Lessons Learned From Baking 5,000 Holiday Cookies

The week after Thanksgiving should be a time of rest and recovery, a few glorious days' respite before the second wave of holiday craziness crashes down. Not so in my family. Each year, my mom and I take on a task of Herculean proportions: baking, boxing, and delivering dozens of Christmas cookie care packages. This year, we made 40.

The tradition began in 2011 or 2010—reports vary—when we decided to revive our long-lapsed tradition of making a handful of seasonal favorites to give out to friends and family. A wise person would have started small, just a few batches. A prudent person would have added one or two recipes at a time. I dove into recipe research with the enthusiasm of a Labrador puppy, much to my mother's chagrin, and before long, we had an inaugural Christmas bake-a-thon recipe list of over 20 types of cookie. The list has changed over the years, but the spirit remains the same, and we've been holiday bakers ever since.

You can't make that many cookies for that long without picking up a tip or two. Here is what I've learned.

1. It has to be fun

Christmas baking at this scale is hard work! It requires tremendous focus and attention to detail and, oh man, is it expensive. It needs to be worth it. Choose recipes that you love and are excited to share. Put on your favorite music and belt out a chorus or two. Rope in friends and family to help, but only if you trust them to actually aid in the process and deliver cookies up to your standards.


Most importantly, know yourself, and bake accordingly. Will a glass of wine help the process or slow you down and make you sloppy? Should you power through one more recipe, or are you starting to fade and likely to burn whatever you put in next? Are you just not feeling it this year? We certainly weren't in 2016. Take a year off, and come back next Christmas. Make sure you'll be happy with the process, and the journey will feel worth it.

2. Start early in the season

We learned this our first year. Lots of people give out sweets in the holiday season. Most of them will not be as fabulous as your homemade tray of deliciousness. Avoid other people's cookie fatigue and seeing the soul-crushing look of, "Oh no, another tray!" flit across their eyes by starting your baking early and cranking those suckers out as quickly as you can. Our first year, we made 22 recipes, each delectable and beautifully executed. And we handed them out at Christmas, at which point even we were ready for a sugar detox. The next year we got 'em out by December 10 and we haven't looked back since. You'll get a much more enthusiastic reaction and you'll be able to enjoy the process without the other demands of the season pressing down on you.


3. Do your homework

If I could pass on one lesson and one lesson only, it would be this: Do not assume everyone wants baked goods at the holidays. Ask. Again, this kind of baking is hard work, and putting that effort in and delivering a tray you take tremendous pride in, only for it to not be appreciated sucks. Finding out someone ended up throwing half of it away, or that they can't eat it due to food allergies, can feel like having your life sucked away à la The Princess Bride.


Yes, it's fun to surprise people with cookies. That's what the office is for. But friends and family? Just ask, and if they say, "Thanks, but I'm trying to eat healthy right now," or "I'd love some, but remember, I have that thing with nuts?" or "I'm not a big sweets person," believe them and give them a gift card instead.

Related: Look into gluten-free and nut-free options. There's no reason not to have at least a couple dependable recipes for each category. And if you're contending with a serious nut allergy, play it safe and buy them something made in a certified nut-free kitchen or factory instead.

4. Don’t multitask

Just don't. You'll think you can answer that one email while the cookies are baking, but you'll wind up burning the edges every time. Set aside time to focus on this one activity, unplug from social media, and treat the work as a meditation. Stay on top of dishes, double check your recipe before you start each batch (a mid-batch trip to the grocery store is no one's friend), decide on a reasonable recipe list, and do not stray. If you let the perfect become the enemy of the good, you'll be making and remaking batches all December. Set an end date, or end condition, and stick to it.


5. Consider the delivery

Can you stack the cookies on a plate, or will the icing cause them to stick together? Are you hand-delivering, or shipping cookies through the mail and if so, can your recipes survive the journey? I air-pop popcorn to use as packing peanuts, making sure the cookies we ship have plenty of cushioning so they don't break. I also print out a cookie menu, with pictures of each recipe and pertinent allergen information, so that people know what they're eating, and potentially what to avoid.


Nothing compares to baked goods fresh out of the oven, but most recipes will stay fresh for a certain period of time. Put each batch in air-tight containers as soon as possible and keep those suckers closed until it's time to compile your plates. We use a lot of strong flavors in our baking, and we realized after a few years that the product we were delivering, while still tasty, was nowhere near as good as what we'd boxed; unless people cracked into the cookies immediately, recipes with more delicate flavors were overwhelmed by their neighbors in the box. Now for the plates we know won't be immediately devoured, we use sandwich bags to isolate each recipe and avoid flavor contamination. It's a hassle, and nowhere near as visually appealing, but much tastier.


6. Debrief

Lastly, once you're done with everything, and maybe after a couple days' recovery, do some post-game analysis. Assess each recipe and cut the ones not worth the effort. Make notes on your recipe cards about the tips you picked up this year. Which recipes really need parchment paper, and which had a significantly different bake time than printed? You will not remember these details next year.


And if you didn't have fun and it was too much, stop! Life's too short. I have a wonderful time baking with my mom each year, but as soon as she's ready to move on, we'll find a new tradition.

Until then, you can find me in the kitchen with my mom the start of each December, chopping dried cranberries and pecans for mini Cranberry Hooteycreeks, or shelling pistachios for Pistachio Ribbon Bars (when I can't find 'em pre-shelled but unsalted, as happened this year), or struggling to temper too-small batches of chocolate for Peppermint Bark, singing carols and having a wonderful start of the season. And if you're very lucky, maybe you'll make the delivery list.