In this post, I want to take you through my calendar strategy that takes 3 years of selling and designing calendars into account, so that if you want to start selling calendars (or boost existing calendar sales), you have a road map to get from illustrations to finished calendars. Let’s dive right in!
where I started
When I thought about designing my first calendar in 2023, I had already decided it would flop. I mean, only big-name, professional designers who went to design school can design sellable calendars, right?
I mustered the courage to do it anyway and was surprised to find that I enjoyed the process so much that I didn’t even care if I sold many calendars.
Surprising Result: I sold 400 calendars in my first calendar season with only one calendar for sale.
Tip:
You will never feel ready to design a calendar. At some point you just have to rip off the Band-Aid and design your first imperfect calendar, so you can move on to the fun part and get into your calendar design groove.
my second year strategy
The first year of designing calendars was fun, yes, and the calendars sold, yes, but would it work again? I didn’t want to invest a lot of time into something that could be a total waste of energy and effort.
So I decided to design 1 new calendar, and just re-date my first calendar with 2024 dates.
Surprising Result: I sold 800 calendars in 2024. It started to feel like the math was simple—each new calendar creates 400 sales.
Tip:
Before you go all in on a plan for selling your work, do some testing first by creating one design/collection. This helps you make sure that you both love designing the product and that it will sell. I always start out with one or two test products before I dive deeper into any new product!
Midyear strategy
In addition to designing a new calendar each year, I’ve added into my strategy a midyear re-dating (yep, just changing the numbers and re-listing on Etsy) of each calendar since many people like to buy July-June calendars.
I expected to sell a few of these, but I was shocked to see that with only 2 calendars in my shop, I have already sold 800 calendars in 2025 (writing this in September) thanks to the big boost that academic calendars gave me.
Tip:
It is more than worth it to re-date your calendars in late spring (March to April is the best time)! This opens up your calendars for a whole other selling season, so you can make even more use of the time you spent designing the calendar pages.
this year's potential life-altering strategy
The first year, I played really small and designed 1 calendar. The second year I went a little bigger and listed 2 calendars (1 new, 1 redated), but this year I am taking all I’ve learned and applying it to FOUR new calendars (leaving me with 6 total calendars in my library).
Am I making a huge mistake by putting so many eggs in this basket? I seriously doubt it! Historical sales data has shown me that people want my strange and funky calendar designs, and I’m leaning into that in a big way this year.
Tip:
Once you have clear data that your product is selling well, it’s time to do a deep dive. Many creatives get stuck in the cycle of always starting something new, but it’s much better to dive deeply into what you’re already doing well! When I realized that my botanical calendars are selling well, I thought of as many botanical related themes as I could and made four calendars around that concept!
The new formats
I believe in repeating what is already working as a core strategy BUT there is always room for experimentation. This year I am introducing two new formats. One is an art print style calendar, where the customer can cut the top off the print and frame it in a standard frame. The other is a smaller square calendar. The big bonus of this square format is that re-dating will be much simpler because I won’t have to adjust any illustrations to account for the varying number of weeks on each month!
Tip:
Each month of the year has a different number of weeks. It ranges from four weeks to six weeks, which can make it tricky to fit your designs on the top of the page, especially when it comes to re-dating designs for next year! Consider starting with a calendar format that keeps the dates and illustrations separate, so you don’t have to worry about adjusting your illustrations when it’s time to re-date your calendars.
get these templates
I have already gone to the trouble of making all of these templates for you, so you don’t have to worry about calendar formatting or figuring out the dates! All you have to do is pop your artwork into these templates. Come grab them inside The Studio.
Come grab my calendar design & selling schedule
- See my whole schedule and process for designing and selling calendars
