We recently connected with Shannon Tillmann and have shared our conversation below.
Shannon, thanks for joining us, excited to have you contributing your stories and insights. Are you happier as a creative? Do you sometimes think about what it would be like to just have a regular job? Can you talk to us about how you think through these emotions?
This is one of my favorite questions because my education background is in chemical engineering and yet, here I am a full-time Calligrapher and Artist making money from what I love!
I grew up hearing all the lies surrounding art: artists can’t make money; you don’t want to be a starving artist; you might as well get an ordinary job and let that pay for your hobbies; etc. So, I put art on the side and went for engineering because engineers get paid well, right?! I got my first internship my junior year at a large international company. They reached out to me wanting to hire me following graduation of my senior year so I accepted it for job security. I was at that job for four and a half years and grew more miserable by the day. I was exhausted, burnt out, and felt like all I did was sleep and work every day. I was reorg’d so many times that I had five different managers during that four-and-a-half-year timeline. I remember being on calls as early as 6:00 a.m. and also having to pick the phone back up some evenings from 8:00 to 9:30 at night to hop on another call to discuss work for the 6:00 a.m. call the next morning. I knew I needed something different and I was already working on calligraphy at the time, but I didn’t think I could make it full-time; I planned on it being a side hustle.
I switched jobs following one of my former managers to a different company and it was such a night and day difference in company culture that it actually felt better to work! I didn’t hate the days or stare at the clock waiting for 5:00 to roll around. I did a lot of data cleansing, Python coding, and dashboarding at that time; dashboarding was by far my favorite because it combined the science and math with a little bit of art and color to tell a story visually, but it still didn’t give me that same joy that running my own business does. After less than a year at that company, my department was let go due to budget cuts. It was such a soul-crushing experience I don’t wish on anyone.
Our department was offered professional coaching that covered how to tailor our resume, practice for interviews, and better prepare ourselves for our next job. I learned after two sessions that their coaching was not for me. After each of the two sessions I would immediately close my laptop and cry for what seemed like hours. It felt brutal, impersonal, and I know I have a softer heart that I can’t callous. It was during those weeks that my husband really encouraged me to pursue my business full time. He knew I had the drive and persistence needed and would really dedicate my time to the business as if it were a full-time job. He decided he would go pick up whatever he needed to in order for us to pay our bills so that I could pursue the business. I am so thankful for his support and encouragement during this time in our lives!
If I was going to turn my side hustle into a sustainable business, I knew I needed a business coach to help me grow my business and that’s exactly what I did: I hired a business coach. She pushed me outside my comfort zone, worked with me on my mindset, and guided me to booking business-to-business opportunities. Ever since that layoff, my business has been my full-time job. It’s hard work, there’s long days, potential clients ghost me, I have to wear multiple hats, I’m the boss and the employee, but I get paid to do art, travel for work, get groceries midday, take my sick days as needed, go the gym during the day, and take a vacation without asking permission! I love the work that I do in my small business!

Shannon, 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’m a calligrapher and artist specializing in on-site and in studio painting, engraving, and heat foiling to create personalized experiences that bring joy to my clients through the art of calligraphy. Let me tell a story.
I’ve loved art since I was two years old painting at my little blue table. Growing up I tried every art form and media I could get my hands on! In 2008 my art teacher introduced us to Gothic calligraphy and it caught my attention because of how ornate each letter was. I didn’t know that was only the tip of the iceberg.
In college, my roommate and I picked up calligraphy kits at Michaels to destress between our studies. I wasn’t very clear on what to do with the strange tools or how to achieve the look I was going for, but I tried my best to copy what I found on Pinterest.
In 2020 I was working from home and desperately wanting to build more therapeutic art into my daily life. With the support of my husband, I decided to purchase an 8 week online modern calligraphy course for my birthday. It was during those 8 weeks that calligraphy clicked! I was using the wrong tools to achieve the look I wanted and never knew there were basics I missed in my self-learning days. My instructor gave us a list of ways to make money with calligraphy and it really sparked the idea that this could be a real business opportunity!
In the new year of 2022, all I had was the name Shannon Scripts and an Instagram page following my progress of learning calligraphy. My Etsy attempt crashed and burned so I decided to get some help and accountability. I took a business course called the Calligraphy Business Accelerator founded by Dina Lu. I setup the business basics during that time, the highlight being registering my business and officially becoming an LLC in May!
In this stage, I waited for people who liked my work to find me through Instagram or Facebook and hoped they would place an order on my website or inquire via DM. However, this so-called strategy wasn’t working. I was ghosted after a quote and had inconsistent sales that were not enough to sustain me to voluntarily leave my day job.
I knew I needed to push past the minimal marketing and waiting game. This led me to hiring my business coach and mentor Irene of Curated to Create in early spring of 2023. The biggest impact was transitioning from primarily a business-to-consumer model to a business-to-business model. Irene’s coaching focuses around connections, relationships, and networking. None of that comes easy for me, but it has been the best decision for my business!
All of that has led me to where my business is today. I now focus on live event artistry through calligraphy, engraving, heat foiling, and painting as well as in-studio work. My mission is to provide an amazing experience through artistry to my clients, their customers, and guests. I want to make events leave a lasting impression on people who walk through their doors. I serve as an extension of a brand’s team to help them transform their brand experience into a one-of-a-kind personal experience for their customers. It all boils down to making every person feel seen, loved, and appreciated.

What’s the most rewarding aspect of being a creative in your experience?
If I have to pick only one, it’s getting to be a part of making people’s day and celebrating milestones, big and small! The excitement of being able to be a small part of gifts for birthdays, anniversaries, graduations, and so many more life milestones to celebrate is so rewarding. Most of the time it’s a surprise and I get to be in on the secret! My most recent project was to engrave a whiskey bottle for my client’s brother graduating from nursing this month. It turned out beautifully and my client loved the finished product! She is so excited to give it to her brother!
One of my favorite interactions at onsite events is the personal touch reactions. It’s October of 2023. I’m at a new Ralph Lauren store for opening day. I was there primarily to heat foil initials or monograms on leather products, but on day two we decided to add customers’ names in calligraphy on their email sign ups that doubled as cute ornaments with the iconic Ralph Lauren bear . During the day I had so many sweet people come in who said they never find their name on anything, and it broke my heart. I’ve had my name on everything growing up like pencils, a ruler, stationery set, keychains, and so many other personalized things. These people missed that childhood experience I had, but I had the pleasure of giving them that experience right before their eyes. Seeing the joy on their faces as I handed them their custom ornaments was one of the best feelings! It still brings tears to my eyes.
I love going on a life journey with a single customer. My friend from college and I were both chemical engineering students and she loved my lettering! She requested that I letter a clipboard for her sister as a birthday gift. I didn’t think much of it at the time. Over the years my skills improved, I learned new techniques, and that same friend came to me for many more gifts for her sister to celebrate milestones! She purchased a new home and I painted a wooden sign with hydrangeas as a housewarming gift. When her bachelorette party came around, I heat foiled glasses sleeves for the party gifts. When time came for the wedding, I engraved and painted a perfume and painted a matching champagne bottle. The following Christmas she found out she was pregnant with a boy and I engraved a crystal ornament celebrating her pregnancy! It’s such a joy to be a part of not only my friend’s life but to also celebrate all the different seasons of life her sister is going through, all the way back to that first unassuming clip board.

Are there any resources you wish you knew about earlier in your creative journey?
Definitely to read more entrepreneurial books, listen to podcasts, and actively seek out education resources to understand how to better my business. I attended free mini courses and summits that align with my interests and time availability, like the Calligraphy Business Summit. I listen to creative and entrepreneurial related podcasts such as The Calligraphy Podcast, Event Ready Podcast, Calligraphy Biz Corner, and The Professional Creative. A few of the books I’ve read and thoroughly enjoyed are “Atomic Habits” by James Clear, “The One Thing” by Gary Keller and Jay Papasan, “Steal Like an Artist” as well as “Show Your Work” both by Austin Kleon, and “The Chillpreneur” by Denise Duffield-Thomas. When my business grew and the income followed, I attended virtual conferences like Bonnie Christine’s Immersion Live Conference.
As for the skill-based creative resources, I utilize the internet and social media. I find creators on Instagram and YouTube who are educators with a skill I want to learn. First, I find out what resources are available for free like a course preview or a promotion they are running on their course. That really helps me identify who as an instructor is a good fit between their teaching style with my learning style. Next is the price and what is offered. Do I feel like the price is justifiable or if it fits my budget at the time? Is there an alternative free option on YouTube to try first or a cheaper Skillshare course that covers some of the basics to test it out?
As a creative entrepreneur, it’s really easy to get shiny object syndrome and want to try all the courses all at once! One way I help overcome these feelings is to weigh the course out in my handy dandy Excel spreadsheet! I keep a running list of courses I want to take, the teacher, where the instructor is located, course type, price, amount of instruction time, how long the course is accessible, skill type, what I get in the course, pros, and cons. I weigh business skills a lot higher on my ranks of importance as I feel that’s something I will find growth and will have a lasting effect on my business. I weigh out the return on investment: is it short term or long-term investment? Is it something I could eventually figure out on my own given enough time? And other similar questions to evaluate whether or not I need to take the course. I also have a nifty price total if I took all the courses and that’s enough to deter me from taking them all! After comparing each course with respect to the whole list, I remove courses from the list to prioritize the ones I know would be beneficial to the next stage of my business.
There’s a saying that you become an average of the 5 people you most closely surround yourself with. I’ve found that I need to be surrounded by fellow creative entrepreneurs and invest my time with them. I look up to people who are ahead of me and do my best to share my knowledge with people who aren’t where I am at yet. I meet with small micro communities within a larger community on a regular basis, some weekly and others monthly. Many of these people I call friends I met in a course or at a conference.
If I could recommend one thing to an aspiring creative entrepreneur is to invest in education and find likeminded communities as soon as possible! It doesn’t have to be going back to school for a 4-year program in business, but doing the homework and finding ways to grow personally and professionally will be a huge benefit.
Contact Info:
- Website: www.shannonscripts.com
- Instagram: https://www.instagram.com/shannonscripts
- Facebook: https://www.facebook.com/shannonscripts
- Linkedin: https://www.linkedin.com/in/shannon-tillmann/
Image Credits
Made by Glyde

