Frequently Asked Questions
When should I start thinking about Medicare if I’m approaching 65?
Generally, Michele recommends starting 6–3 months before you’ll need coverage. If you’re going to retire and go on Medicare at 65, begin learning and planning during that window so you understand enrollment periods, penalties, and your options. If you’re working past 65 and staying on employer coverage, start 6–3 months before your planned retirement date.
Do I have to sign up for Medicare at 65 if I’m still working?
Not always. It depends on:
- The size of your employer
- The quality and cost of your employer plan
- Whether you (and your spouse) will continue working
In many cases, you can delay some parts of Medicare without penalty if you have qualifying employer coverage, but the rules are nuanced. That’s why Michele’s firm encourages a Medicare 101 conversation well in advance.
What is IRMAA and why might my Part B premium be higher than my friends’?
IRMAA stands for Income-Related Monthly Adjustment Amount. Social Security looks at your tax return from two years ago to see if your income exceeds certain thresholds. If it does, they add a surcharge to your Part B (and sometimes Part D) premiums, which can push your total monthly cost into the $500–$600+ range.
Can I appeal IRMAA if my income has dropped?
Often, yes. If you’ve had a qualifying life-changing event, like retirement, reduced work hours, marriage, divorce, or a significant income reduction, you may be able to appeal IRMAA and have your premiums recalculated. Michele frequently helps clients understand whether they’re eligible to appeal and how to complete the process.
What’s the difference between Medicare Advantage and a Medicare Supplement?
In brief:
- Medicare Advantage (Part C) plans are offered by private insurers and typically wrap your Part A, Part B, and often Part D into one plan with networks and copays.
- Medicare Supplement (Medigap) policies work alongside Original Medicare (Parts A & B) to help cover deductibles and coinsurance; Part D is usually a separate drug plan.
The best option depends on your doctors, travel patterns, medications, budget, and risk tolerance. Michele’s firm walks clients through the pros and cons in their specific situation.
How does a Medicare broker like Michele get paid?
Typically, Medicare brokers are compensated by the insurance carriers when a client enrolls in a plan. Clients usually don’t pay brokerage fees directly, which means you can get professional help comparing plans without an additional out-of-pocket advisory charge. That said, it’s important to work with someone who is independent and focuses on fit, not just commissions.
Why should my HR or benefits team care about having a Medicare partner?
Employees turning 65 often bombard HR with questions about:
- Whether to stay on the group plan or go to Medicare
- How COBRA interacts with Medicare
- Timing, penalties, and plan options
Partnering with an independent broker like Michele gives HR a trusted expert to:
- Run Medicare 101 sessions for staff
- Provide individualized guidance
- Help employees avoid costly mistakes
That can reduce HR’s workload and improve the overall employee experience.
How can a high-income year affect my Medicare premiums?
Medicare uses a tax return from 2 years earlier to decide whether you owe an income-related surcharge on certain premiums. That means a large income event in your early 60s, such as a stock sale, a deferred compensation payout or a Roth conversion, can show up in what you pay once you're on Medicare. Our blog When Does a Roth Conversion Actually Make Sense? Find Your Tax Window covers how we think about timing income. This is general education, not tax or insurance advice, and thresholds change each year. [VERIFY]
What should I do about health coverage if I'm laid off or leave a job before 65?
Start by listing your options and their deadlines. Common ones include COBRA, a spouse's plan or an individual policy, and each has its own cost and timing rules. Michele notes that a layoff can leave very little time before coverage ends, which is why she suggests learning the basics before you need them. COBRA is generally not treated the same as active employer coverage when it comes to delaying parts of Medicare, so confirm the rules for your situation with Medicare.gov or a licensed insurance professional. [VERIFY]
How does Medicare fit into a retirement plan?
It belongs in several places at once: your expense budget (premiums and out-of-pocket costs), your tax planning (income in the years that feed income-related surcharges) and your timeline for stepping back from work. We build those into one plan using our Life-Driven Planning process. Our video Hybrid Retirement Plans Explained: Make Work Optional? shows how we think about a phased transition. If you'd like to talk through your own numbers, book a Free Wealth Strategy Call with Tailored Wealth. It's a low-pressure conversation about your situation.