Medicare Planning
Navigating Medicare's enrollment windows, plan options, and income-based surcharges — integrated with your retirement income strategy to protect your savings and minimize lifetime healthcare costs.
Clearing the Medicare maze
Medicare can feel daunting — there are a slew of terms to decipher, costs to consider, and a variety of options to evaluate. Each decision you make, from when you enroll to which plan type you choose, carries consequences that follow you for years. We are here to assist you in clearing the Medicare maze and setting you down the right path.
Medicare planning doesn't happen in a vacuum. Your enrollment timing interacts with your Social Security strategy, HSA contributions, Roth conversion plan, and overall retirement income sequencing. Getting the order wrong can trigger permanent premium penalties or unexpected tax costs. Getting it right means lower out-of-pocket exposure and a more predictable retirement budget.
Who qualifies for Medicare?
Medicare is available to U.S. citizens and legal permanent residents who have resided in the U.S. for at least five consecutive years. You must also meet one of the following requirements:
- You are age 65 or older
- You are under 65 but have a qualifying disability and have received Social Security Disability Insurance (SSDI) for 24 months
- You have been diagnosed with End-Stage Renal Disease (ESRD) or Amyotrophic Lateral Sclerosis (ALS), regardless of age
Original Medicare — and beyond
Original Medicare, encompassing Parts A and B, is administered by the federal government. Part A covers inpatient hospital care, skilled nursing facility stays, hospice, and some home health services. Part B covers outpatient care, doctor visits, preventive services, and medically necessary services. Together they provide a foundation, but they leave significant coverage gaps — including no cap on out-of-pocket spending and no prescription drug coverage.
Additional coverage can be obtained through private Medicare or Medicare-related plans. Understanding the differences between these options is one of the most consequential decisions you'll make at retirement.
Medicare Supplement (Medigap)
Works alongside Original Medicare to cover out-of-pocket costs — deductibles, copays, and coinsurance. Plan G, the most comprehensive option for new enrollees, covers virtually all costs after the Part B deductible, providing highly predictable expenses. Accepted by any Medicare-accepting provider nationwide.
Prescription Drug Coverage
Standalone Part D plans help cover prescription medication costs — an area not covered by Original Medicare. Plans vary significantly in formulary, cost-sharing, and pharmacy network. Missing the Part D enrollment window can also trigger a permanent late enrollment penalty.
Medicare Advantage
An alternative to Original Medicare provided by private insurers. These plans bundle Part A and Part B coverage into a single plan and often include prescription drug coverage. Many offer additional benefits such as routine vision, dental, and hearing — though they operate through provider networks and may require prior authorizations.
IRMAA Surcharges
Part B and Part D premiums are income-tested. If your modified adjusted gross income exceeds certain thresholds, you pay higher premiums through IRMAA — based on a two-year lookback. In 2024, surcharges can add up to $594/month per person at the highest income tier. Proactive income planning can minimize or eliminate this exposure.
The right coverage combination depends on your health profile, financial situation, provider relationships, and retirement income plan. There is no single right answer — but there is a most appropriate answer for your specific circumstances, and that determination requires a thorough analysis.
Medicare integrated with your retirement strategy
We don't approach Medicare as an isolated checklist item. Every enrollment decision, plan selection, and income management strategy is evaluated in the context of your broader retirement income plan — ensuring all the pieces work together from day one.
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Enrollment timing and window planning
We map your Initial Enrollment Period (IEP), identify whether a Special Enrollment Period (SEP) applies based on active employer coverage, and coordinate Medicare enrollment with your HSA contribution strategy — including the Part A retroactive lookback that requires stopping HSA contributions at least 6 months before enrolling.
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Plan comparison and selection
We evaluate the Medigap vs. Medicare Advantage decision in the context of your health profile, provider relationships, travel patterns, and risk tolerance. For Medigap, we analyze Plan G and Plan N cost structures. For Medicare Advantage, we assess star quality ratings, network adequacy, out-of-pocket maximums, and prior authorization requirements.
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IRMAA and income management
We model the multi-year impact of your income decisions — Roth conversions, RMDs, capital gains, and property sales — on Medicare Part B and Part D premiums. We help you smooth income across retirement years to stay within lower IRMAA brackets, and advise on filing Form SSA-44 to appeal surcharges triggered by life-changing events.
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Coordination with Social Security and retirement income
We sequence Medicare enrollment alongside Social Security claiming decisions, Roth conversion timing, and retirement account distributions. These decisions interact directly — and evaluating them together rather than in isolation is the only way to arrive at an optimal retirement income strategy.
Frequently Asked Questions
What clients ask most often about Medicare enrollment and planning.
If you are already receiving Social Security or Railroad Retirement Board benefits when you turn 65, you will generally be enrolled in Medicare Parts A and B automatically, and your Medicare card will arrive by mail. For everyone else, you need to actively sign up during your Initial Enrollment Period (IEP) — a 7-month window that begins 3 months before the month you turn 65, includes your birthday month, and ends 3 months after. You can enroll online at SSA.gov/Medicare, by phone, or at your local Social Security office.
The main exception is active employer coverage. If you are still working and covered under an employer group health plan at a company with 20 or more employees, you qualify for a Special Enrollment Period — you can delay Medicare enrollment without penalty until you lose that coverage, and then have 8 months to enroll. Important: COBRA coverage and retiree health plans do not qualify for this exception. If you retire before 65 and use COBRA, you must still enroll in Medicare at 65 as scheduled to avoid permanent Part B penalties.
Original Medicare (Parts A and B) is administered by the federal government and covers hospital care and outpatient services. It does not cap your out-of-pocket spending, does not cover prescription drugs, and leaves meaningful cost-sharing gaps. From there, you choose how to fill those gaps.
Medicare Supplement (Medigap) policies work alongside Original Medicare, covering deductibles, copays, and coinsurance. Plan G, the most comprehensive option for new enrollees, covers virtually all out-of-pocket costs after the Part B deductible — providing predictable expenses and the freedom to use any Medicare-accepting provider nationwide. The tradeoff is a higher monthly premium, typically $150–$350 depending on age and location.
Medicare Advantage (Part C) plans replace Original Medicare entirely. Offered by private insurers, they often feature low or $0 premiums and may include dental, vision, and hearing benefits. However, they use provider networks (HMO or PPO), may require prior authorizations, and have variable out-of-pocket maximums that can exceed $8,000 per year. The right choice depends on your health, providers, travel habits, and financial situation — and it is worth modeling both before you enroll, as switching out of Medicare Advantage back to Medigap in later years can be subject to medical underwriting in most states.
IRMAA stands for Income-Related Monthly Adjustment Amount — a surcharge added to Medicare Part B and Part D premiums for higher-income beneficiaries. In 2024, IRMAA surcharges begin for individuals with modified adjusted gross income above $103,000 ($206,000 for married couples filing jointly). At the highest income tier, surcharges add up to $594 per month per person — over $14,000 per year for a couple. Source: Centers for Medicare & Medicaid Services, 2024.
The critical planning detail is the two-year lookback: your 2024 Medicare premiums are based on your 2022 MAGI. A large Roth conversion, IRA distribution, capital gain realization, or property sale in any given year can push you into a higher IRMAA bracket two years later. The most effective avoidance strategy is to smooth income across retirement years — spreading Roth conversions over multiple years to stay within safe brackets rather than doing them in single large amounts.
If your income has materially decreased due to a life-changing event — retirement, death of a spouse, divorce, or loss of income-producing property — you can appeal your IRMAA surcharge using Social Security Form SSA-44. A successful appeal uses your current year's income rather than the two-year lookback and can immediately reduce or eliminate the surcharge.
Medicare decisions are permanent. Get them right.
Missing an enrollment window, choosing the wrong plan type, or ignoring IRMAA exposure can cost tens of thousands of dollars over a retirement. Let's build a strategy that gets every piece right.