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Retirement Income

Medicare Planning for Retirees

Medicare eligibility begins at age 65, and missing your enrollment window can cause lifelong penalties. Your retirement income also matters: higher income two years prior triggers IRMAA surcharges.

Medicare eligibility begins at age 65, and missing your enrollment window can cause lifelong penalties. Your retirement income also matters: higher income two years prior triggers IRMAA surcharges on your Part B and D premiums, so Medicare and tax planning should be coordinated.

When should I enroll in Medicare?

Your Initial Enrollment Period spans the seven months around your 65th birthday. If you are still covered by qualifying employer insurance you may delay without penalty, but otherwise late enrollment can mean permanent premium surcharges. Plan the timing alongside your Social Security decision.

What are the parts of Medicare?

Part A covers hospital care, Part B covers outpatient/medical, Part D covers prescriptions, and Part C (Medicare Advantage) bundles them through a private plan. Many retirees pair Original Medicare with a Medigap supplement; others choose Advantage — the right choice depends on your doctors, travel, and health.

How does income affect my Medicare premiums (IRMAA)?

IRMAA surcharges raise Part B and D premiums when your modified adjusted gross income from two years earlier exceeds set thresholds. Strategic tax planning — managing Roth conversions, capital gains, and withdrawals — can help you avoid crossing a bracket and overpaying.

Frequently Asked Questions

Do I need Medicare if I have retiree health coverage?

It depends on the coverage. Some retiree plans require Medicare as primary at 65 — we help you confirm before the deadline.

Can tax planning lower my Medicare costs?

Yes — because IRMAA is income-based, managing taxable income can reduce surcharges. We model this in your plan.

Ready to talk through your situation?

Schedule a complimentary, no-obligation introductory call with a San Diego fiduciary.

Stuart A. Schiffman, CFP®, RICP®

About the Author

Stuart A. Schiffman, CFP®, RICP®, TPCP®

Founder, Senior Wealth Advisor, Compound Wealth Advisors — San Diego

I run a boutique, fee-only fiduciary practice for individuals and couples age 50 and older, helping them navigate the critical years before and during retirement with clarity and confidence. I hold the CFP®, RICP®, and TPCP® designations and an MBA, and have been quoted in Forbes, Investopedia, U.S. News, and Nasdaq.

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