Healthcare Planning
Medicare, explained like you're new to it
Navigating Medicare
The parts, the deadlines, and the decisions that actually have money attached to them — written the way I'd explain it at a kitchen table. About twenty pages, no plan names.
What I can help with
Turning 65
Working out your enrollment windows, whether to delay anything, and what to do first.
Still working
Whether your employer coverage lets you delay Part B without a penalty — a question where the answer depends on details worth checking.
Reviewing what you have
Plans change their costs and drug lists every year. A yearly look is free and sometimes finds real money.
The deadline is the part that costs people money.
Not choosing the wrong plan — choosing late. One of your enrollment windows only opens once, and most people find out it existed after it closed.
Where this fits
- Medicare Planning
- Short-Term Care and Critical Illness
- Individual Healthcare Solutions
Medicare guides
7 guides · scroll or swipe
- Medicare 101
Medicare 101: the four parts, in plain English
What Parts A, B, C, and D actually are, and which ones you have to think about.
6 minute read - Enrollment windows
When you can sign up — and what happens if you miss it
Your enrollment windows, the one that only opens once, and the penalties that last for life.
7 minute read - Your two paths
Original Medicare or Medicare Advantage: the two paths
The one real fork in the road, what each path trades away, and how to tell which fits.
8 minute read - Supplements
Medicare Supplements (Medigap), explained
Why a Plan G is a Plan G everywhere, what supplements actually cover, and the timing that matters most.
7 minute read - Drug coverage
Part D and your prescriptions
How drug plans decide what they cover, why the same medication differs between them, and the yearly check worth doing.
6 minute read - Working past 65
Still working at 65? What to do about Medicare
When you can safely delay Part B, when delaying costs you permanently, and why employer size decides it.
7 minute read - Social Security
Social Security and Medicare, and how they interlock
Automatic enrollment, the premium deduction, the two-year income lookback, and the HSA trap.
6 minute read
