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How to Organize Your Holiday Shopping

 & Jill Duffy Contributor

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The lead-up to the end of the year can be a magical time, filled with lights, songs, winter decorations, and family get-togethers. But let's not pretend it doesn't also stir up feelings of stress, anxiety, and panic. You can't have control over every aspect of the holidays, but with a little organizing, you can be in control of your budgeting and spending. (Note that by "holidays," I'm referring to the six-week stretch from American Thanksgiving to New Year's Day.)

Planning what you'll buy, deciding how much you'll spend, and figuring out the best time to complete your holiday checklist will inject a little bit of order into an otherwise chaotic time of year.

What Do You Need to Buy?

Before you start picking out the cutest little pair of ballet pointe shoes for your three-year-old niece, make a rough list of everything you need to buy this holiday season. As you do, estimate how much it will cost.Get Organized I use a spreadsheet to create a holiday budget. Seeing all your estimated expenses in one places allows you to curb any unnecessary expenses before you incur them. Here are some of the most common holiday expense categories:

  • Gifts. Make sure to include family; friends; staff, co-workers, bosses, and secret santa assignments; hosts and hostesses of parties and dinners you attend; and people you tip, such as doormen, building superintendents, and service industry workers with whom you interact regularly.
  • Greeting cards and postage. Make sure to budget for not only expenses, but also the time needed to write holiday cards.
  • Decorations. Some people buy new holiday decorations every year, and some panic when they realize they don't have a clean tablecloth the day before hosting a party. Think ahead. Be prepared.
  • Food and drink. If you're hosting, you need a game plan for buying food and drink. If you're not hosting anything, it's helpful to buy a few bottles of wine or tins of sweets to keep as emergency gifts. They somehow never go to waste.
  • Travel. Keep in mind that booking travel may take up a good chunk of your budget and time, and during the holiday season, time is a precious commodity.

What to Buy When

The next step is to plan your time. Some purchases, namely travel, are best made as far in advance as possible. But other holiday items you might need to buy drop in price at fairly predictable times of year.

Before November
The earlier you figure out your holiday travel plans, the better the price you'll get from flight, hotel, and car rental booking sites. Last-minute deals are highly uncommon in the U.S. for domestic travel during November and December.

Early November
Early November is a good time to stock up on items that won't go on sale, such as decorations (well, they'll go on sale after the holidays, but that's no help to you now). It's also a good time to get a jump on items that the recipient is unlikely to return, like emergency gift bottles of wine or other non-perishable food gifts.

Black Friday
Black Friday tends to be the best time to buy electronics, especially high-ticket items, like HDTVs, most laptop computers (more on what's excluded in a moment), kitchenwares, and home goods (except furniture). Some analysts predict there will be a handful of exceptions in 2015, stuff that's normally on sale on Black Friday that won't be this year. Those items include most smartphones, ultraportable laptops, gaming laptops, and the latest round of Apple devices, including the latest iMac.

Cyber Monday
If you're an online shopper, Cyber Monday is your day to shine. Get all your online shopping done. One consideration, however, is whether you'll have gifts shipped to you or directly to the recipients. Cyber Monday falls on November 30 this year, meaning gifts will arrive roughly by the week of December 7, and that's a pretty conservative estimate. If that's too early, consider how much it's going to cost you to deliver the gifts on your own. It might not be worth the discount you're getting by shopping on Cyber Monday. I also think Cyber Monday is the earliest possible date to mail holiday cards.

Early and Mid December
The first and second week of December, expect clothing prices to drop in stores. There's a catch, though: Stock starts to dwindle then. If you're a dynamite shopper, it's a great time for bargains. But the thought of digging through sales racks for the right size sweater makes you want to pull your hair out, stick to shopping for clothes online on Cyber Monday instead.

December 15
Pack up and ship gifts by December 15 for Standard Post and December 19 for First Class mail, if you're using the U.S. Post Office for holiday shipping. Going to your local Post Office could be a nightmare, but you can skip the lines by printing your own postage at home. All you need is a scale (a kitchen scale works wonderfully; a bathroom scale will do in a pinch for larger boxes), a printer, and an account at USPS.com. Accounts are free to create with an email address.

Late December
Here's a huge tip: Leave yourself some unplanned time in late December so you have wiggle room in case something goes wrong. How often have you forgotten to buy a gift or been invited to a party at the last minute and didn't have anything to wear? Leaving a few days open will ensure you can take care of whatever problems arise. Also, mid to late December is a great time to cash in any unused personal or vacation time you might have accrued at your job. Let those days be an ace up your sleeve.

Apps and Services for Holiday Organizing

What apps and services can help you stay organized this holiday season? You'll find a number of dedicated holiday shopping apps if you search for "holiday shopping" in your favorite mobile app store, but I like to use tools that are so strong and flexible, they work just as well for organizing your life during the holidays as they do other times of year.

Google Drive is my go-to service for organizing my holiday shopping and planning. I use a simple Google Sheets spreadsheet to plan out my budget and purchases, and rely on Google Drive mobile apps to make it available to me no matter which device I have on hand.

Pinterest helps visually-oriented people collect ideas for holiday parties, recipes, crafts, and gift ideas.

Trello, the kanban-style project management app, is another tool that's so flexible, you can even use it to organize holiday shopping.

About Our Expert

Jill Duffy

Jill Duffy

Contributor

My Experience

I'm an expert in software and work-related issues, and I have been contributing to PCMag since 2011. I launched the column Get Organized in 2012 and ran it through 2024, offering advice on how to manage all the devices, apps, digital photos, email, and other technology that can make you feel overwhelmed. That column turned into the book Get Organized: How to Clean Up Your Messy Digital Life. I was also the first product reviewer at PCMag to test fitness gadgets, including everything from early Fitbits to smart bras.

Currently, I'm passionate about the meaning of work and work culture, and I enjoy writing about how managers and employees can communicate better, with or without software. My most recent book is The Everything Guide to Remote Work. I also love a good workplace drama. 

In addition to writing about work, I cover online education, focusing on learning for personal enrichment and skills development. I have a soft spot for really good language-learning software. Although I grew up speaking only English, some twists and turns in life led me to learn Spanish, Romanian, and a bit of American Sign Language. I've studied at the university level, as well as at the Foreign Service Institute, where US diplomats and ambassadors learn languages.

My writing has also appeared in WIRED, the BBC, Gloria, Refinery29, and Popular Science, among other publications.

Follow me on Mastodon.

The Technology I Use

Squeezing every last bit of usage out of the devices I already own is the only way I can tolerate my personal consumption. In other words, I do not own the latest cutting-edge technology. I buy things that will last and try to take care of them.

My life is organized by Todoist, and my notes live in Joplin. Where would I be without Dashlane as my password manager? Probably locked out of all my many online accounts—I have more than 1,000 of them.

When I share my contact information, it's an excruciatingly long list of phone numbers, messaging apps, and email addresses, because it's essential to stay flexible while also remaining somewhat mysterious.

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