November 20th, 2017

How to Shop Cyber Monday Like a Pro

How to Shop Cyber Monday Like a Pro

If you’re an avid online shopper, Cyber Monday is like your Super Bowl. But do you have a game plan for your shopping binge? Here’s how to put one together like a pro.

As travel lovers and outdoor enthusiasts, many of us have adopted a minimalist attitude — or at the very least we know to look for bargains whenever possible. It’s a skill that travel hones, and one that will serve you well during the holiday season, too. So get your clicking fingers ready and your credit card information auto-filled, because Cyber Monday is around the corner and it’s time to do the Western equivalent of bargaining for the best deals like you would at a market overseas.

Cyber Monday grew as a “why leave the house” foil to Black Friday — the day after Thanksgiving and the single biggest shopping day of the year. Cyber Monday is now a major phenomenon, and it works very much the same way: at the stroke of midnight on the Monday after Thanksgiving, online retailers unleash crazy deals. Expect bargain prices, buy-one-get-one deals, free gifts with purchase, money off your entire bill, free shipping promotions, or some combination thereof. Going into Cyber Monday without a plan is risky, because the chance of both overstimulation and excessive impulse purchases are high. Here’s how to put a game plan in place now, courtesy of a veteran Cyber Monday shopper.

Have a plan

Well in advance of actually opening your laptop, phone, or PC on Cyber Monday, you should know what stores or deals will complete your to-buy list. Unlike Black Friday, where wandering the mall uncovers amazing deals at every turn and you might be tempted to buy a little here and a little there, doing the same on Cyber Monday could end in a personal financial meltdown. Most sites have thresholds for free shipping, encouraging you to add a “little more” into your virtual cart each time. The receipts quickly add up this way. Know what you are shopping for and where you want to do it, then stick to your plan.

Make a list, check it twice

It’s likely that most of your Cyber Monday shopping is holiday gifts for other people, but it’s also a great time of year to replace your worn out travel gear or buy needed items for your next vacation. For planning others’ gifts, make yourself a tangible list of who you need to shop for and what you have already bought them, including the dollar amount you spent. I have a hard copy of this list in my day-planner, but there’s no reason you can’t go 21st-century and make a spreadsheet. Then pull your travel gear from the closet and make a list of items that might not last another season or that you need for a planned trip—perhaps replace that rain jacket with a hole or treat yourself to a new backpack or duffel while they are on sale.

Once again, it’s easy to get swept up in the Cyber Monday madness. If you know that you have already bought your aunt a fantastic cashmere sweater, there’s no need to go crazy with the “buy 3 get 3 free” promotion at that fancy candle store. Likewise, if your hiking shoes are still that perfect combination of “worn in but holding up nicely,” don’t even venture to the online shoe stores. As you shop, update your lists assiduously with every purchase so you know where you stand.

Buy it while you can

This tip runs a little bit contrary to what we’ve just recommended, but exercise good judgment. If you are waffling over a potential Cyber Monday purchase, check the site’s return policy. If it is a good one, you might do best to buy now and waffle later. To clarify: These are time-limited deals that are unlikely to be matched for the rest of the year. You may not have the chance again to get the item you want at such a good price. If you are seriously vacillating, pull the trigger. You can always return it later, but you probably won’t get another chance to buy it at such a low price.

Your turn, Cyber Monday pros. What sites will you be shopping on Cyber Monday? (Don’t forget Eagle Creek!) Let us know in the comments!

by Shannon ODonnell

Shannon O'Donnell is a long-term traveler who has been on the road since 2008; she travels slowly and supports grassroots tourism along the way. She is an acclaimed travel speaker and works with universities and businesses all over the U.S. to talk about supporting developing countries.