How I Turned My Calligraphy Side Hustle into a Six-Figure Business

There are moments in life when you can clearly see the path ahead.bFor me, that path wasn't always obvious. When I started Letters from Elliott in December 2017, I never imagined it would grow into the business it is today. At the time, I was a full-time teacher and librarian with a passion for modern calligraphy, working evenings and weekends on what most people would have called a side hustle. Today, I travel throughout the Midwest and beyond, working with luxury brands, Fortune 500 companies, event planners, retailers, and private clients, providing live calligraphy, hand engraving, bottle painting, hot foiling, wood burning, leather personalization, and watercolor fashion illustration services. Looking back, it's amazing to see how a hobby turned into the career of my dreams.

My Love of Lettering Started Long Before My Business

I've always loved beautiful handwriting. Growing up, I was always drawing and doodling and loved practicing my handwriting and being creating with lettering. As a teacher, I found myself lettering classroom signs, bulletin boards, and anything else I could get my hands on. There was something so satisfying about creating beautiful words by hand. Art has always been part of who I am, but I also had a wonderful example to look up to. My uncle, Kelly Hume, is an incredibly talented professional lettering artist who has built a remarkable career creating hand lettering and logos for movies, sports teams, and brands recognized around the world.

Some of my favorite projects he's created include:

• A Bug's Life movie title

• The Nightmare Before Christmas movie title

• The World Series logo from 2025

While our careers have taken different paths—his professional work today is primarily digital while mine is rooted in handcrafted, live artistry—he has always been a huge inspiration to me. Watching someone in my own family build a creative career made the idea feel possible. Kelly lives on Bainbridge Island, just off the coast of Seattle, and although we don't get to see each other often, we stay in touch whenever we can. I continue to admire his work and learn from his creative journey. (I'll link to his website here so you can see some of his incredible work.)

Starting My Calligraphy Side Hustle

In 2017, I finally decided to take the leap. I had spent countless hours practicing modern calligraphy and hand lettering and felt confident enough to begin offering my services. At first, my clients were friends and family. Then came Facebook. I started posting examples of my work online, and little by little, people began reaching out.

My earliest jobs consisted of:

• Chalkboard signage

• Storefront signs

• Restaurant menus

• Personalized gifts

• Wedding pieces

Several local small business owners took a chance on me before I had much of a portfolio. They hired me to create signage for their shops and even allowed me to sell personalized gifts in their stores.

Looking back, those early supporters helped launch my career more than they probably realize.

I'll always be grateful for their belief in me.

Towards the early part of my creative career I created hand-lettered greeting cards. Long before luxury events and engraving, I spent evenings designing cards, prints, and gifts that helped turn my passion into a business.

As my confidence grew, so did my offerings. Before I ever engraved a perfume bottle or personalized a luxury handbag, I built Letters from Elliott around handcrafted products. I created greeting cards, stickers, art prints, ornaments, and personalized gifts featuring my own hand lettering and illustrations. I was fortunate to have local shops carry my work, and over time I expanded into wholesale, shipping products to customers and retailers across the United States and even internationally. Those products helped fund the next chapter of my business while teaching me invaluable lessons about branding, customer service, pricing, and creating products people genuinely loved. Many of those items are still available in my shop on my website today, even as my business has grown into live event calligraphy, engraving, bottle painting, hot foiling, and watercolor illustration.

Working Two Full-Time Jobs

For several years, my life looked something like this:

Teach all day.

Come home.

Work on calligraphy until bedtime.

Repeat.

Weekends?

More calligraphy.

Vacations?

More calligraphy.

I loved every minute of it—but it wasn't going to be sustainable forever. I was essentially working two full-time jobs and didn't have time for much else. I also wasn't feeling like I was doing either job to the best of my ability which stressed me out. I had to try to find some kind of healthy balance.

As my confidence grew, so did my projects. Personalized home décor and custom signage introduced me to commissioned artwork and helped build lasting relationships with clients.

Finding Craft Academy

One of the biggest turning points in my business came in 2019 when I became a founding member of the Craft Academy. There, I met an incredible community of professional calligraphers and artists who were building businesses just like the one I dreamed of creating. Under the coaching of Rosie Ramirez of the WanderCrafter, I learned skills that completely changed my business. Instead of trying to offer everything to everyone, I learned how to niche down. Instead of pricing based on fear, I learned how to price based on value. Instead of wondering whether I belonged, I slowly learned to overcome impostor syndrome. Those lessons changed everything for me and for Letters from Elliott. Read more about my journey with the Craft Academy here.

Finding My Niche

Rather than focusing solely on commissioned calligraphy, I began specializing in live event calligraphy and hand engraving. It was a natural fit. I loved interacting with people. I loved the excitement of events.

And I loved creating personalized keepsakes using my calligraphy that guests could take home immediately. As my confidence grew, so did my list of services.

Today, I also offer:

• Hand engraving

• Bottle painting

• Hot foiling

• Wood burning

• Leather personalization

• Watercolor fashion illustration

• Custom artwork

Every new skill has opened doors to clients and opportunities I never expected.

Learning hand engraving completely changed my business. What started as lettering evolved into creating custom artwork on luxury products for brands and private clients alike.

Working with Luxury Brands

One of the things I'm most proud of is earning the trust of luxury brands.

Over the years I've had the privilege of working with companies such as:

• Dior

• Burberry

• Parfums De Marly

• Maison Francis Kurkdjian

• Johnnie-O

• Neiman Marcus

• Nordstrom

• And many others.

Every event challenges me to continue improving my craft. No matter how many events I've completed, I still approach each one with the same excitement I had when I booked my very first client. I feel like that is how I know I am doing what I am meant to do.

The Biggest Decision

Eventually, I reached a crossroads. There simply weren't enough hours in the day. I loved teaching. I loved the library. I loved my students. But I also couldn't ignore what was happening with my business. Every week, more inquiries came in. Every month, my calendar filled further into the future.

I realized I had a decision to make. Would I continue treating Letters from Elliott as a calligraphy side hustle? Or would I bet on myself? It was one of the hardest decisions I've ever made. Instead of leaving education completely, I chose a path that allowed me to keep both parts of my identity. Today, I continue serving as the District Teacher Librarian in the same school district where I once attended school and later taught reading and fourth grade. My role is very part-time, which allows me to stay connected to education while dedicating the majority of my time to growing Letters from Elliott. It has been the perfect balance. I still get my "kid fix." I still get to help students discover books and learn important research and media literacy skills. And I also get to pursue the creative career I've always dreamed of. Looking back, it was absolutely the right decision for me.

Every new skill opened another door. Bottle painting allowed me to combine illustration, lettering, and personalization into one unforgettable keepsake.

Looking Ahead

I've now been providing live event calligraphy and engraving since 2020, and I truly consider this my area of expertise. I'm constantly learning. Constantly refining my craft. Constantly adding new services.

This year, I'm on track to reach another major milestone—earning six figures doing something I genuinely love. That still feels surreal to write. None of this would have been possible without the support of my husband, my family, my incredible clients, and the many people who believed in me before I fully believed in myself. Most of all, I'm grateful to God for giving me both the talent and the opportunities to use it.

If You're Dreaming of Starting Your Own Side Hustle…

Start before you feel ready.

Practice often.

Invest in learning.

Charge what your work is worth.

And don't be afraid to dream bigger than you think is possible.

You never know where one "yes" might lead. For me, it led to a business I absolutely love. And I can't wait to see where the next chapter takes me.

Ready to Create Something Together?

Whether you're planning a luxury event, corporate activation, wedding, or private celebration, I'd love to help create an unforgettable experience through live calligraphy, hand engraving, bottle painting, hot foiling, watercolor illustration, and custom personalization. Let's create something beautiful together. Contact me today!