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

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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 ...
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13 - Lucky Tip #13: Win a little money with free contests and giveaways!

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Most smart savers know the basics of clipping coupons and finding deals, but here’s something a little different—using contests, sweepstakes, and giveaways to win extra cash or prizes, all without risking your hard-earned money! There are plenty of ways for deal hunters to add excitement (and savings) to their daily routine, just by giving luck a little nudge.

Here are a few of my favorite ways money savers can play the odds—without any risk:
  • Sign Up for Birthday and Spin-to-Win Promotions
    • Thrifty folks can rack up freebies just for signing up for birthday clubs, loyalty programs, or in-app games at restaurants and stores. Think free desserts, gift cards, or a “spin” for surprise prizes. For example, places like Starbucks, Denny’s, or your local pizzeria often have special rewards each year for members. You’re not spending extra—just taking a chance on a little free happiness!
    • Example: The McDonalds app asks for your birthday and offers you a free treat every time that day on the calendar comes around.
  • Take a Chance on Receipt and Online Surveys
    • After you shop, don’t toss that receipt! Many stores have a code at the bottom inviting you to fill out a quick survey for a shot at a cash prize—for example, winning $500 or even $1,000 in a monthly drawing. Deal hunters know that the couple minutes spent on these surveys can sometimes pay off in a big way, and you’re only entering once per purchase, so it never feels risky. Online brands do this too—look for “feedback” links in your email after orders.
    • Example: Burger King receipts offer a free Whopper when you fill out their online survey.
  • Try Out Free Scratch-Off and “Prize Card” Offers
    • Money savers, you don’t need to buy lottery tickets to get a little thrill! Watch for promotional scratch-off cards or prize games that come with mailers, are handed out at store grand openings, or given away during community events. Almost every card is a winner—sometimes it's a small discount, a free drink, or even a bigger cash prize. It’s free, there’s no purchase required, and it’s a fun little moment that could lead to surprising wins.
    • Example: I get one in the mail all the time. Usually, they are just promotional materials where everyone is a "winner" but occasionally it offers actual savings, prizes, or special deals.
    • Example: Kohl's used to have a "Peel Off" on their mailers that gave you 20-30% off. (Recently, I've just been getting 30% offers without a sticker.)
  • Play Loyalty App Bonus Games and Seasonal Promotions
    • Smart savers keep their favorite apps installed, because many brands run special games or contests—like McDonald’s Monopoly Game, grocery chain bingo contests, or limited-time virtual “spinners.” Often, just making your normal purchase (or sometimes just logging in) enters you into drawings for free food, prizes, or discounts. Checking the “Promotions” or “Games” section in these apps can turn your everyday habits into lucky opportunities.
    • Example: Don't get me started on Temu's spinner! That's a perfect example of an in-app (or online) marketing strategy to get you to spend more, not save you money! Don't be fooled!
  • Start a “Lucky Savings Jar”
    • Here’s a fun idea: Every time you win a prize, score a freebie, or save a few dollars thanks to luck or a contest, stash the amount you “won” into a jar (or digital wallet). At the end of the year, celebrate just how much your thrifty luck has paid off! For families, turn this into a group game and see who collects the most surprise winnings.
    • Example: My dad used to put all the money he won at the casino or the race track (he was a  very casual bettor) into a bowl and when it started to look too full, he would pick one of us to do something we wouldn't do otherwise. He took me to a Cubs Convention one year with this "found money", and we ended up going several more time after that!
  • Join Local Giveaways and Community “Acts of Kindness” Groups
    • Thrifty friends should check Facebook, Nextdoor, or other community sites for local business giveaways or “random acts of kindness” events. You’ll find gift card raffles, sports tickets, and even cash prizes occasionally with little more than a comment or quick signup. These are especially great around the holidays or store anniversaries and can bring unexpected wins to thoughtful, positive-minded savers.
    • Example: Freecycle.org is like a local eBay where everything is free. Just have to drive over and pick it up. Facebook Marketplace offers free and cheap items as well in your local area.
Luck alone never pays the bills, but a little curiosity—and a couple lucky breaks—sure make the thrifty life more fun. If you’ve ever won something surprising or have a favorite contest, share your story in the comments! Let's help each other turn these lucky chances into real savings.

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