Should I Enroll in Medicare if I am still working?

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In a perfect world, the day you turn 65, you retire, stop your work medical coverage, and start Medicare. While this is great in theory, most people do not live this lifestyle. According to the  U.S. Bureau of Labor Statistics, 40% of people over age 55 are still working, with this number expected to increase. This number does not even account for the couples where only one spouse is working but both are still utilizing the work health insurance. A large amount of our clients continue working throughout their 60’s and even 70’s and 80’s and we take them through the process outlined below of signing up for Medicare no matter their situation.

You will be retired when you are 65:

First, let’s go over the easiest scenario. If you are not working when you turn 65, and you are not covered by your spouse’s work coverage, then signing up for Medicare is an easy decision. If you are already talking Social Security, you should automatically be enrolled in Part A and Part B. You then need to decide if you want to go with a Medicare Supplement and drug plan or with a Medicare Advantage plan, but be sure to make this decision carefully.

You are still working when you turn 65:

While Medicare is designed to start the month you turn 65, there are exceptions, especially if you are still working and have creditable coverage, which most work coverage is. If you have creditable coverage, you can postpone Medicare without any penalties. This allows you to not pay for Medicare while also paying for work coverage. It is important to note that COBRA is not creditable coverage – if you lose work coverage past age 65 you must sign up for Medicare within 8 months to avoid penalties!

Signing up for Medicare Part A, which covers hospital insurance, should be considered by working seniors. Part A is free for most people, as long as you or a spouse has worked for 10 years. This coverage works in conjunction with your work coverage, with Medicare being the second to pay. There is really no downside to taking Part A while you are still working, unless you are contributing to a health savings account, or HSA.  

On the other hand, Medicare Part B, which covers doctors and outpatient services, is not free. There is a monthly premium as well as yearly deductible, which is why most people with work coverage are not going to want to sign up for this. Also, it is important to remember that once you start Part B, your Medicare Supplement Open Enrollment period begins for 6 months. This period allows you to apply for a Medicare Supplement without answering health questions. You only get this period once, and if you start Part B when you are working, you will have to answer health questions if you want to get a supplement when you retire.  

If you are still working and already talking Social Security before you turn 65, you will automatically be enrolled in Part A and B the month you turn 65. You will need to contact Social Security to opt out of Part B. For Part A, your red, white, and blue card will come in the mail 3 months before your 65th birthday.  

One exception to all this is if you work for a company with under 20 employees. For these companies, Medicare will become employee’s primary source of coverage once they turn 65. In this case, you should take the same advice we gave to people who are retired at 65 and sign up for full Medicare coverage to avoid any lapse in coverage or penalties.

There are really no advantages of having full Medicare coverage while under work coverage. Unless your work coverage is ineffective, you’ll be paying monthly premiums for Medicare with little or no return. These premiums can be even higher than normal when working, due to IRMAA premium surcharges.  It can be beneficial to compare the costs and benefits of both your work coverage and Medicare to see what makes the most sense. For a small amount of people, full Medicare actually is less expensive.

Once you decide to retire, you’ll have an 8-month Special Enrollment Period to sign up for Medicare before you are penalized. You can even get working on this a few months before you retire, especially if you know the exact month your work coverage is going to end.

Your spouse is still working when you turn 65:

If your spouse still has work coverage when you turn 65, you have a few options. The first is just to stay on your spouse’s work coverage and delay taking full Medicare. In this case, you would follow the same instructions we gave above for people who are still working when they turn 65.

If you spouse is still working but their work coverage does not cover you, or it is cheaper to start Medicare instead of staying on this coverage, you should follow the advice above for people who are retired when they turn 65. Your Initial Enrollment Period starts three months before the month you turn 65 and lasts three months after your birth month. During this period, you can sign up for Medicare. You should also look into a Medicare Supplement Plan as well as a Part D Drug plan.

Medicare enrollment comes with a lot of deadlines and timelines paired with penalties and taxes if you miss these. If you are not sure of what decisions to make, consult a professional. It could save you thousands of dollars in the long run.

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Should I Enroll in Medicare if I am still working?

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Understanding the Upcoming 2026 Income Tax Increase: What You Need to Know

A Brief History of the Tax Cuts and Jobs Act (TCJA)

In today’s Cardinal lesson, we’re discussing the significant changes coming to income tax rates in 2026. This isn’t a proposal but a law already set in motion. The Tax Cuts and Jobs Act (TCJA), passed in 2017 and effective from January 1, 2018, brought about substantial reductions in income taxes. However, these reductions were only funded for eight years, meaning they will expire at the end of 2025.

What Changes to Expect in 2026

As of January 1, 2026, the tax rates will revert to their 2017 levels, adjusted for inflation. Key changes include:

  • The 12% bracket will increase to 15%.
  • The 22% bracket will rise to 25%.
  • The top rate of 37% will revert to 39.6%.

Not Just a Proposal

It’s crucial to understand that this change is already the law. Many people mistakenly believe that the tax rate increases are still under discussion. However, unless Congress enacts new legislation, these higher rates will take effect as scheduled.

Implications for Your Financial Planning

Impact on IRAs and 401(k)s

With the current lower tax rates, now is the time to consider strategies like Roth conversions. By converting funds from a traditional IRA to a Roth IRA now, you can potentially save a significant amount in taxes over the long term.

Why Planning Ahead is Crucial

For individuals with substantial retirement savings, understanding these changes is vital for effective tax planning. The window to take advantage of the current lower tax rates is closing, and planning ahead can make a significant difference.

Case Studies and Planning Opportunities

Hans Scheil and Tom Griffith discuss specific case studies and planning strategies in our latest video. These examples illustrate how different scenarios can be managed effectively:

  • Case Study 1: A married couple with an adjusted gross income of $150,000 in 2024 can convert part of their IRA to a Roth IRA, taking advantage of the lower current tax rates.
  • Case Study 2: High-net-worth individuals with large IRAs can save substantial amounts in taxes by planning conversions over the next two years.

Estate Tax Considerations

The TCJA also doubled the estate tax exemption, which will revert in 2026. This change can significantly impact high-net-worth individuals, making estate planning more crucial than ever.

Action Steps to Take Now

  • Review Your Current Tax Situation: Analyze how the upcoming changes will affect your finances.
  • Consider Roth Conversions: Take advantage of the lower tax rates before they expire.
  • Plan for Estate Taxes: Assess your estate plans in light of the changing exemptions.

Conclusion

The changes coming in 2026 are significant, but with proper planning and informed decision-making, you can navigate these changes effectively. Watch our video for more detailed insights and personalized advice.

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Contact us today with any questions, concerns, or just to stay connected.

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