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. Hi! I have read and reread this post so many times! I decided to start Handlettering as a side business after sending out Christmas cards last year. I LOVE your idea of contacting realtors though- I’ve gotten supplies ready to go, but I’m wondering if you have any suggestions for the note itself. I’m struggling with not writing too much, getting straight to the point, in a way that is memorable to them!

    1. So glad you found this helpful! I completely understand not wanting to write too much. On the inside I usually write in my own normal handwriting (nothing fancy) For realtors I keep it short and simple. I write something to the effect of “Want to get your clients attention? I can help with that.” I will add my business and contact info. I usually throw in a business card or two as well. Something that shows them the value of the service will also work “Did you know you can get triple the response rate with hand addressed envelopes?”. Short and simple usually works best. I would try a couple different things and see what works best. Good luck!

      1. Hey! Quick question. Were you writing the realtors address on the envelope or they’re clients addresses? What would they typically put in the envelope?

        1. Clients addresses. Realtors usually send birthday cards, Christmas cards, anniversary cards and direct mail marketing. Some of the realtors send out monthly newsletters and others use them just to send updates on their past clients about their property prices. Some also send out post cards and flyers to neighbors when they list a home in the area or sell one.

      2. I have a question.. so what address do you write? The clients or realtors? They give you a list of addresses and names??

    2. Hello from London

      I have just started calligraphy at age 55 and I’ve only ever hand painted old English lettering and as you so rightly say there’s so many different ideas especially when you consider everyone’s hobby business etc.

      Wish you all the best

      Johnny Mac

  2. I’m an event designer part time but I want to start a side business for calligraphy. This post gave me the extra boost I needed to start right away. Do you have any other advice for someone just starting out?

    1. My first tip is don’t be afraid to start. You never know what can happen. There are so many opportunities for hand lettering and you never know what it can become until you try it. Second, practice every single day even if you’re already a professional. Over time it becomes like muscle memory. It becomes easier and the better you get the more you can make. Lastly, in my business I started with real estate agents but get creative with your marketing and clients. Being an event designer, you could definitely start with brides to be just to test the waters. I hope these tips help you.

  3. My love!
    This article gave me soo much encouragement with this article! Iam also starting a calligraphy business and I struggle a bit but you gave my a real push! Your marketing ideas are BRILLIANT!
    I have a question: Did u have a lot of likes on fb back then what you send the letters to the real state agancy? Do you think that u have to have a big fan community to advertise yourself? Cause this takes time and i was wondering if you need it or can start right away?

    Big hugs and greets from Spain! ,,


    1. After I made the page I invited my Facebook friends and family. I think a little over 100 of my friends liked my page at the time. That was a decent start. I had the page for a couple of months before I sent out my first set of cards so I had filled it with some photos and posts at that point. I completely understand not wanting to go the Facebook route. You could opt for a small, one page website that just explains a little about you and has samples of your work. That way you don’t have to worry about building a fan base first.

    2. Can I ask where you got those “hello” cards? They really seem perfect for introducing yourself to potential clients and I can’t seem to find anything like them online. Thanks in advance!

  4. Thanks for this great article. For Realtorsome, we much of the cards were personalized. I.e. “I hope you loved the house at 2500 Cleary Lane. Let me know if you want to see it sgain. ” or did you only customize the envelopes for them?

    1. For me, I’ve only done envelopes completely hand lettered. But I have done some lettering for some greeting cards like birthdays and anniversaries and had them printed for realtors. It saves me time in the long run to do them this way. I usually do 3 different designs so there is still variety. They still have a custom organic, lettered feel to them but it takes a lot less time for me to do them. Everyone I’ve talked to about them has still loved them. In my case, the realtor has usually written their own greeting on the inside anyway or had it printed. They usually know the client better.

      1. When you say you do lettering for cards and have them printed, how do you do this? Where do you get the card? How do you get it duplicates?

        1. I designed the greeting card in photoshop with my own digitized hand lettering. I sent it to Staples to have them print it on greeting cards. You can have greeting cards printed at any print shop or office supply store.

  5. Chelsea, I am so happy I found this post! Thank you for willing to share your knowledge!! Any tips on how to price my work? I have no idea how much to charge. If you could please at least give me an idea on where to find this I would really appreciate it. Thank you!!

    1. My basic starting price is $3.00 per envelope but I give discounts the more envelopes that are ordered. I go all the way down to $2 per envelope if more than 500 are ordered. I up-charge for different envelope colors, materials, return addresses and greeting cards.

      The basic formula for pricing should be cost of supplies + cost of your time. For example if you want to make $75/hour and you can letter 30 envelopes in an hour that’s $2.50 per envelope. If cost of supplies (don’t forget your marketing) is $0.20 per envelope you should be charging at least $2.70 per envelope.

      Hope this helps!

  6. Hi! I am a teenage who wants to start a business in hand-lettering but I have NO IDEAAAA where to start! Please help!
    Thanks <3

  7. Thank you so much for writing this! I really want to make extra money that doesn’t involve driving around (my car is on its last leg) so I’m going to try this in my area. My question for you is: did you offer different envelopes for them to use or did they supply the envelopes or was it some other arrangement?

    Thank you for answering. 🙂

    1. I completely know what you mean about making extra money but not wanting to drive. I hate driving it would be a nightmare for me! I do offer envelopes, I have a supply of white, cream and tan colored envelopes but some of the realtors and other businesses I work with want their own color of envelopes for branding purposes. When they want their own color I often ask for a sample first to make sure I have a brush pen that will work on it and that can be read. I don’t except an order from anyone using their own envelopes before getting a sample first to ensure I can maintain good quality.

      1. What is a good brand of envelope to start out with that won’t hurt my brush pens? And where can you get them in bulk at an affordable price? Thank you for this encouraging post!

  8. Thanks so much for this!! I have had encouragement from family to start selling my handlettered stuff! One of my favorites is addressing envelopes! I would like to get better at it but I really like the idea of selling to realtors!! What type of card did you put in it, was it one you created? And what exactly did you advertise in the card if you don’t mind me asking? I would love to hear a little more! Thanks so much 🙂

  9. I’m so glad I came across this article to help me push my small business even further. If you don’t mind me asking, what specifically did you offer to these realtors — addressing envelopes for whom? And where do you normally get your envelopes from! For me I think it’s hard to offer business if I can’t find great quality materials that also sell in bulk as well. Thanks!

  10. Hey! This really inspires me, your page is so sweet and full of great tips! I’ve always had a good handwriting, so I feel like I can take classes and do this on the side! Love love love it, thank you so much 🙂

  11. Hi, Chelsea!

    I am starting a hand-lettering side business and I’d really like to push envelopes as one of my biggest sellers. I was wondering where you buy your envelopes? I’d like for mine to be good quality (obviously) but not break the bank! 😉


    1. I have bought from several places and trust me all envelopes are not created equal! Sometimes people provide the envelopes for me, this is my least favorite and I usually refuse to do dip calligraphy on those ones. It’s brush pen or hire someone else haha. But my favorite place right now for envelopes is Paper Papers I buy lots of speciality papers from them. They have nice quality envelopes and they are well priced.

  12. This is a brilliant post – congratulations on being brave enough to push out and gaining your customers! I’m not too familiar with Photoshop but I have a MacBook Pro. Do you mind me asking, how easy did you find to to add your own lettering to PS? Do you draw your own patterns and have these printed into cards? Big thanks from the UK!

  13. Hi Chelsea,
    Thank you for this amazing article and comments you have left so far! I still have a couple questions that you haven’t answered yet/ haven’t been asked. Did you have a trademark when you first started and do you have one now? These things are pretty expensive and not in my budget, but I’m not sure how necessary they are. Also, did you set up a contract with the realtors that reached out to you? Sorry for all the “legal” questions, but these popped into my mind when reading your article!
    Thank you in advance!!

    1. Hi Lisa, So glad you enjoyed the article!

      In response to your questions, I did not and still do not have a trademark. I personally use my name and that works for me. I’ve thought about filing for one but it has never really seemed worth it to me personally but I can totally understand why people do and I think if you’re really serious about branding it definitely helps and it makes you look more professional.

      As far as a contract goes, I have an order form that has a small contract/disclaimer on it that clients do have to sign and I definitely do recommend this for any type of service you provide. It’s important that you and the client are on the same page as to what services are going to be provided, the cost and turn around time.

      1. Hey Chelsea!
        Do you have a sample of your disclaimer that you give clients? I am trying to draft one and do not know where to start I do not want it to sound like an aggressive binding contract but I do want to be taken seriously.
        Katie C.

        1. All contracts require a 50% nonrefundable deposit of the total design cost to begin work. The initial payment is due upon acceptance of this contract. The final payment is due upon completion of the final project. The finished project will not be shipped or delivered until final payment is received regardless of the contracted completion date.

          All materials and styles will be decided on before work begins and are outlined in this contract. Calligraphy styles cannot be rechosen after work has begun and material costs cannot be refunded.

          If proofing is requested, please note that your timeline will be pushed back by 1 week or more for each round of proofing. The estimated time of completion is based on current workflow.

          Please double check your address list and deliver it to us in a timely manner using the provided template.

          Due to the stylized nature of calligraphy and mass mailing, it is possible that up to 3% of your envelopes could be undeliverable. We are not responsible for any envelopes that cannot be delivered.

          1. Hi Chelsea,

            Thanks so much for all of the information. I was just reading your disclaimer that your include on your invoice/contract to your clients and it mentions that it is possible that up to 3% of envelopes could be undeliverable. Can you please explain this? Thanks!

            Tamara Swinford

      2. Thank you for the reply! I highly appreciate it.
        I am going to be doing some research to find realtor addresses in the near future as well as finish setting up my website!
        Did you get the business cards you included in your first envelopes made at Staples too?

  14. Hi Chelsea!
    Love your grit and dedication towards your passion!
    A few questons I would like to know: Will one have to get a liscense for this type of business? What about taxes? Or is it as easy as setting up a website and reaching locals to build up customers?

    Thanks so much

  15. Hi Chelsea,
    Do you only sell digital copies of your lettering, or at times do you sell individually crafted envelopes (is that what you did at the start?)? Also in your disclaimer, why isn’t it your responsibility for undelivered envelopes? Thanks =)

  16. Hi! This post has really inspired to get my hand lettering out there! I was wondering, when you send the initial letters out do you address them to the individual realtors or the company?

  17. Hi Chelsea!

    Your article is really inspiring! After being and actively working as an art director for more than 12 years, I’ve realized that I wanted to have my own small business where I could use my hands to create things. So, I will definitely use your advice and push myself to go further in this field.
    My question is going to be the same as the last person here. Could you tell more about the legal side of your business? Do we need a license or start a company online?

    Thank you!

    1. I am definitely not a lawyer and I highly encourage you to talk to one. Check out Annette Stepanian. There are lots of legal resources there. I also recommend Calligrafile as a resource to finding just about anything calligraphy business related.

      What I do is freelance work. In addition to hand lettering I also do graphic design and photography. When I first started, I did this as a sole proprietorship but later made an LLC. I was very, VERY broke in the beginning and just trying to make some money. So that’s what worked for me.

      Definitely, talk to a lawyer and do your research to determine the best option for you and your business and budget. The rules for doing something like this could be different depending on the country or state you live in.

  18. Hi Bella here!
    I love this post and am looking into selling my calligraphy (wedding envelopes, birthday cards, inspirational quotes etc.) and i was wondering where you got your envelopes from and how much they were keep going with your business your amazing !!

  19. I’ve done something similar where I’ve reached out to local businesses to redesign their chalkboards! I have never thought of reaching out to realtors and I will definitely have to try that after I graduate!

  20. Hi Chelsea!
    Your post is so inspirational and motivational! This may be a dumb question, but how do you design your envelopes? To clarify, what do you draw/write on the envelope to grab the readers attention? Also do you have any other ideas for what kind of businesses/individuals to target if I’d like to sell lettered things?
    Thank you!

  21. Hi Chelsea!
    Your post is so motivational and inspirational! This may be a dumb question but how do you decorate the envelopes? Like what exactly makes the reader want to open them?
    Also, do you have any other ideas for individuals/local businesses to target for a calligraphy business?
    Thank You!

  22. Thanks so much for this article. Question – do you think it is weird to offer calligraphy using just the calligraphy pens, as opposed to ink? Like do you think you would charge less for this, or is it not even offered by anyone and most calligraphers only offer it with the ink? Also, how did you advertise your work online? Etsy? Thank you!!!!

  23. This class has been removed. Skillshare class: Introduction to the Art of Modern Calligraphy by Molly Jacques.

    Do you recommend one similar to this one?

  24. Chelsea,
    I love your hand-lettering blog and have followed it for a few years.
    You mentioned in your orders for small Contract/Disclaimers that clients have to sign, something about the “provided template?” Is the template something you provide the realtor for them to send you their potential customer mailing list? Where do you get the template from?
    Also, inside the folded card, is the content the realtor sends their potential customers in the form of a printed sheet that you either insert (paste) or write, or digitally print into the folded card?
    Thanks, Rae

  25. I really need some help choosing the right envelopes! You included a couple of links to vendors, but I don’t know which finishes are best for the Tombow dual brush markers or the Tombow Fudes I just bought! I understand I want a smooth finish paper to keep the tips in good shape…. Thanks! Fataima

  26. Hey Chelsea! Your post is really inspiring. I really want to learn this beautiful art. I have been reading quite a lot about it for a while now, watching videos and perusing blogs. I find it very fascinating and I know this is what I want to do too. Please tell me how and where to start learning it. I am a total beginner and have no idea where to begin. Could you please point me in the right direction?

  27. Wow!! This is inspiring! I am a beginner with calligraphy and I love it so much that I think if this is something I could do everyday, I’d be so happy 😍 thank you for sharing your story with us, Chelsea ❤️

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