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What is a prompt?

"A prompt is the input or instruction you give to an AI system, computer program, or person to guide what response or action you want."

ChatGPT

Medicare Made Simple, Clear and Easy for Do-It-Yourselfers Using AI

What You'll Find Here

Everything on this site is free. No sign-up, no sales pitch. Use the table below to go directly to what matters most to you.

#TopicWhere to Go

Are you a Medicare do-it-yourselfer?

You're in the right place. AI assistants have completely changed what it means to navigate Medicare on your own. You now have a patient, knowledgeable tutor available 24/7 — one that answers your questions, not generic ones. No more wading through government guides written for everyone and useful to no one.

Born November 14, 1961? Your AI assistant knows exactly when your Initial Enrollment Period opens and closes — and will walk you through enrollment step by step, in plain English, at your pace. On COBRA? It'll explain what that means for your situation and flag the enrollment trap it can set before it becomes a costly mistake.

At Medicare Do-It-Yourself, we show you how to use AI as your own personal Medicare tutor — one that's never too busy, never rushes you, and never makes you feel silly for asking. You can even ask it to quiz you to make sure everything's sinking in.

Not sure where to start? We've done the heavy lifting.

We've built a library of over 430 ready-to-use sample prompts — just copy one, add your specific situation, and get a personalized answer in seconds. Claude generated 250 prompts drawn directly from the Medicare & You 2026 handbook, covering the full range of enrollment, coverage, and plan decisions. Perplexity contributed 180 more, built from CMS's Choosing a Medigap Policy guide (March 2026), focused on supplement coverage options. Together, they give you a running start no matter where you are in the Medicare journey.

Ready? Use the table of contents to get started. We're glad you're here.

Table of Contents
1.Are you new to Medicare?
2.Are you already a Medicare participant?
3.Are you new to AI?
4.A guide to Medicare prompts
5.AI Assistants
6.DIY Medicare enrollment at medicare.gov
7.Working with an agent or planner
8.Saving on prescription drug pricing
9.Prompts for Medicare & chronic illness
10.Other government-written Medicare resources
11.About Jim
No sales pitch — ever Not affiliated with any insurer Plain language, no jargon Based on official Medicare information

Have a question?

Feel free to reach out directly — I'm happy to help.

Jim Sullivan
(800) 820-9232 Ext. 2800Call between 9 am and 5 pm CST
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Disclaimer: Medicare Made Clear is an independent educational website and is not affiliated with, endorsed by, or connected to the U.S. government, the Centers for Medicare & Medicaid Services (CMS), or any insurance company. Content is provided for informational purposes only and does not constitute insurance, legal, or financial advice. Always verify plan details at Medicare.gov or consult a licensed insurance professional.