I’ve worked with Medicare clients for more than a decade, and one thing I’ve learned is that Medicare becomes much easier when you stop looking at it as one enormous decision. It’s really a series of smaller decisions that happen at different points in your life. That’s one of the reasons we created MedicareChecklist.com.
It’s a free website we’ve been developing where you answer a few questions about your situation, and the website creates a Medicare checklist specifically for you. Your situation is not the same as your neighbor. If you are on Original Medicare with a supplement and you take two generics, your checklist looks different than someone on Advantage who takes six prescriptions and sees three specialists. A generic check list helps neither of you
Enrolling in Medicare requires careful timing, so I built this free tool to make it simple for anyone, anywhere in the country. The home page quiz asks up to four quick, plain-language questions – one at a time – and recommends the checklist that fits you best.
Are you already enrolled in Medicare?
When do you turn 65? Are you or your spouse still working?
Are you moving? What coverage do you have today?
Get the Medicare checklist that fits you best.
When you finish, you get a personalized letter from me, a step-by-step action checklist tailored to your dates, and the option to schedule a free Medicare review with a licensed advisor – at no cost to you.
If you’re approaching age 65 or retiring soon, this section is for you. The threshold for Medicare eligibility includes turning age 65 or having a qualifying disability, such as receiving social security disability insurance benefits. Getting the timing right during your initial enrollment is where most costly mistakes happen. All five tools in this section live under the New to Medicare category.
Your initial enrollment period lasts seven months: it starts three months before your 65th birthday, includes your birth month, and ends three months after. For example, if you turn 65 on June 21, your IEP runs from March 1 to September 30 – and you can enroll in Medicare three months before turning 65. Missing this window without qualifying coverage can trigger lifetime Part B and Part D late enrollment penalties. The Social Security Administration handles the application process for Medicare enrollment, and if you’re already receiving social security benefits, you may be automatically enrolled.
My team and I use these same timelines with clients to compare medigap plans, Medicare Advantage plans, and prescription drug coverage so their coverage starts the first day they need it. You can enroll in Medigap within six months of starting Part B – that’s your Medigap open enrollment period, and during those six months no insurance company can turn you down or charge more for pre-existing conditions.
The Medicare open enrollment period – officially called the Annual Enrollment Period – runs every year from October 15 through December 7. Changes made during this window take effect January 1. MedicareChecklist.com has a specific checklist for each type of change.
⚠ One important detail: if you enroll in a new Medicare Advantage or Part D plan during this period, Medicare automatically cancels your old one on January 1. But a Medicare Supplement (Medigap) is the one plan you must cancel yourself – by calling the insurance company directly and asking for written confirmation.
You should review your current health plan coverage before making any changes, and determining Medicare coverage involves assessing total costs beyond premiums – including deductibles, co pays, and what you’ll pay for your specific medications.
My team at Medigap Seminars can help you understand your medicare annual notice and compare medicare plan options – at no cost to you. We work with multiple insurers as an independent broker, so the guidance is unbiased.
Moving to a new state, county, or even a nearby area can change your plan options, especially for Medicare Advantage and Part D plans. MedicareChecklist.com has a dedicated checklist for this situation.
The Moving with Medicare checklist asks whether you have Original Medicare only, Original Medicare with a medigap plan and Part D, or a Medicare Advantage plan, and builds the steps around your answer.
Your window to switch begins the month before you move and continues for two full months after.
The window starts the month you notify them and continues for two months.
⚠ Never cancel any existing Medicare plan before new coverage is confirmed. The checklist helps you time the change so there’s no gap. This tool is especially useful for retirees relocating to be closer to family, people moving to a new state, or anyone whose doctors or pharmacy options will change. For snowbirds, I’ve also written about Medicare for Florida Snowbirds.
Every MedicareChecklist.com tool follows the same simple structure. Each starts with a few basics – your ZIP code, date of birth – then asks questions specific to your situation: your employment, employer size, or the type of Medicare coverage you have today.
A letter from me explaining the Medicare parts and plan types that apply to you - in plain English.
Concrete deadlines, such as when to enroll in Part B to avoid a late enrollment penalty or when to submit a medigap application.
Reminders about official forms (like Form CMS-L564), which enrollment period you're in, and when coverage starts.
The option to schedule a free review with a licensed advisor who can compare plans, premiums, and networks.
Using MedicareChecklist.com is free, there is no obligation, and the help from my team comes at no additional costs to you.
You don’t need to memorize every Medicare rule. Just match your situation to a checklist and let it guide you:
| Your situation | Start with this checklist |
|---|---|
| Turning 65 in the next year | Turning 65 Roadmap and Birthday Month |
| Working past 65 with group coverage | Working Past 65 and Part B at 65 |
| Contributing to an HSA | Part A at 65 |
| Switching plans this fall | Annual Enrollment checklists |
| Medicare Advantage plan canceled | My Plan Was Canceled |
| Moving to a new state or county | Moving with Medicare |
If you’re still not sure, start at MedicareChecklist.com and answer the four quick questions – it will send you to the right checklist.
After completing a checklist, review the personalized letter and action plan. Then either follow the steps on your own or schedule a free Medicare review with my team. Either way, you’ll have a clear medicare enrollment checklist built around your dates and your health needs.
Visit MedicareChecklist.com now, choose the checklist that matches your situation, and use it as your Medicare roadmap for 2027 and beyond.
MedicareChecklist.com serves both groups. The New to Medicare checklists cover your initial enrollment period and when to enroll in Part A or Part B. The Annual Enrollment Period checklists help current enrollees review their annual notice, evaluate whether their current plan still meets their health needs and budget, and switch between Medicare Advantage and medigap plans. Even long-time Medicare beneficiaries benefit from reviewing their medicare benefits each fall.
No. The tool explains which type of Medicare decision you’re facing, which enrollment period applies, and gives you a checklist of steps and deadlines. After completing it, you can talk with a licensed advisor at Medigap Seminars who will compare specific Medicare Supplement, Medicare Advantage, and Part D plans in your ZIP code. The guidance is educational and independent – there’s no cost for using the checklists or for the plan comparison and enrollment process through my team.
Yes. You should always check if your doctor accepts Medicare before enrolling in any plan. Healthcare providers must accept Medicare for coverage under Original Medicare plans, but Medicare Advantage plans use provider networks that vary by plan. The checklists remind you to verify that your primary doctor and other providers are in-network before switching, and my advisors can help you check networks during a free review.
Medicare has other enrollment periods. The general enrollment period runs from January 1 through March 31 each year, with coverage starting the month after you sign up – but late enrollment usually means lifetime penalties. You can enroll in Part D from April 1 to June 30 during the Part D general enrollment period as well. A special enrollment period may apply if you’re losing active employer coverage or moving. Because these rules are strict and time-sensitive, anyone who thinks they missed a deadline should complete the relevant checklist and contact Medigap Seminars right away. For more on costly Medicare mistakes and how to avoid them, I’ve written a separate guide.
MedicareChecklist.com is completely free, and there is no obligation to enroll in any Medicare plan. Medigap Seminars is paid by the insurance companies if you choose to enroll, so there are no fees to you for quotes, comparisons, or enrollment help. The goal behind every checklist – and behind my team – is to help you choose Medicare coverage with confidence, based on your own doctors, your current medications, and your budget, with every key date clearly explained and no pressure. You can enroll online or with the help of an advisor – whichever you prefer.
Still have questions? Talk with a licensed advisor - at no cost to you.
