How to Cyber Monday Shop Like a Boss

‘Tis the season for unabashed consumerism….fa la la la…oh, hi there!  If you’re like me, you may have departed with a significant portion of your hard-earned moo-lah to take advantage of great Black Friday deals today.

BUT if you’ve still got some shopping left to do, particularly online shopping, let me share my secrets for how to get the most bang for your holiday-buying buck.

  1. Fill your online cart, sign in, then leave it for another day.

The first step in making sure you get the very best deals when online shopping is to have some patience. A lot of retailers now use a marketing strategy called “abandoned cart re-capture,” a practice whereby the retailer will email you about items you left in your cart — and often include a coupon to further sweeten the deal.


If there are a few items that you have your eye on, go ahead and fill your cart, and proceed to checkout through the step where you either sign in or provide your email address. Then, simply close the tab on your browser.

If you’re lucky, within anywhere from 30 minutes to 24 hours, you may receive some goodies in your inbox. I’ve seen brands as varied as Kate Spade to Dick’s Sporting Goods use this tactic; you just never know when it might pay off. Alternately, if you’re not quite sure what you want to buy yet, but you do at least have a specific retailer in mind? Many retailers will give you a one-time use coupon code for subscribing to their email list.

  1. Shop through a rewards portal.

The other real advantage to filling your cart in advance is that, so long as you have cookies enabled on your browser, the items should still be there if you open the retailer’s website in another tab or window. This makes it very easy to shop via a shopping portal for your favorite rewards-earning credit card or travel loyalty program.

For example, I made a purchase today at Petsmart. But first, I went to the Southwest Airline Rapid Rewards Shopping website, logged in, and did a quick search for the retailer I wanted.


And what did I find but the ability to earn 4 points per dollar spent, so long as I launch the retailer’s site through their link. (If you have an Adblock software on, you may want to disable it first.) Note that these bonus points are in addition to any points that you may get by spending money on your credit card — so if I made a $20 purchase, I could end up with 80 RapidRewards points from the shopping portal and 20 Chase points for using my Chase Sapphire Reserve card, all on the same transaction.

One final note on this: a lot of shopping portals like this have recently changed their terms of service to say that you won’t receive points if you use a coupon code on the transaction. In my experience, though, you often still do. So go ahead and give it a try anyways, just don’t be mad if it doesn’t work out if you’re also using a coupon code.

  1. Coupon codes are your friend.

And speaking of coupon codes, these are like the cardinal rule for saving money online. Even better, the process of finding coupon codes has gotten much easier recently, with the invention of browser add-ons like Honey, which will automatically detect when you’re on an e-commerce checkout page and attempt to try any coupon codes they have in their database for that site.

Using Honey usually picks up the biggest codes, but if you’re not seeing any good discounts, I recommend also checking on RetailMeNot. And of course, don’t forget to add in any of the one-time coupon codes you got during step one.

  1. Do what it takes to get shipping for free.

I’m pretty much of the opinion that you should never actually pay for shipping these days. It’s just too easy to get it for free.

For everyday items, there’s always Amazon Prime, which not only gives you free shipping, but also usually gets you those shipments within two days. Between the free streaming shows, free Cloud storage, and free shipping benefits, our annual Prime membership more than pays for itself.

For sites other than Amazon, though, you may want to see if you’re eligible for free ShopRunner services through an existing credit card. AmEx cardholders in particular can get access free 2-day shipping at more than 140 retailers through the service.


If you don’t have either of these services, be on the lookout for the “free shipping threshold.” Often times, sites will offer free shipping once you reach a certain amount in your shopping cart – say, $50. Shipping may cost you anywhere from $5-$15, on average. So if you find yourself with $40 in your cart that will require $10 in shipping costs, you may consider getting yourself a “freebie” item to make up the deficit between your cart and the threshold. The cost to you will be the same either way.

Finally, if none of the above works, but the online retailer has a brick-and-mortar presence in your area, you may want to see if they offer a “ship-to-store” option. At sites like Wal-Mart and many others, they’ll waive your shipping fees if you’ll go pick it up in person, rather than having the item delivered to your house.

  1. Use Honey or other sites to get cash back on your purchases.

Once you’ve made your purchase, you’re all done, right? Wrong. Those same browser add-ons that helped you find a coupon code may also give you cash back for clicking on them during the checkout process. Honey, for example, gives you between 1%-11% cash back on most purchases in a currency they call “HoneyGold.”  You can redeem HoneyGold for Amazon gift cards once you’ve accumulated a decent amount.

So there ya have it. One final thought, though: remember that every time you make a purchase, you’re voting with your dollars. Across all my Black Friday shopping, I voted not to endorse any businesses that does business with the Trumps, and participated in the #grabyourwallet boycott. I’d encourage you to do the same.

Author: Mrs. Millennial

I'm Whitney, writer of Mrs. Millennial. While I've got an advanced degree and a job in the tech industry, I'm usually happiest in my kitchen, garden, and home, or else on a crazy travel adventure. I hope you enjoy my recipes, home improvement tips, travel stories, musings, and more. You can also see what I'm up to in my professional life at Need to reach me? Shoot an email to whitney (dot) magnuson (at) gmail (dot) com.

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