
Today we’d like to introduce you to Jessica Yee.
Hi Jessica, it’s an honor to have you on the platform. Thanks for taking the time to share your story with us – to start maybe you can share some of your backstory with our readers?
Well, if I start at the beginning, I’ve been lettering since I was 14. The first job was addressing envelopes for an insurance company because I had good handwriting. Then I took art classes and I honestly was unremarkable at painting and drawing but when we did lettering it was like breathing for me. Effortless. I was hooked, devoured it, studied it, practiced it. Then about ten years back I decided I was going to take a shot at making my calligraphy a full-time job. So I did, with a brand new baby, a new place to call home, I hung up my shingle. I took all the advice of previous folks in the art biz and did as they said. For the first year, I networked with every group I could get to. I needed to get my name out there. Drank gallons of coffee to get to know other business owners’ stories and so they could get to know mine. Within three years I had replaced my corporate salary doing what I loved. I was doing well, expanding my services than 2020 hit. Like most small businesses I started to prepare to pivot. Had some business savings to lean on, Streamlined expenses, prepped for whatever helps that was available for small business. On March 24th my father was diagnosed with COVID, a week later my mother had contracted it. On April 3rd my father died and on April 11 my mother died. My parents lived in NY, I watched my mom’s last moments via facetime, and I watched my parents’ funeral via facetime. I never got to say goodbye. All pivoting stopped. After all the prep, I mentally and physically could not think about the brand new world we, as a nation, were being thrust into. But despite my inability to network via zoom, my clients still called and new referrals were being sent…All the years of building relationships with networking kept my business afloat with work, without me actively looking for the sale. I was blessed that way. I didn’t make millions but I wasn’t out. With the help of family and friends, I am back at full throttle. Business is picking up and I am out and about again (zooming) and networking to get my brand out there. I like to say I am a professional (not starving) artist. One of the things I love to do is share my story and my knowledge and experience with other entrepreneurial artists so they know that it can be done and still love it. With that focus, I help with the Artist Alliance of the Triangle, and organization that helps artists of all levels by cultivating vibrant communities by supporting emerging artists through education, engagement, and exhibition. This is how I get to share my experience and knowledge as an artist-entrepreneur.
Would you say it’s been a smooth road, and if not what are some of the biggest challenges you’ve faced along the way?
The struggles…..art school doesn’t prepare you to run a business. So I had to learn it by educating myself, experience, and the advice of others.
As an artist, our work is personally entwined with who we are, so rejection is the first thing you must learn to grow a thick skin for it. We must, as artists, remember that not everyone will love our work and that’s ok. Not everyone will be your client. Sometimes you have to choose between eating Ramen for a week or dealing with a toxic project.
As stated before 2020 wasn’t a great year…between losing my parents, having shingles, and permanent nerve affecting the part of my face. I must say I got by with a little help from my friends.
Thanks – so what else should our readers know about your work and what you’re currently focused on?
I specialize in lettering arts. I am a professional calligrapher. I focus mostly on pointed pen calligraphy, copperplate, Spencerian, and modern styles. My art is not limited to just that I also do signs for businesses and events. To date, the most exciting chalkboard I did was for a couple who were big into gaming. They gave me guidelines and I got to design a six-foot by six-foot chalkboard design. It was so much fun!!! I get excited about teaching my skills to others and seeing my students flourish in their love of calligraphy. I have kept in touch with lots of my students and their artwork takes my breath away. Just knowing that I had a small part in their journey fills me with gratitude. What sets me apart from others, easy I don’t believe in competition. Everyone is my business partner and because of that, I have built a network of lettering artists across the globe. Because of this, I am able to share work or refer clients to the perfect artist for their projects.
Is there anything else you’d like to share with our readers?
I saw this recently and it is the way I was raised to live my life. What if the question wasn’t what are you grateful for? But how are you going to change the world because you are so grateful? It makes a huge difference in how abundant your life can be.
Contact Info:
- Email: jessica@theobliquepen.com
- Website: www.theobliquepen.com
- Instagram: @theobliquepen
- Facebook: @theobliquepen
- Twitter: @theobliquepen
- Youtube: @theobliquepen


Peggy Kring
August 26, 2021 at 12:07 am
Thank you for interviewing Jessica. She is one of the most encouraging people I have ever met. She wants everyone to succeed. She encourages her students by pointing out what is good about their work and stresses the importance of practicing to achieve successful.
Carolyn
August 28, 2021 at 3:36 am
Great story! Loved reading about Jessica! Thank you for sharing!