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Starting a modern calligraphy side business can seem daunting with all the legal and financial logistics involved.
But fear not, creative friends!
Today, I’m breaking it down into manageable steps to help you transition from hobbyist to professional calligrapher with confidence.
=Disclaimer: I am not a practicing attorney or a tax expert. Please consult your own lawyer or accountant for individualized advice=
TABLE OF CONTENTS
- 2) Decide on a Legal Structure
- 3) Business Licenses, Permits & Registrations
PART 1: Legal Essentials for Your Calligraphy Business
It’s best to build your lettering business on a solid legal foundation, so you can set it up, check in every few months, and then NOT WORRY ABOUT IT!
1) CHOOSE A BUSINESS NAME
QUICK SUMMARY: Don’t get stuck too long on this! Keep it simple, use your own name when in doubt, and do your research first.
Keep it Clear: Opt for clarity over cleverness. Your business name should instantly communicate what you offer. Simple is better.
EXAMPLE: “Laura’s Lettering & Calligraphy” is instantly understandable while “Laura’s Luminous Lines” is more vague. It sounds nice and has alliteration, but is Laura a painter? A clothing designer? A retailer of LED strip lights? Customer’s attention spans are short, so you need to capture their interest right away.
Using Your Own Name: If you’re truly stuck on choosing a business name, just use “[YOUR NAME] Calligraphy” to start with. You can always change it later!
BONUS TIP: If you use your own name as part of your business name, you might be able to avoid the requirement of a “Doing Business As” registration (more on that later!)
Search Availability: Do some basic research to ensure your chosen business name isn't already taken.
PLACES TO SEARCH: Google, social media sites, your state’s business database, and the US Patent and Trademark Office.
The USPTO Trademark Search website - one important place to search to see if your business name is already being used
2) DECIDE ON A LEGAL STRUCTURE FOR YOUR CALLIGRAPHY BUSINESS
QUICK SUMMARY: For most new professional modern calligraphers, a sole proprietorship will make the most sense. (But, if you have a complicated tax situation or personal assets that need more protection, consult tax & legal professionals.)
Sole Proprietorship:
PROS: Simple and cost-effective to file and maintain
CONS: Provides no protection of your personal assets (if your business gets in trouble, you get in trouble)
LLC (Limited Liability Company):
PROS: An LLC means your business is treated as a separate legal entity. So if you ever get sued or have to pay for damages as a business, no one can come after your personal assets.
CONS: More paperwork required to file and maintain. Can also be quite expensive (in California, it’s $800 every year just to maintain your LLC)
S-Corp: This is something your tax professional can set up to potentially lower your tax liability on the money you make from your business. You usually don't have to think about this until you’re paying yourself a consistent and generous salary.
My experience:
I started Crooked Calligraphy as a Sole Proprietorship with a DBA filing. Then around Year 3 of my business, when I was finally making enough money to go full-time, I decided to switch to an LLC.
Stick figures are highly underrated, IMHO
3) THE EASY APPROACH TO BUSINESS LICENSES, PERMITS AND REGISTRATIONS
QUICK SUMMARY: Getting all the right business permits and registrations might feel overwhelming, so here’s my approach. Start from the TOP level (the federal government) and work your way DOWN to the local level to ensure you’re meeting all the requirements.
Some things that MIGHT be required at each level:
Federal: IRS Tax Filing, Getting an EIN
State: Business Registration, LLC Formation, Seller’s Permits
County: “DBA (Doing Business As)” or “Fictitious Business Name” Filing
City/Town: City Taxes, Police/Fire Permits, Local Business Registration
PRO TIP: Many government websites offer guides and resources for starting a small business. Most even have a dedicated phone number you can call to ask questions.
Remember that governments WANT more small businesses, so it’s in their interests to help you start one. Use the resources they provide!
PART 2: Financial Management to Make Money with Calligraphy
Once the legalities are squared away, it's time to get your financials in order so you can start making money. Here's what you need to know:
1) SEPARATE YOUR FINANCES
QUICK SUMMARY: Trust me, you’re going to want to keep your business finances separated. Both for tax reasons and to track profitability (‘cause making money is the whole point, right?)
Bank Account: Use a dedicated checking account for all your business expenses and deposits. It doesn't have to be an official business account - any separate checking account will do, at least in the beginning.
PRO TIP: If your business is an LLC, then you might need to open an official business bank account for it.
Credit Card: Run all business purchases through a separate credit card. Again, it doesn’t have to be a card specifically for businesses.
2) TRACKING FINANCES & INVOICING TO MAKE MONEY
Beginner DIY Method: Spreadsheet + PayPal
Keep careful track of every single business expense and sale on a spreadsheet.
PayPal is great for free invoicing, so customers can pay you easily online.
Upgrade as You Grow: It's a good idea to invest in QuickBooks Self-Employed once you've outgrown the DIY method. It makes it easy to track your business expenses and income. It also lets you send more “professional” looking invoices and and keep track of the payments.
PRO TIP: An Etsy shop is a great option for calligraphers starting their business with physical or digital products, because it has the payment method, tracking system and sales tax help already built in!
CRM Software:
Honeybook and Dubsado are examples of more sophisticated Client Relationship Management tools - these are great for guiding a client through a custom ordering process, like bespoke wedding invitations and save the dates. You definitely don't need these in the very beginning.
PRICING:
This is a complex topic. What you would charge vs. what others are charging vs. what the clients want and expect? Whew!
For now, check out this post called “Pricing Your Calligraphy (with a real case study)” - I’ll add more about this topic in future posts!
My experience:
In the very beginning, I typed invoices in Word, turned them into PDFs and emailed them to the client to sign and pay via Chase QuickPay, PayPal or physical check. DON’T DO THIS! It’s labor intensive and hard to track - and it’s more inconvenient for the customer. Use an invoicing software like PayPal instead. It’ll It’ll really save time..
3) CONTRACTS NEEDED TO START A CALLIGRAPHY BUSINESS
A quick legal primer on contracts. Technically, a “contract” can be formed, even without an official, signed document in place. If you and a customer come to agreed terms and the customer pays you in return for something of value, that makes a “contract” in the eyes of the law. The reason you want a contract in writing is because it serves as EVIDENCE. You want to be able to show a court clear documentation that there was an agreement.
Bare Minimum: If you haven't made much money doing calligraphy yet and don’t want to spend hundreds of dollars on a contract, at the very least do this.
Step 1: Write down all the key terms of what you and the customer agreed to and put it in an email (dollar amount, deliverables, timing, etc).
Step 2: Ask the customer to REPLY to the email with a clear acknowledgement of the terms.
Step 3: Finally, put the key terms into the invoice that the client signs and pays.
Official Contract: A well-written contract protects you legally, but it also gives your customers more trust and confidence in working with you. Both parties know exactly what is expected of them, as well as the consequences of late deadlines, missed payments, etc.
Helpful Links:
📑 CLICK HERE TO PURCHASE A CONTRACT TEMPLATE JUST FOR CALLIGRAPHERS (My affiliate link for The Contract Shop).
😳 Read my BLOG POST about how a client refused to pay me thousands of dollars… all because I didn’t have a contract
4) BUSINESS INSURANCE FOR CALLIGRAPHERS
The first question to ask is: “What is your actual potential exposure given your calligraphy services and products?”
Low potential liability: If you work from home and mostly create paper goods like place cards and custom quotes… what could you possibly be liable for? A missed guest name or late birthday present? The risks are pretty low.
Higher potential liability: Now, if your work involves more risk of damage to property or people, maybe you want to consider general business insurance. Here are some instances where the potential for damage—and hence the need for insurance—increases.
Example: Going on-site to restaurants to create murals, where you might spill paint on expensive furniture.
Example: Engraving on high-value items like perfumes and candles, with a drill tool that might injure someone in freak accident.
Example: You have a physical studio where customers can trip and injure themselves
My experience:
I didn’t get any business insurance until Year 3, when I landed a big collaboration with a popular brand. I would be doing calligraphy on tote bags with a fabric pen and worried that the ink might rub off on some fancy lady’s expensive white couch. Now, I pay about $500 a year for general business insurance.
Understanding Types of Insurance
General Business Insurance: Offers broad coverage for your day-to-day operations. It can protect against various unforeseen events that might otherwise financially harm your business.
“Day of” Certificates of Insurance: These are cheaper (as low as $30) and cover just a single day or event.
Example: If you're hired to perform calligraphy services at a wedding or a corporate event, the venue may require you to present a day of insurance certificate.
5) SALES TAX FOR SMALL BUSINESSES
HOW IT WORKS: When you purchase a candle from Bath and Body Works, you pay sales tax on top of the item's price. The Shop is responsible for collecting this tax and then remitting to the government.
When Does Sales Tax Apply?
Physical Products: Generally, sales tax is applicable if you are selling physical products. Whether it's calligraphy supplies, greeting cards, or other tangible goods, these sales are subject to sales tax.
Digital Products: The rules around digital products are quickly evolving and vary state by state. If your calligraphy business involves selling digital downloads or services, do your research to stay updated on the latest tax laws affecting these products.
PRO TIP: Sales tax is one factor to consider when you’re deciding what type of business you want. (i.e. physical products, digital products, or calligraphy services.)
Where Does Sales Tax Apply?
When your business has a “nexus” with a state. In other words, if your business has a physical presence in a state, you are required to collect sales tax from customers in that state.
These might qualify as “nexus”:
Your home state, when you live and operate your business
Traveling to another state to sell at a pop-up market there
Having an employee or a business location in another state
Complying with Sales Tax Requirements
Collecting and Remitting Sales Tax: If you have a nexus in a state, you must collect the appropriate sales tax from customers and remit it to the government.
State and County Variations: Sales tax rates can vary significantly from one state to another and even between different counties within a state. It's essential to research the specific sales tax rates applicable to your business locations.
My experience:
Ok, real talk. Sales tax is a PITA. When I sold greeting cards in California, I had to determine the COUNTY that each individual customer purchased in, and apply a slightly different sales tax rate to that purchase. It’s one of the significant reasons that I pivoted from physical products to digital products and services.
Finally, a note of encouragement:
Lettering and calligraphy can offer some really easy ways to make money from your creative outlet. And there’s never a better time to start than NOW. Even if you’re unsure of yourself, don’t forget that you’re creating something beautiful and brand-new. And that takes time and courage. The sooner you begin, the more chances you have of gaining repeat business and discovering ways to make money that you didn't even know about.
In my next post, I'll talk more about ways to make money and attract potential clients.
This includes practical advice on:
building your portfolio,
taking photos of your work, and
making your own website to start promoting yourself.
I'll also go over potential lettering services like:
handmade greeting cards
hosting calligraphy workshops
creating placecards and envelopes for brides
I'd love to hear if this post was helpful. Let me know in the comments!
Love,
Hey I’m Shinah!
Harvard lawyer turned sassy calligrapher and multi-million-dollar business owner.
I make calligraphy & biz more DOABLE, so you can go after your dreams!
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Practical advice from a former lawyer on the legal & financial steps to officially setup your calligraphy business. Everything you need to get your lettering and calligraphy side hustle off the ground. There's never a better time to start and soon you'll be calling yourself a professional calligrapher!