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  • Writer's pictureRyan P. Cleary

How to Win Cyber Monday in 2020

The 2020 shopping season has been an odd one. Retailers have been offering deals all month with many available online and in-store. While different than a normal year, 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, managing debt, and finding the time to do so. We’ve put together a guide to help you win Cyber Monday.

Before You Start: Set Expectations

Now is the perfect time to discuss eliminating presents, setting maximum values, and setting expectations with friends and family. This can be an uncomfortable conversation to initiate, but this year many people are open to the idea of cutting back or agreeing on limits.

It is also acceptable to not participate in holiday gift exchanges if you are struggling. It is 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! Here are some steps to follow:

1. How much debt do you have?

Looking at debt isn’t fun, but it is 100% necessary. Before you think about anything else, determine how much you owe- particularly on credit cards and high interest loans (>12%). If this amount will take more than a month to pay back you may be better off focusing on paying it down and only buying small gifts (if you buy any at all). Also consider your long-term debt obligations- what is your monthly payment for student loans, mortgages, auto loans, etc?

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 are paid hourly or on contract, this will be more challenging. Look at how much you earned during the last holiday season, what you expect your schedule to be like, and focus on your low estimates- with COVID-19's unpredictability it is important to estimate on the low end.

3. What is your baseline spending?

If you don’t have a budget already, take an hour to check your bills and use this worksheet for inspiration.

4. How much can you afford spend?

Once you know your income and your baseline spending, it is easy to figure out how much you can spend!

To find that number all you have to do is subtract baseline spending from income: (Expected Income) – (Baseline Spending) = Total Budget

We suggest reducing that budget by about 10%, just to account for any forgotten expenses or unexpected emergencies.

If you plan to use Black Friday & Cyber Monday to purchase gifts for the holidays, you can record a list of all friends, family members, and co-workers who you plan to buy for this holiday. Assign a gift amount for each of them- the total of these amounts should be less than or equal to your gift 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 places to reduce your holiday spending!

Here is 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, use for gifts, or be put into savings. You have to be careful, because sometimes "deals" aren't really deals on Black Friday and Cyber Monday. Here are some tools and places to look:

Price and Deal Tracking Tools

Have you ever wondered if the “sale” on an item is actually really a sale? Price and deal tracking services can help you know if there 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 a browser extension. Keepa is also allows you to set price drop and availability alerts for specific items.


CamelCamelCamel is very similar to Keepa, but is focused primarily on the US Amazon store. With a simpler interface, CamelCamelCamel may be less daunting than Keepa for some users.


TechBargains updates their site with deals, sales and coupons with a team constantly curating the site. Even though the site name says “Tech,” many other types of products are covered.

Coupons & 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 many sites online offering collections of digital coupons!


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


Groupon is also well known. Like RetailMeNot, it offers online discounts and coupons. 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 retailer websites. While Honey is free for users, it does collect a small commission from some merchants.

Have a list of interest items going in 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 see an interesting product that you can picture yourself owning with a seemingly good price and add it to your cart without thinking. This is what retailers like Amazon count on: impulse purchases. When the item arrives in 1-2 shipping days, you may have some buyer’s remorse.

The good news is that you can avoid this by keeping a shopping list of items you normally buy or have been looking for a good deal on (household items you often buy at the grocery store, a new tablecloth because your old one is showing its age, a replacement for your dying toaster, etc.). Using this list you can have the best of both worlds: great deals and planned for purchases.

The Best Things to Buy on Cyber Monday 2020

There are lots of great deals to find, but always make sure you shop around a little online and use tools such as Keepa and CamelCamelCamel to make sure it really is a deal. Something else to remember is that many of these items go on sale throughout the year so even if you miss out today, there will be other great sales.

Apple Products

Apple is not known for offering discounts on products; Black Friday and Cyber Monday are two of the few sales where you can find them significantly discounted. Many major retailers offer good deals on the latest models and great deals on older models they are trying to move off the shelves. 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 long been one of the best shopping days for TVs, though quantities are often limited in-store and it is difficult to catch one of the doorbusters. Instead, we suggest reviewing TV prices online and looking up non-doorbuster sales. Tablet sales are similarly great to keep an eye our for. Smartphones are heavily discounted this year, whether they be iPhones, Samsung, or Google. Almost anywhere you look will have a good or great deal running. Make sure what you’re buying is actually of good quality. This year, speakers are reportedly one of the better buys for Cyber Monday compared to other electronics.

Gaming System Bundles

If you have a gamer you’re buying for, this is one of the best weekends of the year to pick up a new console with some games. Do some research on the bundle though. With new consoles being released, there may be some great deals but due to many people buying consoles during lockdown they may not be as discounted as prior years.

Home Appliances

Large home appliances often are heavily discounted (though three-day holiday weekends are also great times to buy them!) Small appliances are on sale at very competitive prices nearly everywhere.

Travel Deals

Check airlines and online sites for some very competitive pricing if you know you'll have to travel next year.

What to Skip on Cyber Monday

While there may be tempting looking offers in the ads, certain product categories aren't worth you time.


There are great deals on some toys and if you see an item already on your shopping list it may be worthwhile to pick it up. However, most of the best toy sales are December. With that said, the deals do look better than normal this year.


While you can find decent deals on Cyber Monday, you may have better luck purchasing on in August during back to school sales.


While tempting, the lowest prices on bedding and linens appear in January. If you can hold off until then sales tend to hit as low as 70% off.


Mattresses are best priced on President’s day sales and during the summer holidays.

Outdoor Essentials

These tend to be best priced right near the end of summer or during Labor Day sales. Other options are “Spring Black Friday” sales which many home improvement stores run.


Furniture tends to be best purchased in late December or in January during this time of year and in July.


While there can be many great sales, we advise waiting until later in December. Often you can find sales that are close to the same discounts plus you'll have time to try clothes on and make sure you are getting the right sizes. Another consideration is that many "doorbusters" are of poor quality and will wear out quickly. We strongly suggest shopping exclusively at normal clothing stores for these.

Holiday Decorations

These will hit the clearance rack immediately after the holiday season is over. Stock up then! If you want small festive decorations we love getting creative with our friends at Readers Digest.


The best deals tend to be near the end of the year or during three-day holiday weekends (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 may require you to fill out a mail-in rebate. This means that you must front the cost of purchasing the item and then remember to mail the rebate form in along with a copy of your receipt. There often is also a time limit to do so. During a crazy holiday season this may not be the best option.

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