Turning 65
Your Complete Medicare Enrollment Guide
A step-by-step roadmap to enrolling in Medicare on time, avoiding costly penalties, and choosing coverage that fits your life — with a local advisor by your side every step of the way.
Don't Go It Alone
Why working with an advisor matters more than you think
Turning 65 triggers one of the most complex decisions of your financial life. Most people navigate it alone, armed only with confusing government mailings and a flood of TV commercials. You don't have to.
Medicare is genuinely complicated
There are multiple parts, dozens of plan options, strict enrollment windows, and permanent penalties hiding around every corner. Most people turning 65 are handed a Medicare card and left to figure it out from a stack of confusing mailers. An experienced advisor has guided hundreds of people through this — and knows exactly which questions to ask and which pitfalls to avoid.
One wrong decision can cost you for decades
Miss an enrollment deadline and you could pay a higher premium for the rest of your life. Choose the wrong plan type and you might be locked out of the one you actually wanted. These aren't small mistakes — they compound year after year through retirement. Having someone in your corner who does this every day is the difference between enrolling with confidence and hoping you got it right.
We stay with you long after enrollment
Turning 65 isn't a one-time event — Medicare plans change every year, your health changes, your prescriptions change. We review your coverage every Annual Enrollment Period and reach out proactively if we see a better fit. You're not on your own after you sign the paperwork. We're still your advisor in year one, year five, and year ten.
You deserve someone who works for you, not a carrier
When you call a Medicare plan's 1-800 number, the rep on the other end works for that company and can only sell you their products. An independent advisor like Jenkins IR works with 10 carriers and has no quota to fill. We show you the options available in your zip code and recommend only what genuinely fits your situation — even if that means recommending a plan that pays us less.
Enrollment Timeline
Your 7-Month Enrollment Window
The Initial Enrollment Period (IEP) is a 7-month window centered on your 65th birthday. This is your most important Medicare moment.
3 Months Before
Your Initial Enrollment Period Opens
Month You Turn 65
Your Medicare Coverage Can Begin
3 Months After
Your Initial Enrollment Period Closes
Step-by-Step
10 steps to Medicare enrollment
Click each step to see the details. Steps marked "Important" have the highest penalty risk if skipped.
Avoid These
Permanent penalties you want to avoid
Medicare late enrollment penalties are permanent and add up over decades of retirement.
Part B Late Enrollment Penalty
Penalty Amount
10% per 12-month period delayed
Duration
Permanent — added to your Part B premium for life
How to Avoid
Enrolling during your Initial Enrollment Period, or having qualifying employer coverage
Part D Late Enrollment Penalty
Penalty Amount
1% per month without creditable coverage
Duration
Permanent — added to your drug plan premium for life
How to Avoid
Enrolling in Part D as soon as you have Part B, even if you take no medications
Medigap Premium Increase
Penalty Amount
Varies — potentially denied or charged more
Duration
Outside your Open Enrollment Window, you may face medical underwriting
How to Avoid
Enrolling in Medigap within 6 months of Part B enrollment
These are the exact situations we help clients avoid every single day. Talk to us before your enrollment window closes.
Complete Transparency
How we get paid — and why it costs you nothing
One of the first questions people ask is: "What's the catch?" There isn't one. Here's exactly how independent Medicare advisors work — and why the system is set up to benefit you.
You pay us nothing — ever
Independent Medicare advisors are compensated directly by the insurance carriers, not by clients. When you enroll in a plan through CRSG, the carrier pays us a commission. You pay the exact same premium whether you use an advisor or enroll entirely on your own. Our guidance is genuinely free.
Our commission never changes the price you pay
Federal law prohibits insurance carriers from charging you more because you worked with an agent. The premium is the same on every channel — Medicare.gov, calling the carrier directly, or enrolling through us. There is no markup, no hidden fee, and no fine print. The only thing that changes is that you have someone looking out for you.
We are legally required to act in your best interest
Licensed Medicare advisors are bound by state and federal regulations — and by the Centers for Medicare & Medicaid Services (CMS) — to recommend plans that are suitable for each client's individual needs. Recommending a plan that isn't in your best interest isn't just bad practice, it puts our license at risk. Your interests and ours are genuinely aligned.
Trust is built on transparency — so here's ours
We tell every client exactly how we're compensated. We tell you which carriers pay us and which don't. If there's ever a reason a certain plan might not be the best fit, we say so — even if it costs us the sale. We've built our business on referrals from satisfied clients, and that only works if we earn your trust first.
"You pay the same premium whether you call the carrier directly, go to Medicare.gov, or work with us. The difference is that with us, you have a licensed advisor who knows your situation, answers your calls, and reviews your coverage every year."
— Jordan Jenkins, Jenkins Insurance & Retirement
Many people also review their life insurance or final expense coverage around the time they enroll in Medicare.
Helping a parent through this instead? See our guide for adult children and caregivers →
Content reviewed against 2026 plan-year figures. Dollar amounts change annually — we'll confirm the current numbers in your consultation.
Free Guides
Go deeper on this topic
Plain-language guides from our free resource library — no email required to read.
You don't have to figure this out alone
Medicare is complicated on purpose — and the stakes are high. One missed deadline or wrong plan choice can follow you into retirement for decades. We've helped hundreds of Wyoming and Utah families navigate this exact moment. Let us do the same for you — at absolutely no cost.
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