The Ultimate Guide to Understanding Cyber Monday

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Updated: October 15, 2019
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The Ultimate Guide to Understanding Cyber Monday

Holiday season in America kicks off with Thanksgiving and runs through New Year’s Eve. The second the turkey plates are piled in the sink, the race to secure the hottest Christmas and Hanukkah gifts is on. The average American will spend $700 on holiday gifts this year, totaling more than $465 billion, the National Retail Federation estimates.


Most retailers, both on the ground and in the cloud, depending on sales from the last 4-6 weeks of the year to make up the majority of their annual revenue. The difference between ending the year in the red (in debt) or in the black (with-profits) is often decided by holiday sales. It’s in their best interest to slash prices and offer deals to get customers in their doors or on their websites. Retailers will put their best sales-forward on the biggest holiday shopping days of the year, known as Black Friday and Cyber Monday.


The Difference Between Black Friday and Cyber Monday, Explained

Black Friday takes place the day after Thanksgiving and is the biggest brick and mortar shopping event of the year. The phrase Black Friday came out of Philadelphia back in the 1950s and soon became a national phenomenon. Door-buster deals and early bird specials have people waking up in the wee hours of the morning and standing in long lines, sometimes overnight, in order to jump on the best deals on the season’s hottest gift ideas. If you enjoy the “thrill of the hunt” when it comes to shopping, then there is no bigger challenge than Black Friday. The tone of the day can be rather aggressive with people fighting over items and rushing through the store to obtain everything on their list before items sell out. Big box stores will offer huge savings on a selection of hot holiday items in order to entice hungry buyers into their shop where they will presumably also buy a lot of other items that are not on sale as well.


If the high stakes adrenaline and early morning antics of Black Friday isn't your cup of tea, then Cyber Monday is here to save the day. Imagine this instead, you wake up at a reasonable hour, pour yourself some coffee and sit down in front of your computer in your pajamas and shop for amazing deals to complete your Christmas gift list in peace and quiet. When is Cyber Monday? Cyber Monday always takes place on the first Monday after Thanksgiving. For the year 2019, that day is December 2nd. Since all major brand stores also have online shops the lines between the two holidays are blurred into one week-long shopping event. Being able to shop online gives you greater access to shop multiple stores and find the best deals through comparative pricing.


Tips For Finding The Best Deals On Cyber Monday

Shopping online makes life easier but there are still a few ways you can make it even better. Here is a short list of tips and hacks that will save you, even more, time and money this year.


Stalk Your Favorite Stores

Cyber Monday deals are promoted well in advance. Take advantage of that fact by stalking your favorite brands on social media. Stores will talk about their upcoming deals on Facebook, Twitter, and Instagram. You can also sign up for the email list of your favorite stores on their websites and get deal alerts sent right to your inbox.


Make A Plan

Make sure to have your holiday gift-giving list made out and ready to roll. Group your items by which online shop you’re most likely to find them. You can also list them online deals you know are coming up. Google sheets are a great place to store and organize your list for free and then you can access it easily from your computer, tablet or phone. If you want to save even more time on the big day, make sure that you have a user account set up on all the websites you’ll be shopping at. Lag time is a huge pain point on Cyber Monday so this will make sure you have a smoother transaction.


Get Started Early

While you won’t need to wake up crazy early or spend the night sleeping outside your favorite store in a hold-out line, you do need to get started reasonably early if you have any hot-ticket items on your list. Online stores have a larger capacity but they still run out of stock on popular items eventually. Make sure to hit the high dollar items where you get the biggest savings first thing.


Real-Time Price Comparison

Get real-time price comparisons that show up on the page your shopping from to make sure you’re getting the best deal. You can download free toolbars and apps that help you do this. A free google chrome add-on you can use is called Shoptimate.

Stack Your Deals

Many online sites allow you to stack your deals, meaning you can still use coupon codes at checkout even on Cyber Monday. You can find coupon codes at sites like and Another great Google chrome plugin is called Wadav.


Stock Up On Discounted Gift Cards

Sites like and allow you to buy discounted gift cards for your favorite stores. Stack your deals like a pro buy scoring a Cyber Monday deal, adding a coupon code at checkout and then paying with a gift card you got for 30% off its face value.

Get Rewarded for Shopping

Want even more savings or rewards for shopping on Cyber Monday? Use a credit card with a killer cashback or reward point system to complete your purchase. For security reasons, you should not use your debit card when making online purchases. Choose a credit card with a low-interest rate and a great reward system. Make sure not to overspend because you’ll want to pay off that holiday balance as soon as the first bill arrives.