Two years ago today, I jumped into the unfamiliar waters of self-employment to pursue a career as a full-time artist. Upon quitting my stable desk job, I found myself feeling simultaneously terrified and liberated. I had the time and the studio space to create, but every day felt like a gamble. Would I sell enough to make ends meet? Should I apply for another job? Could I find a community to support me? Just like a painting, I started my career with a mess of unanswered questions and focused on the process. Now I’m finishing up my second year. The journey from the first year to today took me deeper and further into a creative exploration than I ever thought possible - a journey I’d like to share with you.

Two Years of Making Art : Dream It or Live It

When your life resembles a rollercoaster of drastic ups and downs, it makes for a great story. I’ve re-written this essay three times thinking, “how on earth do I condense an entire year into a brief essay?” Therefore, instead of giving you a methodically structured essay, I thought I’d stitch together stories and reflections from my year to share what has changed and what I’ve learned, beginning with an excerpt from the essay “Dream It or Leave It”  by Dorothea Tanning, a mid-20th century American surrealist painter.

“I dreamt again that I flew. It was the same dream as before. It involved the same effort of will, the same sense of special purpose. But this time there was a unique and elegant detail. I found, abandoned under a pile of flat stones in a shadowy glade, a sort of harness made from bands of cloth knotted together. It was dark red and very beautiful. I was fascinated by the intricacy of its design and after satisfying myself of its proper position, I quickly put it on. It was immediately clear to me that it was a sort of flying gear, for without even raising my arms or making any effort, I rose into the air and floated easily there.”

This essay affects me. I think her imagery of picking up the flying harness, putting it on, and floating in the air is similar to how I’ve always viewed being an artist. I don’t want to romanticize what I do because I think that alienates people, but for me, art was the means to flying, to being fulfilled. Tanning’s words reminds me that each of us possesses a talent or skill that makes us fly, but there’s also a need for practicality. You can’t fly on your own. You need a harness, your talent or skill, to get you in the air. This can turn a crazy, seemingly impossible idea into something a little bit more tangible, into something real. It’s a choice to find the means to fly, that’s why I imagine the title of her essay to be “Dream It or Live it.”

As a kid, art showed up everywhere, from school art contests to coloring on the front porch with my friends. It was always simply there, waiting inside me for an opportunity to show itself. Later, as an adult, I realized if creating was the means to flying, opportunity was how high I could go. I’m somewhat embarrassed to admit this, but I waited for opportunities to appear, thinking if I kept waiting and kept working, something big would happen.

But I grew impatient waiting. The more I painted, the more fluid my thoughts became, and the more eager I was to share my projects. Therefore, I began creating my own opportunities, taking how high I could fly into my own hands. I used non-traditional platforms to get my work seen, to garner diverse connections and feedback. And, I believe that publicly sharing my ideas and work played a major part in my success this year.

As I saw the benefits of creating my own opportunities, I was also learning about another, more subtle type of opportunity. For me, there are two types: opportunities that you yourself seek out, find, and usher through the door; and those that you don’t see come in and take you by surprise. The later are sometimes difficult to find, especially if you aren’t looking. I learned, through reflection, that experiences can also be opportunities, especially if you take what you learn and apply it practically. A perfect example of this happened about a year ago, before I owned a car or had many gallery contacts. A collector had come to my studio to look at art, and felt strongly drawn to two paintings, struggling to decide between the two of them. I offered to bring them to her space so she could make the final decision. A week later I hauled those paintings from my studio in Oakland to my apartment in San Francisco, needing a bike and a train to do so. The next morning, I rented a car to take them to the collector. After I presented the work, the collector decided that she would purchase both.

This was such a big moment for me. My bank account was running low, exhaustion levels high. I was still waiting on several payments from galleries and rent was due soon. That collector not only gave me a feeling of temporary financial security, but also the confidence that I was craving. I’m not sure if she realized what an impact she had on me, but I don’t think I’ll ever forget it.

There’s something to be said for being confident in your work, but it takes encouragement from others to know you’ve found the right track. It’s humbling and gratifying to do the work I do and receive encouragement from others, but that feeling of vulnerability, of sticking your neck way out, never leaves. It can either scare you off, or spur you on. I decided to use that vulnerability as an opportunity, letting it inspire me.

Taking my newfound inspiration and the desire to create a new body of work centered around nature, I decided to get vulnerable. This year, I went on numerous solo camping trips along the coast and in the desert, feeling terrified every time tucked myself into my tent. Being alone in the dark with only the symphony of nature sounds occupying your imagination made the nights long. But, the next morning I found myself in a new environment and with a new sense of pride. The courage I found on each trip built on the courage from previous trips, until I felt there was no trip I couldn’t tackle. I learned how challenging myself to feel vulnerable could inspire creation, so I took my studio on the road, painting and sketching along the way. Stepping out of a comfort zone is a great way to expand your creative reach. It’s about figuring out new ways to apply your work in unfamiliar territories.

Nature, self-expression, and the idea that most things are completely out of our hands are sources of vulnerability that inspire me. I’ve found a deep parallel between being vulnerable and the creative process. To create, there has to be a little fear and a little security; one needs to be constantly moving from one end of this spectrum to the other. For me, this perpetual movement transfers onto the canvas—from uncontrollable moments of making rapid marks to logistical controlled motions.

This organic process in my work has also affected my personal life and business as an artist. It’s pretty seamless these days, a complete turnaround from my first year. I enjoy the overlap from the studio to personal life, but it took me a while to adjust to this lifestyle. After I left my design job to practice art full time, I felt pressured to work the typical nine to five hours. But trying to constrain myself and my process to a particular schedule felt too rigid. I realized that I needed to redefine “normal working hours.” Now, at seemingly odd times, I work on several projects at a time, starting early and finishing late, usually with a nap in the middle. Some days I work up to fifteen hours, but then I might take the next day off. To be honest, the past four months I worked seven days a week and took on more that I should have. My mind was always on work with little to no periods of rest, and only recently have I found a good rhythm. Between painting and time in the studio, traveling, gallery shows, and working on collaborations with brands, it’s easy to lose balance.

Collaborations with brands represents another area of growth and change this year. As a fine art artist, I battled with a sense of identity crisis and confusion on how I’d be viewed if I accepted partnerships with companies. I didn’t want to be seen as a corporate sell-out. Therefore, I took time to decide how to approach partnerships, while maintaining an artist’s creative integrity. The conclusions I came to formed an open letter that I published on my blog. I wanted to be transparent with the people interested in my work.  

Ultimately, I want to change ideas about how artists can work and create. We live in a time where it’s ok for an artist to work as a singular entity, without fear of being a “sell out” by accepting partnerships and without depending solely on galleries to survive. As sources of support and encouragement, galleries are so valued and important to artists, and I look forward to strengthening relationships with them. But collaborations with companies are also beneficial. They keep me open minded to new processes and new people. It’s so easy to get stuck working in the privacy of my own studio with the same music and podcasts playing every day. Collaborations have allowed me to travel to new places and meet people different than me. They’ve added complexity to my process. Plus, partnering with brands secures funding for more experimental projects outside of painting, which is valuable because of the buffer created between the need to expand artistically and the need to earn a living. Collaboration has been a vehicle for major expansion.  

Each facet of the last year has challenged me, helped me succeed, and bettered my ability to create. From realizing how much of my success was dependent on my choices to reworking a schedule that fit me best, if I could sit down with you in person and try to summarize my second year as an artist, I think I’d simply want you to know how satisfying it is to be fulfilled not only in what you do, but also by the process it took to get there. In year two I flew higher than I thought possible. I decided to take my career, my opportunities, and my life in my own hands, falling at times and succeeding in others. My career thus far has been both humbling and gratifying, and I still have so much to learn. If you only take one idea away, I want it to be this: Be vulnerable, put on your flying harness, and try. Take a crazy idea and make it real.

Two Years : Dream It or Live It

A Small Selection of What I've Read and Listened to This Year: 

Artist in Conversation with Portia Zvavahera / Bomb Magazine

Don’t Shoot The Messenger / Art Forum

Dream It or Leave It by Dorothea Tanning / Public Space

Ellsworth Kelly, Who Shaped Geometries on a Bold Scale.. / New York Times

Episode 11 with Stefan Sagmeister / Nice To Meet You Podcast

How “Hamilton” Creator Lin-Manuel Miranda is Making History / Fast Company

It’s Not My Own Trip : Lily Baldwin / SheDoes Podcast

Janine Antoni : Short Film / Art Forum

Kim Brandt / Art Forum

Marina Abramovic’s Method Blew Our Minds / Note To Self Podcast

New Minnesota Street Galleries Boost SF Art Scene / San Francisco Chronicle

Placement in Politics in Brooklyn Museum Reinstallation / New York Times

The American Edit Podcast Series - You can also listen to my episode here.

We Desire Magic / Art Forum

Why We Have Too Few Women Leaders : Sheryl Sandberg / Ted Talk


So Many Thanks to These Kind People :

Sophie Knight : Studio Manager 

Hannah P Mode : Studio Assistant

Katherine Holthouser : Writer and Editor 

Justin + Tami / Twin Collective : Web Design

Jen Kay : Photography 

Vanessa Hellmann : Video

Athen B. Gallery : Oakland CA

Tappan Gallery : Los Angeles CA

Uprise Art : New York, NY


Written by Heather Day. Edited by Katherine Holthouser. Studio Portrait by Jen Kay.  For all inquiries, please contact You can read last year's essay, here.