Medicare Planning
Fiduciary Wealth Management
The Healthcare Decision Most Plans Get Wrong.
Medicare is one of the few retirement decisions you can't easily undo. Miss your enrollment window and the late penalties follow you for life. Pick the wrong plan and you'll find out at the worst possible moment, usually when a prescription, procedure, or specialist isn't covered. And every January, the rules and plan structures change again. Most retirees navigate Medicare alone, with a 30-minute call to an agent who sells plans, not coordinates them.
We handle Medicare differently. Our in-house Medicare specialist walks you through Parts A, B, C, and D in plain English, compares Medigap against Medicare Advantage against your actual situation, times your enrollment to avoid penalties and IRMAA surprises, and connects every Medicare decision back to your income and tax strategy. Because the income you report today determines the Medicare premium you pay two years from now. Most plans miss that connection entirely.
WHO THIS IS FOR
Built for Anyone Approaching (or Already Inside) Medicare.
Clients within twelve months of turning 65, recently enrolled and uncertain whether they made the right plan choice, or already inside Medicare and surprised by an IRMAA letter or a coverage gap. Particularly valuable for households with $500K+ in retirement assets, because income reported from those accounts directly determines your premium under IRMAA rules. If you've never had Medicare modeled against the rest of your retirement income plan, this is the conversation to have.
Pillars of Your Medicare Strategy
Medicare isn't one decision. It's six decisions stacked on top of each other, each one affecting the next. Here's how we handle each layer.
Enrollment Strategy & Timing
Most people enroll in Medicare during their seven-month Initial Enrollment Period around age 65. But if you're still working past 65 with employer coverage, the rules change. If you delay Part B without qualifying coverage, the late enrollment penalty adds 10% to your premium for every twelve months you waited, for the rest of your life. We analyze your specific situation, current coverage, projected retirement date, spouse's coverage, COBRA timing, and determine the right enrollment strategy. No guessing. No penalties.
Medigap vs. Medicare Advantage
This is the biggest plan decision most retirees make, and the one most agents simplify to whichever they earn the most commission on. We walk through the actual tradeoff: Medigap offers broader access, predictable costs, and freedom to use any provider that accepts Medicare. Medicare Advantage often has lower upfront premiums but uses narrower networks and prior authorization. The right choice depends on your health, your providers, your travel patterns, your prescription needs, and your budget. We compare both against your situation, not against a sales target.
IRMAA Coordination
IRMAA, the Income-Related Monthly Adjustment Amount, is the surcharge added to your Medicare Part B and Part D premiums when your income crosses certain thresholds. The catch: it's based on your tax return from two years ago, and the brackets are cliffs. One dollar over a threshold and your premium jumps significantly. A poorly timed Roth conversion, an unexpected capital gain, or a one-time IRA withdrawal can trigger thousands of dollars in extra Medicare costs you didn't see coming. We model your Medicare premium two years out, every year, against your projected income decisions.
Let's Build Your Medicare Plan
On your Chain Reaction Audit, Jonathan walks through your current coverage, your enrollment timing, and your IRMAA exposure. Then we show you how Medicare decisions can be coordinated with the rest of your retirement plan. No pressure. No product pitch. Just clarity.
Layer 01
Coverage Strategy
Enrollment timing, plan structure, and supplemental decisions handled together. Whether you're approaching 65, transitioning off employer coverage, or reassessing the plan you chose three years ago, your coverage gets reviewed against your actual healthcare needs and your retirement timeline.
Layer 02
Income & Tax Coordination
Medicare premiums are determined by income from two years ago. That means Roth conversions, RMDs, capital gains, and account withdrawal decisions all affect what you pay for Medicare. We coordinate income decisions with your Medicare premium across a multi-year horizon, not just the year you make them.
Two layers. One coordinated decision. The kind of work most Medicare agents don't do because they're paid to sell plans, not plan strategies.
What's Included
Medicare Handled End-to-End.
- Initial Enrollment Period strategy for clients approaching 65
- Working-past-65 coordination with employer coverage
- Medigap and Medicare Advantage plan comparison
- Part D prescription drug plan analysis
- IRMAA bracket monitoring and multi-year coordination
- Annual plan review during Open Enrollment
- Coverage gap and provider network audits
- Coordination with tax, Roth, and income strategy
The Coordination Advantage
Medicare Doesn't Live in a Vacuum.
The Medicare decisions you make are shaped by income, taxes, and Social Security choices happening elsewhere in your plan. Here's how it all connects when one team handles all of it.
IRMAA is a tax problem disguised as a healthcare premium. A Roth conversion done in the wrong year can push you across an IRMAA threshold and add thousands to your Medicare bill two years later. Our CPAs and Medicare specialist coordinate every income decision against the IRMAA brackets.
Tax Planning
When you claim Social Security affects what counts as income for IRMAA. Delaying Social Security to age 70 to maximize the benefit can interact with your tax-bracket strategy and your Medicare premium in ways that aren't obvious. We model the full picture before either decision gets made.
Social Security Planning
The years between retirement and age 73 are usually when Roth conversion strategy moves the most money. But those same years are when your Medicare premium is most sensitive to extra income. A conversion plan that ignores IRMAA can cost more than it saves. We coordinate both, year by year.
Roth Conversions
Why Choose Leonard Financial Solutions?
There are a lot of Medicare agents available. Here's what makes this one different.
Fiduciary by Law
As a fiduciary Registered Investment Advisor, our advisory recommendations are legally required to be in your best interest. Not in the interest of an insurance carrier. That's the standard we hold ourselves to on every recommendation.
In-House Medicare Specialist
Medicare planning is handled by an in-house specialist, not a referral. Twenty-plus years of military discipline applied to enrollment timing, plan comparison, and IRMAA coordination. You work with the same person on day one and every year after.
Coordinated With Everything Else
Most Medicare agents end the conversation at plan selection. We start there. Medicare is one decision inside a coordinated retirement plan that also handles your taxes, your income, your Social Security, and your investments. One team. One plan. One direction.
Your Chain Reaction Audit: Three Simple Steps
A coordinated income plan starts with one conversation. Here's how it works.
Book Your Audit
Choose a time on Jonathan's calendar. Two minutes, no prep work required.
We Map Your Income Sources
Jonathan walks through your full retirement picture, including your Medicare enrollment timing, current coverage (or projected enrollment date), and IRMAA exposure. When the Medicare specifics call for it, our in-house Medicare specialist joins to handle the plan-comparison detail.
You Get a Clear Picture
No product pitch. Just an honest read on whether your current Medicare strategy is right for your situation, where the gaps are, and what a coordinated plan would look like.
No cost. No obligation. Just the information you need to decide what to do next.
Common Questions Answered
Got a question? Here's where most people start.
When should I enroll in Medicare?
For most people, the seven-month Initial Enrollment Period around your 65th birthday. Missing it can result in permanent late enrollment penalties for Part B that follow you for the rest of your life. But if you're still covered by qualifying employer coverage past 65, different rules apply. We analyze your specific situation (current coverage, projected retirement date, spouse's coverage, COBRA timing) to determine the right enrollment strategy.
What's the difference between Medigap and Medicare Advantage?
Medigap (also called Medicare Supplement) works alongside Original Medicare to cover the out-of-pocket costs Medicare leaves behind, like deductibles and coinsurance. You can see any provider that accepts Medicare nationally, no networks. Medicare Advantage is a private alternative to Original Medicare that bundles your coverage, often with lower upfront costs, but uses defined networks and prior authorization for many services. The right choice depends on your health, providers, travel, prescriptions, and budget. We compare both against your actual situation.
What is IRMAA, and how do I avoid it?
IRMAA is the Income-Related Monthly Adjustment Amount, a surcharge added to your Medicare Part B and Part D premiums when your income crosses certain thresholds. The brackets are cliffs, meaning one dollar over a threshold triggers the full surcharge. The catch: IRMAA is based on your tax return from two years ago, so the income decisions you make today affect what you pay for Medicare two years from now. We model your projected IRMAA bracket annually and coordinate income decisions (Roth conversions, capital gains, IRA withdrawals) to keep you on the right side of each threshold.
Take the Next Step
Start Building Your Medicare Plan
Whether you're approaching 65 or already inside Medicare, getting the coordination right matters more than getting the plan name right. The Chain Reaction Audit is where we start. One session, your situation, no obligation.
