Sometimes you just don't know what you need to know [retirement planning, Medicare, Social Security, income taxes]

Originally I was just going to make this a Medicare question thread but it can be better than that. I robbed the cradle when I got married and nobody told me and I didn’t think about how that would influence the golden years. For instance I am currently working past the “typical” retirement age. My wife doesn’t work outside the home so the main reason I am still working is for the insurance. Gotta few more years to go before she is eligible for Medicare. I’m happy to do it but there are some days I wish I could be at home instead yelling at people to stay off my lawn.

Regarding Medicare, I just applied for Social Security past the the age of 65. Well, yesterday I got a letter from Medicare welcoming me to the program. Turns out, if I’m not mistaken, you get enrolled automatically into Medicare part A when you apply for Social Security past the age of 65. That was a genuine surprise that I had been enrolled. Now I have to figure out dealing with my HSA because one cannot contribute for 6 months prior to enrolling in Medicare and I have been.

I had no idea you could have Medicare and commercial insurance at the same time under certain conditions.

Well, what kind of things were you “supposed” to know but didn’t? Not limited to Medicare.

Medicare starts at the first of the month of your birthday.

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How many years until your spouse is 65?

If you want to retire you could see what an ACA plan would cost?

I certainly understand.

My husband is transitioning to Medicare this year. I’ll be on an ACA plan for 3 more years. It’s not cheap, the coverage isn’t great but I feel blessed that we have this option and we can afford to pay.

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We purposely didn’t apply for Medicare B until zH had fully retired at 70. I do believe you are auto-enrolled & premiums auto-deducted from SS.

DH and I both applied for Medicare A when we each turned 65, but stayed on his private health insurance through his employer. DH DID stop contributing to his HSA once he turned 65, and waited more than 6 mos after that before he applied for Medicare A. Our mistake was initially forgetting to discontinue the high deductible insurance plan for that year, so we got a little bit of $ in an account called an HRA (health reimbursement account) but then moved to a low deductible plan so fixed that.

DH is retiring at the end of the month and we both just applied for Medicare B. Because I had decided to take my SS a few years ago (I was well past FRA), my monthly premiums and IRMAA will come out of my SS. But DH is waiting until he is 70 to take his, so we will be billed by Medicare for his premiums/IRMAA (and IIRC we can pay by credit card with no service charge, and then reimburse ourselves from our HSA. Reason to use a CC is that I am chasing medallion level on Delta). So it might be worth checking if you are only in Medicare A (most likely) but yes, stop contributing to your HSA. When you do apply for part B, your card will show your effective start date for Medicare A, and then
separately your effective date for Medicare B. My DH and I filled out the paperwork (and attached his CMS L564 from his employer showing that he was covered by the private insurance, and a letter from his HR department showing his last date of coverage). So for us Part B will start Sept 1, and we now (now that my part B was FINALLY processed) have to pick our supplemental, RX and dental/eye plans (if it’s worthwhile to do those last 2- probably will).

Like you, I robbed the cradle. My DH is younger than I am!

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I am following. I turn 65 in March. I have talked to Medicare advisors. We are in a transition so won’t know for sure if I will take part b right away. But totally looking forward to Medicare(did I really say that lol)…paying like $25,000 for two of us for Blue Cross is getting old. My wife will continue on ACA plan for 2 year’s. I am older.

Many of us have always had jobs where our federal and state taxes were automatically paid from our paychecks to the appropriate authorities by our employers. Once we start receiving SS and drawing from our IRAs, we need make sure we pay the appropriate taxes on a quarterly basis. Failure to do so can result in a penalty. (We have our taxes withheld and remitted automatically by our financial advisor.) I’ve known several recently retired people who were surprised at tax time.

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That happened the first year of retirement.

Took out too little. Our accounts have an option for withholding but it under estimated.

Now I’m extra cautious about making sure that I’ve paid enough in taxes.

The IRS gives you a year if you mess up, I won’t make that mistake again.

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I’m used to checking that now. Whenever the big changes were done in trump’s first term, the school system did some wonky to H’s withholdings. They were taking out a little under 5% for federal taxes. I just compensated by taking out more out of mine, as it was easier dealing with our finance dept than his.

And last year there was a news report that the school system had taken out ZERO federal taxes out of approximately 200 teachers. And many didn’t notice until tax time. I guess with direct deposit people don’t look at their pay stubs anymore? The school system chalked it up to typos. They said they had to enter everything manually for every person. Seems strange. Glad H is retired!

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Great suggestion. Heading towards retirement so just learning now. When you say financial advisor are you speaking about your accountant or person that is helping you invest like a financial planner?

We pay quarterly. Maybe I should have taxes taken out of my SS.

Our financial advisor. He does all of the money movement for us, deciding how to withdraw, then moving it into our bank account & remitting the taxes. We’re not DIY on our investments. But many are, which is what prompted my post.

In medicine we called it- sometimes you don’t know what you don’t know. When I am getting something repaired or a purchase I ask- what have I not asked that I should?

The reason I ask is we are interviewing “Financial Advisors” and I don’t think they do like the taxes or transfer for that. Something for us to think about.

Learning more I didn’t know about Medicare and Social Security. I was aware that if you have a high deductible insurance plan and an HSA you must terminate HSA contributions six months before applying for Medicare. What I did not know (and this is probably repetitive) is that if you apply for Social Security after the age of 65 you are automatically enrolled in Medicare. You can reject part B but you cannot reject part A or you must terminate your Social Security. So my new learned lesson today is terminate your HSA contributions six months before applying for Social Security if your are older than 65. So now I have to deal with refunding HSA contributions and having the payroll department adjust W2 info. I have a call scheduled tomorrow our insurance broker’s Medicare “expert” to see where we go from here. So the key point here is if you have an HSA make sure you terminate contributions six months before applying for Medicare and if you are going to apply for Social Security after the age of 65 terminate HSA contributions six months before that application. Wish I had known. :slightly_frowning_face:

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As you plan for future financial decisions, study up on IRMAA

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Oh I know one that hit me hard, and I’ve been spreading the news with my coworkers. Many of us are eligible to retire before 65 & Medicare. I can go at 55. Originally this was the plan. But then I started getting cold feet, and when I found the following out it put the final nail in the coffin.

I knew buying health insurance on the exchange was pricey. I finally got the nerve to check and was pleased it wasn’t near as bad as I thought. We aren’t high income people. But what I didn’t know was….

The exchange insurance doesn’t cross state lines.

This is a dealbreaker living here. We live in a small community on the state line. I don’t want to say every doctor is horrible. Some are friends! But in general, you don’t come here for health care. You run anywhere else, especially if it’s even somewhat significant like a colonoscopy.

Fortunately for us, we have three great cities with excellent to outstanding health care within 1:00-1:30… but they are all across the state line. If you want a comparable health care system in my state, it’s 2:30 hours away.

For me this still isn’t a HUGE deal, except 10 years is a long time to hope nothing goes wrong. But H has CLL. He has a fantastic doctor in an outstanding place that I’m not ready to give up.

So now my plan is to work until I’m 60 and H is 64. Maybe COBRA outs for a year, or if H is doing well try to time appointments and skip a calendar year. Or work until I’m 61.

A coworker called me yesterday asking about H’s shoulder surgery. That we actually do in-state, 1:30 away. I love that ortho facility. This coworker is getting ready to retire in his early 60s and found out the same thing. Can’t go to any of the doctors people in my town are used to going. And he needs a new ortho.

But nobody around here (my world IRL) seems to know this restriction!

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The other thing with picking a plan on the marketplace is that many are HMO’s. We went with a PPO which is very expensive because with the HMO, we would have to get referrals to see every one of our specialists.

That’s fine but we see specialists in different medical systems. The provider list would be one medical system and so we would have had to switch our primary and all of our specialist except one or two.

My husband was transitioning to Medicare in the 9th month and me a year and half later. We would have spent the whole time switching between specialties to then go on Medicare.

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We met with our financial advisor last week and went through the IRMAA stuff because I’ll be going on Medicare next year (H is already on it). For whatever reason, this seems to be the year we’ve withdrawn more than usual from our 401k investments and we’re planning ROTH conversions. Because of the expected values for 2027, we have to be sure we don’t hit that for our 2025 income.
So, no conversions this year. Barring #2D either getting married or buying a house in 2026, we should be ok to start next year.

We did find out that our advisor’s company has both CPAs and attorneys who can help us with some of this at no additional cost; it’s all in the fees we pay.

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Some couples with this situation have opted to have the wife find a job that comes with medical benefits. But… under that plan, the husband needs to be willing to pick all the cooking/cleaning chores at home.

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