How to Win Cyber Monday in 2020

The 2020 shopping season has been an odd one, for obvious reasons. Learn how to make the best of the deals and offers availabe this Black Friday and Cyber Monday.

Ryan P. Cleary
Spending Hacks
January 26, 2022

Originally posted on November 29, 2020

The 2020 shopping season has been an odd one, for obvious reasons. Retailers have been offering deals all month, with many available online and in-store. While the COVID-19 pandemic has led to a lot of changes, much of our normal advice for Black Friday and Cyber Monday shopping still holds.  

Many of our readers are facing hard decisions about spending, where to buy gifts and managing debt, as well as struggling to find the time to do so. That’s why we created this guide to help you to win Cyber Monday.

Before You Start: Set Expectations

With so much change happening all around us, it’s the perfect time to discuss eliminating presents, agreeing on maximum values and setting expectations with friends and family. It can be an uncomfortable conversation to initiate, but it’s an important one to have and many people are open to the idea of cutting back. 

It’s perfectly fine to not participate in holiday gift exchanges if you’re struggling. It’s far better to send an uncomfortable message than to find yourself paying 20% or more in interest due to credit card debt. If anyone is upset, try to communicate your situation honestly. You aren't alone: up to 54% of Americans take more than a month to pay off an average of $1,054 of credit card debt.

Set a Budget

Before searching for deals, it helps to understand how much you can afford to spend. Get started by asking yourself the following questions.


1. How much debt do you have?

Looking at debt isn’t fun, but it’s necessary. Before you think about anything else, determine how much you owe, particularly on credit cards and high interest loans (>12%). If it will take you more than a month to pay it back, you might be better off only buying small gifts (if you buy any at all). Also consider your long-term debt obligations, such as your monthly payment for student loans, mortgages and auto loans.


2. How much income will you have in the next few months?

If you earn a salary, look at your pay stubs or bank account and use that to estimate your income during the season. If you’re paid hourly or on contract, it’s a little more complicated. Look at how much you earned during the last holiday season and what you expect your schedule to be like, then focus on your low estimates. With the pandemic’s unpredictability, it’s important to estimate on the low end. It’s better to be safe than sorry!


3. What’s your baseline spend?

If you don’t have a budget already, take an hour to check your bills and use this worksheet for inspiration. You need to know your baseline spend so that you can compare it to your income and figure out how much will be left over.


4. How much can you afford to spend?

To figure out this magic number, subtract your baseline spending from your income: (Expected Income) – (Baseline Spending) = Total Budget. 

We suggest reducing that budget by about 10% to account for any forgotten expenses or unexpected emergencies. If you plan to use Black Friday and Cyber Monday to buy gifts, you can write a list of everyone that you plan to buy for. Assign a gift amount for each of them and check that the total amount is less than or equal to your budget: (Total Holiday Budget) <= (Non-Gift Holiday Costs) + (Gifts).

If the total cost of gifts and non-gift holiday costs is greater than your total holiday budget, you need to tweak your numbers and find ways to reduce your spending! To help you with that, here’s a holiday budgeting worksheet from The Penny Hoarder.

Make Sure You’re Getting Deals

Why spend more than you have to? Every dollar saved can be used to pay off debt, to buy gifts or to be put into your savings. You have to be careful, because sometimes "deals" aren't really deals on Black Friday and Cyber Monday. Here are some tools you can use and some places to look.


Price and Deal Tracking Tools

Have you ever wondered if the “sale” on an item is actually what it says it is? Price and deal tracking services can help you to know if there’s a better time and place to purchase an item.



Keepa is ideal for Amazon shoppers, tracking the pricing on over 600 million products. You can look up a specific product, view a detailed graph of historic pricing and even install it as a browser extension. Keepa also allows you to set price drop and availability alerts for specific items.



CamelCamelCamel is similar to Keepa but focusses on Amazon US. With its simpler interface, CamelCamelCamel can be less daunting than Keepa for some users.



TechBargains regularly updates its site with curated deals, sales and coupons. Even though it has “tech” in the name, it also covers plenty of other product types.

Coupons and Promo Codes

Even in the digital era, coupons still offer excellent savings opportunities. Check your local newspaper, retailer ads and websites for coupons and promo codes. There are also specialist sites that offer collections of digital coupons!



RetailMeNot is an industry giant when it comes to couponing and deals. You can search almost any brand or retailer to find online codes and in-store coupons.



Groupon is also a well-known website and like RetailMeNot, it offers online discounts and coupons. But Groupon goes a step further by using geographic location to find the “best” deals in that area.



Honey is a browser extension that compiles online promo codes and applies them automatically at the checkout on retailers’ websites. While Honey is free for users, it collects a small commission from some merchants.

Have a list of interest items and stick to it

Remember that “savings” from sales aren’t really savings if you weren’t already planning on buying an item. It can be easy to spot something at what seems like a good price and to add it to your cart without thinking. These impulse purchases are what retailers like Amazon count on. The problem is that when the item arrives, you can end up experiencing buyer’s remorse.  

The good news is that you can avoid buyer’s remorse by keeping a shopping list of items that you normally buy or have been looking for a good deal on. For example, you could look out for household items that you often buy at the grocery store or a replacement for your dying toaster. If you stick to this list, you can get the best of both worlds, taking advantage of great deals for planned purchases.


The Best Things to Buy on Cyber Monday 2021

There are lots of great deals out there at the moment, but you should still shop around and use tools like Keepa and CamelCamelCamel to make sure that the deal you’re looking at is really a deal. It’s also worth remembering that many of these items go on sale throughout the year, so even if you miss out today, it doesn’t mean that you won’t have another chance to save money in the future.

Apple Products

Apple generally doesn’t offer discounts on its products, and Black Friday and Cyber Monday are two of the few exceptions where you can often find them at a significant discount. Many major retailers offer good deals on the latest models and even better ones on older models that they’re trying to sell to make room for new stock. Walmart, Target and Best Buy all have great deals on iPhones this year.


Electronics (TVs, Tablets and Other Devices)

Black Friday and Cyber Monday have been one of the best shopping days for TVs for years, though quantities are often limited in-store. Instead, we suggest shopping for TVs online.

It’s also worth looking out for smartphones and tablet computers, whether you’re an Android or an iOS user. This year, smart speakers are experiencing significant discounts, so it’s worth looking out for those, too. Just make sure that whatever you buy is high quality.

Gaming System Bundles

If you’re shopping for a gamer, this is one of the best weekends of the year to pick up a new console or some video games. If you’re buying a bundle, be sure to do some research to see how much you’re saving versus buying each item individually. You should also bear in mind that there may be fewer discounts this year due to more people buying consoles during lockdown.


Home Appliances

Large home appliances are often heavily discounted over Thanksgiving, although you can also often find deals during three-day holiday weekends. On Black Friday and Cyber Monday, small appliances are on sale at competitive prices from most retailers.

Travel Deals

Given that the travel industry has taken a major hit during the pandemic, travel companies are more keen than most to run promotions to rebuild their customer base. If you’re planning on travelling next year, spend some time checking both airlines and comparison sites to see whether you can get a better deal from going direct or using an aggregator.


What to Skip on Cyber Monday

It can seem as though every brand under the sun is offering up deals for Cyber Monday, but not all of them are worth your time. Here are just a few of the categories that you’re going to want to skip.


There are great deals on some toys, and if you spot a discount on an item that’s already on your shopping list then feel free to pick it up. Just bear in mind that most of the best toy sales are in December, even though the deals look better than normal this year.



While you can find decent computer deals on Cyber Monday, you can often get a bigger discount if you buy in August during the back to school sales.


We’ve found that the best deals on bedding and linens tend to hit the market in January. If you can’t wait then it’s better to buy on Cyber Monday than to pay full price, but if you can hold off until the new year then you can expect up to 70% off the RRP.



While they’re often discounted on Black Friday and Cyber Monday, mattresses generally have the best discounts on President’s Day and during the summer holidays.

Outdoor Essentials

If you want to get the best deal on your outdoor essentials, try to hold off until Labor Day or the end of summer, when companies are trying to get rid of old stock to make room for their fall and winter inventories. You can also look for “Spring Black Friday” sales, which can often be found at home improvement stores.



You’ll find the best deals on furniture in late December, early January and July. If you spot a particularly good Cyber Monday deal then feel free to take it, but bear in mind that you may be better off holding out for a better one.


While there are plenty of great sales on clothing during Cyber Monday, we advise waiting until later in December. You can often find sales with the same discounts, but they tend to run for longer and so you’ll have plenty of time to try them on and make sure that you’re getting the right sizes. You should also bear in mind that "doorbuster" clothing is often of a poor quality and will wear out quickly. It’s much better to shop at normal clothing stores.


Holiday Decorations

These hit the clearance rack as soon as the holiday season is over, so it makes a lot more sense to stock up then. All it takes is a little forward planning and you can get everything you need for the next holiday almost a year in advance and save a small fortune while you’re at it. If you’re looking for small festive decorations, we love getting creative with our friends at Readers Digest.



For vehicles, the best deals tend to be near the end of the year or during three-day holiday weekends like Labor Day and Memorial Day.

A Final Note: Skip Mail-in Rebates

Always read the fine print on deals. Some small appliances, electronics and other items will require you to fill out a mail-in rebate. This means that you need to pay full price for the item and then mail in the rebate form, along with a copy of your receipt. The paperwork can get lost in the rush around the holidays, and there’s often a time limit to do so. We recommend skipping these where possible and going with a more accessible option.

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