Tricks for Making Holiday Shopping Fun, Never Stressful

I believe the year was 2008 when I realized I was dangerously teetering one candy cane’s width away from the edge of true holiday insanity. I had a 1-year-old and a 3-year old climbing all over me in a house littered with moving boxes we still hadn’t fully unpacked yet as I reviewed my list of family members I had to shop for.


It was 49 people long.

Forty. Freaking. NINE. People. Long.

Parents, grandparents, siblings, nieces, nephews, cousins, second cousins…it was completely out of control. What can I say? I married into a family of breeders who were overly generous during Christmastime, and the number kept creeping up over the years. Just thinking about that number hitting 50 made my eye start twitching in stress to the beat of “Little Drummer Boy,” so I put my foot down, called one of my husband’s cousins, and begged for mercy. I told her what my number was, and pleaded with her to be okay with us no longer getting each other gifts, and could she please help me tell all the extended family that we need to stop the insanity? SHE HUGGED ME THROUGH THE PHONE. She, too, was feeling like it was out of control. She, too, felt unfairly stressed by all the generosity that was expected of us.

Holiday shopping was no longer fun. It was all about finishing an exhaustive checklist without breaking the bank, then making time to deliver all those gifts or ship them, hoping the recipients liked them, and it was all too much. We agreed to spread the word that gifts were no longer happening to anyone outside of immediate family, unless it was food handed over to each other at a family gathering (it’s a big Italian family, so food is always a given and I will never complain about free delicious food).

Once we got off the phone, I started looking at my shortened list in a new light. I was so used to holiday shopping being an aggravating task, and that was a mega holiday cheer destroyer. I decided then to make it not only easier on myself, but also enjoyable. FUN.

It took a bit of time for me to get into a new rhythm, but now I can say that holiday shopping is something I actually look forward to these days. Here are some of the tricks I have up my sleeve that completely turned around what used to be a stressful job. 

1. Make a list of people you need to get gifts for. Scratch that: Make a SHORT list of people who need to get gifts for. Here’s a good way to see if your list is too long: Does it resemble Santa’s list of every kid everywhere? Yes? Then chippity-chop it down. Yay! Isn’t all this streamlining a hoot?

2. Take notes. Throughout the year, create a private holiday shopping list on Amazon, or secret Pinterest board, of goodies you find for people on your holiday shopping list. If someone mentions she likes something she sees while you’re within earshot, write it down. It’d be a great surprise for her to see it in her stocking months later. I keep a note in my phone all year long with a list of exactly this type of thing under a misleading label to deter snoopers, making me feel like a secret agent.

3. Shop ridiculously early. Come across something that’d be a great stocking stuffer for your sisters and mom in June? Grab them! Do you like it, too? Grab one for yourself as a reward for getting things done way ahead of time. WEEEE PRESENTS FOR MEEEEE! In January, you will find a lot of the cool gifty things specially packaged for the holidays on clearance at your local stores. Why not stock up on those now, while the prices are low?

4. Keep a special spot for Christmas gifts all year long. I have a cardboard box on a shelf in one of my closets that is specifically for this purpose. This way, items I buy way early never got lost (because I lose all the things every day of my life), and I can always poke my nose in it to see how I’m doing once I get closer to the actual holidays.

5. Make your shopping trips as efficient as possible. Find a store that has something for everyone under one roof, like Old Navy, where you can get totally cute, cozy sweaters for every member of your family at prices that don’t make your wallet do sad faces at you. Bonus: You all will look so adorably coordinated in them on Christmas day!

6. Have the kids make their own lists. Hand over the iPad and open up a link to their favorite toy store and tell them to add everything they want this year to the shopping cart. Make sure they prioritize their top three to six very favorite items. Maybe also make sure all those items are not ridiculously expensive? I like to ensure there are things on their lists that range from only a few dollars on up, covering all budgets. Then I create an online wish list of all those items that family can shop from, adding in notes as to which are the kids’ favorites, what else they might want, and clothing sizes.

7. Make YOUR list—and one for your husband. It feels weird at first, but it’s only practical. PRACTICALLY AWESOME. You’re pretty much guaranteeing everything under the Christmas tree will be exactly what you want. How does this not make you want to high-five yourself? Now stalk your husband’s web browser for the golf shoes he keeps eyeballing or the gadget you never knew even existed but that he loves. Add both of your lists to the online wish list you made for your kids.

8. Now use those lists. Shop for what you (and Santa) want to get for the kids. Get it delivered to your house. Prevent yourself from having to fight fellow shoppers in puffy coats, sweating and hating life while holiday music burns holes in your ear dums as you wait in endless lines to buy things at the mall you can totally just buy online in the comfort of your holey sweatpants and no-bra-ness.

9. Send the lists to loved ones. What is more frustrating than being inundated with texts and phone calls from all the siblings and grandparents and in-laws who are in the store right now and want you to recite—from memory—exactly what your family wants for Christmas? GAH. Prevent that from happening by emailing and texting links to your tidy and accurate wish lists to everyone, letting them know that it covers everyone and is there if they want it.

10. One more checklist! Keep track of all the people you are shopping for and what you got them or what’s shipping to you soon, so you know exactly when you are done shopping. I use the one in my phone that I keep for ideas throughout the year: I just add the things I do end up getting to it, so I know what’s what.

11. Let’s talk about wrapping it up now. If you loathe wrapping gifts, see if the places to shop or order from can do it for you. Yes, it might not always be free, but worth it? YEP.

But if you don’t mind it, you can make it even more fun by making little dates with yourself to get it done in small batches. Turn on your favorite dance music, pile wrapping supplies on one side of you, gifts on the other, and your checklist in front of you, and get jiggy with it while prettifying those packages for your loved one.

Happy holidays! Oh, and don’t forget to bundle up before you head to the stores. Check out this cute outerwear from Old Navy:


From top, clockwise: Men’s puffer coat, $44.50; Baby’s one-piece, $12; Women’s puffer coat, $55; and Girl’s Wool coat, $46; Hat, $8 and up; Mittens, $10 and up; Scarf, $12

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Content is sponsored by Old Navy. Thoughts and opinions are my own.