5 Things To Do When Starting Your Calligraphy Business That Work

Mar 26

Taking the leap to start your own calligraphy business takes guts. That first year is full of emotional ups and downs, and sometimes, it can feel like you're just slinging spaghetti at the wall! Saying yes to anything, Googling everything, and excited to see where you'll end up. I remember that feeling so clearly because I was right there, six years ago. No fancy business plan, no sales pouring in, and only four months of lettering under my belt.

But even without a perfect plan, I made a few moves that first year that helped me quickly turn my dream into a successful calligraphy business. And, looking back, I wish there had been a resource that told me all of these from the get-go. So, I decided to share these with you!

Here are the five things I did when I started my calligraphy business that worked.

*Photo of me doing calligraphy on my first wooden sign*

Some of the links in this post are affiliate links. I may receive a small commission if you make a purchase through those links - and, you may receive a special offer, so win-win! I only promote products that I believe in. Thanks for supporting my business in this way!

1. I built relationships that turned into referrals

I didn’t have a huge portfolio or hundreds of Instagram followers when I started my business. But, coming from client-facing roles in a large tech company, I did know how to build genuine relationships. So, that’s what I focused on!

Instead of only trying to get seen by everyone in a sea of scrolling, I put energy into getting to know a few planners and wedding professionals in my area. I went to networking events and set up coffee chats, reached out to them personally to introduce myself, and looked for ways to start conversations. (I dive into networking tips more here.) Over time, those micro-touches turned into real connections — and, eventually, referrals. Some of my earliest wedding jobs came from tapping into my network and building relationships with local planners and wedding pros. I quickly learned that the fastest way to book the right clients is by getting referred by someone who trusts you enough to recommend you - time and time again.

2. I found community with other calligraphers

When I first started my business, I came from a corporate background, and everyone else I knew worked 9-5 jobs. The people I did know who were running their own businesses were seeking venture capital funding. I didn’t know anyone who was doing something creative for a living, let alone who understood what it was like having to find your own income. It felt like I was building a business in a vacuum. It was so lonely!

So, I decided that I needed to make calligrapher friends. Instagram was the first place I turned to. I ended up forming a small friend group with three other calligraphers in different stages of business. We’d hop on Zoom once a month to talk about what we were learning, what we were struggling with, and what was working. That group is where I first learned about styled shoots, what to include in contracts, and how other calligraphers were pricing and packaging their services. We still keep in touch nearly six years later!

Community was what kept me going. Finding people who understood what I was building made all the difference. It gave me a place to ask questions, get feedback, and feel less alone in the process. We don't do monthly Zoom calls anymore, but that experience stuck with me. So much so that I made community a core part of my Pro Wedding Calligrapher course. Because building a business is hard enough…you shouldn’t have to do it alone with no guidance.

3. I participated in lots of styled shoots

Styled shoots were one of the best things I did for my business in year one. I didn’t even know they were a thing until one of my calligrapher friends brought it up after I asked her how she got such gorgeous photos of her work! A styled shoot is when a few wedding pros get together and contribute their talent to create a faux wedding scene that a photographer captures. Each person gets professional photos from that shoot to use on their website or Instagram. And trust me, having amazing photos of your calligraphy makes it nearly sell itself.

Once I figured out what they were and how to get involved, it all clicked. Styled shoots gave me the chance to get amazing photos and connect with photographers, planners, and other vendors I wanted to work with. I got professional photos of my work, built connections that went deeper than meeting someone at a networking event, and started showing up in other people’s portfolios and posts — without paying for ads or listings. And styled shoots also helped me get published! Just over a year into my business, my work from two styled shoots was featured in prominent national and international publications, CosmoBride and Style Me Pretty!. Win, win, win!

Now, I should warn you, not every styled shoot is worth it or leads to clients. You have to pick and choose. But the right ones can absolutely open doors. I learned how to choose shoots that aligned with the kind of weddings I wanted to book and how to communicate my value to the other vendors involved. Over time, those photos and relationships helped position my work for the kind of clients I actually wanted to attract. Now, I teach others how to get the most out of styled shoots in my course, Pro Wedding Calligrapher.

*Photo by Sarah Ching Photography, Left - from my first styled shoot. Right - me with my first attempt to do calligraphy on fabric. It took forever!*

4. I stopped selling calligraphy on Etsy

Like a lot of calligraphers, I started out thinking I needed an Etsy shop to make money. It seemed like the obvious first step. I listed a few products and waited to see what would happen.

One of my first orders? A table number. Just one.

Who orders just one?! It didn’t take long to realize Etsy wasn’t going to be the thing that built my business. Clients on Etsy tend to be budget-focused and price-shop, which made it hard to stand out or charge what you needed to be worth your time. And the platform doesn’t help! Etsy will show your listing right next to a cheaper competitor’s product. That type of competitive gamble may work for some, but I quickly recognized it was a race to the bottom and wasn’t how I would build a profitable, sustainable business.

The real turning point came when I started talking to other calligraphers who weren’t selling on Etsy and realized there were other options. By repositioning myself as providing a service, especially for weddings, I had the chance to guide clients through a more personal experience. I wasn’t just selling a product or commodity anymore, I was offering a luxury service. A service people sought out.

If you’re leaning toward services and wondering how to start booking higher-paying clients without relying on Etsy sales, my free masterclass is for you. In it, I walk you through exactly how I made the shift into services and how you can do it too.

A Funny Side Note: It should have been a clue for me, but my first paid project wasn’t even from Etsy! My first paid job from a total stranger came through Thumbtack. I’ll never forget it. Someone wanted Shakespeare’s Sonnet 116 written in calligraphy on beautiful paper (yep, the full 113 words). I charged $160 for it, and he said yes immediately. It took me forever. I was so nervous! But that one order gave me a huge confidence boost. Would I charge more for it today? Absolutely. But I’ll never forget the feeling of someone valuing my art and loving what I created for them. If $160 seems like a lot to you now, just know it was a lot to all of us at some point, too.

5. I started using Dubsado

Toward the end of my first year, I realized I needed a better way to manage inquiries, contracts, and payments. At the time, I was using PayPal for estimates, HelloSign for contracts, and manually emailing everything back and forth. It worked…but it wasn’t smooth for me or my client. I had to do a lot of manual work and click between accounts to get anything done. It definitely didn’t make me feel like a polished, high-end service provider.

Switching to Dubsado changed all of that!

Dubsado is a CRM (client relationship manager) built for creatives. With Dubsado, I was able to send a proposal, contract, and email an invoice all in one place. It looks professional to just have to send one link, and it cuts down your work because you can save packages and email messages to reuse again and again.

But beyond streamlining my backend, it also changed the way clients experienced my brand. I could show inspirational photos and mockups in the proposal, which helped clients visualize the final product and feel excited to move forward.

If you want to be paid like a professional, you need to look and feel like one. Dubsado helped me uplevel that part of my business and feel more confident showing up as the business owner I wanted to be, and I still use it today!

If you’re still using PayPal and sending contracts manually, I highly recommend you try a CRM. You can use my code MONSTERAGOLD for 20% off your first month or year!

Final Thoughts On Starting Your Calligraphy Business

Looking back, I didn’t have it all figured out in year one. But I kept showing up, trying new things, and trusting it would all add up. And it did.

I made $10K in my first six months of business. It wasn’t perfect or polished, and it certainly didn't replace the corporate salary I had left behind, but I was happy. It was enough to prove that this is what I was meant to be doing and motivated me to keep going. Less than two years later, I hit six figures in revenue — even with a pandemic in the middle!

So, if you’re still throwing spaghetti at the wall, that’s okay. Keep going. You’re learning, growing, and building something, even if it’s messy right now.

Want a clearer path forward? My free masterclass walks you deeper through the steps that helped me book dream wedding clients without relying on Etsy.

Shaochen | @monstera.gold