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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20 - Smart strategies to slash your internet and cable TV bills!

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One of my least favorite annual rituals is the dreaded call to my Internet provider. Years ago, this meant wrangling with cable companies like Comcast (now Xfinity) or Astound for TV service; today, as a proud cord-cutter, the negotiation is all about broadband. For two decades, these calls have been synonymous with upsells, misquoted rates, and spending at least an hour sifting through confusing charges. Still, it’s worth the hassle to lower my bill—so, like clockwork, I make the call each year.

This year’s story is a bit different. Yesterday, I noticed my mom’s internet bill had mysteriously jumped from $25 to $55 per month, and to my chagrin, it had taken me a couple of months to catch it. I called immediately and managed to wrangle it back down to $38—which, for our area, is about as good as it gets. That win got me thinking about my own bill. I’m with a different provider, so I called them, only to discover an unpleasant surprise: a lingering $55 charge from my previous time with that company.

That $55 was never supposed to be mine. My relationship with Astound (formerly RCN) soured when I tried to cancel with them in February. I signed up as a new Xfinity customer on February 6, but Astound somehow missed my cancellation and let my introductory rate lapse. Suddenly, I was being charged $70 per month for internet I wasn’t even using! Add autopay and paperless billing to the equation, and I didn’t notice the double billing until May—by which point I’d already shelled out an extra $120 to Xfinity as well.

Determined not to pay for Astound’s mistakes, I called in May. I explained that I’d canceled months earlier, but the Astound rep didn’t believe me. He assured me that calls were recorded and offered to review our conversation. Sure of what I had said, I welcomed the review. However, after checking the recording, Astound still sided with themselves, claiming the charges stood. They also demanded $55 for a pro-rated portion of May. That was the last straw: I revoked autopay, pulled my card info, and resolved to let the debt go to collections—a testament to my stubbornness.

But paying extra for someone else’s error goes against my financial principles. With my Xfinity intro rate ending in three months (set to jump from $35 to $60 per month), I began looking for alternatives. Astound, ironically, is offering new customers $30 per month for the next year. The catch? You can’t have been a customer in the last 90 days. So, since I needed to make a “discount call” soon anyway, I figured I’d attempt a switch—saving $5 a month in the process.

Signing up online didn’t go smoothly (I botched the setup), so I dialed Astound’s 800-number. The agent quickly found my old account and the infamous $55 charge. I explained the whole situation once again. This time, instead of the usual stonewalling, the agent read through my account notes, agreed with me, and wiped the $55 debt. On top of that, he credited me another $55 for an earlier overcharge—vindication at last! The agent told me it would take a few days for approval, after which I could try signing up again. Fingers crossed for a smooth transition.

Why am I sharing this saga? Because these calls, while frustrating, really matter if you want to minimize your monthly bills. Good, reliable internet should cost $30–$40 per month—no more. Loyalty to a provider means nothing to me; whoever offers the best price wins my business. Flexibility is key.

Internet companies rarely profit from customers on introductory rates, so they scheme to upsell extras—like WiFi extenders or “premium” equipment—or sneak in surprise charges once a deal expires. These tactics aren’t outright illegal, but they’re manipulative. It falls on us to be vigilant, renew deals, switch if needed, and avoid their traps. Here are a few lessons learned:
  • When discounts expire and you’re on autopay or paperless billing, you might not notice a sudden jump for several months. I was out $300 before catching the change last time.
  • Discounts often expire at different times: service deals might last 12 months, while modem rentals get 18 months—a recipe for confusion and missing out on renewed savings.
  • Sometimes promotions automatically enroll you in paid add-ons (security services, premium support) after a trial period ends, so double-check your statements.
  • Watch for “activation” or “installation” fees even if you already have equipment—these can be added quietly or as a surprise when you make changes.
  • Penalties or higher rates can kick in if you miss a renewal window by even a few days.
  • If there are other tricks you’ve encountered, add them in the comments! Your experience could help someone else spot a hidden fee before it bites.
Additional Smart Consumer Tips (from AI):
  • Set calendar reminders a month before any discounted rates end—don’t rely on vague emails or low-priority notifications.
  • Review each bill monthly for unauthorized charges or new fees, even if you’re on autopay.
  • When negotiating, politely mention current competitor offers; many reps have access to better deals than what’s advertised online.
  • Don’t hesitate to rotate providers annually. Introductory rates beat most loyalty pricing over the long run.
  • Use a throwaway email when signing up so you can easily track and consolidate all provider correspondence—helpful for catching service changes.
  • Take screenshots of every signup or chat confirmation, just in case you need to prove what was offered to you.
  • Make a checklist of all hardware and account changes requested with your provider, and get confirmation numbers or emails for every interaction.
  • Ask for a written summary or emailed breakdown of your new rate and promo expiration—it’s much easier to dispute future mistakes with this in hand.
  • If you frequently switch, label and save your modems, routers, and cables to match each provider; this can speed up transitions and help avoid “unreturned equipment” fees.
  • If a provider offers a loyalty or “retention” team, always politely ask to speak with them for maximum leverage.
Navigating these calls is never fun, but with vigilance, documentation, and a bit of stubbornness, you can win—and save hundreds over time.

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