Surviving Cyber Monday


Black Friday, Cyber Monday, and the days between and around them are always full of incredible deals. This year is no different.  We keep a running list of select deals here: 2020 Black Friday and Cyber Monday deals.  While it seems like I should be excited, I actually find it stressful.  This year I sat out of most Black Friday deals with the thought that there’s always Cyber Monday.  Now it’s crunch time.  Which deals should I pursue?  Below you’ll find my battle plan for surviving Cyber Monday…

Every deal, big or small, takes time and mental focus.  Many deals require multiple steps, spread out over time.  Some require follow up: Did the portal track my purchase correctly? Did Amex credit my account for that Amex Offer?  There’s always a mental cost – not just to understand the deal in the first place, but rather the ongoing weight of participation.  For each deal, there is work to do, usually followed by a feeling that something might have been missed or forgotten.  Did I use the right credit card? Did I use up that gift card before filing it away?  Have I maxed out the bonus spend on this offer yet?

Cyber Monday Battle Plan

In order to weed through deal options and reduce stress, I evaluated available deals using the following criteria:

  1. Is the deal big enough and/or simple enough?  If a deal promises to save only $5, I’ll usually ignore it.  The one exception is when it’s easy and fits with my usual spend anyway.  For example, if there’s an offer to save $5 at a store that I’m planning on shopping with anyway and if there are no big hoops to jump through, then I might as well go for it.
  2. Is the deal limited?  If a deal is likely to stick around for a while or likely to come back regularly, then I don’t need to hurry to snag it.  Only the soon-to-expire deals require my immediate attention.
  3. Do I really need/want this thing? Or will it make a good present?  Over the weekend, Nick wrote about some fantastic deals for new phone service and new phones, but I don’t need either.  A great deal isn’t great if it means buying something that I don’t really need or want.

Deals I’m Going For

With the above criteria in mind, here are the deals I’m planning to take advantage of on Cyber Monday (this list will likely change during the day as we post new deals):

  • Citi to offer 20% off on gift card redemptions: With a 20% discount, Citi ThankYou points are worth 1.25 cents each.  That’s not amazing, but it’s solid enough if you don’t think you’ll use all of your points for potentially much more valuable transfers to airline partners.  I have more than enough Citi points for transfers to airline programs and so I’m willing to spend some for opportunities like this.  I’ll probably redeem points for Apple gift cards both to use for myself and as gifts.
    UPDATE 12:40 pm ET: Done! Redeemed 8K points for $100 Apple gift card.
  • Dell 15X via Rakuten: The Rakuten portal is offering 15X Membership Rewards or 15% back at Dell. In my family we have two Business Platinum cards which each have $200 in Dell rebates yet to be spent before the end of the year plus 10% back at Dell via Amex Offers, plus +1 point per dollar at Dell via Amex Offers.  This means that I can get 100% back from Amex on almost $450 worth of Dell purchases plus 17X Membership Rewards points (15X from Rakuten + 2X from the Business Platinum card).  With Dell undoubtedly offering lots of excellent Cyber Monday deals, this is a great time to spend down my credits to buy presents for others and things I need or want for myself.  For others, I’ll look for deals on bluetooth earbuds and other electronics that might make good gifts.  For myself, I’m considering a new monitor.
    UPDATE: 3:45PM ET: This morning I bought a webcam that was on sale for $25 and then later I bought a monitor for $360 (UltraSharp 27″ Monitor – U2719D).  The monitor will come with a $150 promo egift card.  So, once the egift card arrives, I’ll have to go Dell shopping again!
  • Staples Hyken Mesh Task Chair for $149.99: We actually need a new desk chair and this appears to be a good deal.  While there are plenty of ways to stack Staples deals, my preferred way is to redeem Discover Cashback for the required amount and then click through a portal to Staples to make the purchase.  For example, I can redeem $127.50 of Discover Cashback for a $150 Staples e-gift card.  Then I can click through a portal to Staples (such as RebatesMe, which is offering 4.1% back) in order to get a little kickback.  Hopefully I’ll find even better portal options on Monday (I’m writing this on Sunday).
    UPDATE 8:30 am ET: I should have bought this chair yesterday as it’s no longer on sale today.
    UPDATE 4:45PM ET: The deal is live again. I’m now going to read a bunch of reviews to see if I should get it.
    UPDATE 5:15PM ET: I decided to go for it. I used the GivingAssistant portal for 4% cash back.  And I redeemed $123.25 of Discover Cashback for a $145 Staples gift card.  That, plus a couple of $5 rewards in my Staples account (I don’t know why), plus about $3 on a credit card got it done.
  • Marriott: 15% off gift cards: As noted in our post, this deal will likely stack with the current Chase Marriott offers to earn 10X at Marriott.
    UPDATE 1PM ET: I bought a $500 gift card for $425 with a Citi card (see below)
    UPDATE 1:18PM ET: I bought a $100 gift card for $85 with my Bonvoy Brilliant card. That card has $100 remaining of it’s annual $300 Marriott credits so I’m hoping this will be close to using up that credit.
  • Citi cards: 5% back for online shopping November 24-30: Monday is the last day to take advantage of this one.  I have a few miscellaneous bills that I’m hoping will code as online purchases for this deal.  I’ll also reload my Amazon gift card balance a bit.  That should count for sure.  Frustratingly, I made one big purchase over the weekend and later found out that the item purchased was out of stock and they wouldn’t charge my card until they had the item ready to ship.  This will happen, of course, after this 5% deal is long gone.
    UPDATE 1PM ET: I bought a $500 Marriott gift card for $425 with my Citi AT&T Access More card. I believe this will stack with the card’s usual 3X for online/travel purchases + 2X retention offer + 5% back.
  • Plum Market (local grocery chain) $25 Bonus Card w/ $100 Gift card purchase: I’ll do the max $500.
    UPDATE 12:50 pm ET: Bought the max $500. Paid with Amex Platinum hoping that it will count as grocery but not as gift cards.

Deals I’ve Done

I’ve already taken advantage of the following deals:

  • 20-50% off Amazon with 1 Membership Rewards point!  My wife and I were each targeted for 20% off on up to $100 spend at Amazon.  In each of our accounts I bought a $100 Whole Foods gift card for $79.99 plus 1 Membership Rewards point.
  • Awesome Amex Offer — Get +8 Points Per Dollar at Amazon: This is a great offer and I have it loaded to one of my Amex cards and one of my wife’s cards.  I already spent $79.99 on each card with the above deal and I’ve scheduled daily Amazon reloads with my Everyday Preferred card in order to polish off this deal on that card (and to ensure hitting the 30 charges per billing cycle on that card to get the card’s usual 50% bonus).  I haven’t finished the deal on my wife’s card yet, but we have until the end of the year to do so.  That shouldn’t be a problem.
  • Rakuten: Earn 16%/16x At Saks Fifth Avenue, Stack With Platinum Benefit.  With two personal Platinum cards and a left-over $40-ish Saks gift card, I had a little over $140 to spend at Saks for free.  My wife helped me pick out a few gifts for her and I earned over 2,200 Membership Rewards points.  I used my ShopRunner membership (register for free with any Amex card or Mastercard) to get free shipping.

Deals I’m Skipping (or Delaying)

I’m listing here only the deals that I seriously considered, but ultimately decided not to do.

Follow my progress via comments

I’ll add comments to this post as I make progress with my Cyber Monday battle plans.  If you’re interested in seeing how my plans turned out, subscribe to the comments below or simply check back occasionally.

Your Turn

What are your plans for Cyber Monday?  And, did I miss any awesome deals?  Please comment below.

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