A quick comment on HumbleDollar authors. Jonathan lived, breathed and labored over HumbleDollar constantly, and he probably read every single comment ever made. He was unique, and it was his baby that he was caring for. It was also his livelihood. I don't think Adam or others should (or can) be held to that standard. It is unrealistic. They are still making valuable contributions with what they write.
(And even Jonathan was wrong once in a while, I think... :) )
A thought-provoking list. Even if you don't quite agree with all of them, they make you think. And where I might disagree, it is more a question of degree. One small question I still struggle over is how much cash to hold, knowing its value erodes over time. (The counter to that might be the risk of a giant financial accounts breakdown or hack (AI or otherwise) and records loss, that might make real cash valuable for a while - at least physical cash.).
A good "free breakfast" is a win-win. A good breakfast helps shape a guest's positive experience and builds loyalty for a hotel, and it can offer a good breakfast at a low cost because it has economies of scale. But a guest also benefits from a good "free breakfast" even if it is paid for indirectly. I always found the breakfast time at a hotel to be a great time to get a solid start, and to eat nutritious food instead of the inevitable later mid-morning snacks. It is a great place to discuss or resolve one's final plan for the day when on vacation, and even on some business trips. It is one place where you bond rather than argue on vacation. You also save time running out and looking for something acceptable elsewhere, especially if you have a few people in your party. You also will tend to know what you will order (or grab from the buffet) every day in advance, since you know from day 1 what you like that is on the menu and what the hotel puts out on the buffet. This works for cruises, too. However, even if a breakfast has a separate charge, it may still be useful to pay, since the value to a hotel guest can more than offset the cost. (On the other hand, a breakfast of powdered eggs, rubbery bagels, bad coffee and half-stale pastries will make one think less of a hotel, and lead to a different choice for a place to stay in the future.)
I never liked to owe anybody money. When I was a young man, I borrowed because I needed to - school loans, car loans, mortgages, occasional purchases on credit. But I clawed along until I got free of all those things, and resolved to avoid large borrowings and to pay off my credit cards each month. I know there can be benefits to borrowing, but I like the sense of freedom I have about how I use what I've earned. I save a lot, and I put most of my money to work somehow. My weakness is imprecision. I leave more cash in my local bank account than I need to in order to get all those free services - checking, safe deposit box, etc. I let some of my RMD sit in a money market fund at my broker's, rather than investing it more carefully. I sometimes pay more to have a service done than I know I would pay if I carefully got competitive quotes. In the end, however, I do think I'm pretty efficient with money. I like the tips in the comments. I always pick up a trick or two when I read these posts. Thank you!
Congratulations. I have what I call the definitive Father of the Bride reception speech outline, which covers every possible thing you need to remember to cover (or affirmatively elect to ignore.) I researched it for a month for my daughter's wedding, digging through almost every wedding book in print. (Did you know that Angela Lansbury wrote a really good wedding preparation book?) I've given it to a half dozen friends as their little girls began to get married, and it saved them a lot of work. Anyway, if there is a good (and safe) way to share it with you, I'm happy to send you a copy. (I've looked for a way to publish it online to give it a broader reach, but never really came up with a way to do that.)
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.
Comments
A quick comment on HumbleDollar authors. Jonathan lived, breathed and labored over HumbleDollar constantly, and he probably read every single comment ever made. He was unique, and it was his baby that he was caring for. It was also his livelihood. I don't think Adam or others should (or can) be held to that standard. It is unrealistic. They are still making valuable contributions with what they write. (And even Jonathan was wrong once in a while, I think... :) )
Post: Financial Lessons
Link to comment from September 27, 2026
A thought-provoking list. Even if you don't quite agree with all of them, they make you think. And where I might disagree, it is more a question of degree. One small question I still struggle over is how much cash to hold, knowing its value erodes over time. (The counter to that might be the risk of a giant financial accounts breakdown or hack (AI or otherwise) and records loss, that might make real cash valuable for a while - at least physical cash.).
Post: Financial Lessons
Link to comment from September 27, 2026
Sent you a document today (Sunday). Congratulations again.
Post: A Wedding Too Far
Link to comment from September 21, 2026
A good "free breakfast" is a win-win. A good breakfast helps shape a guest's positive experience and builds loyalty for a hotel, and it can offer a good breakfast at a low cost because it has economies of scale. But a guest also benefits from a good "free breakfast" even if it is paid for indirectly. I always found the breakfast time at a hotel to be a great time to get a solid start, and to eat nutritious food instead of the inevitable later mid-morning snacks. It is a great place to discuss or resolve one's final plan for the day when on vacation, and even on some business trips. It is one place where you bond rather than argue on vacation. You also save time running out and looking for something acceptable elsewhere, especially if you have a few people in your party. You also will tend to know what you will order (or grab from the buffet) every day in advance, since you know from day 1 what you like that is on the menu and what the hotel puts out on the buffet. This works for cruises, too. However, even if a breakfast has a separate charge, it may still be useful to pay, since the value to a hotel guest can more than offset the cost. (On the other hand, a breakfast of powdered eggs, rubbery bagels, bad coffee and half-stale pastries will make one think less of a hotel, and lead to a different choice for a place to stay in the future.)
Post: Free Breakfast
Link to comment from September 15, 2026
I never liked to owe anybody money. When I was a young man, I borrowed because I needed to - school loans, car loans, mortgages, occasional purchases on credit. But I clawed along until I got free of all those things, and resolved to avoid large borrowings and to pay off my credit cards each month. I know there can be benefits to borrowing, but I like the sense of freedom I have about how I use what I've earned. I save a lot, and I put most of my money to work somehow. My weakness is imprecision. I leave more cash in my local bank account than I need to in order to get all those free services - checking, safe deposit box, etc. I let some of my RMD sit in a money market fund at my broker's, rather than investing it more carefully. I sometimes pay more to have a service done than I know I would pay if I carefully got competitive quotes. In the end, however, I do think I'm pretty efficient with money. I like the tips in the comments. I always pick up a trick or two when I read these posts. Thank you!
Post: Locking it in
Link to comment from September 15, 2026
Congratulations. I have what I call the definitive Father of the Bride reception speech outline, which covers every possible thing you need to remember to cover (or affirmatively elect to ignore.) I researched it for a month for my daughter's wedding, digging through almost every wedding book in print. (Did you know that Angela Lansbury wrote a really good wedding preparation book?) I've given it to a half dozen friends as their little girls began to get married, and it saved them a lot of work. Anyway, if there is a good (and safe) way to share it with you, I'm happy to send you a copy. (I've looked for a way to publish it online to give it a broader reach, but never really came up with a way to do that.)
Post: A Wedding Too Far
Link to comment from September 15, 2026
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