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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15 - Some health Insurance premiums can be lowered with activities!

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For the past seven years, I've been on "ObamaCare" (or the Affordable Care Act) for health insurance. When you quit teaching at 42 but aren't old enough to officially retire, you don't get teacher's health insurance (at least not until I turn 55)! I'm super thankful that I found Ambetter because the monthly premiums are inexpensive for a single (I have no idea about family coverage).

In addition to the monthly premiums being reasonable, they also offer ways to reduce that monthly premium each month, called My Health Pays! I, of course, try to take advantage of all of those offers! They offer "Challenges" (large point totals) and "Power-ups" (small point totals), that all earn real money.

Some of the Challenges that I've been offered recently include:

  • See What’s New in 2025!
    • 5 Tasks 750 PTS Points
  • Get to Know Type 2 Diabetes
    • 4 Tasks 1,000 PTS Points
  • Find Your Inner Calm and Earn
    • 4 Tasks 250 PTS Points
Some of the Power-Ups that I've been offered recently include:
  • Be Well: Keeping Your Heart Healthy
    • 250 PTS
    • 5 MIN
  • Financial Wellness: Saving in Style
      • 10 PTS
      • 7 MIN
    • Move More: Enhance Your Walks
      • 100 PTS
      • 5 MIN
    I also get 500 points for my annual "Wellness Visit" (annual physical). Each point is worth ten cents, so I get $50 for turning my head and coughing. ;)

    For 2026, a lot of the rules are changing for health care. I might not be able to keep the same plan I've had for the past seven years because I will need to apply for health insurance through my state (Illinois) instead of through the "Marketplace." 

    Since I might be switching coverage in two months, I am cashing all of my points out now, so I can credit the points towards my last monthly premium. These points and the money earned from the points expire when coverage ends.

    Here are my annual earnings from these activities:
    • 2025: $250 (I just earned $20 on a new 5-minute Challenge today!)
    • 2024: $250
    • 2023: $250
    • 2022: $350
    • 2021: $300
    Several other health insurance companies offer cash-back or rewards programs similar to Ambetter’s My Health Pays. Here’s a list of reputable insurers and their current (2025) wellness reward programs for individual/ACA (Marketplace) plans, with information relevant for Illinois and most other states:

    • Cigna – Take Control Rewards
      • Earn up to $325 per year for completing wellness tasks like annual checkups, flu shots, and online challenges.
      • Rewards are redeemable for healthcare costs or merchandise.​
    • Oscar Health – Step Tracking & Wellness Rewards
      • Sync your fitness tracker with Oscar’s app and earn cash rewards for meeting daily step goals.
      • Additional rewards available for preventive care, like annual wellness visits and health screenings.​
    • UnitedHealthcare (UHC) – Health Perks
      • Earn up to $150 prepaid Visa cards by completing activities such as doctor visits, setting up online accounts, and wellness screenings.​
    • Molina Healthcare – Healthy Rewards
      • Earn $100 gift card for your annual wellness visit and Health Risk Assessment on their member portal.
      • Other activities throughout the year can earn more rewards.​
    • Blue Cross Blue Shield (BCBS) – Blue Rewards
      • Many state BCBS plans offer cash, gift cards, or credit for preventive care visits, annual checkups, and health assessments, though amounts and eligible activities vary.
      • Some BCBS Illinois programs encourage wellness but check details for individual plans.​
    • Aetna CVS Health – Member Rewards
      • Aetna Medicaid and Marketplace plans may offer rewards like gift cards for screenings and preventive care.
      • Example: Earn up to $20 for health risk screening, $25 for diabetes checks, and more (see Illinois Medicaid rewards for local examples).​
    • Meridian Health (Illinois Medicaid) – Healthy Rewards
      • Medicaid members can earn prepaid Mastercard rewards for activities including wellness visits and screenings.​
      • These programs may be less robust for Marketplace/ACA enrollees but are expanding.
    Notes/Tips:
    • The reward values, eligible activities, and claim process may vary from insurer to insurer and by state.
    • Most programs now let you use rewards to offset premiums, copays, or everyday expenses.
    • Always check if programs apply to ACA Marketplace plans in Illinois, as some are still expanding rewards for individual plan buyers.
    For the latest information, always ask the carrier or review member materials after enrollment—these programs change often and new incentives are being added for 2026.​

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