Emails advertising Black Friday Month and early access to holiday shopping sales were delivered the day after Halloween, creating urgency and confusion about what the holiday shopping season playbook should look like this year.  It seems that in the turn of our front porch decor from ghouls to pumpkins signaled to retailers this year to kick off the holidays. 

Ahead of a news report I’m giving on Cyber Monday deals, I’ve been researching what to expect this season and seeing a strategy for you and yours to bring good cheer – and savings. 

The holiday shopping trends look strong

Even with climbing costs and economic pressures, holiday spending is projected to hit at or close to new highs this year.  Strong demand means that there will be pressure on supplies and fewer incentives for retailers to create deep discounts this holiday season.  According to Deloitte’s Black Friday-Cyber Monday survey, consumers will spend 13% more than last year.   Overall holiday retail sales are estimated to climb more than 3% from last year to $957 billion, the National Retail Federation says. Many consumers will do most of their shopping during Black Friday and Cyber Monday. 4 in 10 expect to finish their shopping on Cyber Monday.

This means a little planning and strategizing will help ensure your holiday wishlist is checked off with ease and savings. Here are some ideas:

holiday shopping ai

1. Make a list and check it twice with AI’s help

Experts suggest creating a shopping list ahead of door-buster season’s official kick-off.  This allows you to get organized, research prices and avoid temptation of impulsively purchasing those deals-of-the day with their irresistible prices.  Retailers count on this.  So, having a list ready with some researched prices will help you know if you’re getting a good deal.  

I like leaning on AI shopping assistants (see below) and these from the NYT with deal alerts to do some of this research for me, including price comparisons. 

For this example, you would type something like: “Act as a shopping assistant. I am looking for a coffee bean grinder for French press that is well reviewed. It should cost no more than $200.”

NY Times

2. Ensure you but at the best price with Google Price Tracking

Google has installed new price tracking features in Chrome that allow you to track prices in on any device to ensure you are buying at the best price across the web. Here’s a great tutorial on how to do this and how to disable the feature once you’ve made your purchase. If you have an iPhone, you can enable the feature by:

Google has several price tracking features including price tracking on a site, finding discount codes and managing a shopping list. Here is a quick link on its various features.

3. When to buy? Black Friday or Cyber Monday?

That depends on how hot your items are and what kind of discount you’re seeking. At this point, most retailers offer deals both in store and online on both major shopping days, and the weekend in between.  It is unlikely an item will be further discounted on Cyber Monday.  Your best strategy is to explore sales starting Black Friday throughout the weekend.  If you find an item you desire within your price point, scoop it up! There are no guarantees it will be in stock or at a lower price days later.  

Black Friday deals are usually based on limited quantities available for a short time. Big name retailers are savvy about changing up promotions – so what you see on sale on Black Friday may not be available on Monday.  Though you will see a mix of previous and new deals everyday, culminating on Cyber Monday. 

Be sure to check price matching promises different brands like Peloton and Dyson offer. Don’t forget to read the fine print on whether discounted holiday deals apply to their matching offer. 

4. What not to buy during the holidays

Experts say that Black Friday deals can offer bigger sales on big ticket items like flatscreen TVs, refrigerators, computers and other items.  On Cyber Monday you can see better savings for small appliances, toys, clothing and beauty.  If you’re looking to make a purchase for these before the end of the year, this is the perfect time to it. There is little benefit to waiting for deeper discounts, as you will run the risk of an item selling out or its price remaining static. The overall advice for the season: if you find your desired item and see it a good price, get it.

Gaming consoles, electronics and high-demand toys can often sell out quickly online but can be available in stores.  Be sure to check both. Using a retailer’s app to check in-store availability can be advantageous, as is curbside pick up. 

If you have the ability to wait and push-off purchases, know that furniture and mattresses are heavily discounted over President’s Day. If you’re in the market for a TV, Super Bowl sales often can match – or beat – holiday deals. So you can save yourself the stress, for these items, if on your wishlist.

Happy holidays!