Issue #215: A three-step guide to acing Black Friday

Hi y’all —

Thanksgiving is over a week away, and somehow my inbox is already 99% Black Friday ads. I haven’t even figured out which pies I’m making yet, and retailers want me to think about stocking stuffers? Are they out of their minds?!

I get easily overwhelmed by all the possibilities (of sales, not pies). Every new email with a flashy graphic and a huge discount piques my interest. Before I know it, my Notes-app shopping list is so long I don’t know where to begin — or how to tackle it without going broke.

I don’t want to be a victim of the hype machine, but I also don’t want to miss out on legit deals. How can I evaluate a Black Friday sale and determine whether it’s actually worth it?

Julie Ramhold, consumer analyst at DealNews; Vitaly Pecharsky, head of deals at Slickdeals; and Joanie Demer, co-founder of The Krazy Coupon Lady; helped me create a short guide to sniffing out a good deal. Here are three key steps they recommend.

Putting together a limited list of items I’m hoping to buy on Black Friday and Cyber Monday can narrow my focus. While making this, Ramhold says I should look at all the brand emails and ads for intel on what discounts are to come. Many stores started rolling out their holiday deals in October, so I can already get a feel for whether I have to snag something the first time I see it on sale (or if it’ll likely be OK to wait until later).

On my list, I should also write down what the prices for each item usually are. Ramhold says I can't always trust that slashed-through price on an item's webpage — some retailers will inflate the list price right before big sales so their discounts seem deeper.

If I want to get really serious, Pecharsky says to do a little background research on the merchants that carry my most-desired items, paying attention to what day they typically update their pricing, whether they offer coupons, how they cycle through prices and whether they price-match. (More on this in a sec.)

The goal of doing this homework upfront is to save me time and anguish on the back end — when I see a deal pop up in the coming days, I won’t have to frantically start Googling for info. I can simply pull up my list and I'll instantly know whether the advertised price is a “good” one.

“One day your jeans will be $20, then $15, then $20 again, then $10," Pecharsky says. "You will know at which price to strike.”

When evaluating a sale, I’ll want to keep an eye out for retailers that offer holiday price match guarantees. Target has a nice one: According to its website, if I buy something from Target after Oct. 22 and then Target cuts the price “on or before” Dec. 24, I can request a price adjustment.

This can give me the peace of mind to pull the trigger on a purchase knowing that I’m getting the best price possible. It also means I may not even need to wait until Black Friday to buy an item: If a store has a price match guarantee and it’s already boasting its quote-unquote “lowest prices of the season,” that's a pretty good bet that it won’t drop further.

Even if a store doesn’t have a price match guarantee, Demer points out that it might have an extended return window, which would allow me to swap the item I bought for a “new,” cheaper one.

Of course, DealNews, Slickdeals and the Krazy Coupon Lady all have years of archives and research on every deal imaginable, and I’d be remiss if I didn’t encourage you to check them out.

But beyond that, Ramhold recommends the website Camelcamelcamel, which provides price drop alerts and price history charts for Amazon products. Google Chrome has a price tracking feature that will notify me when things go on sale. And Demer says some sites, like Walmart and Wayfair, have pop-ups or callouts with info like “1,000 people bought this yesterday” or “this is in 100 people’s carts” — signs that other customers also think something is a solid deal.

There are smaller, sneakier ways to use technology to score discounts, too.

Ramhold suggests “favoriting” items that I’m considering buying, or even going so far as to put them in my cart a few days before checking out, because retailers (or the sellers themselves, if you're buying on a site like Etsy) will often email me a promo code to get me over the finish line. On Amazon, I may want to add a desired item to my wishlist and use my Alexa to let me know before it goes on sale.

These aren’t ironclad guarantees, but “it’s definitely worth padding out the different shopping methods you have to see if you can ... jump on those deals before they sell out,” Ramhold says.

It’s possible to save big bucks on Black Friday and Cyber Monday, but I have to be smart and methodical about it.

Part of this is knowing that some retailers simply don’t do sales: For example, Apple is notorious for not running traditional Black Friday sales with discounted appliances, and Pecharsky says it’s hard to save money on Weber grills. On the flip side, he says Old Navy, Under Armour, Kohl’s, Macy’s, Home Depot and Lowe’s tend to boast frequent sales. Demer says Black Friday can be a great opportunity to get a deal on Dysons and AirPods specifically.

Preparation is crucial, and so is self-control.

“You should only buy something that you actually need — you shouldn’t buy an item just because it’s on sale,” Demer says.

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Actress Anya Taylor-Joy confessed to British Vogue recently that she’s obsessed with vintage shopping — or, more accurately, vintage splurging. “Talking about dumb purchases: the amount of velvet vampire capes that I keep buying and trying,” she said. “Honestly, every time I’m about to go out, I’m like, ‘Maybe today is the day for this cape?’ But it’s never the day.” 🧛

See you next week.

P.S. What’s your strategy for deciding whether a deal is “worth it”? Do you have a favorite SpongeBob quote? What’s the strangest piece of clothing you own? Send feedback to julia@money.com, please and thank you.

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