Resource Library

Resources for Every Stage of Coverage

Guides, checklists, key dates, and trusted official sources — everything we’d hand you across the kitchen table, gathered in one place. Take what you need, at your own pace.

Medicare Annual Enrollment opens in
October 15 – December 7 · Changes take effect January 1
--
Days
--
Hours
--
Minutes
The Guide Shelf

No-Cost Guides, Written in Plain English

One guide for every kind of coverage question we answer. The Medicare Guidebook is ready now; three more are on the way — join the waitlist and you’ll get each one first.

Health Market Advocates
Welcome to Medicare
A simple guide to reviewing your options
Available Now

The Medicare Guidebook

Parts A, B, C, and D explained, Medigap vs. Medicare Advantage, the deadlines that matter, and the questions to ask before you enroll.

Health Market Advocates
Coverage Without an HR Department
For the self-employed, individuals & families
Coming Soon

Self-Employed & Family Guide

How Marketplace plans and premium help really work, the options beyond them, and a workbook to size up your household’s needs.

Health Market Advocates
Small Business Benefits, Decoded
Written for owners, not HR departments
Coming Soon

Small Business Benefits Guide

Owner coverage, first group plans, sharing the cost with your team, and the questions to ask before signing anything.

Health Market Advocates
The Family Protection Guide
Life & supplemental coverage, simplified
Coming Soon

Family Protection Guide

Term vs. permanent life, what supplemental coverage is worth, and how to protect the people who depend on you.

Send Me My Resources

Pick as many as you like. Available guides arrive by email right away; coming-soon guides are sent the moment they’re ready.

🔒 Your information is secure and will never be shared or sold.

Medicare Toolkit

Everything You Need for Enrollment Season

Know the dates, do a little homework, and walk into your review ready. A little preparation is the difference between a plan that looks good and one that works for you.

📅 Medicare Key Dates

Oct 15
– Dec 7

Annual Enrollment Period Every year

Join, switch, or drop a Medicare Advantage or Part D plan for the coming year. The most important window for anyone already on Medicare.

Jan 1
new year

New Coverage Begins

Changes you make during Annual Enrollment take effect on January 1.

7 mo.
around 65

Initial Enrollment Period

Three months before your 65th birthday month, the month itself, and three months after. Starting early keeps coverage on time.

Varies
life events

Special Enrollment Periods

Retiring, losing employer coverage, or moving can open a window outside the standard dates. Ask before assuming you have to wait.

From Your Advocate

📝 Your Medicare Homework

Checklist & Real Cost Worksheet

[PRODUCTION HOLD — cover image not supplied: “Cover page of Your Medicare Homework: Checklist and Real Cost Worksheet, a companion to the 2026 Medicare Guidebook”]

A short packet that turns a confusing decision into a clear comparison. Your Health Market Advocate sends it personally, so it comes with someone to call when a question pops up.

  • ✓ A checklist of what to gather before your review: doctors, prescriptions, pharmacies, and current plan details
  • ✓ A Real Cost Worksheet to compare two paths side by side, beyond just the premium
  • ✓ Page references back to the Medicare Guidebook for anything you want to read up on

Already working with an advocate and don’t have it yet? Just ask them for it.

Our Newsletter

The Advocate, Delivered Monthly

Straightforward insurance insights, once a month, from the Health Market Advocates team: a lesson from Your Insurance Professor, the deadlines coming up, and a favorite recipe from Joshua’s kitchen.

Rather Talk It Through?

Guides are a great start, but nothing beats a real conversation. Request a no-cost review and a member of our team will reach out within one business day.

Good Questions

About These Resources

No. Every guide on this page is available at no cost. We write them because people make better decisions when they understand their options first.

Your guide arrives by email. Phone is optional; if you share it, a member of our team may reach out to see whether you have questions, and you can always tell us you’d rather just read.

The Guidebook is the education: how Medicare works and what your choices are. The Homework packet is the action step: a checklist and worksheet you fill in so your review is built around your actual doctors, prescriptions, and budget. Your advocate sends the Homework packet personally.

Because we want you to have the full picture. We don’t offer every plan available in your area, and official sources like Medicare.gov, 1-800-MEDICARE, and your State Health Insurance Assistance Program (SHINE in Florida) can give you information on all of your options.

They’re in progress now. Join the waitlist above and you’ll receive each one the day it’s released.

Accessibility Toolbar