With 2026 starting, this marks my ninth year in business, and there are some really exciting things coming. I wanted to share the full backstory of Simply Lettered and give you a glimpse of what's ahead.
Why You Don't See Me Much on Social Media
I don't show my face a lot on social media because I'm simply not a big social media person. I don't love short-form videos, chasing trends, or creating reels. I like to watch them, but I don't love creatingthem.
YouTube is where I feel more comfortable with long-form videos, teaching, and sharing educational content. That's what I enjoy, and that's where you'll see more of me this year.
From Educator to Entrepreneur
For those who are new here, my name is Cheyenne, and I have a dual bachelor's degree in early childhood and elementary education. When I had my first child, I left teaching to stay home, and that's where my business was born. I needed something outside of the everyday routine of mom life.
In Christmas of 2016, I asked for a set of brush calligraphy markers, and I fell in love. I've always been interested in handwriting and creating fonts - my husband would laugh because I'd write in a different style every time I picked up a pen.
The Early Days: Wooden Signs and Craft Fairs
I started an Etsy shop in 2017 while living in Oklahoma. Like many new business owners, I took whatever work came my way. While I loved stationery and greeting cards, farmhouse wooden signs were incredibly popular at the time.
I made these signs completely by hand - cutting, sanding, painting, and hand-lettering custom quotes. I charged about $40 for them. Looking back, I probably should have charged closer to $300 for the amount of labor involved, but I'm still proud of that work.
During those early years, I tried everything: dish towels, hats, bags, pillows, craft fairs, pop-up shops. If someone wanted something lettered, I was your girl. But I also realized how much I didn't know about traditional calligraphy, so I started studying pointed pen calligraphy and historical scripts seriously.
The Triplet Years and Moving Home
In 2019, my second pregnancy turned out to be triplets. It was a crazy year, and I had to step back from the business significantly. With four little boys under my care, I took about a year off. We also moved from Oklahoma back to Utah during that time.
Finding My Niche: Live Events and Engraving
Once settled in Utah, I started teaching calligraphy classes, but I also live in a place where I have to travel quite a bit to reach an audience. That's when I started researching experiential marketing and live events.
In 2020, I also got into engraving. People kept asking for calligraphy on glass, and I didn't know how to make it permanent. Engraving was the answer. I started practicing and eventually began doing my first perfume engravings.
I drove to Denver for my first live event, initially doing them for free just to build my portfolio. I still do a lot of traveling (about three hours each way to most events), but I've carved out a market where I feel comfortable with my rates and making the travel worthwhile.
The Subscription Box Experiment
In 2023, I launched a monthly subscription box to teach online rather than in person. It was fun but extremely exhausting. I couldn't keep up with boxing one month's items while marketing the next. I was always behind and could never get ahead, so I eventually made the difficult decision to close it.
Leveling Up with The Cursive Connection
After closing the subscription box, I became certified in American Cursive and hired an assistant. That's when I started building The Cursive Connection.
I homeschool my children in a blended program with a charter school, so I'm deeply involved in both the education and homeschool worlds. I knew there was a real need for quality handwriting education that goes beyond just tracing letters.
I developed the curriculum, filmed lessons, built the physical box set, and did a soft launch. I was honestly skeptical because I'd invested so much work, and taking that risk felt scary.
2025: A Breakthrough Year
But 2025 changed everything. Even though you might not see me much on social media, a lot happens behind the scenes. Last year, I sent The Cursive Connection program to over 100 students through charter schools, homeschools, and private schools.
The response has been incredible, with so many requests for programs for other grades and additional resources.
What's Coming in 2026
During my three-hour drives to events, I do a lot of thinking. An idea has been brewing that I'm really excited to bring to life this year. I can't share all the details yet, but here's a sneak peek: I'm expanding our offerings to include not just cursive, but print resources as well.
During an event, I scribbled the entire vision on my white sticky notes (the same ones I use for orders). I came home over Christmas break and mapped everything out. There are big projects in the works, and I cannot wait to share them with you.
Why I Don't Share Everything
I'm still doing custom commissions and live events - lots of them. I just don't share much about them on social media because it takes the joy away from creating when I have to stop to film and edit. The work itself is the reward for me.
But I do want to share more behind-the-scenes content this year around growing The Cursive Connection through longer videos, blog posts, and meaningful updates rather than trendy reels.
I'd Love Your Input
I'd love to hear from you. Are you a student, homeschool parent, or educator? How long have you been following Simply Lettered? What stage did you come in at - the wooden signs, the subscription box, or The Cursive Connection?
Your feedback helps shape what we create next. Comment on the YouTube video, send me an email, or reach out on social media.
Looking Forward
I've always considered Simply Lettered a very small business, but I hit some really big goals last year that I wasn't anticipating. Now I'm excited to grow in ways I never thought possible and create more educational resources for all of you.
Thank you for being here and following along through all the pivots, experiments, and growth. I'm excited to share more this year and continue building something meaningful together.
Here's to 2026 - the year of new resources, big projects, and bringing handwriting education to even more students and families!
—Cheyenne