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7 Mistakes That I Made as a Freelance Calligrapher and Artist

7 Mistakes That I Made as a Freelance Calligrapher and Artist | The Postman's Knock

Last week, I posted a throwback article called 10 Items That I Successfully Sold on Etsy. Writing that post offered a fun trip down memory lane, and I think that people were able to draw some inspiration from it! This week, I’d like to continue that throwback theme by sharing some of the mistakes that I made as a freelance artist and calligrapher. I hope that you can learn from my mishaps if you decide to take on any freelance work, whether it’s just on the side or as part of a full-time gig!

Lindsey Bugbee | The Postman's Knock

For the first four years of TPK’s existence, I did freelance calligraphy and illustration work. I really enjoyed it; working with different people on different projects was fun! Ever since the beginning of 2016, however, the bulk of my time has been dedicated to maintaining this website — which I love just as much.

1. Underpricing

I have always enjoyed creating art and calligraphy, so when it came time to sell my skills, I was reluctant to charge much. It didn’t feel like work, so how could I justify asking what I perceived as a lot of money for what I was doing? In the beginning, I charged $1.00 per envelope for calligraphy. Each envelope took me 10-15 minutes to create, so I averaged a $4.00-$5.00 profit per hour. After a couple of envelope jobs that took me several weeks and rendered very little profit, I finally adjusted my rate to $3.00 per envelope. By the time I stopped taking on freelance work, I was charging $4.50-5.00 per envelope.

Paper Sack Envelope Calligraphy

If your work doesn’t look professional yet, it’s okay not to charge a premium. However, you shouldn’t sell it for a bargain, either. If you’re looking for guidance on pricing, check out The Calligrapher’s Business Handbook.

Those first few underpriced jobs taught me a lot about clients. It seemed that when I charged outrageously low prices for services, the quality of my clients was also lower. They were often less pleasant — and more unreasonable — to work with than subsequent clients that I collaborated with at fair prices. Now, I realize that they just wanted to make sure that they were getting a true blue bargain, which isn’t an expectation that you want from a client as a freelance calligrapher.

2. Not Sending Progress Photos to the Client

My very first (dip pen) envelope calligraphy commission was nerve-wracking. I spent hours on the job and lovingly packaged up the result. Once the client received the package, she wrote me an awkward message asking me to re-do all of the envelopes with 5-6 line addresses. I hadn’t known what to do with the tails on letters like “J” and “y” in the last line of calligraphy, so I let them cut off at the bottom edge of the envelopes. In my inexperience, I thought that was fine, but she (justifiably) felt it looked unprofessional.

7 Mistakes That I Made as a Freelance Calligrapher and Artist | The Postman's Knock

This is a picture of my first dip pen envelope calligraphy job, created using an early version of Flourish Formal Style calligraphy.

After interacting with that client, I realized that I could have avoided miscommunication and awkwardness by sending her a couple of progress photos. If I would have kept her abreast of what I was doing, she could have helped me to ensure that her envelopes looked just like she wanted them to.

3. Selling Calligraphed (Copyrighted) Quotes and Passages

As a first-time Etsy seller, I wasn’t well-versed in copyright laws. Now, it seems so obvious to me that you can’t sell calligraphed quotes or passages from books. Those quotes are generally copyrighted, and you need permission from the publisher to sell them. 

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In general, if a quote is 100 or more years old — like this Shakespeare quote — then its copyright has expired. Theoretically, I could sell this piece. (It’s always best to check first, though!)

In my naïvety, I used the “everyone else is doing it, so it must be okay” logic to go ahead and write out a couple of famous quotes. A couple of weeks later, I got warning emails from the lawyers of Shel Silverstein’s estate, later, Dr. Seuss’ estate. Needless to say, I was much more careful about what I wrote out to sell after that!

4. Not Sending a Pencil Draft to the Client

After a client hired me to create calligraphy and/or an illustration for them, I would explain my plan in detail via email. Communication is always key when working with clients, but verbal explanations are a poor substitute for visuals. I found that out after working on the project below!

7 Mistakes That I Made as a Freelance Calligrapher and Artist | The Postman's Knock

The scan on the left is the original poem/illustration that I created for the client. The scan on the right is the re-do. Sending a pencil draft to the client would have saved me at least ten hours of work!

For this project, the client wanted a poem written out and accompanied by an illustration. We agreed on a weeping willow theme after I (verbally) explained what I planned on doing, and I went ahead and created the piece. After I created the poem and illustration, I sent it to the client, who immediately asked for a re-do. They didn’t like how cluttered the piece was, as they had envisioned a simpler execution of the concept. We talked at length about the client’s priorities for the piece, and I realized that — duh! — I should have sent them a quick pencil draft for approval. After that, I did make a draft that included a simple branch/bluebirds theme, and the client approved of both the draft and the resulting piece.

5. Overcomplicating Projects

As an English major, I used to lean toward being overly verbose. My emails to clients were long and confusing, with many unnecessary questions and superfluous details. Now, I realize that I was probably guilty of adding a lot of stress to more than a few clients’ wedding preparations! It would have been much better to be concise.

Handwritten Wedding Invitations | The Postman's Knock

This wedding invitation client was one of my first. She was very polite about all of the emails that I bombarded her with as a green behind the ears freelance calligrapher! I’m sure that my numerous questions and emails were not much fun to deal with, though.

If there’s one thing I’ve learned, it’s that clients like choices, but not too many. As the calligrapher or artist, there are some creative choices that you should make for them to help make the process easier. For example, I used to ask clients to choose between brands of ink. “Dr. Ph. Martin’s Bleedproof White is more matte, while Ziller White is a little bit shinier … which do you want?” To the untrained eye, there’s barely a difference! You have to feel out your client and see how much control she or he wants of the project. Keep them updated and communicate with them, but don’t ask them to make every single decision for you: you’re the professional.

6. Not Working Directly With the Client

I ran into a strange situation a few years back. A wedding planner contacted me to create invitations for her client. The client wanted invitations that roughly looked like invitations that her grandmother had sent out a century before. I was excited about the project, and forged ahead based on the instructions that I was given! There was only one snafu: the wedding planner didn’t want me to have direct contact with the client.

7 Mistakes That I Made as a Freelance Calligrapher and Artist | The Postman's Knock

On the left, you can see the example invitation that I had to go off of. The right depicts my recreation according to the wedding planner’s instructions.

I didn’t have any of the client’s contact information; every bit of interaction had to go through the wedding planner as a middle man. I suspect that it’s because the wedding planner added a 25% “finder’s fee” onto my services that she didn’t want the client to know about. Whatever the reason, not being able to interact directly with the client led to a wedding suite that the client didn’t like at all. Both the client and myself complained to the wedding planner about not being able to talk to each other. From then on, I only agreed to work with wedding planners if they allowed me to work with the client directly and not force me to go off of the wedding planner’s interpretation of what the client wanted.

7. Not Setting a Schedule for Myself

If you’re working freelance, you need to have good time management skills. As someone who left a 9 to 5 to be a freelance calligrapher and artist, I didn’t understand that. So, when friends would ask me to give them a ride to the airport in the middle of the day, I’d say “Sure.” When the kitchen started to get a little bit messy, I’d stop what I was doing and go clean it.

Calligraphy Guidelines | The Postman's Knock

It’s especially important to schedule time for envelope calligraphy. Once I became disciplined about setting goals (e.g. “I need to do 10 envelopes per day for 10 days to complete this job), my workload got a lot less stressful.

Now, I realize that you need to treat your freelance work as you would a 9 to 5 job. Take it seriously, and make sure you set aside enough time every day to fulfill your responsibilities. Yes, freelance has flexibility perks — but you don’t benefit from over-stretching those perks. Commissions like envelope calligraphy and illustrations take a lot of time to make, so you want to make sure that you give yourself plenty of time to complete them!


Despite the unpleasantness that these mistakes cost me, I wouldn’t trade them for anything. Honestly, mistakes often shape a business much more effectively than victories do. Still — while I think mistakes are valuable, I hope that reading this post helps you to avoid some of mine!

If you have any questions, please feel free to ask. Otherwise, I hope that you enjoyed this post, and I’ll be back on Friday with a creative Mother’s Day card tutorial!

Warmly,

Lindsey's Signature | The Postman's Knock

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