The library

Every article, organized by the decision you're making.

Filter by the topic that matters most to you right now. New articles go out every Sunday.

The signature piece

The Medicare agent intake script — by a licensed agent who ran it

What actually happens on a "free Medicare consultation." The opener, the needs assessment, the carrier-appointed "options," the Scope of Appointment, and the close. Written by a Florida-licensed agent who was trained on the script.

9 min readPublished April 2026

INDUSTRY

The Basics

6 min read

Medicare Parts A, B, C and D — finally explained

The four-part alphabet soup, translated into a 6-minute read. What each part covers, what it costs, and why there's no single "Medicare."

Enrollment

5 min read

The 7-month window: when you can (and must) sign up for Medicare

Miss your Initial Enrollment Period and the Part B penalty sticks with you for life. Here's exactly when your window starts, ends, and what to do if you're still working.

Medigap vs. Advantage

8 min read

Medigap or Medicare Advantage? A fair comparison, without the sales pitch

The honest trade-offs between the two paths most people choose between. Neither is universally better — here's the framework for figuring out which fits your life.

Working past 65

7 min read

Still working at 65? Here's what changes — and what doesn't

Employer size matters more than most people realize. The rules for a 50-person company are different from the rules for a 15-person company, and COBRA doesn't count.

Costs & IRMAA

6 min read

IRMAA: the income surcharge most high earners don't see coming

If your income crosses a bracket threshold, your Medicare premium jumps — sometimes dramatically. Here's how the cliffs work, and how to appeal after retirement.

Part D / Prescriptions

5 min read

The $2,000 drug cap: what changed in 2025 and what it means for you

The old "donut hole" is gone. Part D now has a hard annual out-of-pocket cap. Here's how to use the new Medicare Prescription Payment Plan if your meds are expensive.

Enrollment

4 min read

AEP vs. OEP: what you can (and can't) change each year

Two annual windows, two different sets of rules. Here's a simple table of what's allowed in each — so you don't try to switch at the wrong time.

Medigap vs. Advantage

6 min read

The 6-month Medigap window — and why most people don't hear about it in time

You have exactly 6 months from when you're 65 and on Part B to buy any Medigap plan at the best-health rate. After that, most states let insurers underwrite you. Plan ahead.

Working past 65

6 min read

Medicare and your HSA: the trap no one warns you about

Enrolling in any part of Medicare — even premium-free Part A — stops your HSA contributions. If you're within 6 months of 65 and still contributing, read this first.

The Basics

5 min read

What Part B actually covers (and what it doesn't)

The "medical" part of Medicare pays 80% of approved charges — which means you're on the hook for the other 20% with no cap. This is the single most misunderstood fact in Medicare.

Before you go

Get the free Medicare Decision Map.

The 12 questions to answer before you enroll, in one printable PDF. Delivered in 2 minutes.