New to Medicare? Here Is Exactly What to Do

June 28, 2026 · 8 min read

By Kaleb Boedecker · Licensed Independent Insurance Agent (NPN 20642452) · June 28, 2026 · 8 min read

Getting on Medicare comes down to three moves: enroll through Social Security, learn what Part A and Part B actually cover and cost, then pick a plan to fill the gaps. Understanding how Medicare works is mostly about doing those steps in order instead of all at once.

I talk to people every week who think Medicare just shows up on their 65th birthday like a tax refund. It doesn't. For most folks it is something you have to go claim, and the gaps between the basic parts are where the real money lives. So let me walk you through it the way I would on a call.

The numbers you should anchor to first

Medicare eligibility starts at age 65 for most people. Your Initial Enrollment Period is a seven-month window that opens three months before your birthday month and closes three months after. Part A is premium-free if you or a spouse paid Medicare taxes for at least 40 quarters — about 10 years of work. Part B carries a standard monthly premium of $202.90 in 2026, and there is a late-enrollment penalty of 10% for each full 12-month period you go without qualifying coverage that sticks to you for life. Five numbers. Write them on a sticky note.

Myth: Medicare is free and automatic

This is the single most expensive misunderstanding I run into, so I'll say it plainly. Medicare is neither free nor, for most people, automatic.

If you are already drawing Social Security before 65, you may get enrolled in Part A and Part B without lifting a finger. But a lot of people are working longer now and haven't filed for Social Security yet. If that's you, nobody enrolls you. You have to do it yourself through the Social Security Administration at ssa.gov, and if you miss your window, that Part B penalty I mentioned can follow you for the rest of your life.

"Free" is the other half of the myth. Part A usually has no premium, but it has a deductible every time you go into the hospital. Part B has a monthly premium pulled straight out of your Social Security check, plus it only pays 80% of the Medicare-approved cost, leaving you the other 20%. That coinsurance has no ceiling on Original Medicare alone. One serious illness and that open-ended gap is exactly what lands people in bankruptcy. Keeping people out of that hole is my number one goal.

Step one: enroll through Social Security

The first thing — the thing that confuses people most — is that you enroll into Medicare through the Social Security Administration, not through me, not through a carrier, not through some plan. You go to ssa.gov, or you call Social Security, or you walk into a local office.

This is also the free part I help with. Walking you through the SSA enrollment screen costs you nothing, and there's no commission in it for me. I do it because the rest doesn't matter if this step goes sideways. If you're still on solid employer coverage past 65, there are rules about when you can delay Part B without a penalty, and that's a conversation worth having before you click anything.

Step two: understand Part A and Part B

Original Medicare is two parts, and they split your care down the middle.

Part A is hospital insurance. It covers inpatient hospital stays, skilled nursing facility care after a qualifying stay, some home health, and hospice. What does Medicare Part A cover that trips people up? It is the inpatient side — being formally admitted, not sitting in an ER under observation. Part A is premium-free for most, but it has a per-admission deductible.

Part B is medical insurance. Doctor visits, outpatient care, labs, preventive screenings, durable medical equipment. Part B is where your monthly premium goes, and it's the part that pays a share of approved costs and leaves the rest to you with no built-in ceiling.

Here's the analogy I use. Part A and Part B are two slices of bread. They're real, they're necessary, but by themselves they're a dry sandwich with a hole in the middle and no cap on what that hole can cost you. The plan you choose next is the filling.

Step three: choose a plan to fill the gaps

Once you're enrolled, the question becomes "okay, now what?" There are two roads, and you pick one.

Road one: a Medigap (Medicare Supplement) plan plus a standalone Part D drug plan. Medigap is standardized by letter — a Plan G from one carrier covers the same things as a Plan G from another, so you shop on price and company stability, not on a confusing benefit grid. Medigap has no networks: any doctor or hospital in the country that takes Medicare takes your plan. The tradeoff is that it doesn't include drug coverage, so you add a separate Part D plan for your prescriptions.

Road two: a Medicare Advantage (Part C) plan. These are run by private carriers, usually bundle your drug coverage in, and often add dental, vision, and hearing. Many run a $0 or low monthly premium. The catch is networks — HMOs and PPOs limit which doctors and hospitals you can use — and benefits can change every year.

I go deep on this fork in a separate post on choosing between Medigap and Medicare Advantage, because it's the decision that matters most. Here's the quick version.

Question to ask	Medigap + Part D	Medicare Advantage
Provider networks?	None — any doctor that takes Medicare	Yes — HMO/PPO networks
Drug coverage?	Separate Part D plan	Usually bundled in
Monthly premium	Higher, predictable	Often low or $0
Out-of-pocket predictability	Very predictable	Varies; capped by an annual MOOP
Extras (dental/vision/hearing)	Rare	Often included
Best fit for	Travelers, anyone wanting freedom to choose any doctor	Budget-focused, healthy, in-network locals

One thing I won't let slide: the network on an Advantage plan is not a detail. MD Anderson in Houston, one of the largest cancer hospitals in the country, is out-of-network for every individual ACA marketplace plan in Texas and for all but a small set of Medicare Advantage plans — Blue Cross Blue Shield of Texas dropped it from their Medicare Advantage network in late 2024. If you get a serious diagnosis, the network you picked years earlier suddenly decides where you can be treated. That's why I do the homework on your doctors before you sign anything.

Three things to know before you enroll

1. You have to act. Nobody auto-enrolls most people anymore, and a missed Part B window can cost you a lifelong penalty.
2. The coinsurance gap has no cap on Original Medicare alone. The plan you add — Medigap or Advantage — is what puts a ceiling on what one bad year can cost you.
3. Check your doctors and your drugs first, then choose. Pick the plan around the care you actually use, not around a flashy benefit.

A word on that last one. Some plans get marketed with a shiny "best in the market" badge for one specific perk, and seniors get steered into them by agents chasing a bigger check who never checked whether the client's own doctor was in network. That's the opposite of how I work. I get paid by the carrier, not by you, so I work for you, not for them. A lot of plans are even becoming uncommissionable — they pay me nothing — and I'll still put you in one if it's the right fit. That's what an independent agent actually does for you.

What I'd do if I were turning 65 tomorrow

I'd file with Social Security inside my Initial Enrollment Period, confirm my Part A and Part B start dates, then sit down and list every doctor I want to keep and every prescription I take. Then I'd weigh my Medicare Supplement, Advantage, and Part D options against that list — not against the marketing. And I'd lean on the year-round stuff most people forget exists: an agent helps with billing, eligibility, claims, and an annual review every fall to make sure your plan still fits. One more piece of advice I give everyone: don't ever pay the first bill you get. Always call first.

If you want a real person in your corner who does this in Texas and several other states, that's Kaleb Boedecker, a licensed independent agent, and I'm a phone call away at 281-607-4053.

Frequently asked questions

When do I sign up for Medicare?

Your Initial Enrollment Period runs around your 65th birthday — starting three months before your birthday month and ending three months after, a seven-month window. If you're still on creditable employer coverage, you may be able to delay Part B without penalty, but confirm that before your window closes.

What does Medicare Part A cover?

Part A is hospital insurance. It covers inpatient hospital stays, skilled nursing facility care after a qualifying admission, some home health, and hospice. It does not cover routine doctor visits or outpatient care — that's Part B. Most people pay no Part A premium but owe a per-admission deductible.

Is Medicare really not free?

Part A is usually premium-free, but Part B has a monthly premium pulled from your Social Security check, and Original Medicare typically pays only 80% of the approved cost. The remaining 20% has no annual cap on its own, which is exactly why most people add a Medigap or Advantage plan.

Do I have to choose a plan the moment I turn 65?

You enroll in Original Medicare during your Initial Enrollment Period, and that's also your best window to buy a Medigap plan with guaranteed acceptance. You can change Advantage and Part D plans later during the fall Annual Enrollment Period, but the early Medigap window matters most for your long-term options.

Does using an agent cost me anything?

No. There's no reason not to use an agent. The carrier pays me a commission, never you, and your rate is identical to going direct. I help you enroll, compare carriers, and handle billing, claims, and annual reviews year-round — all at no cost to you.