Sep 15, 2026

Avoiding Medicare Headaches

Medicare can come with plenty of confusion and a little anxiety.

We're going to say something that won't surprise you. Medicare can come with plenty of confusion and a little anxiety.

There are a lot of rules that carry potential consequences for your specific situation. Trying to Google your way through the process can get you a lot of information, but very little of it is clearly structured, and at times it is conflicting and outdated.

That's why we encourage our clients to talk to someone like Katie Keenan, an independent Medicare broker we've worked alongside for years.

Meghan recently spoke to Katie to discuss “What we wish every retiree knew about Medicare.”  Here’s the full interview with Katie, along with the cliff notes below.

Sixty-five is the deadline, not the starting line. Katie meets people at 62 and 63. Her advice: understand your options well before 65, even if you plan to keep working and stay on an employer plan. Medicare penalties are permanent. Getting the timing wrong once follows you for every month you're on Medicare after that.

Working past 65 will change the math but not the deadline. If your employer coverage and drug plan meet Medicare's standards, you may be able to delay Part B without a penalty. The catch: eligibility depends on employer size and plan specifics. This is the kind of decision Katie says needs someone knowledgeable to confirm, not a guess based on what a coworker did.

A layoff will change timing significantly. If you're laid off at 64 and a half, the Social Security Administration's application clock becomes the most time-sensitive part of the entire process. Coverage gets backdated to your application date, but Katie's advice is to move immediately: the earlier you apply, the earlier you're protected while it processes.

Lifetime penalties and Part B enrollment often get missed. Lifetime penalties are almost always the result of someone getting incomplete information at the wrong moment. The initial Medicare Part B enrollment window is one of the only times certain plans are guaranteed regardless of health history. Decisions made outside that window may not be reversible later.

Every one of these decisions gets easier with someone in the room who does this for a living, alongside someone who knows your full financial picture. That's why we bring Katie in, rather than sending people to research it alone.

If you're within a couple of years of 65, or your employment situation just changed, we'd be glad to walk through it with you.



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The Retirement Game Plan is the planning process we take every client through. If you'd like to talk through what asset location means for your own plan, a good place to start is a complimentary conversation with one of our coaches. You can schedule one at financialcoachgroup.com/contact.

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Investment Advice offered through FC Advisory LLC, a registered investment adviser doing business as “New Wealth Project” and as “Financial Coach”.  This content is provided for informational purposes only.  Views and opinions expressed are those of the authors and do not necessarily reflect those of FC Advisory, LLC.  Information provided is not and should not be interpreted as investment, tax, legal, or other professional advice or recommendation by FC Advisory, LLC or the members of our firm.  Always consult the appropriate professional regarding your specific situation before implementing any options presented or inferred.  FC Advisory LLC, All rights reserved.

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Investment Advice is offered through FC Advisory, LLC, a registered investment advisor doing business as Financial Coach and doing business as New Wealth Project.

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Memberships

Services

Fee-only Financial Planning; Retirement Income Planning; Asset Allocation and Investment Management; Estate and Legacy Planning; Charitable Gifting Strategies; Education Consulting; Tax Planning; Insurance and Survivor Needs Analysis; Retirement Benefits, Social Security, Pension, and Medicare/Medicaid Planning


Investment Advice is offered through FC Advisory, LLC, a registered investment advisor doing business as Financial Coach and doing business as New Wealth Project.

© 2025 FC Advisory, LLC

Designed by Slices.Design

Memberships

Services

Fee-only Financial Planning; Retirement Income Planning; Asset Allocation and Investment Management; Estate and Legacy Planning; Charitable Gifting Strategies; Education Consulting; Tax Planning; Insurance and Survivor Needs Analysis; Retirement Benefits, Social Security, Pension, and Medicare/Medicaid Planning


Investment Advice is offered through FC Advisory, LLC, a registered investment advisor doing business as Financial Coach and doing business as New Wealth Project.

© 2025 FC Advisory, LLC

Designed by Slices.Design