Sarah had everything figured out. After 35 years of practice, she retired at 63 with a solid financial plan. Her portfolio was positioned correctly, her withdrawal strategy was tax-efficient, and she’d even mapped out her Social Security claiming strategy.
What she didn’t figure out? Medicare enrollment.
When Sarah finally enrolled at 65, she discovered something that made her stomach drop: because she’d missed her Initial Enrollment Period by a few months, she’d be paying an extra $67 per month in Part B penalties. That’s over $800 annually.
Forever.
For a lawyer who’d spent her career mastering complex legal concepts and advising clients on intricate matters, this felt particularly frustrating. I see variations of this story more often than I’d like to admit.
The reality is that Medicare can be confusing for even the sharpest of minds.
Parts A, B, C, D.
Medigap.
IRMAA.
Enrollment periods that overlap but have different rules.
Penalties that compound over time. It’s a bureaucratic maze that makes tax code look straightforward.
Getting this wrong has the potential to cost you thousands of dollars annually throughout retirement. So let’s cut through the confusion and focus on what actually matters for your planning.
One last item before we dive in: This is a comprehensive Medicare guide, and it’s a lot to cover in one sitting. If you’d rather get the highlights, you can subscribe to our Money Meets Law newsletter anytime. We’ll be sharing a streamlined Medicare guide with subscribers over the next few weeks.
Medicare Basics: The Quick Overview
I’ll try not to bore you with a comprehensive Medicare 101 lesson. You can read the government pamphlets if you want that level of detail. Here’s what you need to know:
Part A (Hospital Insurance) – Usually premium-free if you worked 40+ quarters. Covers hospital stays, skilled nursing facilities, hospice care.
Part B (Medical Insurance) – Requires a monthly premium (standard is $202.90 in 2026, but we’ll talk about why you might pay much more). Covers doctor visits, outpatient care, preventive services.
Part D (Prescription Drug Coverage) – Separate drug coverage with multiple plan options. You choose a private insurer’s plan.
Part C (Medicare Advantage) – An alternative to Original Medicare that bundles A+B+D through private insurers. Think of it as Medicare through an HMO or PPO.
Medigap (Medicare Supplement Insurance) – Fills coverage gaps in Original Medicare. These are standardized plans sold by private insurers.
The fundamental decision you’ll make: Original Medicare (Parts A+B) + Medigap + Part D, OR Medicare Advantage (Part C). We’ll get to which makes sense for you shortly.
But first, let’s talk about timing — because this is where uninformed lawyers make expensive mistakes.
The Critical Enrollment Periods (Where Mistakes Happen)
Initial Enrollment Period (IEP)
Your Initial Enrollment Period is a 7-month window: the three months before your 65th birthday month, your birthday month itself, and the three months after.
Let’s say you turn 65 in June. Your IEP runs from March 1st through September 30th.
Enrolling during the first three months of your IEP means your coverage starts on the first day of your birthday month. Waiting until your birthday month or after can delay when your coverage begins.
If you miss this window entirely — that’s when you trigger the permanent penalties Sarah faced. For every 12-month period you could have had Part B but didn’t enroll, you pay an extra 10% on your Part B premium. Forever.
The Part B penalty might not sound devastating at first — 10% of $202 is only about $20 monthly. But remember, Medicare premiums increase over time. That 10% penalty grows with every premium increase for the rest of your life. Over a 25-year retirement, we’re talking thousands of dollars in unnecessary costs.
Special Enrollment Period (SEP) – The Working Lawyer Exception
If you’re working past 65, things get a bit more nuanced:
If you’re still working AND have group health coverage through an employer with 20 or more employees, you can typically delay Part B enrollment without penalty. When you finally retire, you get an 8-month Special Enrollment Period to sign up.
But — and this is critical — solo practitioners and lawyers in small firms need to pay attention. If your firm has fewer than 20 employees, your group coverage likely doesn’t count as “creditable coverage” for delaying Medicare enrollment. You might need to enroll at 65 regardless of your employer coverage.
Let’s look at an example of how this may play out. A retiring lawyer elects COBRA, assuming it will neatly bridge the gap to Medicare at 65. COBRA can be helpful for that purpose if you retire at or before 65. But because it’s continuation of employer coverage, some retirees assume it also counts as creditable coverage for delaying Medicare Part B. It doesn’t. That misunderstanding often isn’t discovered until later — when penalties show up and the “strategy” turns out to be an expensive mistake.
If you’re working past 65, get a certificate of creditable coverage from your insurer. Keep this documentation. You’ll need proof that your delay was legitimate.
The Part D Prescription Drug Trap
Even when delaying Medicare Part B is appropriate due to employer-sponsored health coverage, Part D may still be necessary if that plan does not offer creditable prescription drug coverage.
Going without creditable prescription drug coverage for 63 consecutive days or longer triggers a permanent penalty: 1% of the national base beneficiary premium for every month you went without coverage.
This penalty might seem small initially — we’re talking a few dollars per month. But like the Part B penalty, it’s permanent and grows with premium increases over time.
Calculation Example:
Number of months without coverage × 1% × current year’s national base premium = your monthly penalty.
And yes, this compounds. If you miss Medicare Part D enrollment for 2 years, you’re paying roughly 24% more than the standard premium. Forever.
The IRMAA Problem (Common with Lawyers)
IRMAA stands for Income-Related Monthly Adjustment Amount. It’s Medicare’s way of saying, “You made good money, so you’re going to pay more for coverage.”
The Two-Year Look-Back
Your 2026 Medicare premiums are based on your 2024 Modified Adjusted Gross Income (MAGI) from your tax return. This two-year look-back creates a unique problem for a retiring lawyer. Your high-earning years as a practicing attorney directly affect your early retirement Medicare costs.
Let me show you what this looks like in 2026 for married couples filing jointly.
If your 2024 MAGI was:
| MAGI Range | Part B Monthly Premium | Part D Monthly Surcharge |
| ≤ $218,000 | $202.90 | $0 |
| $218,001 – $274,000 | $284.10 | $14.50 |
| $274,001 – $342,000 | $405.80 | $37.50 |
| $342,001 – $410,000 | $527.50 | $60.40 |
| $410,001 – $749,999 | $649.20 | $83.30 |
| > $750,000 | $689.90 | $91.00 |
For single filers, these thresholds are roughly half.
Notice the jump from the standard $202.90 premium to $284.10 once you cross $218,000 in MAGI. That’s an extra $974 annually per person. For a married couple, you’re looking at an additional $1,948 per year just for crossing that first threshold.
The Roth Conversion Conflict
For those that follow my work, you know that I often write about tax-smart Roth conversions as a potential means of lowering lifetime taxes within tax-deferred accounts. But as it relates to Medicare premiums, these conversions can increase them.
They count as income for IRMAA purposes.
This creates a genuine planning dilemma. You might execute a Roth conversion in 2024 that saves you thousands in taxes over your lifetime. But two years later, in 2026, that conversion income could push you into a higher IRMAA bracket, increasing your Medicare premiums for that year.
This doesn’t mean you shouldn’t do Roth conversions. It just means you need to be strategic about the timing and size of your conversions, especially in the years immediately before Medicare enrollment.
The window between retirement and age 65 might be your best opportunity for larger Roth conversions — you’re no longer earning W-2 income, but you’re not yet subject to IRMAA surcharges.
Life-Changing Event Appeals
There is good news: you can appeal your IRMAA determination if you’ve experienced a “life-changing event” that reduced your income.
Qualifying events include:
- Marriage
- Divorce or annulment
- Death of a spouse
- Work stoppage or reduction
- Loss of income from income-producing property
- Loss or reduction of certain kinds of pension income
“I retired” absolutely counts as a life-changing event.
If you retire in 2024 and your income drops significantly, you can file Form SSA-44 to request a reduction in your 2026 IRMAA. You’ll need documentation showing the life-changing event and your new expected income.
This is one area where being proactive pays off. Don’t just accept the IRMAA bill—if your circumstances changed, file the appeal.
Medicare Advantage vs. Medigap: The Real Decision
This is the choice that actually matters for your long-term retirement healthcare strategy, and there’s no universal right answer. The decision depends on your health status, travel habits, risk tolerance, and how you think about insurance generally.
Medicare Advantage (Part C)
Medicare Advantage plans are offered by private insurers and replace Original Medicare entirely. Think of them as Medicare delivered through an HMO or PPO structure.
The upside:
- Lower monthly premiums (many plans are $0 premium)
- Built-in maximum out-of-pocket limits (Original Medicare has no cap)
- Often includes extra benefits like dental, vision, hearing
- Prescription drug coverage typically included
- One card, one plan, simpler administration
The downside:
- Network restrictions — you’re limited to certain doctors and hospitals
- Prior authorization requirements for certain services
- Plans can change benefits and networks annually
- Less flexibility if you travel frequently or split time between locations
- May have copays for each service
Medicare Advantage is a good fit for lawyers who:
- Are comfortable with managed care and network restrictions
- Primarily stay in one geographic area
- Want predictable, lower monthly costs
- Don’t mind navigating prior authorization processes
- Are generally healthy and don’t anticipate frequent specialist visits
Original Medicare + Medigap
This is the traditional approach: Original Medicare (Parts A and B) plus a supplemental Medigap policy to fill coverage gaps, plus a standalone Part D prescription drug plan.
The upside:
- Complete freedom to see any doctor or specialist who accepts Medicare (which is most of them)
- No referrals needed for specialists
- No network restrictions — perfect if you travel or maintain multiple residences
- Coverage is consistent and doesn’t change annually
- More predictable costs once you know your premiums
The downside:
- Higher monthly premiums (Medigap policies typically cost $150-$350+ monthly depending on location and plan)
- No built-in out-of-pocket maximum (though Medigap covers most costs)
- Three separate pieces to coordinate (Medicare, Medigap, Part D)
- Slightly more administrative complexity
Original Medicare + Medigap is a good fit for lawyers who:
- Travel frequently or maintain residences in multiple locations
- Want maximum flexibility in choosing providers
- Have complex health conditions requiring multiple specialists
- Prefer predictable costs and comprehensive coverage
- Can afford higher monthly premiums for peace of mind
The Medigap Underwriting Window (Critical Timing)
You have a 6-month Medigap open enrollment period that begins the first month you’re both 65 or older AND enrolled in Medicare Part B.
During this window, insurance companies cannot:
- Deny you coverage based on health conditions
- Charge you more due to pre-existing conditions
- Make you wait for coverage of pre-existing conditions
If you miss this window, insurers in most states can use medical underwriting. If you’ve developed health issues, you might face:
- Coverage denial
- Significantly higher premiums
- Exclusions for pre-existing conditions
- Waiting periods
This is why the “I’ll just start with Medicare Advantage and switch to Medigap later if I don’t like it” strategy can backfire. You might not be able to get Medigap coverage later, or you’ll pay substantially more for it.
If you’re on the fence, my advice is to start with Medigap during your guaranteed issue period. You can always switch to Medicare Advantage later without underwriting. But going the other direction gets complicated.
The most popular Medigap plan is Plan G, which covers nearly everything except the Part B deductible ($283 in 2026). Plan N is also worth considering if you’re comfortable with small copays in exchange for lower premiums.
Strategic Considerations for Lawyers
If You’re Retiring Before 65
Retiring before Medicare eligibility creates a coverage gap you’ll need to address:
COBRA – You can continue your employer coverage for up to 18 months. It’s expensive (you pay the full premium plus up to 2% administrative fee), but it maintains continuity until Medicare enrollment at age 65.
ACA Marketplace – Depending on your state and income, marketplace plans can be competitive. If you’re managing your taxable income strategically in early retirement, you might qualify for subsidies.
Spouse’s Coverage – If your spouse is still working with good employer coverage, this might be your best option.
Part-Time Work – Some firms offer continued health benefits for of-counsel or part-time attorneys. This could be valuable if you’re pursuing a phased retirement.
The key is ensuring you don’t have a gap in creditable coverage that triggers Medicare penalties later.
If You’re Working Past 65
First, confirm your coverage is actually creditable. Ask your HR department (or your own records if you’re self-employed) for a certificate of creditable coverage. You’ll need this documentation when you eventually enroll in Medicare.
For small firm owners and solo practitioners: You probably need to enroll in Medicare at 65 even if you’re still working. The employer size matters for creditable coverage, and self-employed coverage typically doesn’t qualify.
For partners in larger firms: Verify that your partnership insurance actually counts as group coverage. Some partnership arrangements are structured in ways that don’t meet Medicare’s definition of employer group coverage.
Keep detailed records. When you eventually enroll during your Special Enrollment Period, you’ll need to prove your delay was legitimate to avoid penalties.
Coordination with Health Savings Accounts
If you’ve been using an HSA as part of your retirement strategy, enrolling in Medicare ends your ability to contribute.
This can get tricky. Medicare Part A coverage is retroactive up to six months from when you apply (or back to when you first became eligible, whichever is shorter).
This means you should stop HSA contributions six months before you plan to enroll in Medicare to avoid an IRS penalty for contributing to an HSA while covered by Medicare.
But don’t worry, you can still withdraw from your existing HSA tax-free for qualified medical expenses, even after enrolling in Medicare. Many retirees effectively use their HSA as a tax-free healthcare ATM throughout retirement.
Geographic Considerations
Medigap premiums vary significantly by location. The same Plan G policy might cost $180 monthly in one state and $280 in another.
Medicare Advantage plan availability and quality also differs dramatically by county. Some areas have excellent MA plans with broad networks; others have limited options.
If you’re considering relocation in retirement — perhaps moving to a lower cost-of-living area or closer to family — factor Medicare costs and plan availability into your decision. This is one of those details that seems minor until you’re locked into expensive coverage.
Common Mistakes I See Lawyers Make
1. Assuming they can “figure it out later”
Medicare has strict deadlines and permanent penalties. This isn’t an area where you can afford to procrastinate. Start researching at least a year before you turn 65.
2. Treating Medicare like employer insurance
Medicare is fundamentally different. The enrollment rules, coverage options, and costs operate on completely different principles than the employer insurance you’ve had your entire career.
3. Not accounting for IRMAA in Roth conversion planning
Those tax-efficient Roth conversions can trigger higher Medicare premiums two years later. You need to coordinate your tax planning with your Medicare timeline.
4. Enrolling in Part A while still contributing to an HSA
This is an IRS violation that can result in penalties and taxes on your HSA contributions. Stop contributing six months before enrolling.
5. Choosing Medicare Advantage without understanding network restrictions
The $0 premium looks attractive until you’re traveling and need care outside your network, or you want to see a specialist who isn’t in-network.
6. Missing the Medigap underwriting window
Health issues can develop quickly. If you miss your guaranteed issue period, you might not be able to get Medigap coverage later — or you’ll pay significantly more for it.
7. Forgetting about Part D
Even if you don’t take many prescriptions now, you still need creditable drug coverage to avoid permanent penalties. Your medication needs will likely increase as you age.
Your Action Timeline
Three Years Before 65
- Understand how your current financial strategy (Roth conversions, income timing) will affect IRMAA
- Maximize HSA contributions while you still can — this is your last window
- Research Medigap premiums in your area to understand what you’ll be paying
- If you’re planning to relocate in retirement, factor Medicare costs into your decision
One Year Before 65
- Get certificate of creditable coverage if you’re planning to delay enrollment past 65
- Estimate your Modified AGI for IRMAA planning — look at your projected income two years post-retirement
- Review your prescription drug needs to help with Part D plan selection
- Decide between Medicare Advantage and Original Medicare + Medigap
- If choosing Medigap, research which plan (Ex. G vs. N) makes sense for your situation
- Set calendar reminder to stop HSA contributions if enrolling in Part A (six months before)
Three Months Before 65
- Enroll during your Initial Enrollment Period — don’t wait until the last minute
- Stop HSA contributions if enrolling in Part A (six months before to be safe)
- Finalize your Medicare Advantage plan selection or choose your Medigap + Part D combination
- Set up automatic premium payments to avoid coverage lapses
At 65
- Confirm your coverage started and you have your Medicare card
- Keep documentation of all enrollment confirmations
- Set calendar reminders for Annual Enrollment Period (October 15 – December 7) to review your coverage
- File IRMAA appeal if your income dropped due to retirement
Ongoing
- Review your coverage annually during the Annual Enrollment Period
- Monitor your prescription drug needs—your Part D plan might need adjustment
- Keep track of IRMAA brackets if your income is near a threshold
- Reassess Medicare Advantage vs. Medigap if your health or travel situation changes significantly
The Bottom Line
Medicare planning isn’t sexy. It doesn’t have the same appeal as discussing investment returns, Roth conversions, or tax optimization strategies. But getting this wrong can cost you thousands of dollars annually throughout retirement — money that could fund travel, hobbies, or time with family.
The good news is that unlike some aspects of retirement planning, Medicare has clear rules and definite deadlines. You just need to understand what they are and plan accordingly.
Start researching now, even if you’re still several years from 65. Understand the enrollment periods, decide between Medicare Advantage and Medigap during your guaranteed issue window, coordinate with your HSA strategy, and plan for IRMAA if you’re a higher earner.
If you found this Medicare breakdown helpful, you’ll love my weekly newsletter Money Meets Law. It’s designed for lawyers who want thoughtful, no-nonsense guidance on retirement, tax, and investment planning decisions that actually matter.
Over the next few weeks, we’ll be offering subscribers a curated Medicare guide that brings all of this information together in one clean, organized resource — plus ongoing insights each week. You can opt-in (or out) at any time here.
Additional Resources:
New York Times: Medicare’s Private Option is Gaining Popularity, and Critics
DISCLOSURE: The information in this article is not intended as tax, accounting, retirement or legal advice, as an offer or solicitation of an offer to buy or sell, or as an endorsement of any company, security, fund, or other securities or non-securities offering. This information should not be relied upon as the sole factor in an investment making decision or your decision to retire. Medicare rules and premiums change annually; consult Medicare.gov or a licensed insurance agent for current information.
David Hunter, CFP® is a CERTIFIED FINANCIAL PLANNER™ and owner of First Light Wealth, LLC, a financial planning & wealth management firm with a unique focus on serving attorneys nationwide. David has over a decade of experience helping clients build financial plans and has been featured in publications such as Attorney at Work, ThinkAdvisor, MarketWatch, Financial Planning, and InvestmentNews. David also writes weekly to attorneys in his popular Money Meets Law newsletter. For more about David, visit firstlightwealth.com/lawyers or connect with him on LinkedIn.
The post Medicare Enrollment For Lawyers: What You Need To Know Before 65 appeared first on Above the Law.