Why it's useful
Medicare is complicated, and mistakes can be expensive. This prompt gives you a personalized, easy-to-understand roadmap so you avoid penalties, choose the right coverage, and budget accurately for healthcare in retirement.
Who it's for
Anyone approaching age 60–65
Anyone confused about Medicare Parts A, B, C, and D
People deciding between Medigap and Medicare Advantage
Those wanting clear costs, timelines, and coverage recommendations
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copy the entire prompt in italics below
paste into ChatGPT, Gemini, or your favorite AI app
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Prompt
I want you to help me understand my Medicare options and create a personalized pre-65 plan. Begin by asking me these questions one at a time:
What is my current age?
When do I expect to retire?
Will I have employer or retiree health coverage before Medicare starts?
Do I have any ongoing medical conditions or prescription needs?
What is my estimated income in retirement (to determine IRMAA impact)?
Am I more concerned about monthly premiums or out-of-pocket costs?
Do I prefer more flexibility with doctors or lower upfront costs?
After collecting my answers, do the following:
A) Explain Medicare Parts A, B, C, and D in simple language
B) Tell me when I need to enroll and whether I qualify for premium-free Part A
C) Calculate my expected monthly costs (including IRMAA if applicable)
D) Compare Medigap vs. Medicare Advantage based on my needs
E) Recommend the best coverage approach for my situation
F) Provide a clear checklist for what to do at 12 months, 6 months, and 3 months before turning 65
Finish with two personalized scenarios:
• A conservative scenario (higher healthcare use, greater protection)
• A moderate scenario (average use, balanced costs)
How this helps you
Instead of navigating dozens of government pages or relying on generic advice, you get a personalized Medicare roadmap that tells you exactly when to enroll, what it will cost, and which type of coverage fits your health needs and budget.
