How I Turned a Hand Lettering Hobby into a Money Making Business

How I started a Hand Lettering Business |

I have been practicing calligraphy for over two years now. It is such a beautiful hobby I couldn’t help but want to learn how to do it myself. It is a classic story really, that all started with a boy and a girl falling in love.

How I got started with Calligraphy

It all started after I got engaged and started planning the wedding. After picking a date, the invitations were the next priority. After spending weeks browsing through invitations the only thing I knew was that I wanted the envelope to be so beautiful that it immediately set the tone for the wedding with beautiful hand addressed calligraphy and vintage stamps.

Being a do-it-yourself kind of gal I set out to learn calligraphy. I had done some old school calligraphy when I was much younger. You know, the kind with the flat marker that requires you to turn the marker a certain way to get the right kind of line but I wanted beautiful modern calligraphy and I knew nothing about it. I didn’t even know what kind of supplies I needed.

My first lesson in Calligraphy

I started doing tons of research and I came across the Skillshare class: Introduction to the Art of Modern Calligraphy by Molly Jacques. It was exactly what I was looking for complete with a list of supplies and lessons that started from absolute beginner to lettering on envelopes and using different color inks.

I took the course over a week and spent an hour or two everyday just practicing. I started with straight lines and then circles until I was writing full letters and eventually words. It wasn’t easy. I filled up pages and pages of practice letters until my hands started moving on their own. It was almost like muscle memory had kicked in and each letter I would write would just flow right from the nib.


In addition to learning on Skillshare I also picked up the book Modern Calligraphy by Molly Suber Thrope. The video class was great because I could actually see it being done. It gave me a better understanding of what I was doing. The book was geared more towards applying what I’d learned on actual projects and using it for the wedding. It came with several pages of letters with different styling. This book really helped to develop my style.

Addressing my wedding invitations

After a few weeks of practicing I set out to address some envelopes. I hand addressed both my save the date cards and the wedding invitations. All of them. It was great real world experience. I learned that not every envelope is easy to address. My save the date cards were done on a kraft paper envelope. The result wasn’t horrible but it was difficult to write on and I ended up wasting a lot of envelopes. So I switched to a beautiful gold linen envelope for the actual invitations that was much smoother and easier to write on.

I received tons of compliments on both the invitations and the save the date cards. I began to wonder if this was something I could do part time to make some extra cash. Lots of people getting married and lots of people need letters addressed so why not.

Starting a Calligraphy Business

I decided to start using hand lettering to make money about a year ago. I wanted to address letters and make cards to sell online and at craft fairs. There are so many ideas for hand lettering businesses. I believe that everyone should find their own passion and turn it into a business. It’s easy to start with just a Facebook page, Etsy store and a business card.


Generally, when you sell lettering services on Etsy most clients that you get will be engaged brides looking for wedding invitation addressing. I choose to go a different route because I wanted to get repeat business. I didn’t want to have to search for my clients every single month, I wanted them to come to me.

Hand Lettered Envelope |

Direct mail marketing is still one of the most popular forms of marketing for local businesses. If you really want your business to stand out and ensure that your letters are opened, sending a hand addressed letter is the best way possible.

I decided to start with realtors. Why realtors? First, because their information is easy to find and because they are constantly marketing with direct mail. So I went to Google and gathered up 25 local realtors names and addresses. I focused more on luxury realtors because they are more focused on presentation and making a good impression to higher end clients. I sent just 25 hand made cards in beautifully addressed envelopes.

Grabbing Their Attention

Hello Greeting Card
Here is a sample of what I write in my cards.

Hi Larissa,
Looking to get your clients attention? I can help with that! My name is Chelsea and I’m a local calligrapher looking to build lasting relationships with local businesses. I absolutely love what you’re doing with your marketing. Did you know that you can get triple the response rate with hand addressed envelopes? My business focuses on delivering beautiful, hand addressed envelopes that your clients will adore. I have included my business card and with pricing information. I’d love to chat with you, please give me a call or shoot me an email.

I received 4 orders from my first 25 cards and those 4 realtors ordered a total of 1150 envelopes. At this point I’d spent maybe $250 on supplies and mailing materials. I made over $4,000 from those 4 calls. One realtor ordered 500 envelopes! I charged differently depending on colors desired, envelopes and volume. It took me roughly one week to complete all of the envelopes, working around 4 hours a day. To save time, I generally calligraphy just the name and write the address with a thick pen. $4,000 was a good extra chunk of change in my pocket, especially for around 20 hours worth of work.

Growing a Hand Lettering Business

I started to wonder if I could turn this into a part time job with full time pay. To grow the business, I expanded out to other cities and followed the same model of sending out about 2 dozen cards with my information and business card. I’ve also tried the same with other companies that send me direct mail marketing but realtors have by far been my best clients. I’ve grown my little hand lettering business to a point where I work around 3-4 hours per day and make enough for ends meat. It’s rewarding, I love making pretty things.


I also visit local farmers markets, mailing stores and boutique paper shops to sell my hand made cards. These are usually really simple cards that I can make and duplicate in just a minute or so. I’ve gotten great feedback from these.

If you have any questions please feel free to ask. I will post another update soon with all of the frequently asked questions I get about hand lettering.


  1. Dear Chelsea,
    Thank you Soooo much for the wonderful article! It has a wealth of information and it is super-inspiring! I have looked up online for the course that you’ve mentioned that you took (by Molly Jacques), but unfortunately it is no longer available. Have you heard by any chance of an alternative course that you might recommend for someone to begin with hand lettering and calligraphy? There are so many out there and I’m unsure which one to choose.
    Thank you so much,

  2. I have read this blog several times and I am also wanting to address envelopes as a side job. I do have questions that I can’t seem to find answers to. Does the customer provide the envelopes (and invitation/card) to me? Do I provide the envelopes? Do I mail the envelopes back to the customer or do I mail the envelopes directly? Any advise would be greatly appreciated.

  3. Hey Chelsea! I loved reading this post! Thanks for all the good ideas and inspiration! I really liked your idea about sending lettered marketing to local realtors. Such a great idea that I hadn’t thought of! Did you send these letters to realtors’ offices’ addresses? Were there any other industries you had luck sending this advertising to? I’d love to hear any tips you have with this! Thank you!!

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