By the second week of February, my Santa suit's back from the cleaners, my beard's had its trim, and my calendar for next December is sitting there completely empty. Same as every year since I started doing this in the mid-2000s. For a long time, I let it sit there empty until fall.
I built Kringle Tracker in 2022 mostly because I got sick of not remembering which kid was scared of the reindeer or which family asked for a Hanukkah mention alongside the visit. Along the way I learned something that cost me actual families to figure out: if you want to manage your Santa bookings well, February beats September every single time. Not because of some marketing trick. Because of memory.
The Year I Waited Until Fall
For years I ran things the way most seasonal Santas do. Season ends, I sleep for two weeks, and I don't think about next December again until Labor Day rolls around and the corporate party inquiries start trickling in. Made sense to me at the time. I told myself the families knew where to find me. They'd call when they were ready.
Some did. A lot didn't.
One family I'd visited four years running, the Lewis family, booked another Santa the following November because I hadn't reached out since the previous January. Four years of history, gone, because I couldn't be bothered to send one email in February.
Four years. Gone.
That one stuck with me. Still does, honestly.
Why February Beats September, Every Time
Here's what I didn't understand back then. In February, a family's December memory is still sharp. The kid is still telling his teacher about the Santa who knew his dog's name. Mom still has the photos as her phone background. That family is primed to say yes to next year, fast, because the feeling hasn't faded yet.
By September? You're competing with back-to-school chaos, a full summer of vacations, and whatever else happened in the six months since. And you're competing with every other Santa who already locked that family in back in the spring. I lost count of how many families told me, kindly, "oh, we already booked someone for this year, sorry Roger," when I finally got around to reaching out in October.
The families most likely to rebook aren't new inquiries. They're not the ones who found you on a directory. They're the people who already trust you, who already have you in their phone, who already know what a visit with you feels like for their kid. That trust doesn't expire exactly, but it does have a shelf life, and September is well past it.
Know Who You're Talking To
This only works if you actually kept track of last season. Not a mental note. An actual record: family names, kids' names and ages, what they asked for, anything specific from the visit (the kid who wanted to know if the elf on the shelf was real, the mom whose husband was deployed and wanted extra kindness that year, whatever it was).
I used to keep this in my head and in a battered spiral notebook, which is exactly as reliable as it sounds. I'd show up to a return visit and blank on a kid's name mid-conversation, which is a special kind of panic when you're supposed to be Santa Claus and Santa Claus knows everything. That's the whole reason Kringle Tracker exists now, honestly. I needed somewhere to put this stuff that wasn't my own memory, because my own memory was garbage by August.
Whatever you use, even if it's a plain spreadsheet, write the details down while they're fresh. In January. Not in October when you're trying to reconstruct who these people even are.
The Actual Outreach
Here's roughly what I send, usually within the first few weeks after the season wraps.
For families I want back:
Subject: Saving your December date
Hi [Name],
[Kid]'s face when I remembered his dog's name last December is still one of my favorite moments from the whole season. I'm opening up my calendar for next year now, before I post availability anywhere public, and I wanted to give you first pick of your date. Dates are locked in with a signed performance agreement. Let me know if you'd like [same date] again, or if another Saturday works better this year.
Hope the kids are doing great,
Santa Roger
The Timeless Santa
For the more casual, local families, a text works better than an email:
Hey [Name]! Hope everyone's doing well since December. Building my calendar for next year and wanted to grab your date before it fills up, any interest in locking in [date] again?
Neither of these is complicated. That's kind of the point. You're not selling anything new. You're reminding a family who already loves what you do that the window's open, and that it's closing.
The Fall Trap
Wait until fall and you lose people two ways. Half of them already booked somebody else, because somebody else emailed them in March. The other half genuinely forgot they wanted to rebook at all, not because they didn't love it, but because six months is a long time and Christmas hasn't crossed their mind since the tree came down.
I get it though. February feels early. It feels a little aggressive to be talking about Christmas while your neighbor's still got Valentine's decorations up. But the families don't think it's early. They're still in the glow. Use it.
It Doesn't Have to Be Fancy
You don't need anything complicated to do this right. A notebook works if you actually use it. A spreadsheet works better. A CRM built for tracking this kind of thing works best, mostly because it won't let you forget the details the way a shoebox of scribbled notes will. What matters far more than the tool is the timing.
Send the email in February. Not the fall. Your future December self will thank you, and so will Tommy, who's already started asking his mom when Santa's coming back.