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Whether you’re turning 65, retiring early, or wondering if your current plan still fits – get answers from Health Market Advocates. No pressure, no jargon, no homework.
Different starting points, same goal: coverage you understand and doctors you keep.
Your mailbox is full of Medicare ads and every one says something different. We’ll cut through the noise: what your deadlines really are, what Original Medicare covers, and how to compare Advantage and Supplement paths calmly – months before anything is due.
Leaving work early means bridging the gap until Medicare begins. We’ll map your options – COBRA, marketplace plans, private coverage – and the real costs of each, so early retirement doesn’t come with a coverage surprise.
Plans change every year – premiums, networks, drug lists. If you haven’t reviewed yours since you enrolled, you might be paying for coverage that no longer fits. An annual review takes 20 minutes and often pays for itself.
Everyone talks in letters. Here’s what the letters actually mean.
Covers inpatient hospital stays, skilled nursing care after a hospital stay, and hospice. Most people pay no monthly premium for Part A if they’ve worked and paid Medicare taxes long enough.
Covers doctor visits, outpatient care, preventive services, and medical equipment. Part B has a monthly premium, and enrolling on time matters – late enrollment can mean a permanent penalty.
Private plans that bundle Parts A and B – and usually D – often with extras like dental or vision. Networks and costs vary by plan and county, which is exactly why comparing matters.
Covers your medications. Every Part D plan has its own drug list and preferred pharmacies, so the right plan depends entirely on the prescriptions you actually take.
Medicare runs on enrollment windows. Miss one and you can face gaps or lifetime penalties – know them and everything gets calmer.
7 months around your 65th birthday
Starts 3 months before your birthday month, includes your birthday month, and ends 3 months after. This is when most people first enroll in Parts A and B – and starting early in the window means your coverage begins on time.
October 15 – December 7, every year
The yearly window to join, switch, or drop Medicare Advantage and Part D plans for the coming year. This is when an annual review with our team earns its keep.
When life changes
Retiring and losing employer coverage, moving to a new area, and certain other life events open personal enrollment windows outside the standard dates. If something’s changing in your life, ask before assuming you have to wait.
Prefer to learn by watching? Our Medicare 101 session covers the essentials – right here on this page.
New Medicare 101 Video Coming Soon!
Joshua Ruiz founded Health Market Advocates to make Medicare easier to understand and less stressful to navigate. As your Insurance Professor, he helps people approaching 65 understand enrollment timelines, compare their coverage options, and avoid costly mistakes. Joshua has built a team of licensed advocates who share his education-first approach. When you reach out, a qualified HMA team member will explain your options clearly, answer your questions, and continue supporting you after enrollment with annual reviews, claims guidance, and real help from real people.
Our Medicare guidebook covers what Medicare does and doesn’t cover, the enrollment windows above in more detail, the Advantage-vs-Supplement decision, and the questions to ask before you enroll.
Read it at your kitchen table. Bring your questions whenever you’re ready.
By submitting my information, I consent to receiving this educational Medicare Guidebook about Medicare, Medicare Supplement, Medicare Advantage, and Prescription Drug Plans from Health Market Advocates.
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The questions people actually ask us – answered the way we’d answer them in person.
Ideally about 6 months before your 65th birthday. That gives you time to understand your options, check your doctors and prescriptions, and enroll early in your window so coverage starts on time – no deadline stress, no rushed decisions.
Not always – it depends mainly on the size of your employer and whether your current coverage counts as “creditable.” Many people with solid employer coverage delay Part B without penalty; others need to enroll on time to avoid one. This is one of the most common (and most expensive) places people guess wrong, so it’s worth a 10-minute conversation with our team before your window opens.
Two different philosophies. Medicare Advantage (Part C) changes how you receive your benefits – usually lower monthly premiums, often with extras, but with plan networks and plan rules. A Supplement (Medigap) works alongside Original Medicare – typically higher premiums, but broad doctor access and more predictable costs. Neither is better for everyone; one usually fits your health, budget, and travel habits better than the other. That’s the heart of the conversation we’ll have.
Original Medicare (Parts A and B) generally does not cover most outpatient prescriptions. Drug coverage comes through a standalone Part D plan or through a Medicare Advantage plan that includes it. Every drug plan has its own list of covered medications, which is why we check your exact prescriptions before recommending anything.
No – our guidance comes at no cost to you. We’re compensated by insurance carriers when you enroll, and that doesn’t change your premium. Because we’re independent and compare many carriers, our recommendation is built on what fits you.
Yes – that’s when the relationship really starts. Our team provides ongoing support with claims questions, an annual review to make sure your plan still fits, and a real person in your corner whenever something changes in your life or your coverage.
