55 - The Calendar Strategy: How to Automate Your Dining Discounts (And Never Pay Full Price Again)

I recently did something a little crazy—but financially brilliant. During the holiday sales, I stocked up on restaurant gift cards. You know the ones: “Buy $100, Get $25 Free.” I bought them for my favorite local spots: the Irish pub around the corner, the pizza place we love on Fridays, and the nice steakhouse we save for special occasions. Mathematically, I was already winning. By getting $125 worth of food for $100, I had locked in an instant 20% discount on my future meals. But then I thought: How can I stretch this even further? The gift cards are great, but they are only one part of the equation. Most of these restaurants also offer weekly specials—Half-Price Burgers on Mondays, Taco Tuesdays, Kids Eat Free Wednesdays, or Happy Hour appetizers. If I used my discounted gift cards only on nights when the food was also discounted, I wouldn’t just be saving 20%. I’d be saving 50%, 60%, or even 70% off the regular menu price. The problem? I can never remember which restaurant has the ...

14 - Learn what the gimmicks/draws are for each business that you frequent.


Some of my favorite stores, restaurants, and fast food chains have specific gimmicks or ways to draw customers in. Once you know what the gimmick is, you can maximize its use and minimize overpaying for non-gimmicks. I'll share a few of my local business' gimmicks and you can use these examples to help you in your location.

Menards is a home improvement store nearby. They run an "11% Off Everything" special approximately 11 months out of the year, but it's refunded to you in the form of a store credit rebate. You pay full price at the register, including sales tax. You save your receipts, and you send them all in within six months of purchase and they send you a postcard with your store credit. Here are some of my tips for maximizing the savings with this gimmick:
  1. Keep your receipts in the same place so you don't lose any! 
  2. If you buy anything online, be sure to print out the receipts to get your credit.
  3. I have one credit card devoted to "home improvement" stores (it's the Citibank Custom Cash card which identifies one category that you spent the most in that month, and it give you 5% cash back in that category each month. I restrict my usage of this card to ONLY home improvement stores like Menards, Home Depot and Lowes. (I have another one of these cards in my mom's name and use it only for gasoline.)
  4. Menards sells groceries too, so I get 5% cash back, plus an 11% rebate on groceries, which is better than I can get anywhere else (and their prices are often as good or better than nearby grocery stores!).
  5. I keep all of my Menards rebate postcards in one place in my home and only use them in the month (usually December) that doesn't offer 11% off! That way, I'm not losing out on an opportunity to earn 11% cash back for those purchases. And, since I've already paid tax on that money, the items I buy using the rebates have no sales tax!
  6. Their previous gimmick was including a paper bag in the Sunday newspaper that said, "Everything you can fit in this bag is 20% off!" They still sometimes run this gimmick, so if you see it, be sure to save! 
Kohl's has 20-30% off days when you bring the card or coupon in from a mailer. They send these to almost everyone by me, but once you get a Kohl's credit card, they send you one almost every month! Kohl's usually offers $10 back for every $50 you spend as well. This can't be spent until the 30% off sale is over, however. That's their way to get you to come back in and spend even more! Here are some of my tips for maximizing the savings with this gimmick:
  1. I like to shop on the first day of the sale in the Clearance sections (which are huge and filled with perfect clothes for me!) Being there on the first day ensures the best selection.
  2. Although most of their products have ridiculously expensive suggested retail prices, they don't really expect to sell many things at that price point. 30% off is usually on top of a sales price of 40% off or something like that (which does not equal 70% off - 40% off of $100 means it costs $60. 30% off $60 is $18, so it costs $42. 70% off would be $30.) Be able to do math like this in your head (or on your phone) so you know what you'll be paying at the counter.
  3. If you're close to a total (before sales tax) of a multiple of $50, be sure to buy something small (like a candy bar) to get over the hump and earn another $10 (for every $50 spent). They expect you to do this and are happy when you do! But we can both be happy! I like buying a $2 candy bar that gives me $8 to spend next week!
  4. There are some exclusions with the 30% off coupon, like Nike, UnderArmor, Sephora, etc. So, I use the $10 off coupons for those purchases during the next week (which are often allowed). I find the pair of shoes that are 25% off regular price and use my $30 in "Kohl's Cash" earned the week prior to get my new Nikes for $45 (or whatever).
  5. The Amazon Drop-off is located within my Kohl's store, so whenever I have an Amazon return I go there (and have to go to the back of the store!). This means I have to walk past all of their products for sale. Your Amazon return receipt includes a Kohl's coupon (they're hoping to convert you to a customer on a day you weren't planning to shop there). The reward varies depending on the day of the week and store location. I like the $5 off coupon, because I end up getting something for $5 and only have to pay sales tax on it! Here is what AI has to say about it.
    • Saturday to Monday: Many Kohl’s stores give you $5 Kohl’s Cash (to use in-store, usually within 7 days).​
    • Tuesday to Friday: Most stores give a 25% off single in-store purchase coupon (valid on almost anything, usually for 7 days).​
    • Some locations or times may be random—there are reports of slight variations (sometimes 15–25% off instead of $5 Kohl’s Cash).​
Jewel-Osco is notorious for offering great sales prices on certain staples and advertised products, while charging more than most competitors for everything else. Using the app mitigates this to a large degree these days, but most of their regular prices are still more expensive than they should be. (Remember the $11.99 I spent on two ounces of pine nuts?)
  1. Figure out what Jewel sells cheaper than other stores and try to stick to buying only those items. (Duh!) 
  2. Avoid impulse buys or convenience purchases ("I'm here. It's easier than going to another store.").
  3. I use Jewel simply for buying things on sale in their app. These are often at competitive or better than competitive prices compared to other stores in my area. I will also buy certain sale items, like when they sell an entire pork loin for $8 (got that last week), or two ribeye steaks for $15 (they usually have one cut of beef on sale every week - just check the labels), or lobster tails for $5 each (once or twice per year they sell small, but not tiny, lobster tails for $5 each and I get a few to enjoy). 
  4. I try to buy my other groceries at other stores (e.g. We have great produce markets in my area, so when I want produce, I prefer to shop at Caputo's or Valli Produce. I got everything I needed to make two dozen homemade enchiladas verdes yesterday at Caputo's for $15 (a rotisserie chicken, tomatillos, peppers, cilantro, tortillas, etc.)!
  5. If you end up buying things not on sale at Jewel, like soda, deli meats, cheese, baked goods, etc., you are likely to pay 25-75% more here than you will at a competitor that sells those items cheaply as their gimmick! Meijer sells soda cheaper and Walmart offers better deals on baked goods (especially their marked down products that are near the expiration date). I buy deli meat and cheese from the produce stores for a third of the price of Jewel!
Taco Bell will be my final example for this blog post. Taco Bell's prices have gone up a lot over the past 20 years. I've been a loyal customer this whole time and I'm starting to become weary of paying their prices ($15 for two items?!?!). But they do have a couple gimmicks that might be of interest to you. 
  1. First is their box deals. Popular in England, some restaurants offer some of their most popular dishes in a box (like a combination platter). Taco Bell currently offers three levels of box deals: $5, $7 and $9 each with a few ways to customize the choices. On their app, they even have a custom box deal that I believe is different from these three options. 
  2. Also on their app are some "Online Order Only" deals. These vary, but have included new items, flashback items (80's, 90's, 00's items that were not on the menu at the time), and special Taco Tuesday drops that change each week. 
  3. If you order through the app, you also accrue points towards free food (although I have yet to earn enough points to cash out so far). We'll see if it ends up to be worth the extra trouble.
  4. Finally, they have a "Cravings Value Menu" which offers inexpensive options (at $3 or less) like Cheesy Roll Ups, Spicy Potato Soft Taco, Cheesy Bean and Rice Burrito, and even Loaded Beef Nachos! Stick to this menu if trying to save a few bucks!
When it comes to stretching your dollars, knowing a store’s “gimmick” is like holding a secret map—one that helps you avoid overpaying for everyday items and lets you scoop up the real bargains. The more you pay attention, the more you’ll see patterns and play along instead of playing into their hands! Whether you’re a thrifty shopper, a resourceful saver, or simply someone who enjoys finding clever ways to spend less, these strategies add up over time. Don’t be afraid to ask questions, compare offers, or experiment to see what stores in your area are doing—you might find hidden promotions or special deals that others miss.

A Few More Ways to Outsmart the Gimmicks (AI-generated):
  • Sign up for store loyalty programs and email lists. Brands love sending exclusive offers, coupons, and “member-only” gimmicks that sometimes don’t get advertised in-store.
  • Follow your favorite stores and restaurants on social media—they often announce flash deals or show secret menu items for their fans.
  • Use price comparison apps (like Flipp, ShopSavvy, or Google Shopping) before you buy anything advertised as “on sale.” Sometimes a neighboring store is running a competing promo on the same item!
  • If you see a great offer—like “buy one, get one free” or a rare discount on an item you use often—stock up if your budget allows. Just don’t fall for the trap of buying things you wouldn’t want otherwise (or that expires!).
  • Keep your eyes peeled for special events like grand openings, customer appreciation days, or seasonal clearances. These can come with supercharged discounts, giveaways, or bonus rewards you won’t see during regular shopping. (I got $5 off $30 every week for six months when Caputo's moved into my neighborhood!)
  • At the end of the day, a savvy shopper treats every sale, promo, or so-called “gimmick” as an opportunity—not an obligation. And remember, it’s not about denying yourself—it’s about spending smarter so you have more for what really matters to you.
If you’ve cracked the code on a local store’s savings strategy, share your tips below! The more we learn from each other, the more fun—and rewarding—this smart savings game becomes.

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