AUTHOR: John Katz on 2/27/2025 FIRST: Jonathan Clements on 2/27/2025 | RECENT: 1michaelm on 3/5/2025
Comments
I had a friend, a retired detective who took a job as a security consultant for large trade shows well into his 60s. He was busier in that job than he was in his previous 'day job.' At any rate, he said his mother very much wanted to go to Hawaii at some point in her life. She died before he took her there. He deeply regretted not taking time out to take that Hawaii trip with her. Not exactly Dennis' situation, but on the broader topic of: Listening to mom.
This is also about diminishing returns ... Gross returns don't tell the whole story—you have to factor in the sweat equity. If I have to double my effort just to move from a 9% return to a 12% return, the math doesn't check out for me. I’m interested in maximizing my life, not just a spreadsheet. There’s a point where chasing the extra 3% could turn a passive investment into a second job. For me, the older I get, the steeper the opportunity cost of time.
My experience with Chat and Gemini mirrored Gary's. While I'm certainly aware of AI models being a bit sycophantic, I largely neutralize that by starting conversations with something like this: "Act as a completely objective, fee-only financial analyst. Do not flatter my choices or validate my ideas just to be polite. Your job is to look for blind spots, misalignments, and hidden risks based strictly on the data I provide." Chat and GPT have been very helpful to me on a range of financial topics, in particular, positioning me to be ready to take RMDs in the most beneficial way possible. I've spent hours and hours asking follow-up questions to responses Chat or Gemini gave me. They are not perfect. And you can't take what they say at face value. But they are only going to get better. And they are pretty darn good right now, depending on how you tee up conversations. If nothing else, they help focus the mind on critical issues that provide the best possible blueprint for a discussion with a human CFP or other professional. If I were in the business of providing financial advice, I would be keeping a VERY close eye on AI models - and how younger people in particular were engaging with them.
I totally get your point about finding hidden savings, and I suspect it applies to many, but it’s worth noting how subjective this can be. Anyone could look into another person's cart and find something to disagree with—whether it's a six-pack of beer, a bottle of wine, or an expensive steak. Depending on consumption levels, and the consumer's personal health, you could even argue some of these choices are unhealthy. But the larger point is one person’s 'non-essential' prepared dessert is another person’s hard-earned reward. Budgeting is rarely one-size-fits-all because what we value is so personal. Additionally, we never know the financial reality of the person pushing the cart. Many of those carts are being propelled by people for whom money is simply no object, making the exercise of auditing a stranger's groceries a bit of a moot point.
Like the author, that 93% didn't sound right to me, either. I think the number is probably pretty sound, but I also expect that once you break down 'seniors' by increasing age categories, that number drops. For example, 93% of 65-70 year-old seniors might be aging in place, but I seriously doubt 93% of 85-90 year-olds are.
You're highlighting a classic trade-off: simplicity versus flexibility. One universal plan would definitely eliminate confusion, but losing the pre-tax option removes a major tool people use to manage their current tax brackets. Also, that 'generous limit' is highly relative—what’s generous for one person's situation might not be for another. There would be a LOT of concern paid to where that limit got set initially, and how it would adjust over time.
Where I worked, if we wanted to create a new position, we had to budget the salary of the person, of course, and also had to add 35% of the position's salary for benefits. Very, very few people who got hired, I imagine, had any idea of the value/cost the organization placed on those benefits. It took a while for me, at least, to fully understand how valuable they were.
On the subject of 'expect to change jobs and careers', I would add, "Life is not a straight line. Expect lots zigs and zags in all areas of your life, not merely your career. It will not go as planned."
In your last paragraph, Richard, you apparently make an assumption about the financial literacy on the part of a lot of people. You seem to assume that they know, or should know, how to determine what income they need to supplement their social security payments. I know many people, some of whom are college educated, who have no idea how to figure out when to claim social security, let alone how much additional money they will need to finance a particular lifestyle. They are clueless. Meaning, for some, it's an information deficit - not necessarily one of priorities and financial discipline (though I suspect that misguided priorities and lack of discipline are along for the ride). We can say it's their responsibility, it's their problem to figure this out. And that's true. But it's also society's problem. This country does little to prepare people for even the most rudimentary financial planning.
I agree with your general approach. But how does one know when they will need social security most? Life isn't a straight line. That said, I agree that many people treat this issue of when to claim as a traditional investment account where they want to "get their money back" as quickly as possible. Viewing it as a hedge against outliving your assets is a much more robust strategy for long-term stability. That was my approach.
Comments
I had a friend, a retired detective who took a job as a security consultant for large trade shows well into his 60s. He was busier in that job than he was in his previous 'day job.' At any rate, he said his mother very much wanted to go to Hawaii at some point in her life. She died before he took her there. He deeply regretted not taking time out to take that Hawaii trip with her. Not exactly Dennis' situation, but on the broader topic of: Listening to mom.
Post: Close to Everything I Need
Link to comment from June 21, 2026
This is also about diminishing returns ... Gross returns don't tell the whole story—you have to factor in the sweat equity. If I have to double my effort just to move from a 9% return to a 12% return, the math doesn't check out for me. I’m interested in maximizing my life, not just a spreadsheet. There’s a point where chasing the extra 3% could turn a passive investment into a second job. For me, the older I get, the steeper the opportunity cost of time.
Post: Risk Adjusted: The Family Ledger
Link to comment from June 19, 2026
My experience with Chat and Gemini mirrored Gary's. While I'm certainly aware of AI models being a bit sycophantic, I largely neutralize that by starting conversations with something like this: "Act as a completely objective, fee-only financial analyst. Do not flatter my choices or validate my ideas just to be polite. Your job is to look for blind spots, misalignments, and hidden risks based strictly on the data I provide." Chat and GPT have been very helpful to me on a range of financial topics, in particular, positioning me to be ready to take RMDs in the most beneficial way possible. I've spent hours and hours asking follow-up questions to responses Chat or Gemini gave me. They are not perfect. And you can't take what they say at face value. But they are only going to get better. And they are pretty darn good right now, depending on how you tee up conversations. If nothing else, they help focus the mind on critical issues that provide the best possible blueprint for a discussion with a human CFP or other professional. If I were in the business of providing financial advice, I would be keeping a VERY close eye on AI models - and how younger people in particular were engaging with them.
Post: ChatGPT’s Portfolio Advice
Link to comment from June 7, 2026
I totally get your point about finding hidden savings, and I suspect it applies to many, but it’s worth noting how subjective this can be. Anyone could look into another person's cart and find something to disagree with—whether it's a six-pack of beer, a bottle of wine, or an expensive steak. Depending on consumption levels, and the consumer's personal health, you could even argue some of these choices are unhealthy. But the larger point is one person’s 'non-essential' prepared dessert is another person’s hard-earned reward. Budgeting is rarely one-size-fits-all because what we value is so personal. Additionally, we never know the financial reality of the person pushing the cart. Many of those carts are being propelled by people for whom money is simply no object, making the exercise of auditing a stranger's groceries a bit of a moot point.
Post: Shopping carts again…but not what you think
Link to comment from June 4, 2026
Like the author, that 93% didn't sound right to me, either. I think the number is probably pretty sound, but I also expect that once you break down 'seniors' by increasing age categories, that number drops. For example, 93% of 65-70 year-old seniors might be aging in place, but I seriously doubt 93% of 85-90 year-olds are.
Post: Percentage that “age in place”
Link to comment from May 25, 2026
You're highlighting a classic trade-off: simplicity versus flexibility. One universal plan would definitely eliminate confusion, but losing the pre-tax option removes a major tool people use to manage their current tax brackets. Also, that 'generous limit' is highly relative—what’s generous for one person's situation might not be for another. There would be a LOT of concern paid to where that limit got set initially, and how it would adjust over time.
Post: Time to scrap IRAs, 401k, 403b and all the rest
Link to comment from May 22, 2026
Where I worked, if we wanted to create a new position, we had to budget the salary of the person, of course, and also had to add 35% of the position's salary for benefits. Very, very few people who got hired, I imagine, had any idea of the value/cost the organization placed on those benefits. It took a while for me, at least, to fully understand how valuable they were.
Post: Benefits Young Adults Should Look at Before Taking a Job
Link to comment from May 13, 2026
On the subject of 'expect to change jobs and careers', I would add, "Life is not a straight line. Expect lots zigs and zags in all areas of your life, not merely your career. It will not go as planned."
Post: Jonathan’s Advice for 2026 Graduates
Link to comment from May 8, 2026
In your last paragraph, Richard, you apparently make an assumption about the financial literacy on the part of a lot of people. You seem to assume that they know, or should know, how to determine what income they need to supplement their social security payments. I know many people, some of whom are college educated, who have no idea how to figure out when to claim social security, let alone how much additional money they will need to finance a particular lifestyle. They are clueless. Meaning, for some, it's an information deficit - not necessarily one of priorities and financial discipline (though I suspect that misguided priorities and lack of discipline are along for the ride). We can say it's their responsibility, it's their problem to figure this out. And that's true. But it's also society's problem. This country does little to prepare people for even the most rudimentary financial planning.
Post: The great COLA debate-maybe not the expected solution.
Link to comment from April 27, 2026
I agree with your general approach. But how does one know when they will need social security most? Life isn't a straight line. That said, I agree that many people treat this issue of when to claim as a traditional investment account where they want to "get their money back" as quickly as possible. Viewing it as a hedge against outliving your assets is a much more robust strategy for long-term stability. That was my approach.
Post: Rethinking the “Right” Time for Social Security
Link to comment from April 24, 2026