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Published: Nov 27, 2019 6 min read
Illustration by Jade Schulz

Welcome to Dollar Scholar, a personal finance newsletter written by a 27-year-old who’s still figuring it out: me.

Every week, I talk to experts about a money question I have, whether that’s “What if I don't have a 401(k)? or “How many credit cards do I need?” As I learn, I share simple ways to improve your financial life… and post cute dog photos.

This is (part of) the 20th issue. Check it out below, then subscribe to get future editions of Dollar Scholar every Wednesday.

Thanksgiving is great, but I'm already looking ahead to Friday: the official start of holiday shopping. Some 165 million people shopped between Thanksgiving and Cyber Monday in 2018, and this year is sure to generate a similar crowd.

But I'm not sure I'll be in it.

I purchased one item on Black Friday last year: a pair of supersoft ankle leggings from Express. They weren't a present; they were for me. 😇 The leggings were discounted from $39.90 to $14.90, which made the price juuust low enough I could justify buying something I wear only when I'm feeling too lazy to put on real pants.

However, that's the extent of my experience with Black Friday shopping. I've never really done the get-up-at-2-a.m.-to-fight-over-a-TV thing. As someone with a relatively normal gift list and a pretty standard budget, is shopping on Black Friday and Cyber Monday worth it? Are there actually huge savings at stake?

According to Michael Bonebright, a consumer analyst with, yes.

"Black Friday is going to 100% save you money if you actually commit," he says. "You don't really have to devote a lot of time to it, though. There are people who gear up for the whole week and go hardcore, but if you give yourself an hour of really focused shopping online, you can basically knock out your entire Christmas list."

In fact, Bonebright recommended pulling out my wallet way before Friday. He said most major stores begin their Black Friday sales on Thanksgiving, and some begin slashing prices even earlier. Clothing prices generally drop the Monday before Thanksgiving, while prices for tech products like video games and headphones don't fall until Thursday.

Bonebright recommended I keep a running list of gift ideas throughout the year and prioritize it before Thanksgiving. He said I should do some research by checking out various retailers' ads, then log onto the computer for a contained, focused period of shopping. (He did acknowledge that some doorbusters are only available in stores.)

Either way, I shouldn't beat myself up if the price drops after I check out.

"Stores design these sales to feel very frantic, and you have to forgive yourself," he says.

Casey Runyan, the managing editor of Brad's Deals, also recommended I chill out.

"So much of Black Friday is focused on those big-ticket items and not as much on the smaller things," she says. "It's definitely worth it to try to shop on these days, but you don't want to assume everything you're seeing is going to be huge savings."

Runyan identified a couple of categories where I'm likely to see the best deals on Black Friday and Cyber Monday. Among them are small kitchen appliances, floor care equipment (like vacuums) and apparel (specifically cashmere and pajamas). For comparison's sake, last year's top deals included video games, Blu-Ray movies, Instant Pots and iPads.

Runyan also said shoppers should check out smaller retailers, too, because the holidays may be the only time they offer discounts. Glossier, for example, is known for running its lone sale of the year over Black Friday/Cyber Monday.

If I miss out on a particular deal, there's no need to panic. Runyan pointed out that most stores continue to offer discounts throughout December. Places like Kohl's and Macy's even participate in price matching, where they'll discount a product if I find it for cheaper elsewhere, or price adjusting, where they'll give me a refund if the cost drops within a certain time period.

Even so, Runyan told me she sticks to a budget so she doesn't get caught up in the inevitable chaos.

"At the end of the day, it's not going to change my life if I got a pair of boots at 75% off," she says.

I can skip waking up early the morning after gorging on turkey. If I research sales ahead of time and target my purchases in certain categories, I can score some significant discounts this week. But I can probably do that next month, too.

"Shopping should be fun. I think it's a mistake to put too much pressure on yourself," Runyan says.

Photo by Peter Ardito