Why Medicare Deserves the Same Attention as Your Investment Portfolio

By Dan Gould | Three Streams Financial — Independent, Fee-Only Fiduciary Advisor

When people build a retirement plan, most of the conversation centers on savings rates, investment returns, and Social Security timing. Healthcare costs often get treated as an afterthought – something to figure out “when I turn 65.” That’s a mistake I see often in my work with retirees across Kansas and Missouri, and it’s an expensive one.

Fidelity’s research consistently estimates that the average 65-year-old couple will spend several hundred thousand dollars on healthcare throughout retirement, and that figure doesn’t include long-term care. Without a plan, these costs show up unpredictably – a surprise premium increase, an underwriting denial, an IRMAA surcharge you didn’t see coming – and they can quietly drain the nest egg you spent decades building.

The good news: nearly all of this is predictable and manageable with the right strategy. As a licensed Medicare expert with over 10+ years of experience helping Kansas and Missouri residents enroll in and manage their Medicare coverage, I built my senior healthcare planning process specifically to keep medical expenses from derailing your retirement.

It Starts With the Correct Medicare Strategy – Not Just “Signing Up”

Enrolling in Medicare isn’t a single event; it’s the first decision in a strategy that will affect your healthcare costs for the rest of your life. The choices you make in your Initial Enrollment Period – Original Medicare with a Medigap supplement versus a Medicare Advantage plan, which Part D drug plan, whether to layer on additional coverage – set the foundation for everything that follows.

Get this decision wrong, and it can be difficult or expensive to correct later. This is especially true if you’re in Kansas: unlike Missouri, Kansas does not offer an annual guaranteed-issue window for Medigap, so outside of your Initial Enrollment Period, switching supplement plans typically requires medical underwriting, and a health change could leave you stuck with a plan that no longer fits.

That’s why I sit down with clients before they ever submit an application. We map out your prescription needs, preferred doctors and hospitals, travel habits, and budget, then build a Medicare strategy designed around your actual life – not a generic recommendation.

Comparing Rates and Every Option Available – Not Just One Carrier’s Pitch

One of the biggest mistakes I see is retirees enrolling through whichever agent or call center reached them first, without ever comparing rates across the market. Medigap premiums for the identical, federally standardized plan letter (Plan G, for example) can vary significantly from one insurance carrier to another for the exact same coverage. Medicare Advantage plans differ widely in provider networks, drug formularies, and out-of-pocket maximums, even within the same Kansas City metro county.

As an independent, licensed Medicare expert, I’m not tied to a single insurance company. My role is to shop the market on your behalf – comparing:

• Original Medicare (Part A & B) with a Medigap supplement, and the true price differences between carriers offering the same plan letter
• Medicare Advantage (Part C) plans, including network coverage, star ratings, and total annual out-of-pocket exposure
• Part D prescription drug plans, matched against your actual medication list, so you’re not overpaying for coverage you don’t use
• Dental, vision, and hospital indemnity add-ons where they genuinely fill a gap

The goal isn’t just finding the cheapest premium – it’s finding the plan that delivers the most value for your specific health picture and financial situation.

Why Annual Reviews During Enrollment Period Matter More Than People Realize

Here’s something that surprises a lot of clients: the plan that was the best fit the year you enrolled is not guaranteed to be the best fit five years later. Carriers adjust premiums, networks change, drug formularies shift, and your own health and prescription needs evolve.

Every year during the Medicare Annual Enrollment Period (October 15 – December 7), I review each client’s coverage against what’s currently available in the market. In many cases, that review turns up meaningful savings or a better network fit. In Missouri, clients who already hold a Medigap policy also have access to that state’s Anniversary Rule, which allows switching to an equal-or-lesser plan letter with a different carrier – without medical underwriting – during a 60-day window around their policy’s anniversary date. That’s a valuable tool for Missouri residents looking to reduce premiums over time, and it’s one more reason an annual review pays for itself.

Skipping this annual check-in is one of the most common (and costly) mistakes retirees make. A plan on autopilot is a plan that’s quietly costing you money.

Managing Income to Minimize IRMAA Surcharges

Here’s a piece of the puzzle that rarely gets discussed outside of a real financial planning relationship: the Income-Related Monthly Adjustment Amount, or IRMAA. If your Modified Adjusted Gross Income exceeds certain thresholds, the Social Security Administration adds a surcharge on top of your standard Medicare Part B and Part D premiums – and that surcharge is based on your tax return from two years prior.

This catches a lot of retirees off guard, particularly in years when a Roth conversion, a large capital gain, required minimum distributions, or the sale of a business or property pushes reportable income above a threshold – sometimes by just a few dollars, triggering a full jump into the next surcharge bracket for both spouses.

Because I work with clients on both their Medicare strategy and their broader retirement income plan, I can help you:

• Time Roth conversions and capital gains around IRMAA thresholds rather than against them
• Sequence withdrawals from taxable, tax-deferred, and tax-free accounts to manage reportable income
• Plan two years ahead, since this year’s income decisions determine your Medicare premiums two years from now
• File a Medicare IRMAA appeal (Form SSA-44) when a life-changing event – retirement, divorce, loss of income – justifies a reduction

Managing IRMAA isn’t about avoiding taxes owed; it’s about avoiding an unnecessary Medicare surcharge resulting from decisions made without the full picture in mind.

Connecting Medicare to Your Long-Term Care and Retirement Income Plan

Medicare and Medicare Advantage plans cover a lot, but they were never designed to cover extended long-term care – and that’s often the single largest, least predictable healthcare cost retirees face. That’s why Medicare planning shouldn’t happen in isolation. It needs to connect to your broader retirement income plan, your long-term care strategy, and your asset protection goals, so a health event later in retirement doesn’t force you to liquidate investments at the worst possible time or burden your family with difficult decisions.

About Three Streams Financial

I’m Dan Gould, an independent, fee-only fiduciary financial advisor based in Overland Park, Kansas, serving families throughout the Kansas City metro and across Kansas and Missouri. For over 10 years, I’ve specialized in helping people enroll in Medicare and manage their Medicare strategy year after year, always as part of a complete retirement income and healthcare cost plan – never on commission, and always with your interests first.

If you’re approaching 65, already on Medicare, or simply want a second opinion on whether your current plan and income strategy are still working in your favor, I’d welcome the conversation.

Schedule a complimentary Medicare and retirement healthcare review with Dan Gould »

Remember, there’s no one-size-fits-all approach to investing. Conduct thorough research, consider your personal circumstances, and consult a fee-only financial advisor before making any investment decisions.

We do not offer every plan available in your area. Currently, we represent five organizations that offer over twenty products in your area. Please contact Medicare.gov or 1-800-MEDICARE to get information on all of your options.