A common question we receive is in regards to when you should start charging for your calligraphy work and how long before you turn your hobby into a business. 
If you are serious about getting started with your calligraphy business (or getting things more legal & organized if you’re already in the early stages), we very highly recommend Calligraphy Business Bootcamp. It’s run by our friends at Modern Calligraphy Summit and we teach a few weeks worth of content in the course. I also recommend Molly Suber Thorpe’s book The Calligrapher’s Business Handbook: Pricing & Policies for Lettering Artists.
Here is some general advice, though, to consider when you think you’re ready to start charging for your work. I will preface this by saying that I do not recommend the route that I took. I personally started pointed-pen calligraphy by doing a “client” order back in the early 2000s. The client was my best friend, and I was paid with a Nordstrom gift card. I continued to focus on client work instead of improving my pointed-pen technique and the quality of my work suffered. Sure it looked “fine”, but honestly I would have been much better served by practicing drills and letter shapes than simply addressing envelopes. To be fair to myself, no one was offering courses focused on this (our 5 to 11 week Calligraphy Practice Plan is dedicated to truly elevating your skills all around), and I didn’t have anyone guiding me with advice on calligraphy at all and definitely not in terms of building a career around it. Ultimately I ended up doing client work on the side from my 9-5 job for two years before taking the leap and running Laura Hooper Calligraphy full time.
With that all of that said, in theory you can accept money for your calligraphy as soon as people are willing to pay you for it, though I do not necessarily recommend this, especially if you have to undercut your industry colleagues with your pricing. If your calligraphy is “not good enough” (this is subjective but something we hear when this conversation takes place!) to command industry standard rates, then you should focus on improving your technique and your skills so that your work is at a level high enough to command pricing that will allow for a live-able wage. When you undercut your industry colleagues, you are telling consumers that calligraphy should be “cheap” and not only are you damaging the industry, but you are shooting yourself in the foot by training your clients to devalue your work. They are telling their friends and family your “cheap” rates and that’s what people will expect of you, even when you are ready to attempt to go full time.
If you aren’t sure what industry standard rates are, consider looking at the websites of a few well-established calligraphers doing this full time, both in your area and nationwide. Many stationers and calligraphers share their pricing, or at least starting rates, online. Many people say $3 bare minimum for an outer envelope mailing address (no, this does not include a handwritten return address – that should be pre-printed with the rest of the stationery suite!), but even that number is becoming a bit outdated. We charge $4.50 per guest address and others in our area charge anywhere from $4-$6+ per address. Again, this does not include the return mailing address, nor does it include calligraphy for inner envelopes. Digitally printed envelopes cost people $2.50-$3….handwritten scripts should absolutely not be at the same investment point as a computer! This is an artistic skill that requires hours and hours of dedicated practice, financial investment in learning and improving your craft.
Something else to consider is when you are doing work for friends and family for free or at a discount. If you are doing this to gain experience and build a portfolio, you should still be creating and providing an invoice to them that reflects the value of the work you are doing. This will help you get in the habit of pricing your work and creating invoices, and also shows others that they should value your work (and the amount they should be telling their friends who ask about your services!). 
Ultimately the timing to turn your calligraphy hobby into a business is a personal one, but laying the groundwork from the start can help make it a smooth (and legal!) transition.
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