
Today, I want to focus on a question that I often receive via email: “How do you know if you’re ready to sell your calligraphy?” The answer is that you will probably never feel completely ready, and that’s okay. If you fit the following criteria, however, selling your calligraphy is certainly worth a go!
1. You Can Create Calligraphy
Listen, your calligraphy doesn’t have to be out-of-this world in order for you to sell it. No matter what you make, you’ll always see flaws in it. I’ve been creating calligraphy for years, and I can still point out flaws in any given project that I churn out! As long as what you make has some character, it’s ready to go out into the world.

Don’t feel inferior to others because you weren’t mentored by X big shot calligrapher or you didn’t attend Y workshop. Art and calligraphy aren’t brain surgery — if people like what they see, they’ll buy from you, whether you’re “qualified” or not. As long as you do a good job, that’s what counts!
2. You Are Able to Ignore Insecurities and Worries
When you take those first few steps to sell your calligraphy (setting up an Etsy shop, potentially sending samples out to wedding planners), you will probably feel like a total “poser”. Acknowledge that feeling, then let it go. Beauty is in the eye of the beholder, and you should initially think of selling your calligraphy as a “paid internship”. Don’t feel like you’re cheating the customer with your lack of experience; they’ve seen examples or photos of your work, so they know exactly what they’re getting.

Furthermore, for some reason, we often worry that other people will judge us for starting a business or side hustle. It’s weird — I know — and I’ve been there. Don’t worry about it; you’re being adventurous and trying something new, which is good for your happiness and personal growth! If other people don’t respect your venture, then that’s on them.
3. You Have a Product/Service Idea (or Two or Three …)
Think about what products or services you can offer. Envelope calligraphy is a safe bet because clients love sending out calligraphed envelopes to announce their events (and there are always events going on)! But — you should also try to think outside of the box when brainstorming products.

A little tip for after you come up with your product/service idea(s): don’t compare your stuff to others’. You will always find someone out there who is selling something that you perceive to be much more amazing than your own offerings. First: remember that there’s room for everyone to take on custom calligraphy work. Second: remember that there’s always going to be someone out there who will prefer your calligraphy/art to another person’s calligraphy/art.
4. You Have Worked Out a Selling Process
Let’s say that you’ve started an Etsy shop, and a potential client contacts you to work on a project. What happens next? Do you take a flat deposit? Send over a quote? Have a rock solid process ready to go, and give the client a good idea of that process ahead of time in your item description. (You can find tips about developing a selling process in the How to Make Extra Income Selling Calligraphy article.)

The more well-thought-out your selling process is, the more trust you’ll elicit from the client. You’ll also be more confident as an artisan and a business person if you have a plan to lean on. I recommend dedicating plenty of time to coming up with a selling process for each product or service that you offer. Think about exactly what you’re going to do once a client makes an inquiry or places an order. Also, consider any hiccups you may encounter and how you might remedy them!
5. You Have Realistic Expectations
Most businesses start out slow. TPK was no exception — for the first few years, it was really more of a hobby than a business. But: as you build your reputation, your portfolio, and your experience, your business will likely start to blossom. Maybe it won’t evolve beyond a “side hustle”, but that’s okay!

Sometimes, doing something as a side hustle and not a full-blown business keeps it enjoyable. And there’s no better feeling than splurging on something you’ve wanted for a while and thinking “my creativity bought this for me”!
Business Spotlight: Eileen Graphics
I recently received the following email from Eileen Korney, proprietress of Eileen Graphics. Her success story is inspirational, so I want to share it with you (with her permission)! I love that Eileen just went for it and is experiencing so much success:
One year ago I discovered TPK, and your guidance has truly sculpted my small business (Eileen Graphics) that has blossomed during the past 12 months! I began my own greeting card line and have gotten into a number of stores.

[My card] designs consist of my original illustrations, but it was the calligraphy education that you shared with the public that helped make my hand lettering so much stronger. The handwriting has truly contributed to the success of my line- after I learned about faux calligraphy techniques that are present on the TPK blog. When I have a bad day (in the day job that helps pay my bills currently) my spirits lift when I read about your newest projects. Without sounding too corny, a light truly goes off inside of me and I am filled with the eagerness to create because of the knowledge that you so generously share with this online community. Thank you so much for the inspiration.
You can follow Eileen on Instagram and/or find her Etsy page by clicking here.
Have you taken the plunge to start a business or side hustle (big or small)? If so, did you feel like you were ready when you started it? Others will benefit from your input, and I — personally — am interested to hear, so please comment/share!
Thanks so much for reading TPK, and enjoy the rest of your week!
Warmly,