you’re highly sensitive and perfectionistic like me, it’s definitely worth checking out the reviews of the book.

Regardless, during this time, I was sometimes unable to hold a fork with my right hand. I adjusted by starting to work with my left hand, training it to trace with a ballpoint pen and do other household tasks. I found great comfort reading about the late artist Francis Tsai. He was also Asian American, had to overcome parental pressure to go into a more “stable” field, and ultimately made the transition from architecture into concept and comic art. In his 40s, he was diagnosed with ALS and gradually started losing movement in one limb, then another. Even when totally paralyzed, he kept making art, eventually using an eye tracker to draw and color shapes in Photoshop. I was like, “If this man can keep going, so can I.”

And I did: I kept trying to make art, even if it was a 5-minute study with my right hand, and I kept an open mind while trying to treat my wrist. Sometimes I forget entirely that all this happened, so I’m glad to remind myself not to take my mobility for granted.

We often hear about learning lessons – but just as important is unlearning lessons. Have you ever had to unlearn a lesson?

I had to unlearn that being a strong independent woman means never asking for help. It’s some classic eldest daughter shit—I was praised for being highly self-sufficient (aka trained out of having needs or ever bothering anyone by asking for help) and while that mentality has made me a highly competent person, some parts of my life have just been more difficult than they strictly needed to be. I remember starting a mural at my pole dance studio and fretting about figuring out how I, a 5’2” person, would move a 15-foot ladder back and forth from the storage room and the studio every day without injuring myself. My friend was like, “Uh, why don’t you just leave the ladder propped up in a corner?” It’s jarring to look back and observe how it did not occur to me that I could ask for something that would be a minor change to everyone else (an eyesore in the corner) that would make my own life so much easier. There’s a simultaneous egotism and martyr mentality wrapped up there that I’m still working to shed.

Contact Info:

• Website: https://jessicao.me/
• Instagram: https://www.instagram.com/jessicao.studio/

Image Credits

Michael Lin, Jessica Cao, Dexter Bradford, Sophie Cao