Tax Season: The Not-So-Pretty Side of Running A Luxury Calligraphy Business

Not to burst your bubble, but…

Most of luxury calligraphy is characterized by all the pretty things. There are the tools and supplies, the wardrobe, the event-day glow up for live-event calligraphers, and the lovely designs calligraphers create for their clients.

But, every year, there comes a time that’s ugly. It’s the messy-hair-don’t care tax season. It’s the bald-headed stepchild most well-natured artists who wouldn’t hurt a fly want to starve, lock in the closet, and never let see the light of day again.

Unfortunately, they have a big brother called Uncle Sam of which you want no parts.

I’ve just survived my most recent tax season and it was nasty.

For days, I was buried in paperwork and scouring my online accounts to upload documents for income, expenses, mileage and the like…all of which I tracked in a very minimal way. I itemized all I could itemize until I couldn’t itemize no more.

In my defense, this business was a side hustle. I only anticipated making a few bucks here and there…And while I made certain I had my license to operate and the like to be sure I was doing things above board, I didn’t foresee all of the i’s I’d have to dot nor the t’s I’d have to cross for a side hustle that decided it could do better than a couple dollars here and there.

Many times, my workspace looks as pretty as a picture…like at the Jo Malone event I just had last weekend. But, during tax season, it’s not so. My laptop was all but glued to my hands on my living room sofa as I muddled through everything to make the deadline my new accountant set for me.

In the end, I got through and I made it to the other side. But, it could have been a lot easier with some tools in place…

In an effort to make your next season more painless, let’s chat about some tools that you might consider, and those I have chosen for now to see if next tax season could be a little more bearable to look at (like the pretties in this little recap video).

Tax Binder/Checklist

It has been said that if you have a positive mindset, your brain will look for ways to confirm its inclination. It will look for ways to prove that what you believe is true. It’ll do the same for a negative mindset. But, that’s a lesson for another day. Now that I have an idea of what I’m supposed to look for, I’ll definitely be more alert when I see those items. It then triggers me to keep those things set aside for the next tax season.

I also bought a checklist to be sure I collect what I need. I can orgranize all these items in a binder now for when the time comes to use them.

Bookkeeping/Accounting Software

This could come in the form of good, old spreadsheets or an app like Quick Books (or similar).

This year, I’ve committed to using this Easy Bookkeeping Spreadsheet by Visual Planners on Etsy. I must admit. I had this well before tax season and never got around to using it until after tax season. But, when I first saw it, I liked that it was a one and done purchase that could be used year-to-year. I also liked that it had monthly and annual overviews, and could be used to track financial goals, etc.

Since I’ve started tracking my business expenses, I’ve found it pretty easy to use so far. I’m still deciding between bi-weekly or monthly updates to keep it current. But, it should definitely help me not to lose my mind trying to gather all of my info next year.

Mileage Tracking App

I had to go back and map the mileage I had over each event from last year. Not fun. And….there’s an app for that. A few, actually. But this year, I’m giving Driversnote a spin. At the time of this writing, there is a free plan for up to reports for 15 trips per month as well as a paid plan that will give the ability to track an unlimited number of trips. I enter my home and work/school location and live life as usual. Later, when I have a moment, I update the app on which trips were business or personal trips. When it’s time to report the information, just export the documentation. While it feels a little creepy for an app to follow every move I make in the car, overall, it’s a much better option than trying to compile and compute all that information during spring break! Love it!

Get Your Tax I.Q. Up

If entrepreneurship is a permanent fixture in your future, it may be a good idea to get some education on finances and/or accounting for your business.

There are a few classes that tackle taxes and finances specifically for calligraphers. Most of these resources offer more than information on taxes. Take a look and see which would be most beneficial to fill in any gaps in your learning.

The Business of Calligraphy by Kestrel Montes - I’ve eyed this course for a couple years now. In the end, I chose another direction. But, I have taken a course with Kestrel before and it was exceptional! The list of what is covered in this course is near-endless and the paperwork section is well-stocked. It covers permits, which kind of business entity to consider, taxes, tracking expenses, copyrights, etc.

Ink & Income by The Lefty Writer - This pop-up course was by Magen, aka The Lefty Writer. Magen, a fellow Craftie and one of our freshly minted coaches in The Craft Academy, has a passion for helping calligraphers learn the ins and outs of their finances as it pertains to the calligraphy industry. The course debuted it’s first run in November 2023, in the thick of the holiday season for live-event calligraphers…and while there is no definitive ETA on the next round, you know I’ll be looking out for it. 👀 If you happen to be seeing this post during tax season, and you’ve waited until the last minute to prep, it’s possible a course like this could save your bacon.

The Craft Academy by Rosie Ramirez - While there is no module specifically for taxes, financial goal-setting is one of the most important tenets of this group. This comprehensive coaching program is also a wonderful resource to lean on for finding information on operating successfully as a calligrapher during tax season and beyond. If you are interested in an ongoing program where you can ask any question related to taxes, finances, pricing and the like, this may be the one for you. Coaching calls regularly tackle these items on a weekly basis.

Conclusion

One thing is for sure, tax season holds little attraction for most creative types and calligraphers are no exception.

But, once your affairs are in order, you’ll be one less headache away from getting back to sitting as purr-ty as these kitties. That’s certainly worth the trouble. 😌