A Holiday Shopping Strategy Guide To Get The Best Deals

holiday shopping strategyAlthough the community won't let me spend money, I still enjoy buying things for others throughout the year and during the holidays. To love is to give after all!

Like many of you, I absolutely hate physically shopping for things during sales. Places like WalMart, Target, and Best Buy go absolutely crazy! From the stress of finding a parking spot to the pressure to buy something quickly before selling out, feeling anxiety while shopping just isn't worth it.

Shopping online is the absolute way to go. That said, I always go to the store to test out the product anyway, especially if it's an electronics product like a TV. Seeing is believing and I don't fully trust the quality descriptions of products written online just yet.

The following outlines my holiday shopping strategy that maximizes discounts and minimizes stress. I'd love to read about your shopping strategies as well.


1) Always buy around a week before the projected sale. Black Friday is November 29 this year. Knowing this, I went to Best Buy to test out a bunch of 50″ and up LED Smart TVs. My parents have a beasty 32″ CRT TV from 20 years ago which I thought was time to finally replace. I ended up buying a 50″ Vizio M-Series 240hz LED Smart TV with 3D for $799, $150 off the “normal” retail price.

You won't get the best deal before the projected sale, but you will still likely get a good deal because retailers begin to gradually discount before the major sale weeks before. You should be able to get some good deals which will make you feel pretty good about your purchase. Buying one week before is just a good guideline. You can buy as early as the return policy allows until the projected sale e.g. Best Buy has a 15 day return policy, so buy as early as 15 days before the sale.

On Thanksgiving day, I went online to monitor the latest pricing of my new TV because Best Buy does a price match guarantee. Lo and behold my TV is now on sale for $599! I returned on Saturday, 11/30 with my original receipt and got the $200 discount price match. Don't go on the actual Black Friday because they are swamped and will not give a price match that day. I

If you don't want to risk getting rejected from the price match, just buy before the sale and during the sale online. You've now got two of the same items and can just return the unopened item. It's a pain to return to the store, but for an extra $200 in savings in my case it's worth it.

2) Always take a picture of the sale online. It's not enough to copy and email the link of the sale item to yourself to show to the vendor when you ask for a price match. The reason is because once the supply runs out online, vendors REMOVE the URL! I went back to the link I e-mailed showing the $599 deal and it was gone! Those bastards.

Luckily I took a picture of the deal with my phone and also took a screen shot so I could simply show them the price match guarantee. Without the screen shot, Best Buy would have been less than honorable to give me such a match because they have a “no price match for Black Friday” guarantee. But again, Best Buy would rather move inventory and provide the $200 discount to me rather than go through the restocking hassle and potential non sale of the item since it's already been used.

3) Leverage Amazon all day long. Amazon is clearly the best online shopping website around. They have the best deals and the largest inventory of product due to their shear size. In addition to the Vizio 50″ LED TV, I also got a Vizio Soundbar with wireless subwoofer, a 32″ LED Samsung Smart TV, a Samsung Blu-ray DVD player, a Chocolate HDMI cable, and a Acer C7 Chromebook for my mother.

I use Amazon as the pricing backstop for whatever I buy, not just electronics. Always leverage the internet's largest dealers to get the best price possible.

4) Don't get attached. Desire is the cause of suffering. It's best not to get attached to the things you buy because you must be able to return the product and walk away when push comes to shove. There will always be another sale, another vendor, another person who will provide you a deal. Once the vendor realizes you are willing to return everything, they will be more amendable to giving you a deal.

5) Be patient and courteous. The salespeople and return staff have tremendous power to do whatever they can to please the customer just like how a cop has the ability to let you go with a warning. The staff can't bend over backwards for everybody, but they will for people who are patient, courteous, and kind.  With social media, large vendors are becoming very sensitive to customer service.

Offer to write a positive online review for the person helping you out. Tell them you'll Tweet out your name and CC the vendor and say what an awesome job you've done. Tell them you have this massive blog which is read by hundreds of thousands of people a month. You'll be surprised how much more helpful they will be if you offer to help them help you help them.


Shopping gives me little pleasure because I'm a savings addict. The worst is when I buy something for X and see the same item at a discount a week later. I feel scammed when this happens, which is why I make sure this never happens again through strategies like I've just described in this post. Maybe this is one reason why I hardly ever buy anything. If you don't spend money, you'll never feel ripped off.

I'm ecstatic I've helped my parents join the 21st century with a couple of new LED Smart TVs and a new Acer Chromebook. There weren't that many deals to be had at Best Buy when I went because they were all sold out. Large retailers plan for disappointed consumers to “carry over” their spending and acquiesce to buying something else since they are there already. It's hard to leave empty handed!

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Related: Great Things To Buy With Your Massive Investment Gains

Updated for 2020 and beyond.

20 thoughts on “A Holiday Shopping Strategy Guide To Get The Best Deals”

  1. What’s the deal with that chocolate hdmi cable? I have always heard buy the cheapest hdmi cable because quality is always the same. It either transmits signal or it doesn’t.

  2. Rebecca @ Stapler Confessions

    I used to buy things and return them, but I just ran out of time to be able to do that anymore. Now I rarely buy with the thought that I’ll return it later if I find a better price. I purchase for keeps!

    1. I don’t buy with the intention of returning, only of the product ends up below expectations or there’s a sale during my return window and they don’t price match.

      I admit I enjoy returning stuff bc it replicates the feeling of saving money!

  3. Since I avoid shopping completely, I do not have a strategy. My wife is pretty good at getting bargains and I jjust leave it to her. I have bought appliances near Thanksgiving and they usually have a 60 or 90 day price match policy.

      1. We stopped buying gifts some time a go. We celebrate our birthdays (they are 2 weeks apart) with dinner or a weekend away. We enjoy these experiences much more than a gift.

  4. I cannot stand to go shopping. I do like to buy gifts for my friends and family though I make a lot of gifts. Most of my family members and good friends don’t need anymore clutter or trinkets, so I give homemade jams and jellies or hand sewn/knitted/crocheted/ items. We grow peaches, plums, pears, apples, blackberries and persimmons. What I don’t grow, I buy from local farmers.

    When it comes to shopping, I try to stick to online purchases. I don’t like wasting time in stores and while I rarely cave to impulse buys (years of training myself) I simply don’t enjoy maneuvering busy roads and bustling crowds. I have no problem strategically using return policies. I always check when I’m buying something. We live pretty far out in the country, so I’d rather buy while I’m out and then comparison shop at home. I typically have 30 days to return the item with most local stores and we can always work returns into our regular shopping schedule, so no wasted gas making a special trip.

  5. Dee @ Color Me Frugal

    Great advice, especially about taking pictures of sale ads! I never thought of that but it makes a lot of sense.

  6. I love online shopping for the convenience. The downside for me is that I spend way too much time trying to decide what to buy, literally hours, it’s bad. I read review after review and check multiple websites whenever I can. All of the choices make me really indecisive. I guess that’s better than the opposite and pulling the trigger too fast, and overspending and overpaying.

    I do love getting things on sale though! I like Amazon because of the save for later feature and wish lists. I was bummed they raised their free shipping minimum to $35. But it’s still way lower than a lot of other sites!

  7. There’s a much easier way to get the deal without every stepping foot into the madness than what is outlined here.

    If you have a Discover it® card, they will price match the same item you see in any BF ad on the day of BF. They snail mail you a form and you have to complete it and return it but they refund up to $500 per purchase and up to $2500 in a year. Pretty nifty.

  8. Thank goodness for return policies! I’ve found that every time I go Best Buy for a “sale” everything is sold out and they try and get you with inferior sales just to move inventory.

    Returning goods is one of the best feelings.

  9. Hey Sam,

    Excellent summary as usual. Dont forget though, if you shop exclusively online you are more likely to stick to your budget. Thats one benefit of not leaving the house!

    1. But the more I spend the more I save! :()

      I haven’t noticed any budget busting spending habits yet online vs offline. I often want to hurry up and get the hell outta there when it is offline shopping. If argue that it’s much easier and dangerous buying online!

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