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"3 Costly Mistakes At 65 Many Accidentally Make Starting Medicare You Should Avoid"
By Andrew Hibbard
YES! A Real, Happy And Helpful Human Wrote This (No AI Software Was Used)
Updated On: August 1, 2026
TIME TO READ: 5 MINUTES
By Andrew Hibbard
YES! A Real, Happy And Helpful Human Wrote This (No AI Software Was Used)
Updated On: August 1, 2026
TIME TO READ: 5 MINUTES
YOUR SUMMARY OF KEY TAKEAWAYS
- There are 2 key rule changes passed by Congress which affect EVERYBODY applying for their Federal Medicare Part A and B benefits for the first time now.
- Mistake #1: Not knowing your timeline and required “to-do” list for signing up for Medicare at age 65 (or after 65)…and waiting too long to get started without realizing it.
- Mistake #2: Assuming you will not pay a permanent late penalty for life because you’ll keep working past 65 with Employer Group Healthcare Plan coverage (EGHP) --- which is not always true anymore.
- Mistake #3: Not being aware of, or paying attention to, the NEW process to apply for your Federal Part A and B benefits.
Signing up and starting Medicare for the first time is way more complicated and way more confusing today than ever before because of TWO KEY RULE CHANGES Congress passed which affect EVERYBODY applying for their Federal Medicare Part A and B benefits.
The first rule change was hidden in the four-part Consolidated Appropriations Act (CAA), which made significant changes to the Medicare penalty period deadline and what is considered "creditable coverage" if you will work past age 65 with Employer Healthcare coverage, ESPECIALLY for those who will wait to collect Social Security benefits until later in life...
The second rule change came in the Inflation Reduction Act (IRA) effective January 2025, allowing Social Security offices, across the country, to significantly reduce (and severely restrict) in-person appointments for Federal Medicare Part A & B applications, leaving legal, tax-paying, U.S. Citizens without the help they thought they would (and should) have.
The combination of these new rule changes has created, and continues to create, a serious concern for those turning 65 not knowing what to do, when to do it, and how to get things done.
After helping over 2,100+ folks and families in Erie County and those living in the surrounding area, I can tell you there are 3 costly mistakes many are accidentally making starting Medicare you should avoid.
COSTLY MISTAKE #1: Not Knowing Your Timeline And Required “To-Do” List For Signing Up At 65 (Or After 65)…And Waiting Too Long To Get Started WithOUT Realizing It…
The unfortunate reality when people call me is, they are nervous and stressed, not sure where to start, and have procrastinated and put things off, waiting until the last-minute causing deadline to be missed because things were not done EARLY enough.
It might be surprising to you, but many people apply for their Federal Medicare Part A and B benefits at the wrong time.
Whether applying at age 65, or older than age 65, there are very specific timelines, UNIQUE to your situation you must follow to avoid paying penalties --- this is different for everybody, so what your friend, or neighbor, or coworker, or even your spouse did, is not the same thing you need to do.
COSTLY MISTAKE #2: Assuming You Will NOT Pay A Permanent Late Penalty For Life Because You’ll Keep Working Past 65 With Employer Group Healthcare Plan Coverage (EGHP)…
As I mentioned earlier, the Consolidated Appropriations Act (CAA) changed the rules to what is considered “creditable coverage,” specifically with Employer-sponsored prescription drug benefits embedded into employee healthcare coverage.
With this rule change, many traditional and standard plans that have been offered may no longer meet the new standards exposing you to pay permanent late penalties for life is not coordinated correctly.
These changes in “creditable coverage” may affect you if:
- You have a high-deductible healthcare plan (HDHP) at work with an H.S.A. …and either you, or your employer (or both) are contributing where you receive a write-off for a reduced tax-return…
- You retired before age 65, were offered to maintain your Employer Healthcare Plan through COBRA coverage for up to 18 – 36 months…
- You banked sick days or paid-time-off (PTO) to cover keeping your Employer Group Healthcare Plan (EGHP) after your retirement date, but are no longer an “active” employee…
- You are married with younger spouse the one still working providing the healthcare plan for both, and the older spouse is eligible for Medicare benefits…
These are all situations you need to check and double check to be certain you steer clear of any government “gotcha’s.”
Remember what they say about when you assume anything?
COSTLY MISTAKE #3: Not Being Aware Of, Or Paying Attention To, The New Process To Apply For Your Federal Part A & B Benefits…
With the passing of the Inflation Reduction Act, the old advice of going to Social Security is DEAD!
It hard to hear, but it’s true and in my opinion, the options you are left with, aren’t really good anymore. You're either frustrated trying to apply by phone -- OR -- challenged trying to apply by computer.
By phone, you can call and talk with phone robots, which is obviously very frustrating and rather infuriating. A recent analysis done by ’65 Incorporated’ (independent research firm advocating for American seniors), reported average wait time when calling Social Security is 2 hours and 32 minutes…with 25 million calls reported being disconnected withOUT speaking to anyone and no service received.
And, if you are lucky enough to get ahold of Social Security, and not hung up on, you do not actually apply for your Medicare benefits same day, instead, you are scheduled a future phone interview appointment with average wait between 9 to 12 weeks, that’s 2 to 3 months they make you sit around, and twiddle your thumbs, before you can get done what you need to do.
You can also make the alternative choice to go online, which has turned out to be challenging, and a huge, complicated chore…especially if the security settings on your home computer are not correct.
It’s even worse using a tablet or smartphone. A lot of people can only go so far, and can get locked out, not able to complete their application completely.
The online application has not streamlined, or made anything simpler, as promised, it has only created more headaches and hassles, and leaves a lot of room for error and wasting a lot of time.
** NOTE** The good news is, you don’t have to do anything with Medicare on your own. As the one and ONLY approved Certified Starting Medicare Specialist™️ for Erie County, my office does offer the benefit of Medicare SmartApp application services on-site where we are authorized to, not only complete and submit your Federal Medicare applications FOR YOU --- FREE, but we also have the ability to speed up the time it takes for approval, shortcutting the typical 2-3 months down to 2-3 weeks, sometimes as fast as 2-3 days. Let me take away the stress of you trying to tackle anything with Medicare on you own! We are always happy to help in any way we can, you just have to ask…
Due to our reputation and popularity being voted #1 best Medicare planning service in the area for the last 6 years in a row, appointments are limited and fill up fast. To see if you qualify to use the free, nationally-recognized and 5-star rated, Medicare SmartStart Program™️ I manage, call my local office in Clarence right now at (716) 833-0252. (Really the only people I can't help and the ones who never call).
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Who Is Andrew Hibbard?
Since 2015, Andrew has helped over 2,100+ WNY'ers through the free, 5-star rated and nationally recognized Medicare SmartStart Program™ to take away all the stress folks suffer with trying to tackle Medicare on their own. His impressive record of success has Andrew featured in Forever Young Magazine and the BEE Group Newspapers, exclusive interviews on WECK Radio's Senior Matter's Program, nominated to Buffalo Business First 40 Under 40 (2023), and listed in Marque's Who's Who In America (2024). He is the author of the award-winning #1 best-selling book, "Starting Medicare Smartly," which reveals the new, confusing rule changes for signing up for Medicare the first time and how to avoid common mistakes, not mess anything up, and prevent paying a permanent late penalty at 65 or anytime after