We were lucky to catch up with Adrianna Tan recently and have shared our conversation below.
Adrianna, looking forward to hearing all of your stories today. We’d love to hear about when you first realized that you wanted to pursue a creative path professionally.
I have always been an creative person, but I hadn’t really considered it professionally at the start. I always considered having art and music as my hobbies, something I could always enjoy without the pressures of needing to monetize it. I studied Business Management with minors in Japanese and International Business, and in order to solidify my Japanese Language joined the JET (Japan English Teaching) Program in 2016.
When I moved to Japan to teach English to K-9th grade students I also started teaching modern brush calligraphy. Japanese calligraphy always inspired me, but I found that my students and even local community members were just as intrigued by English calligraphy styles as well. In 2017, I started teaching calligraphy workshops on a regular basis for free and I decided to start an Instagram to show my work as a hobby artist. It was a great way to build new connections and share parts of a culture that I hadn’t given much thought to in the past.
Through a lot of cheering from my students and the local Art teachers, they told me I should start to sell my workshops and make cards or stickers with my work. It was something new and definitely scary, but incredibly fun at the same time.
When I finally returned to the states, I made the decision to continue working towards making Penditude a business. It was a great way to cover the cost of my student loans while doing something I loved and enjoyed outside the typical grind of a work day. And that is how Penditude was officially born in 2020 during the pandemic, and I became a professional artist!

Adrianna, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?
I am a calligrapher and hand engraver! When I was younger I had missed cursive classes because I needed to attend speech therapy, and I was lucky enough to live close to my Grandfather at the time who had the most beautiful handwriting I had seen. He was the one who taught me the importance of good penmanship, and that flourished all the way to 2020 when I started doing calligraphy professionally.
I initially specialized in modern brush style calligraphy, and over the years expanded my works to include pointed pen calligraphy, hand engraving, and watercolor portraits for wedding bouquets and house illustrations.
I serve local brands heavily through brand activation events, providing on-site live calligraphy and engraving services to provide a unique and memorable experience for customers. This has been in the form of engraved perfume bottes at Neiman Marcus, hand lettered boxes and cards at Tiffany’s, and custom house portrait commissions for local real estate agents in the Chicago area.
I also love the joy of weddings, and providing custom signage, mirror seating charts, and handwritten envelope calligraphy for invitations and save the dates helps balance out the year with all kinds of projects.
The event I am most proud of to date, was a brand activation event in Downtown Chicago with Guinness for St. Patrick’s Day where I engraved roughly 350 names on pint glasses to celebrate. It’s my largest and most exciting booking to date because they reached out to me 5 months in advance, were referred by a past client I worked with, and was the largest quantity of custom engraved items I’ve performed at a live event!

What do you find most rewarding about being a creative?
Honestly seeing my own progress. I think it’s completely natural and common for artists to be our own worst critics. We have to have an eye for detail, and part of the process is naturally understanding what you can do better next time.
Especially when it comes to calligraphy, there are a lot of subtle rules and guides that can really make or break your foundation in developing a unique style that still looks professional and clean.
Every year that I get booked for more events and take pictures I love to look back at my posts from when I first started sharing my work in 2018 and the progress year after year is incredibly rewarding. To me it’s not only a testament to how consistency in a craft pays off more than being an immediate master, but it also means I am continuing to provide my customers with greater quality and experience. It’s truly the best feeling ever!

Learning and unlearning are both critical parts of growth – can you share a story of a time when you had to unlearn a lesson?
When I first started out with Penditude, I was fortunate enough to have had a business degree. I had experience working in sales and marketing, and with my parents being entrepreneurs a lot of the day to day business aspects came very easily to me. This made it incredibly easier to run my business as a side-hustle while I continued to work my full time job in SEO.
But if there was one major lesson I had to unlearn when I first started out, it was feeling the pressure to say yes to projects I didn’t absolutely love for the sake of bringing in income. Especially, for the creatives who are still balancing a creative business on top of other work, I think it’s extremely important to learn how to set parameters for projects that are worth your time and effort, that you enjoy, and that are charged at the right price point that compensates you fairly.
I hate the word Niche. It feels incredibly restrictive especially when it comes to being a creative, but when it comes to running a business it’s definitely a necessity to pick and choose the projects you want to monetize, and the creative hobby works you want to keep private and do for fun. Setting those boundaries will not only be impactful on your mental energy and workload, you’ll also end up finding the clients you enjoy working with, and make more money along the way!
Contact Info:
- Website: https://penditude.com/
- Instagram: https://www.instagram.com/penditude/
- Other: TikTok @penditude
Image Credits
Ashely Lauren Photography https://alaurenphoto.com/services-i#services-i And Penditude

