Good topic for those who want to retire just a little bit early. If your planned retirement is more than 18 months before you turn 65, or you have another situation where the COBRA bridge might not help you, you may face a gap period in insurance coverage. You could elect to take the risk if the time gap is small and you are in good health. But from what I recall, if you want or need continuous coverage, the private sector options are mostly very costly for one-off customers. It pays to do your homework on this issue in advance, even if you are healthy and don't need specialized medical care often. (Medicare itself isn't really free, either. What makes it seem cheap is that the costs involved are usually deducted from your Social Security each month, so you get used to the lower Social Security net payment, and don't notice it as much.)
I will move one more time. This is a great article, but for me the financial considerations are still significant. As I age, it is less about the income, sales and real estate taxes, and a lot more about the estate taxes. That will be the big one - larger than years' worth of the other taxes. My current state (MD) has both estate and inheritance taxes, and the "grab" is growing to cover state overspending elsewhere. I want my kids to get what I have, not a rapacious and inefficient state government.
I wish I had done some conversions 10 or 15 years ago, in the period I was coasting toward retirement and let my income decline. But there is an age you reach at which you can no longer expect the Roth tax free benefits will offset the tax payments and other cost impacts from conversion. IMHO, I am now well past that age, so I'll live with what I've got and live with the tax implications. It was a fairly simple calculation to reach that decision.
Great article. Lots of good detail. My weakness is that I just don't like spending lots of time calculating at this level of detail for some of these options. Too much work for too little impact for me. So, I stay out of individual stocks and follow some of these rules with a broader brush. (No 351 for me - it may save you taxes, but IMHO you could be left with a mess of cats and dogs.) Still, I have a few mutual funds with huge tax overhangs from years of accumulation. Some of my charity gifts come from these funds' lots with the lowest basis. I'll leave the rest to my kids with the inheritance-related step up in basis, or just pay Uncle Sam down the road. These investments have served me well.
That's the format of an old joke. Kids must be much stronger than when I was small years ago. When I was a kid, it was really hard for me to carry $70 worth of groceries. But these days, my young grandson seems to have absolutely no problem with that.
Two quick points: (1) I often feel that I am not at financial equilibrium unless I have any extra money that comes my way snatched away from me by unexpected repairs, replacements or other home- or property-related events. (2) Dr. Atul Gawande, author of the best seller Being Mortal, says the most important rule as one gets older is "Don't fall down!" That seems to have cascading bad impacts on the health of aging people. Even healthy and athletic seniors should play it cautious when falls are possible. That may not keep you off a roof, but it may lead you to secure the ladder and inch up and down more slowly, with two hands on it.
I'd love to donate more of my time, but I don't want anything close to a mandated schedule or a place I need to be on time. The non-profits in my area mostly don't impress me. I keep looking around, but I'm not going to jump into something unless I deeply feel the merit.
I understand the skepticism, but there are reasons Costco works for some. Like any subscription arrangement, you have to balance the cost against savings every year for Costco (as you need to do for Amazon Prime and similar things). I have a small numbers of things I particularly like at Costco, and buy over and over for the savings - like Advil, certain breakfast cereals, Keurig pods and gas for my car. There are a handful of others. I first went there for eyeglasses - great service and much lower prices. Periodically, I buy individual things for better prices, like lawn fertilizer, printer ink, canned olives, dried mango and in the spring, plants. I don't buy much else. The eyeglasses alone saved me much more than the annual fee. Cheaper gas is always about 15-20 cents a gallon better than local stations. My gut calculations tell me I am better off each year, since I don't load up on things unnecessarily. But the Costco advantage is not a giant advantage. One thing I do notice is that Costco is also a destination for many non-profits that serve the poor. I often see people with three and four loaded carts at a time, all with essentials and no impulse item. I think that when those people load up their carts with food essentials, they should be applauded for using their contributions wisely.
There is joy in reading a compelling or interesting book, usually accompanied by some sadness when it is finished. We want more, but there is no more. But we have memory, and that must satisfy us. This is true of Money and Me.
My mother was a professional artist, and my daughter is highly talented in that area. I have a number of pieces done by each of them. No cost. They are priceless, and give me great pleasure. They get preferential placement. I also now collect fine art. I follow auction notices I receive through the site called Invaluable, and have favorite artists and favorite forms of art. I research what I like. I bid at auctions and have built quite a good collection. While I can tell you what pieces I paid too much for and what pieces I got at a bargain, the totals I've spent are not especially high. And I don't really care about whether my collection appreciates. What really drives me is a work that I know I will love to look at every day, and that I will never grow tired of. I am patient. I know every art owner's preferences are different. So I often see bidding on things I don't care for at all, and sometimes am surprised that there is little competition for things I really want. I tend to appreciate highly real artistic skills that are evident. Not everyone can accurately reproduce a specific human's face. Not everyone can throw a tall wide pot with a very thin wall. Not everyone can carve realistically in three dimensions. All of these things and more make art collection a special form of ownership. It may be worth a dip in the art auction market - it is far more fun than gambling or speculation.
Comments
Good topic for those who want to retire just a little bit early. If your planned retirement is more than 18 months before you turn 65, or you have another situation where the COBRA bridge might not help you, you may face a gap period in insurance coverage. You could elect to take the risk if the time gap is small and you are in good health. But from what I recall, if you want or need continuous coverage, the private sector options are mostly very costly for one-off customers. It pays to do your homework on this issue in advance, even if you are healthy and don't need specialized medical care often. (Medicare itself isn't really free, either. What makes it seem cheap is that the costs involved are usually deducted from your Social Security each month, so you get used to the lower Social Security net payment, and don't notice it as much.)
Post: COBRA insurance: No need to fear the bite
Link to comment from August 18, 2026
I will move one more time. This is a great article, but for me the financial considerations are still significant. As I age, it is less about the income, sales and real estate taxes, and a lot more about the estate taxes. That will be the big one - larger than years' worth of the other taxes. My current state (MD) has both estate and inheritance taxes, and the "grab" is growing to cover state overspending elsewhere. I want my kids to get what I have, not a rapacious and inefficient state government.
Post: Before Someone Else Decides
Link to comment from August 9, 2026
I wish I had done some conversions 10 or 15 years ago, in the period I was coasting toward retirement and let my income decline. But there is an age you reach at which you can no longer expect the Roth tax free benefits will offset the tax payments and other cost impacts from conversion. IMHO, I am now well past that age, so I'll live with what I've got and live with the tax implications. It was a fairly simple calculation to reach that decision.
Post: Roth Conversions and Taxes
Link to comment from August 9, 2026
Great article. Lots of good detail. My weakness is that I just don't like spending lots of time calculating at this level of detail for some of these options. Too much work for too little impact for me. So, I stay out of individual stocks and follow some of these rules with a broader brush. (No 351 for me - it may save you taxes, but IMHO you could be left with a mess of cats and dogs.) Still, I have a few mutual funds with huge tax overhangs from years of accumulation. Some of my charity gifts come from these funds' lots with the lowest basis. I'll leave the rest to my kids with the inheritance-related step up in basis, or just pay Uncle Sam down the road. These investments have served me well.
Post: Risk and Taxes
Link to comment from August 9, 2026
That's the format of an old joke. Kids must be much stronger than when I was small years ago. When I was a kid, it was really hard for me to carry $70 worth of groceries. But these days, my young grandson seems to have absolutely no problem with that.
Post: Inflation, prices, COLAs, retirement and the last 16 years
Link to comment from August 7, 2026
Two quick points: (1) I often feel that I am not at financial equilibrium unless I have any extra money that comes my way snatched away from me by unexpected repairs, replacements or other home- or property-related events. (2) Dr. Atul Gawande, author of the best seller Being Mortal, says the most important rule as one gets older is "Don't fall down!" That seems to have cascading bad impacts on the health of aging people. Even healthy and athletic seniors should play it cautious when falls are possible. That may not keep you off a roof, but it may lead you to secure the ladder and inch up and down more slowly, with two hands on it.
Post: Reluctantly Saving Money
Link to comment from July 12, 2026
I'd love to donate more of my time, but I don't want anything close to a mandated schedule or a place I need to be on time. The non-profits in my area mostly don't impress me. I keep looking around, but I'm not going to jump into something unless I deeply feel the merit.
Post: Haunted Head
Link to comment from July 12, 2026
I understand the skepticism, but there are reasons Costco works for some. Like any subscription arrangement, you have to balance the cost against savings every year for Costco (as you need to do for Amazon Prime and similar things). I have a small numbers of things I particularly like at Costco, and buy over and over for the savings - like Advil, certain breakfast cereals, Keurig pods and gas for my car. There are a handful of others. I first went there for eyeglasses - great service and much lower prices. Periodically, I buy individual things for better prices, like lawn fertilizer, printer ink, canned olives, dried mango and in the spring, plants. I don't buy much else. The eyeglasses alone saved me much more than the annual fee. Cheaper gas is always about 15-20 cents a gallon better than local stations. My gut calculations tell me I am better off each year, since I don't load up on things unnecessarily. But the Costco advantage is not a giant advantage. One thing I do notice is that Costco is also a destination for many non-profits that serve the poor. I often see people with three and four loaded carts at a time, all with essentials and no impulse item. I think that when those people load up their carts with food essentials, they should be applauded for using their contributions wisely.
Post: Frittering away Frugality
Link to comment from July 12, 2026
There is joy in reading a compelling or interesting book, usually accompanied by some sadness when it is finished. We want more, but there is no more. But we have memory, and that must satisfy us. This is true of Money and Me.
Post: Reminded of Jonathan’s Grace
Link to comment from July 5, 2026
My mother was a professional artist, and my daughter is highly talented in that area. I have a number of pieces done by each of them. No cost. They are priceless, and give me great pleasure. They get preferential placement. I also now collect fine art. I follow auction notices I receive through the site called Invaluable, and have favorite artists and favorite forms of art. I research what I like. I bid at auctions and have built quite a good collection. While I can tell you what pieces I paid too much for and what pieces I got at a bargain, the totals I've spent are not especially high. And I don't really care about whether my collection appreciates. What really drives me is a work that I know I will love to look at every day, and that I will never grow tired of. I am patient. I know every art owner's preferences are different. So I often see bidding on things I don't care for at all, and sometimes am surprised that there is little competition for things I really want. I tend to appreciate highly real artistic skills that are evident. Not everyone can accurately reproduce a specific human's face. Not everyone can throw a tall wide pot with a very thin wall. Not everyone can carve realistically in three dimensions. All of these things and more make art collection a special form of ownership. It may be worth a dip in the art auction market - it is far more fun than gambling or speculation.
Post: Mr Market visits Art Basel
Link to comment from July 5, 2026