• How to Know If You’re Ready to Sell Your Calligraphy or Art

    Many artists and calligraphers grapple with the question of when their work is ready to sell. Rather than waiting for a definitive sign, I encourage you to embrace the journey and consider taking the leap! You might be more prepared than you think to start taking commissions.

    Escort Cards in Amy Style | The Postman's Knock
    This 2013 escort card commission was one of my very first projects.

    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 totally ready, and that’s okay. (Remember, too, that it’s completely valid if you choose to keep your calligraphy or art personal — many create purely for self-satisfaction and mental well-being.) However, if the criteria below resonate with you, venturing into selling your work could be a rewarding next step!

    1. You Can Create Calligraphy

    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.

    Faux Envelope Calligraphy
    TPK Throwback Calligraphy | The Postman's Knock
    I actually started off selling faux calligraphy. No, it wasn’t perfect, but it had a certain sweetness to it that attracted a baby shower client (and Style Me Pretty).

    “Imposter syndrome” is a very real thing. It’s easy to feel inferior to others because you weren’t mentored by a big shot calligrapher or you’ve never attended a workshop. That said, 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.

    How to Know If You're Ready to Sell Your Calligraphy Services | The Postman's Knock
    This 2014 photo accurately represents my skill level at the time. When clients purchased envelope addressing services from me, I felt confident that they understood what they were getting because of photos like this one. (This is all-lowercase Kaitlin Style calligraphy.)

    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

    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 think outside of the box when brainstorming products. 

    You can use an illustrated map to announce an event!
    I’ve received requests from brides/grooms, magazines, and book publishers to create illustrated maps featuring calligraphy. Per How to Stand Out From the Crowd When Selling Calligraphy, the more you think outside the envelope addressing box, the more services/products you’ll likely sell.

    A little tip for after you come up with your product/service idea(s): don’t compare your creations 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.)

    10 Items That I Successfully Sold on Etsy: A Throwback Post | The Postman's Knock
    Let’s say you are selling holiday greeting cards like this one. You would probably require payment for the design up front, then ask the client which names they want on the card and ask them for a vertically-oriented high-resolution photo.

    The more well-thought-out your selling process is, the more trust you’ll elicit from your 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!

    Clothesline Baby Shower Clothespins | The Postman's Knock
    TPK started as an Etsy side hustle. I sold many of these calligraphy clothespins on there! For a list of other items and services I sold on Etsy, check out the 10 Items That I Successfully Sold on Etsy article.

    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”!

    Resources to Boost Your Skill Level

    If you’ve never created pointed pen calligraphy before, I’ve put together a game plan for you to learn calligraphy in two months. If you’ve got the basics down, however, I recommend taking the Intermediate Modern Calligraphy Online Course. In it, you’ll practice everything from coming up with new calligraphy styles to designing bespoke envelopes and café menus for imaginary clients.

    Flourished Place Cards
    TPK’s Intermediate Modern Calligraphy Online Course touches on everything you need to know to vastly improve your pointed pen skills.

    The TPK website also has stylized calligraphy worksheets and a flourishing course that will boost your skill level. Don’t underestimate the utility of the free worksheets and the knowledge available on the TPK website, too! I’ve got articles over how to take DIY photos of your creations, impressive calligraphy projects that double as practice, and tips for staying motivated in your pointed pen endeavors.

    Business Spotlight: Eileen Graphics

    In 2018, I received the following email from Eileen Korney, proprietress of Eileen Graphics. Her success story is inspirational, so I want to share it with you:

    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.

    Cards, Lettering, and Artwork by Eileen Korney | The Postman's Knock
    On the left, you can see Eileen’s cards on display at a local J.Crew store. On the right is an illustration and lettering that she created for Newport Life Magazine.

    [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.

    Last year, Eileen reached out to me to say that she has now opened a brick and mortar store called Sincerely, Eileen in Newport, RI. If you’re in the area, check it out! 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!


    Lindsey's Signature | The Postman's Knock