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

Hi Caitlin, thanks for joining us today. The first dollar you earn is always exciting – it’s like the start of a new chapter and so we’d love to hear about the first time you sold or generated revenue from your creative work?

I love this question because I love telling this story. The first dollar I earned as a creative wasn’t from a client exactly. But a stranger. I could mention so many stories of clients, the grind, the cleverness of getting to a satisfying result; But what I count as my “first dollar” as a creative (as an adult and with my degree) was at this restaurant called “Pure” in Atlanta. It was hours after I walked off the stage, I still had on my robes, cap, tassels, everything. There was a retired art teacher sitting off to the side as my party came in and we took up a large portion of the restaurant. I get gentle taps my shoulder asking where did I and another one of my classmates graduated from, and I told her my art college. She smiled, asked me my major (illustration) and what I wanted to do. I told her I just wanted to inspire, draw, and touch those voices who feel like they aren’t seen often. She smiled, and handed me a dollar. She told me her stories of being an art teacher and how her journey was worth it. But she was sad she never made a dollar off her art. So she gave me my first dollar. Then told me something that truly changed my perspective:
“Take this dollar, and never spend it. This is so that way you have made money off your art. This is so that way [also] you can’t say ‘you don’t have no money’. You at least have a dollar. And it was made off of your art.” To this very day almost 6 years later that dollar is framed and unspent. It truly changed my perspective about money, money talk in the art community, and gave me a bit more of a free spirited, go-with-the-flow mindset about “having to make money” off of my art.

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers

I’m an illustrator, designer, and creative director. I make illustrations (both digital and traditional) for many things. My past experiences have been in comics, covers, illustration prints, sticker designs, paintings, inkings, etc. I also do design work where I love creating the look at feel of a project, topic, brand. It’s how I started dipping my toe into the creative director world as well. Where as you make a brand, it’s like telling a story and encouraging others why they want to be apart of that story. From font choices, color palettes, illustration styles, and user interface design. Making something from the ground up is satisfying.

We’d love to hear the story of how you built up your social media audience?

I don’t have a large audience on social media. I got my following from networking, tabling at conventions, and just leaving my social media cards in coffee shops from time to time. It feels intimate and like “if you found me, what are the odds / chances”.

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

Drawing every day, each day, to “get good”. And if you don’t, you”’ go backwards. (PS, this isn’t how that works.) It’s not wrong. If you practice and draw every day, you will see improvements.
But if art imitates life, and you are not out living & enjoying life, what are you creating? What depth is there to your pieces? What cleverness or happening can you create without being inspired? Having an idea?
Resting is quintessential to the artist’s journey. It rests your hand so you don’t creating irreversible damage; it gives you time to think, imagine, brainstorm more concepts and art that do more than just “imitate a moment in time”; it gives you the “why”. It also reminds you that outside of being an illustrator, you are more than just that. It creates separation and identity. The saddest thing for me to watch isn’t just the illustrator who can’t draw anymore; but couldn’t describe themselves outside of being “kind, funny, silly, an artist”, when there is so much more to anyone than just “the work they do”.
When artists remember to rest; they remember to live, have something to look back on, they help grow their own self worth and esteem, and they start making better art. In every sense. It could start to look better because they start looking at a piece with fresh eyes. It could have better meanings; but also they become prouder in the pieces they create.
That’s what I had to unlearn. All of it. And be more than just an artist. I’m curious, lukewarm at best restaurant connoisseur, a pretty knowledgeable but presumptuous musician, and daydreamer; working to be a travel enthusiast. Oh right! And I am still an illustrator & storyteller.

Contact Info:

• Website: www.pensurfing.com
• Instagram: www.instagram.com/pensurfing
• Twitter: www.twitter.com/pensurfing

Image Credits
These are all my artwork. :)