We were lucky to catch up with Anna Eastman recently and have shared our conversation below.

Anna, looking forward to hearing all of your stories today. Was there an experience or lesson you learned at a previous job that’s benefited your career afterwards?

My first “serious” creative job— I’m adding quotes because I think at the root of it, it’s important to be a little un-serious to make seriously good creative work— was at a cannabis company that also had its own apparel brand. I worked on the apparel side of the company and spent most of my time arranging logos, branded graphics, and designs made by freelance artists onto technical garment files so that they could be approved and then sent out for production.

While I was initially thrilled to have landed a role at a trendy sweetwear business, I quickly realized I didn’t have as much of a creative hand in designing the garments as I had hoped. When it became clear to me that all of the creative, limited-run designs that went on merch were made by artists the company outsourced, I felt like I was assisting other artists in doing the job that I really wanted— making original designs from scratch to go on garments.

I eventually put in my 2 weeks, but not without some degree of reluctance. After all, I hadn’t even really tried to pitch my own original design ideas to my boss. I had somewhat complacently accepted my role as it was and then once I had enough, I threw in the towel and left. Looking back, I could have made so much more of the position I had if only I had been vocal about the projects that excited me. The brand was also partnered with another company that provides creative services —album covers, T-shirts, and event collateral for electronic music artists, and I am still sometimes haunted by the thought of whether I could have created album covers or poster designs for some of my favorite electronic artists if I had stayed and more adamantly expressed my creative desires.

In my next (and current) role, I made sure to be very vocal during the interview stage about how much I love to design my own original apparel concepts. By voicing these wishes early on, my boss threw any and all projects my way that had to do with merch and apparel. On one particularly slow work day, I recalled someone mentioning a holiday candle package that needed designing. I felt like it was a perfect opportunity to flex the kinds of design skills I had been wanting to for a long time, and I pitched a vintage type lockup featuring a retro-style mascot illustration. The design was approved, and my illustrated character quickly became the company mascot. He now lives across all kinds of media, and in my desk drawer I have lovingly saved a holiday party napkin with his very likeness printed on it. I realized his success was in large part due to the fact that there was a fresh, new, and identifiable character now representing a previously faceless brand.

All of this is to say that one of my proudest moments and creative achievements came from the simple act of speaking up and volunteering to make something that no one asked me to make. I think there’s so much more possibility and opportunity in work roles than is initially apparent, and all it takes to extend beyond the reach of your role is sometimes as simple as asking a question or offering to take on a small project.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

To bring it all the way back to the beginning, I have always loved to draw. It was my number one pastime since a child, and has been the through line that’s carried me to where I am now (peppered with occasional breaks —sometimes several years long— and trying out different media). I’ve always had a very strong sense that I belonged in a creative field, regardless of what that particular field might be.

I decided to go to a visual and performing arts highschool and was lucky enough that my parents were always very supportive of my choice to commit to the arts. From there I went to the Rhode Island School of Design to get my MFA in painting, but then decided Junior Year to switch to Illustration. That experience threw me a real curve ball— I had been feeling very lost in the painting department —which placed an emphasis on abstraction and provided very little in the way of technical training. I found my teacher’s assignments vague and at times difficult to latch onto, and I was left fumbling for some sense of direction as an artist. After a certain point I had no idea what to create anymore. I thought that switching to a department that celebrated more figurative and literal representations of people and objects would give me the proper framework to crystalize what it was that I wanted to express. I’ve also always been a believer in the concept of “enabling constraint” and its ability to jumpstart creativity. I felt deeply that my painting curriculum left something to be desired there.

When I switched to Illustration however, I found it to be almost too far gone in the “constraint” direction— we were given mock-editorial assignments where we had to illustrate as if we were being hired to draw the cover of The New Yorker (or another magazine, as it were). I was at a loss for how to find my own voice and style while also entertaining the fake-magazine-cover idea. It was the first time I was actually laughed at by my peers because my work was so bad (and it really was bad). I was even told by my supervisor that my diploma was a lie. Clearly he didn’t think I was cut out to be an illustrator. As a result, I developed a very limited idea of what an illustrator should be, blinding myself to the endless applications and possibilities that come with this actually rather broad term. I ran in the complete opposite direction, and was scared out of drawing for a good 4 years.

Then the pandemic happened. I had just been let go from a job in esports where I worked as a translator for a professional CS:GO team and I happened to have just gotten back into drawing (very lightly and un-seriously). As many of us did during that period, I took the time to re-assess and ask myself truly what it was that I wanted. And honestly? I just wanted to make cool drawings and enjoy the process again. For the entirety of lockdown, I threw myself into illustrator and procreate and from there I began to land design gigs here and there. In one stroke of amazing luck, I reached out to an art director who works specifically on music videos to see if he needed a hand creatively. (I was also entertaining the idea of art directing music videos at the time). He got back to me saying that he specifically needed some illustrated posters for a classroom scene in a music video for Snoop Dogg and would I be interested? Without hesitating I got back to him and promised to have 3 posters ready for him by the very next day. That felt like a miraculous little gift from the heavens that pointed me toward drawing again.

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

A lesson I had to unlearn was, in broad terms, there are no “should”s in art. In fact, if you’re making creative choices according to what you “should” do, then you’re probably not being truly creative. The backstory was one that I touched lightly upon earlier, but during my college years I enrolled in the Illustration department because I was feeling very lost as a painter. Though I didn’t realize it at the time, the classes I was taking were founded upon some slightly dated principles and exercises. I was assigned editorial-based prompts wherein I was to draw a cover or spot-illustration for a made up article or magazine edition. While I’m aware this was an invaluable class for students interested in being editorial illustrators, that was not my case. At the time though, I thought that was the only prospect for being a successful creative, and so when my work failed I took it very much to heart. I felt like if I wasn’t succeeding within the very specific framework, then I wasn’t an artist or creative, and just an overall failure. It took several months of lockdown years later to really face myself and unlearn all my fears and imposed limitations around the creative process. I started to get comfortable with the idea that illustration can actually be anything at all, and that there really aren’t any rules– just things that look and feel more “right” than others. (And even that’s subjective!)

What’s the most rewarding aspect of being a creative in your experience?

I think the most rewarding aspect of being a creative is when you make something that truly resonates, strikes a chord with, moves or excites other people. It’s one thing to make something technically impressive and hear people say, “wow, that’s really great!” I feel like all that does is feed the ego and then everyone else moves on. Plus, the reason I personally  look to art is to feel something real and true— something that transcends the white noise that drones on in my head all day. To know that what you’ve made has had that same effect on other people is the greatest gift— it provides a feeling of connection and mutual understanding. I think at the end of the day I just want to feel seen by others and in being seen, make others feel seen as well. If my art is able to do that, then that’s wonderful! I think that’s what’s so powerful about art on social media— the access we have now to art that hits on very specific cultural experiences at a very niche, micro-level is empowering. There’s an audience waiting for every story that has yet to be told.

Contact Info:

• Website: https://annateastman.myportfolio.com/
• Instagram: @lagraphicstore
• Facebook: Anna Eastman
• Other: https://lagraphicstore.com/ I have an online apparel shop coming soon! Please be sure to keep an eye on @lagraphicstore on Instagram for more updates regarding the official website launch!