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

Chandra, looking forward to hearing all of your stories today. When did you first know you wanted to pursue a creative/artistic path professionally?

I was drawn to art from a young age. I spent hours studying magazines, cereal boxes, book covers, and even others’ handwriting, trying to understand how one could create something so visually engaging. In college, I studied design, envisioning a future where I’d work for a publication or create cards for Hallmark. But, like many artists, I found opportunities in unexpected areas that eventually led me to a career in graphic design. Over time, I rose to become the manager and creative director of a division, all while doing freelance lettering and design projects like wedding invitations, custom prints, and even tattoos in my spare time. Although my career path eventually shifted away from graphic design and into technology and innovation, I continued to nurture my artistic passion. On July 27, 2017, something told me it was time to get serious about my lettering and make my passion a reality. It was in that moment that Big Girl Press was born. I quickly grabbed an acrylic pen, hand-lettered the company name on a mug, and posted it on Instagram with the caption, “I’m too old to make excuses.” I had to be a big girl and live up to the name—and I’ve been striving to do that ever since.

Chandra, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?

My creative journey started with a desire to learn my father’s signature. I would study the line and curve of every letter, constantly practicing until eventually, you couldn’t tell the difference between my handwriting and his. It was this early practice that led me to experiment with different forms of lettering and fall in love with the art form. It’s also what inspired me to turn my lettering into a business. Now I’ll be listening to a song, reading a passage, or simply having a conversation, and certain words will stand out that will make me think of how I can turn them into art.

I specialize in lettering for posters and create custom pieces tailored to express personal messages of empowerment, love, and more. My creative process starts with a great quote I’ve heard or read—I keep a running list of my favorites to have on hand whenever inspiration strikes. I enjoy working in black and white and express my signature aesthetic across a versatile range—from elegant calligraphy to bold, impactful styles and everything in between. Each piece begins with understanding the tone and purpose, allowing the style to take shape from there. It all depends on the project, the audience, and the feeling each message conveys. My goal is to design the words to bring the emotions behind them to life and personally connect with the viewer, all while staying true to my artistic voice—something I learned through the foundational experience of learning my father’s signature.

One piece I’m especially proud of is the mural I designed and painted in 2021 for the Alexandria location of Shop Made in VA. I wanted to create something bold that would serve as the backdrop for what would eventually be hundreds of workshops and pop-ups for creatives and small business owners in the community. I feel like it inspires the people that inhabit the space to be brave and create something new. I’ve even enjoyed selling some of my work and teaching a few lettering workshops there, using my mural to demonstrate to participants what’s possible.

Is there mission driving your creative journey?

Words create worlds, and lettering has the unique ability to bring those worlds into being. It helps us visually express the emotions and power behind our words—expressions that writing or speaking alone sometimes cannot fully capture. What drives me in my work is the desire to make people feel uplifted, inspired, and empowered through the illustrated word. Whether I’m creating my pieces or teaching lettering workshops, my goal is the same: to guide others in reconnecting with their creativity, helping them discover new sides of themselves and walk away encouraged to use their innate gifts. As Andrew Garfield wisely said, “Art can get us to places we can’t get to any other way.”

Learning and unlearning are both critical parts of growth – can you share a story of a time when you had to unlearn a lesson?

Fear once held me back from life-changing experiences, whether it was traveling abroad or advancing in my career. Seneca the Younger’s words resonate deeply with me: “We are more often frightened than hurt, and we suffer more from imagination than from reality.” I spent too much time worrying about what might happen or what others might think, missing opportunities to step into something new and transformative. Looking back, I wonder who I might have become if I had simply taken that next step. Now, I’m determined not to let fear dictate my path. I’ve adopted a new mindset: “What’s the worst that could happen?” I know setbacks are inevitable, but by taking action and putting myself out there, I’m learning to embrace the unknown. And in the end, I’ll be able to look back and say, “I’m glad I did that.” Better yet, “I’m glad I lettered that!”

Contact Info:

• Website: https://biggirlpress.co
• Instagram: https://www.instagram.com/biggirlpress/
• Facebook: Big Girl Press Studio LLC. https://www.facebook.com/profile.php?id=61564050146994
• Youtube: https://www.youtube.com/@biggirlpress418

Image Credits

Image 1 “Another Trip Around the Sun” greeting card: background mockup courtesy of Adobe Stock