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← The Bold Letter Issue #8 · June 16, 2026

The Most Underused Website in America

Hi friend,

If I told you there was a free website that could find you money you’re already entitled to — no strings attached, no one trying to sell you anything — you’d probably use it, right?

Most people would say yes. And yet the National Council on Aging estimates that millions of eligible seniors leave significant benefits on the table every year, simply because they don’t know to look.

Let me tell you about BenefitsCheckUp.

💻 One big idea: there are nearly 2,000 programs and most people don’t know they exist

The NCOA built and maintains BenefitsCheckUp.org — a free, confidential screening tool that searches close to 2,000 federal, state, and private benefit programs and tells you which ones you may qualify for based on your location, income, housing situation, and other factors.

The programs span a wide range:

  • Medicare Part D Extra Help (Low Income Subsidy): Reduces or eliminates drug copays and premiums — worth hundreds to thousands of dollars a year for people who qualify
  • SNAP (Supplemental Nutrition Assistance): Many seniors qualify who don’t realize it
  • LIHEAP (Low Income Home Energy Assistance): Help with heating and cooling bills
  • Property tax relief programs: Many states offer freezes, exemptions, or reductions for older homeowners that most people never claim
  • Phone and internet discounts: The Lifeline and ACP programs reduce monthly telecom bills
  • In-home services: Transportation, personal care, and home modification programs

The income limits for these programs are often higher than people assume. Many people rule themselves out before they even check. The site removes the guesswork.

🌟 One win: it’s private, free, and takes 15 minutes

Here’s what you’ll need to complete the BenefitsCheckUp screening:

  • Your ZIP code
  • A rough household income range
  • Whether you rent or own your home
  • Your age and household size

That’s it. The site doesn’t ask for your Social Security number. It doesn’t share your information. It’s built by a nonprofit whose only mission is connecting older adults with help they’re entitled to.

If the screening finds programs you might qualify for, it gives you the program name, a plain-language description, and directions for how to apply. You take it from there — no one calls you, no one follows up.

🎯 One thing to try this week

Go to BenefitsCheckUp.org and run your own screening, or run one for a parent or someone you know.

One thing I’d add: don’t disqualify yourself in advance. I’ve heard so many people say “oh, I make too much for that.” Maybe. But find out before you assume. The programs exist because they were designed for real people in real circumstances — and the people who built them put the income limits where they did on purpose.

Fifteen minutes. That’s the investment. The potential return could be measured in hundreds of dollars a month.

Age boldly, Robert


Sources: National Council on Aging, BenefitsCheckUp.org program overview; NCOA “Get the Facts on Economic Security for Seniors” (2024); Social Security Administration, Extra Help program data.