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I'm a Medicare-certified health & life insurance agent contracted with multiple carriers to offer many choices. I'm Cheri Head.

I'm also a Registered Social Security Analyst (RSSAยฎ). I help people become savvy about their health insurance & Social Security options.
๐Ÿ’™ As a licensed idependent health & life insurance agent, I help seniors navigate the Medicare maze so they can make the best choices for their health care. I am also certified to offer other life and health insurance products. As a Registered Social Security

06/13/2026

One of the biggest Medicare mistakes I see people make is when they decide to work past age 65 and assume they can just continue on their employer coverage rather than go onto Medicare.

If you remember just one thing, this is it: ** When you turn 65, and forever afterwards, the government requires you to maintain "creditable" coverage for both medical and prescription drugs or else face lifetime penalties. **

Q - What is considered "creditable" coverage?
A - Either Medicare (Part B-medical and Part D-prescription drugs) or coverage that is deemed as good as Medicare.

Q - How do I know if my coverage is "creditable?"
A - If your employer has 20 or more full-time employees, their group insurance is probably creditable. PROBABLY. If your employer gives you a letter stating that your medical AND prescription drug coverage is creditable, you're fine to stay on their coverage if you wish. If they don't state in writing that your coverage is creditable, or if your employer is small, you need to go onto Medicare when you turn 65.

Q - What happens if I don't maintain creditable medical and drug coverage starting at age 65?
A - You will begin to accrue penalties - one for Part B (medical) and one for Part D (prescription drugs) that will follow you forever.

Q - Can I go onto Medicare when I turn 65 even if I have creditable coverage and want to keep working?
A - Absolutely. That's your right. Given the rise in costs for employer insurance, in many cases you might get better coverage and/or lower prices by going onto Medicare than you are getting with your current employer coverage.

Q - What about Part A? Do I have to sign up for that when I turn 65?
A - Most people are entitled to free Part A because they've worked at least 10 years and paid F**A taxes. If that's you, you aren't required to sign up for your Part A, but it often makes things easier when you later sign up for Part B. HOWEVER, if you have an HSA account, you and your employer should stop making contributions 6 months before you retire so as to avoid tax penalties.

Many mistakes can happen when you decide to work past 65: missing the window to sign up for Medicare when you're coming off employer coverage; not getting the proper form from your employer or filling it out incorrectly; missing the short deadline to get prescription drug coverage if you want to stick with original Medicare; using the wrong Special Enrollment Period when enrolling; choosing one Medicare path without learning about both of them; and many more.

Feel free to reach out to me for help. I'm licensed in CA and 9 other states. My guidance is free and comes with no strings. If you already have a trusted Medicare-certified agent or broker, reach out to them. But please don't rely on the well-meaning advice of friends or coworkers or AI or medical offices or any one insurance company. This is a nuanced system and very easy to mess up!

Cheri

06/11/2026

My latest 5-star Google review. I truly meet the coolest people in my business!

05/12/2026

๐Ÿคฉ Cool Medicare Update That Most People Havenโ€™t Heard About Yet ๐Ÿคฉ

A new temporary federal program called the Medicare GLP-1 Bridge is scheduled to begin July 1, 2026, and no one seems to be talking about it, so if you're reading this, you're among the first๐Ÿ˜„

๐“๐ก๐ž ๐ฉ๐ซ๐จ๐ ๐ซ๐š๐ฆ ๐ฆ๐š๐ฒ ๐ก๐ž๐ฅ๐ฉ ๐ž๐ฅ๐ข๐ ๐ข๐›๐ฅ๐ž ๐Œ๐ž๐๐ข๐œ๐š๐ซ๐ž ๐›๐ž๐ง๐ž๐Ÿ๐ข๐œ๐ข๐š๐ซ๐ข๐ž๐ฌ ๐š๐œ๐œ๐ž๐ฌ๐ฌ ๐œ๐ž๐ซ๐ญ๐š๐ข๐ง ๐ฐ๐ž๐ข๐ ๐ก๐ญ-๐ฅ๐จ๐ฌ๐ฌ ๐ฆ๐ž๐๐ข๐œ๐š๐ญ๐ข๐จ๐ง๐ฌ ๐Ÿ๐จ๐ซ ๐š ๐Ÿ๐ข๐ฑ๐ž๐ $๐Ÿ“๐ŸŽ ๐ฆ๐จ๐ง๐ญ๐ก๐ฅ๐ฒ ๐œ๐จ๐ฉ๐š๐ฒ ๐ญ๐ก๐ซ๐จ๐ฎ๐ ๐ก ๐ƒ๐ž๐œ๐ž๐ฆ๐›๐ž๐ซ ๐Ÿ‘๐Ÿ, ๐Ÿ๐ŸŽ๐Ÿ๐Ÿ•.

A few important things to know:

โ€ข This is NOT regular Part D coverage
โ€ข You must already have a Medicare Part D or Medicare Advantage drug plan
โ€ข Your insurance company does not need to โ€œopt inโ€
โ€ข Eligibility is based on medical criteria your doctor must certify

Medications currently included in the program:
โ€ข Wegovyยฎ
โ€ข Foundayoยฎ
โ€ข KwikPenยฎ version of Zepboundยฎ

Important financial details:

Part D deductible & spending cap:
This program sits outside the normal Part D benefit structure. That means the $50 you pay does NOT count toward your yearly Part D deductible or the annual $2,100 out-of-pocket prescription drug cap.

Extra Help / LIS:
Extra Help (Low-Income Subsidy) does NOT apply to this program. Even if you normally pay very little for your prescriptions, the $50 copay under this program is currently a fixed amount for everyone.

In general, eligibility requires:
โ€ข BMI of 35+
or
โ€ข Lower BMI levels combined with certain qualifying health conditions such as heart disease, kidney disease, high blood pressure, pre-diabetes, or prior stroke/heart attack

Because this is a medical program, your doctor must submit the approval request.

Have other Medicare questions or issues? Reach out. I help with all things Medicare, and my services are always free with no obligation or strings.

One important note: this is a brand-new federal pilot program, and details may continue to evolve as additional guidance is released.

I'll put a link to the official site in the comments.

~Cheri Head
[email protected]

05/08/2026

**IMPORTANT PSA for those on Medicare and Medi-Cal **

Something is happening right now in Marin County (and certain other California counties where Kaiser has facilities) that is causing difficulties for those who are dual eligible for Medicare and Medi-Cal.

๐Ÿ‘‰ During the annual Medi-Cal renewal/redetermination process, PEOPLE ARE BEING AUTOMATICALLY SWITCHED TO KAISER'S MEDI-CAL PLAN from their current Medi-cal plan (which is Partnership HealthPlan in Marin county).

This adversely affects people who have ALL of the following:
โ€ข Medicare
โ€ข Medi-Cal
โ€ข A non-Kaiser Medicare Advantage plan

Why this matters:

If your Medi-Cal switches to Kaiser while your Medicare Advantage plan is non-Kaiser, the two systems will not work smoothly together. This can create problems with:
โ€ข Referrals
โ€ข Coordinating care
โ€ข Accessing certain Medi-Cal-covered services and benefits

โš ๏ธ If you want to KEEP your current non-Kaiser Medicare Advantage plan, your Medi-Cal plan must be Partnership HealthPlan (the only non-Kaiser Medi-Cal plan currently available in Marin County). THIS IS VERY IMPORTANT. (If you are in another county, this will be the Medi-Cal plan you have been on.)

Hereโ€™s what to do:
When you receive your annual Medi-Cal renewal/redetermination packet,
โ€ข Read it carefully and immediately
โ€ข The packet often arrives in a yellow envelope around your Medi-Cal anniversary date
โ€ข If you meet the critera above, you need to immediately do the following:

๐Ÿ“žCall Health Care Options: 1-800-430-4263

Say:

โ€œI want to choose my Medi-Cal health plan and select Partnership HealthPlan.โ€ (or whatever your existing Medi-Cal plan is)

If your Medi-Cal plan has ALREADY been changed to Kaiser and you have a non-Kaiser Medicare Advantage plan, follow the same steps above. If approved, the change back to the other plan will generally take effect on the first day of the following month.

Timing matters. Acting BEFORE the effective date on the letter may prevent the switch.

This issue does NOT automatically change your Medicare Advantage plan, but it can absolutely affect how your coverage works day to day.

If I can help, let me know.

04/19/2026

This email warmed my heart today.

03/18/2026

MORE MEDICARE NEWS ---

An issue arose this week (3/17/26) that may affect some of you on Medicare if you have either a Medicare Advantage or Part D Rx drug plan with HealthSpring (formerly known as Cigna).

CMS (the Centers for Medicare & Medicaid Services) advised HealthSpring that because of an issue with Medicare Part A and/or Part B entitlement data in their system, some beneficiaries have been DISENROLLED from their plans.

**** IF YOU RECEIVE A LETTER OF DISENROLLMENT FROM HEALTHSPRING when you didn't ask to be disenrolled, you should FIRST reach out to HealthSpring ASAP and THEN contact your local Social Security office. ****

You can reach HealthSpring at 800-222-6700

The main Social Security Administration number is 800-772-1213. You can try calling your local SSA office, if you have the number, which is unlikely as they are incredibly hard to find. (If you're in Marin county, let me know or check my Nextdoor post, as I DO have that number.)

**** The reason it's important to check with the SSA is because this is an ENROLLMENT data issue with CMS. ๐ˆ๐ง ๐จ๐ญ๐ก๐ž๐ซ ๐ฐ๐จ๐ซ๐๐ฌ, ๐ฒ๐จ๐ฎ๐ซ ๐ž๐ง๐ซ๐จ๐ฅ๐ฅ๐ฆ๐ž๐ง๐ญ ๐ข๐ง ๐๐š๐ซ๐ญ ๐€ ๐š๐ง๐/๐จ๐ซ ๐๐š๐ซ๐ญ ๐ ๐ฆ๐š๐ฒ ๐ก๐š๐ฏ๐ž ๐›๐ž๐ž๐ง ๐š๐Ÿ๐Ÿ๐ž๐œ๐ญ๐ž๐. If this is the case, ensure they fix it ASAP, as Parts A and B are the core of Medicare and required for all plans.

This is what HealthSpring says they will do for those affected:

Member will have "open access to care in their eligibility systems for 60 days.
The member then has 60 days to resolve the issue with the Social Security office.
We will check the CMS system daily to see if the member's Medicare Part A/B coverage has been restored.
Once it is restored, we can reinstate the member's coverage.
If this issue is not resolved within 60 days, we will be required to terminate that member's coverage."

So watch your mail if you have a HealthSpring plan.

03/18/2026

** HEADS UP RE MEDICARE DATA BREACH **

Because of a CMS (Centers for Medicare and Medicaid Services) data breach, a large number of Medicare beneficiaries will be issued new Medicare cards with new Medicare numbers. If you are part of this group, you should receive a new card during the month of March 2026, and your new number will be effective April 14, 2026.

If this happens, please contact your agent/broker to give them your new number. If you don't have an agent or broker, notify your Medicare plan carrier(s) to give them your updated Medicare number.

DO NOT EMAIL ANYONE YOUR MEDICARE NUMBER, as this is highly insecure. In fact, never give anyone that number unless they are someone you trust.

12/04/2025

Hey, Pisces & Aries peeps! ๐Ÿ™‚

Is your milestone 65th birthday coming up in March? If so, your Medicare Initial Enrollment Period just started, and it ends June 30, 2026.

If you sign up for Medicare during December, January or February, your coverage will start as early as the FIRST day of March.

But SHOULD you or do you HAVE TO sign up for Medicare parts A and/or B now? The answer is: MAYBE.

If you have creditable employer coverage (with an employer having 20+ full-time employees), you MAY be able to wait. But you may not want to. Nowadays, employer group insurance has gotten so expensive that Medicare almost always gives you either better coverage or costs less or both. You don't know until you compare.

Reach out to me if you are confused. (And don't feel bad, everyone is!)

You don't know what you don't know...but I do. ๐Ÿ˜‰Best of all my help costs you nothing, as I'm compensated by insurance carriers when I help you choose a plan and enroll. And the cost is the same whether you use an agent or not.

*** I make sure you know and understand ALL your options and make the process as easy as possible for you.

Also... if you were born on the 1st day of any month, you're considered to have been born the month prior, so the seven-month Medicare window starts a month earlier for you. Weird, I know.

PS - If you were born in September of 1960, your Initial Enrollment Period ends on December 31.

11/07/2025

** Medicare Update **

This applies specifically to those losing a UHC Advantage plan at the end of this year, but it is also helpful information if you are losing ANY OTHER Advantage plan, as well.

If you are on Medicare and have a United Healthcare Advantage plan that is terminating at the end of this year, you probably received at least one very confusing and inaccurate letter from UHC. You may have gotten a similar letter from whatever carrier you have.

In the UHC letter, it says that if you want to STAY in your current plan, you'll need to choose a new provider in order for the plan to cover your care. It also says that if you choose to stay in your plan, they can provide you with a list of contracted providers and help you select a new network provider.

BOTH OF THESE STATEMENTS ARE UNTRUE. YOUR PLAN IS TERMINATING on 12/31/25!!
They also say that because your plan is terminating you have the right to return to Original Medicare. This is true, but without additional context, it is very dangeous advice! Why? One, because if you simply return to original Medicare WITHOUT also choosing a standalone drug plan, you will have no Rx coverage and will begin to accrue a lifelong penalty after 63 days without Rx coverage.

And two, if you you simply return to original Medicare WITHOUT also choosing a Medigap/Supplement plan, you will also be responsible for paying 20% of nearly ALL medical costs--with no cap--as well as the sizeable deductions (over $1600) on part A every time you go to the hospital for a different reason.

Having Original Medicare (A&B) all by itself can be a financially dangerous solution.

What you DO have is the right to go into another Medicare Advantage plan---and there are some very good options available in Marin county, California--where I live--for 2026. This is unfortunately not true everywhere, as Advantage plans are specific to the COUNTY in which you live and the plans available there during that calendar year.

You also have the right to GUARANTEED ISSUE (i.e., you don't have to be healthy or answer health questions) to get a Medigap aka Medicare Supplement plan. This choice would require you to get a part D plan also, and the deadline for that is 12/7, so don't wait until the last minute to think about these things.

***** Please...if you have a trusted Medicare-certified agent, reach out to them asap. Or reach out to me. This is what I do. But please don't try to make these decisions on your own unless you completely understand all the ramifications.

All agents are crazy busy at the moment. The sooner you reach out, the better.

11/02/2025

Hey! Aquarius & Pisces peeps! ๐Ÿ™‚

Is your milestone 65th birthday coming up in February? If so, your Medicare Initial Enrollment Period starts today, November 1 and ends May 31, 2026.

If you sign up for Medicare in the next two months, your coverage will start as early as the first day of the month you turn 65.

But SHOULD you or do you HAVE TO sign up for Medicare parts A and/or B now? The answer is: IT DEPENDS.

If you have creditable employer coverage (with an employer having 20+ employees), you MAY be able to wait. But you may not want to. About half of the time, Medicare may give you either better coverage or cost less or both. You don't know until you compare.

Reach out if you are confused.

You don't know what you don't know...but I do. ๐Ÿ˜‰Best of all my help costs you nothing, as I'm compensated by insurance carriers when I submit an enrollment on your behalf. (And the cost is the same whether you use an agent or not.)

*** My job is to make sure you know ALL your options and make the process as easy as possible for you.

Also... if you were born on the 1st day of any month, you're considered to have been born the month prior, so the seven-month Medicare window starts a month earlier for you. Weird, I know.

PS - If you were born in August of 1960, your Initial Enrollment Period ends on November 30.

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