At the turn of the century, Cyber Monday wasn’t even a gleam in the eye of the retail PR team that would create it, and the person commonly credited with coining the phrase was still in college.
Today, Cyber Monday is the United States’ biggest online shopping holiday. Every year, on the Monday after Thanksgiving, tens of millions of deal-hungry holiday shoppers converge on retail websites big and small to take advantage of time- and quantity-limited sales.
It’s no accident that Cyber Monday comes on the heels of Black Friday, its older, brick-and-mortar counterpart. The twin shopping holidays complement each other perfectly. In recent years, the lines between the two have blurred. Many Black Friday deals are available online, though in-store-only opportunities persist. Meanwhile, Cyber Monday is frequently an extension of marathon “Black Friday week” or “Cyber week” promotions. Shoppers have more choice – and more chances to save – than ever before.
Capturing the best Cyber Monday deals takes work though. In this post, I’ll outline some tips to help you plan for your big Cyber Monday shopping bonanza. I’ll share some expert-level secrets that can help you snag great deals before sales end or supplies run out – while staying safe during the worst time of year for identity theft and computer fraud.
How to Prepare for Cyber Monday
You can get started on some of these items weeks or months before Cyber Monday, even before Black Friday deals begin appearing if you’re so inclined. The earlier, the better.
1. Look to Past Years’ Sales for Guidance
Retailers don’t exactly recycle Cyber Monday deals from year to year, largely because consumers are so fickle and product life cycles are too short. But you can reliably predict the types of products on which you’ll find the best deals. Electronics, clothing and apparel, and cosmetics are all Cyber Monday stalwarts.
For more specific guidance on retailers’ wheelhouses, check out prior-year Cyber Monday flyers. Just Google the retailer’s name and “Cyber Monday [year] flyer.” Look for flyers on retailers’ official websites. Screenshotted flyers on shopping blogs and discount aggregators are more likely to have errors or inaccuracies, as retailers sometimes release multiple versions of flyers before Cyber Monday hits.
With access to prior-year flyers, you can begin to compile a tentative Cyber Monday shopping list. More on that below.
2. Bookmark Your Favorite Retailers’ Websites
Bookmark each useful retail website as you go. If you’re shopping for multiple people, you’ll probably accumulate a pretty long list of options. Create a separate Cyber Monday or “online shopping” folder to sequester your retailer bookmarks.
For memory’s sake, I customize my bookmarks’ names with words or phrases reminding me why they’re useful – for instance, my Fry’s Electronics bookmark says, “PC accessories and home entertainment.” I could just as easily use the same label for a Best Buy bookmark, of course. For general-interest retailers, such as Walmart and Target, the actual store’s name might be better.
3. Follow Your Favorite Retailers on Social Media
The best way to stay up-to-date on late-breaking retail promotions at any time of year is to follow your favorite retailers on social media.
This strategy is especially fruitful during the holiday shopping season and just after, when clearance sales are common. (Fun fact: The best time of year to shop for a new TV is actually January, when retailers rush to offload their remaining stock of prior-year models that didn’t sell during the holidays.)
Twitter is probably the best venue for information about time-limited deals and sales on specific products or product categories. I recommend creating a Twitter list specifically for the retailers you follow. It’ll help you filter through the noise and stick to business.
Facebook is better for highly targeted, hopefully relevant offers. Once you follow a retailer’s Facebook page and browse their website with cookies enabled, you’ll likely begin to see promoted Facebook ads for products similar or identical to the ones you’ve already scanned through. If you’ve never experienced this phenomenon, it’s a bit off-putting at first, and it can really threaten your shopping budget if you don’t maintain discipline. But it’s also an amazing time-saver that might just curry favor with your gift recipients.
Pinterest and Instagram are great for visual shoppers who want to see certain types of products in context before they buy, but I don’t use them much for deal-hunting. They’re better for generating useful ideas to pass along to recipients.
4. Sign Up for Retail Newsletters
This old-fashioned strategy is no less useful than following your favorite retailers’ social media profiles.
It costs nothing and takes 30 seconds of your time (at most) to sign up for an email newsletter. Do it for every retailer you’re seriously considering patronizing this holiday season.
Being a newsletter junkie has an obvious downside: lots of promotional emails, especially around the holidays. Your email client probably allows you to create a special folder to keep them sequestered, though, or uses an automatic filter anyway. Gmail shunts all emails deemed promotional into its Promo folder, keeping them out of your main inbox. Set aside a few minutes every couple of days to sort through your promotional emails en masse.
As Cyber Monday approaches, your newsletters will begin touting this year’s top deals. Some newsletters include or link to actual Cyber Monday flyers, so they’re a good centralized planning resource.
5. Make Your Holiday Gift List as Early as Possible
Use your social follows, newsletter memberships, and old-fashioned research skills to build your holiday gift list as early as possible.
Rather than manually monitor websites for updates, you can use an app that automatically alerts you when a specific page’s content changes. App quality varies, and they’re sometimes harder to work with than they sound, so do your research before you select one. The best apps, like visualping.io, generally aren’t free, though they may follow freemium models that allow a limited number of alerts before the pricing structure kicks in.
However you build your list, make sure you have alternatives in place for popular products. If the exact item you want is out of stock or beyond your price range, you’ll want to have a Plan B. Ditto for retailers: You’ll want to know which retailers sell which products, so that you can easily switch if it’s out of stock at your preferred vendor.
6. Stock Up on Discounted Gift Cards
Don’t wait until the holiday shopping season kicks off to start stocking up on discounted gift cards.
The best places to find cut-rate gift cards from your favorite retailers (rather than paying full price in the grocery store checkout line) are online clearinghouses like Raise and CardCash. Both stock physical gift cards and online coupon codes from hundreds of popular retailers, including some of the biggest names in the business. DealsPlus focuses more on online coupon codes, again for some of the biggest U.S. retailers around. Rakuten Rewards, formerly known as eBates, is another fantastic resource that claims to deliver discounts up to 40% at thousands of online stores.
Discounters’ claims notwithstanding, discounting rates generally correlate inversely with retailer popularity. Major home improvement and electronics retailers typically have lower discount rates than niche apparel retailers, for instance. If you’re planning to patronize smaller outlets on Cyber Monday, you can probably find excellent deals on cards from low-key retailers: 20%, 30%, 40%, and even more in many cases.
Before you lock in your gift card purchases, make sure you’re allowed to use them in combination with other offers and that there aren’t any other onerous restrictions to worry about (like prohibitions on using your discounts on Cyber Monday). Coupon stacking, or combining multiple gift cards or coupons to magnify discounts on the same item, is a fantastic and simple way to stretch your holiday shopping budget further. Plus, you don’t want to make it all the way through the checkout process only to discover that your discounted coupon code doesn’t apply.
If you realize at some future point that you’ve gone overboard with your gift card buys, check out our article on what to do with unwanted gift cards and learn how to cut your losses.
7. Research Shipping Policies and Fees
Many retailers offer free shipping on Cyber Monday, even if they don’t at other times of year – “free shipping on all orders” is a very powerful temporary selling point. Unless you’re shopping for products that aren’t available on free-shipping sites, I’d recommend avoiding retailers that charge for shipping on most or all orders.
If your preferred retailer offers free shipping on orders above a certain size, determine whether it’s feasible to spend that much (meaning, whether you would have spent that much anyway) before you place your order.
8. Research Return Policies and Fees
Before you buy, look into retailers’ return policies and fees. Most clearly state their return policies on their websites, but it’s worth calling customer support if there’s any confusion at all.
Return shipping charges and restocking fees really eat into refunds or store credits, leaving less left over to rectify the mistake and fund the rest of your holiday shopping.
They also distort consumers’ decision-making processes. I recently purchased several pairs of bike shorts from a New York State bike shop’s online store in preparation for a long-distance bike ride. Two pairs were a size too large; I saw chafing and discomfort in my future. I looked up the shop’s return policy for online sales and, lo and behold, I’d be responsible for return shipping charges – just under half the total cost of each pair. I decided the added expense wasn’t worth it and held onto the shorts.
Nothing disastrous happened, but I definitely felt the difference by day four. Had return shipping been free, returning the shorts would have been a no-brainer.
Shopping on Cyber Monday
Once your favorite retailers announce the year’s Cyber Monday deals, set these strategies in motion.
9. Set a Firm Budget
The first rule of Cyber Monday shopping is simple: Stick to your budget.
Figuring out how that budget should look in the first place is another matter. The L.A. Times offers some general guidelines on holiday spending: $20 and up for siblings and cousins, $25 and up for nieces and nephews, $20 and up for parents and in-laws. But there’s obviously a big difference between spending $25 on a nice new tableware set for your mother-in-law and shelling out $200 (or more) for a new table.
Your broader financial picture plays a crucial role too. As the Times itself notes, paraphrasing consumer spending blogger Leah Ingram, “A surgeon earning six figures will have a different budget than an elementary school teacher.”
Speaking with The Street, finance executive Elle Kaplan recommends sticking to the 20-30-50 rule: investing 20% of your net take-home pay “in yourself,” reserving 50% for essentials (like groceries), and spending the remaining 30% on “fun” discretionary purchases – including holiday shopping.
Whatever you decide you can spend, keep your actual holiday shopping budget on the conservative side. Try as you might, there’s a good chance you’ll overshoot your projected spending. That hurts less when you have room to spare in your budget.
10. Use a Price Comparison Tool
Don’t pull the trigger on a Cyber Monday purchase until you’re (reasonably) sure you’re getting the best possible deal.
Use a price comparison app or toolbar (if you’re shopping on a desktop) to see which retailers are offering the lowest prices on the big shopping day. One of the best-regarded is PriceGrabber, but plenty of other legitimate options exist, and many have other features specifically designed to help shoppers save.
You can also check consumer blogs and deal aggregation websites. Remember that these sites aren’t necessarily updated instantaneously when new sales hit or old sales go away – you always want to confirm with the retailer itself, especially when deals seem too good to be true.
11. Create a Spreadsheet With Sale Information and Links
If you’re a “spreadsheet person,” this is an evergreen strategy that can save you serious money on online shopping throughout the year.
Create a spreadsheet with site descriptions, links to interesting products (or examples thereof), price ranges and comparisons with competing retailers, discounts and promotions (including Cyber Monday sales), shipping policies, and other pertinent information. Update it whenever you come across a new retail website. In no time, you’ll have an encyclopedic resource customized to your online shopping preferences (and your holiday gift recipients’).
12. Avoid Sites With Poor Security Practices
Don’t gamble with your identity. Stay away from retail sites with lackadaisical security practices. Two key practices stand out in particular: SSL certificates and Verisign domain protection.
SSL is an encryption protocol that renders it much more difficult (though not impossible) for bad actors to steal payment card information and other personal data during the payment process. Look for “https” at the beginning of the site’s URL. You should never enter payment card information on non-“https” pages, period.
Verisign provides site administrators with a modicum of protection against hacking attacks and malware. Like SSL, it’s not foolproof, but it helps. Sites without Verisign protection are vulnerable to man-in-the-middle attacks, spoofing, and other types of cybercrime.
If you don’t already, consider using a web browser that can identify potentially compromised websites. This protection isn’t foolproof – my Chrome browser is overzealous, occasionally returning false positives that prevent me from accessing legitimate sites. But better safe than sorry.
If you’re shopping on a mobile device, download your favorite retailers’ verified apps too. Apps downloaded from a legitimate source, such as the Google Play Store, are much less likely to be compromised.
13. Rise Early or Stay Up Late the Night Before
Most retailers run Cyber Monday sales for at least 24 hours. Many begin them before Cyber Monday itself, or fold them into longer “cyber weeks” or Black Friday weekend sales.
If you’re shopping for common products for which demand is measured, you probably don’t have to get up at (or stay up until) 1am to snag the best deals. However, if you’re worried about items running out of stock – a common problem on the weekend after Thanksgiving – then you’ll want to shop as early as practically possible.
When you shop at inconvenient times, you may also capture deals that you’d otherwise miss. Some retailers are famous for running hourly Cyber Monday sales, each focusing on a different, deeply discounted product category. Want 50% off the latest Sony UHDTV? You might find yourself groggily entering your credit card information at 3:15am on Cyber Monday. The good news is that most retailers release their hourly shopping lists in advance of Cyber Monday, so you can plan accordingly (and hopefully stock up on sleep).
14. Shop in Incognito or Private Mode
Do your actual shopping anonymously(ish) using your browser’s private or incognito mode. This isn’t a foolproof way to mask your identity to retailers, but it can render you eligible for deals not available to someone with your browsing or purchasing history. (Yes, retailers know way more about you than you realize.)
Using your browser’s private mode reduces your exposure when you shop at inappropriate times – like, ahem, at work. Even if it doesn’t directly save you money, avoiding your boss’s ire (and potential disciplinary consequences) is obviously a good thing in the long-term.
If you’re really concerned about privacy, opt for a virtual private network (VPN) or torrenting platform instead. You may have to pay for it (my VPN through NordVPN costs about $70 per year), but it’s well worth the cost for a variety of reasons that I won’t get into here. You can learn more about the benefits of VPNs in our post on the subject.
15. Resist Upsells and Add-Ons
Remember your budget. Always remember your budget.
Successful Cyber Monday shopping requires discipline in spades. No matter where you shop, it’s inevitable that you’ll be swamped by offers to add complementary products to your order or upsold to premium versions – for a premium price, of course.
Unless you were planning to purchase add-on or upsold products anyway, ignore these entreaties, tempting though they may be. This is the single easiest way to avoid exceeding your preset holiday shopping budget.
16. Use a Rewards Credit Card or Cash Back App
The right rewards credit card can significantly reduce the cost of your holiday shopping campaign.
In this instance, though, cards with rotating rewards categories really shine. Every quarter, Chase Freedom Flex pays 5% cash back on up to $1,500 in net purchases in one or two rotating categories – up to $75 in bonus cash back per quarter. Department stores routinely appear in the mix, and the category is broad enough to encompass many of Cyber Monday’s most popular retailers. Amazon and Walmart purchases occasionally make fourth-quarter appearances in the Freedom Flex rotation too.
I keep a Freedom Flex card on standby for eventualities like this. With no annual fee, there’s no downside to letting months go by with little to no account activity, then spending aggressively on favored purchases while the 5% deal is in effect.
If your credit is dicey, or you’re not a big fan of credit cards in general, use a cash back mobile app or browser plugin that doesn’t require a credit check. Ibotta, a personal favorite, works with some of the biggest names in retail – along with travel vendors, such as Booking.com, and others not typically associated with deep Cyber Monday discounts. Capital One Shopping, a popular browser extension that automatically adds coupon codes, is another great choice
17. Monitor Your Bank Accounts, Credit Cards, and Credit Profile for Suspicious Activity
The holiday shopping season is the busiest time of year for credit card fraudsters and identity thieves. If you avoid sites with poor security practices and keep your eyes peeled for potential scams, you’ll reduce your likelihood of victimization, but it’s impossible to cut your chances down to zero. As long as you shop online, the risk is there.
What you can do is proactively monitor your financial profile for red flags. If you haven’t already, start reviewing your account statements and between-statement activity (accessible through your online account dashboards) for unfamiliar purchases and charges. It sounds like overkill, but credit card issuers’ built-in fraud detectors still don’t catch everything.
This is also a good time to review your issuers’ fine print and confirm that you’re protected by “zero fraud liability” (the nomenclature varies by issuer). Credit card companies are required by law to limit cardholder liability for unauthorized purchases to $50 per event, but many waive even that small limit as part of their standard benefits packages. Why part with $50 when you don’t have to?
I recommend using a receipt organizer as well. You can buy physical organizers for a few dollars on Amazon, but for online purchases, a digital version is a better bet. Shoeboxed is a good product; other options abound. If you’re in business for yourself, you’ll want to prioritize this step, as a receipt organizer is a great way to reduce business expenses at tax time. Some digital organizers have built-in mileage trackers too – essential for business owners and professionals who need to travel for work.
Finally, consider enrolling in a free credit monitoring service like Credit Karma. I’m a converted skeptic: I resisted signing up for CreditKarma for a long time because I didn’t like the idea of tailored sales pitches and frequent email blasts, but the service has been relatively unobtrusive. Around the holidays, it’s a useful way to stay on top of changes to your credit profile without actually running reports yourself.
As I mentioned up top, the lines between Black Friday and Cyber Monday blur a little bit more each year. But it’s not accurate to say that all the tips that apply to Cyber Monday shoppers apply on Black Friday (or during Black Friday weeks) as well.
If you’re planning to take advantage of the best Black Friday sales and deals this year, check out our companion post on the top Black Friday shopping tips for frugal consumers. And remember to stay sane during this reliably hectic time of year. Happy shopping!
What’s your top Cyber Monday shopping tip?
Source: Money Crashers / Featured image by freepik