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Retirement Toys

Mark Crothers  |  May 4, 2026

"What? Everyone can’t relate to the tough issues and the dark and depressing side of financial life? 😱"
- R Quinn
Read more »

The reality of Social Security and Medicare- My real life experience.

R Quinn  |  May 4, 2026

"I’m a bit surprised. I thought this post would generate more discussion. Maybe the HD folks are too knowledgeable on the subject. A know the Threads and Facebook crowd sure aren’t though. 🤷🏻‍♂️"
- R Quinn
Read more »

Ageing and the Open Road

ArticleMark Crothers  |  May 2, 2026

RECENTLY I TOOK a free ride on a driverless bus trialling its proposed route, part of my local administration's ten-year rollout plan for self-driving public transport and taxis. I see real potential in this technology, and I'm hoping the infrastructure and implementation stay on schedule. That hope is mostly selfish, I'll admit. In fifteen years I'll be in my mid-seventies, and I'd love to ditch my car and rely on cheap, dependable robo-taxis instead. It would give me freedom precisely in that decade of life when driving starts to become genuinely problematic. I'm planning to change my car in 2027 for a modern hybrid, but in the back of my mind is the thought that it could be my last. If the self-driving rollout hits its targets, I can see the case for never buying another. The advantages for someone in my demographic at that stage of life would be hard to argue with. Think about what car ownership actually costs. There's the purchase price, insurance, road tax, fuel, servicing, tyres, and the occasional bill that arrives like a punch to the stomach. For most people, a car is the second most expensive thing they own after their home. In retirement, when income typically drops and budgets tighten, that ongoing drain becomes harder to justify. This is especially true when the car spends the vast majority of its time sitting on a driveway looking pretty. A robo-taxi model, where you pay only for the journeys you actually take, could represent a dramatic shift in how much personal transport really costs. The numbers, I suspect, will be compelling — with current estimates from real world operations suggesting an 80% reduction in the cost of fares being achievable. Then there's the question of independence. This is the one that matters most to me personally, and I'd imagine it resonates with anyone approaching or already in their later years. Giving up your car keys is one of those milestones that nobody really talks about, but everyone in that demographic understands. It represents a loss of spontaneity and self-sufficiency that can genuinely affect quality of life. The difference with autonomous vehicles is that surrendering the wheel doesn't have to mean surrendering the freedom. A reliable, affordable self-driving taxi available on demand restores something that previous generations simply had to go without once driving became difficult. This could be a trip to the supermarket on a weekday morning or a late evening visit to family. The safety dimension is also worth considering. Reaction times slow as we age. Night vision deteriorates. Concentration over long distances becomes harder. Most older drivers are aware of this and manage it carefully, but there comes a point for everyone where the road becomes a source of anxiety rather than freedom. Autonomous vehicles remove that calculation entirely. You get in, state your destination, and arrive, without the cognitive load of navigating, anticipating other drivers, or worrying whether your responses are still sharp enough. That peace of mind shouldn't be underestimated. There are wider social benefits too. Older people who can no longer drive are disproportionately affected by isolation. Poor rural transport links, infrequent bus services, and the general assumption that everyone has access to a car all contribute to a situation where many retired people find their world gradually shrinking. Autonomous vehicles, particularly if integrated intelligently with existing public transport, have the potential to reverse that. A robo-taxi that can be summoned by a smartphone, or even a simple voice command, could keep people connected to their communities, their families, and their routines far longer than is currently possible. There are, of course, reasons to be cautious. Technology rollouts rarely go entirely to plan. The ten-year schedule my local administration is working to is ambitious, and a lot can change in funding priorities, in public appetite, and in the regulatory environment. The early trials are promising, but promising trials and full-scale dependable infrastructure are very different things. It's worth keeping in mind, with a groan inducing pun: your mileage will vary — literally. Dense urban and suburban areas will almost certainly see reliable services first, and I'm fortunate that describes my situation. For those in more rural communities, the very people for whom isolation is already the sharpest problem, the wait could be considerably longer. I'm hopeful, but I'm not banking on it entirely. Which is why the 2027 hybrid still makes sense. It's a practical hedge, a good, modern, efficient car that will serve me well through the transition years, whatever pace that transition takes. But the fact that I'm already thinking of it as potentially my last car feels significant. A decade ago that thought wouldn't have crossed my mind. The technology has moved from science fiction to credible near-future fast enough to genuinely reshape how I'm thinking about retirement planning. If it delivers, the generation hitting their seventies in the late 2030s could be the first in history for whom ageing and mobility don't have to be in conflict. That's not a small thing. That might turn out to be one of the most personally transformative shifts of the entire autonomous vehicle revolution. It is not about the flashy early adopters or the logistics industry efficiencies. Instead, it is the simple dignity of an older person getting where they need to go, independently, on their own terms. I'm hopeful I'll be taking that ride and certain my children and grandchildren definitely will.
Mark Crothers is a retired small business owner from the UK with a keen interest in personal finance and simple living. Married to his high school sweetheart, with daughters and grandchildren, he knows the importance of building a secure financial future. With an aversion to social media, he prefers to spend his time on his main passions: reading, scratch cooking, racket sports, and hiking.
Read more »

Tax Free Income Trap, Dealing With MAGI

DAN SMITH  |  Apr 21, 2026

"Agree! When it comes to Roth conversions, tax arbitrage is usually the focus of discussion, but “portfolio return“ arbitrage (if that’s a proper term?) is usually less mentioned."
- Andy Morrison
Read more »

A Life You Build

Jeff Peck  |  Apr 19, 2026

"Jeff, That is an incredible article. One of if not the best HD articles I’ve ever read.That moved me. As I was reading I was thinking to mention a couple of the most inspiring takeaways you included but there were so many. Thank you so much for taking the time to write and share this piece with the HD community. Ideally, I hope this reaches way beyond HD. Well done on your life’s journey and well done capturing it here!"
- Andy Morrison
Read more »

How much to provide a college student monthly?

Chris  |  Apr 25, 2026

"I have one child who didn't ask for a lot. We were always like, do you need any money, do you need any money? Decades ago when I was in school, I tracked necessary expenses and then would ask my dad to reimburse me for those. So, then, what is "necessary?" Books, groceries, anything school-related, anything needed to live. Beyond that, I paid for it. I never overbilled him. I hated asking for money. I would have rather had a certain amount sent to me."
- David J. Kupstas
Read more »

Blood Money

Michael Flack  |  Mar 28, 2026

"On April 30 (with WTI closing at $105.07/bbl.) I sold another 10% of my XOM shares @ $154.413 (up nicely from it mid-month low of $146.44). Plan is to continue selling next month."
- mflack
Read more »

New Face, old scam

Jim Wasserman  |  May 2, 2026

"Thanks. Good to see you contributing again."
- Jeff Bond
Read more »

Is saving really that hard? Nope, not for the great majority of Americans. 

R Quinn  |  Apr 28, 2026

"It’s also easy to rationalize. Disney has an estimate on multiple visits, but that’s why I said “many.” In any case, the point is not Disney, but non-necessary spending before the financial house is in order and a plan for the future is in place."
- R Quinn
Read more »

How Far Behind is the IRS?

Larry Sayler  |  Apr 29, 2026

"My mother died in 2021 and we were due a significant refund on 2020 taxes due to medical expenses. We filed on time but it took two years and mutiple phone calls to resolve it. This was before the Trump cuts. Nothing moved until Biden pumped $80 million more into their budget. Before they woukd not even answer the phone. my only advice is to call every 2 months, take names and badge numbers and if no result call again. one agent told me they had everything they needed but nothing happened. Two months later calling back I wastold they needed X form and the lady stood by the fax machine when I faxed it. The refund arrived in two weeks. oh and keep a joint bank acvout open with mom so they can send the money there even if she passes and you can withdraw it"
- Concerned
Read more »

First Place

Jonathan Clements  |  Sep 6, 2024

"I've driven that stretch of road from the north, after a hiking trip to Humboldt Redwoods and Sinkyone on the coast. Very beautiful."
- Edmund Marsh
Read more »

How it all pencils out–or at least, we hope so! (Our Big “Little” Move, Part 3)

DrLefty  |  Apr 22, 2026

"Even with decades of consistent saving and careful planning, the transition from saver to spender is such a psychological challenge when we retire. 🤞🏻"
- Andy Morrison
Read more »

Wall Street Trap

ArticleAdam M. Grossman  |  May 2, 2026

IN THE INVESTMENT world, May 1st is a notable day. It was on May 1, 1975 that the Securities and Exchange Commission deregulated the brokerage industry. For the 183 years prior to that, trading commissions on the New York Stock Exchange had been fixed at uniformly high rates. But when deregulation arrived, competition got going. That’s when discount brokers like Charles Schwab got rolling, and over time, May Day, as it’s now referred to, has delivered enormous savings to consumers. More than 50 years later, though, Wall Street still operates in ways that are often at odds with consumer interests. As an individual investor, what are the obstacles to be aware of? At the top of the list is Wall Street’s fixation with individual stocks. For almost 100 years, the data has been clear that stock-picking is counterproductive. Probably the first to uncover this was a fellow named Alfred Cowles. Cowles came from a wealthy family and wondered whether the investment advice his family had been receiving was worthwhile. He set about answering that question and in 1933, published a paper titled “Can Stock Market Forecasters Forecast?” Cowles’s conclusion: They can’t. More recently, research by finance professors Brad Barber and Terrance Odean came to a similar conclusion. The title of their most well known paper is self-explanatory: “Trading Is Hazardous to Your Wealth.”  Along the same lines, Standard & Poor’s regularly examines actively-managed mutual funds to see how many are able to outperform the overall market. The most recent finding: Over the past 10 years, fewer than 15% of funds benchmarked to the S&P 500 managed to beat the index. Research by Jeff Ptak at Morningstar has found that the more active a fund is, the worse it performs. So-called tactical funds, which shift among different asset classes in response to economic forecasts have, in Ptak’s words, “incinerated” shareholder dollars. This data is fairly well known. The problem, though, is that trading activity generates revenue for the brokerage industry, so it has an interest in keeping investors engaged with the market. That’s why brokerage analysts are on TV every day, offering their forecasts for individual stocks, for the overall market and for the broader economy. To be sure, this makes for interesting television. The problem, though, is that it’s been shown to carry almost no value. According to research by Joachim Klement, the accuracy of Wall Street prognosticators is approximately zero. Why are they so poor at forecasting? For starters, there’s the simple fact that no one has a crystal ball. No one can know what a company—or its competitors—will do a month or a year from now, and how that will translate into stock price gains or losses. Sociologist Ezra Zuckerman Sivan uncovered a more subtle explanation. In research published after the technology selloff in 2000, Sivan found that Wall Street analysts are constrained by two obstacles. The first is that they’re dependent on access to companies’ management teams to help in their research. For that reason, it’s in their interest to maintain positive relationships with the companies that they follow. Investment banks that take a positive view on a company may also be rewarded with profitable mergers or acquisitions work when the need arises. Those factors bias stock recommendations overwhelmingly in the direction of “buy” ratings. Another reason analysts tend to avoid negative comments about the companies they cover: Sivan found that there is a community effect that tends to form among the analysts assigned to a given company, and thus an incentive develops to not “rock the boat” in saying anything too critical. People generally want to get along, and that results in a sort of self-censorship. This research is well understood, and yet Wall Street continues to generate forecasts day after day, year after year. Why? There are two explanations, I believe. The first is that it’s entertaining. I’ll be the first to acknowledge that index funds aren’t terribly interesting to talk about. It’s far more interesting to talk about smartphones or AI and the companies behind them. That makes Wall Street analysts invaluable to the media, who need to fill airtime.  And as long as they’re granted that airtime, forecasters are of great value to the brokerage industry. Since trading activity is profitable for Wall Street, it’s in brokers’ interest to generate continued interest in stocks. That brings in commission dollars for brokers. And even though commissions have shrunk in recent years, brokers benefit in other ways from active trading, including the “bid-ask spread” on each trade. That’s the difference between what buyers pay and what sellers receive, and though these spreads are tiny, they add up for the brokers who collect them. For good reason, then, Wall Street continues to promote stock-picking. At the same time, the investment industry is always busy developing new funds. In the first half of last year, for example, fund companies rolled out more than 640 new funds. Among them: funds that hold single stocks with varying degrees of leverage and other seemingly unnecessary new formulations. The result: There are now many more funds than there are stocks trading on U.S. exchanges.  Many of these new funds follow ever more esoteric strategies. They’re often opaque. And almost invariably, they carry higher fees. In a 2011 study titled “The Dark Side of Financial Innovation,” finance professor Brian Henderson and a colleague looked at one popular category of fund known as a structured product. Their conclusion: These funds were overpriced to the point that their expected return was actually a bit below zero. How were they able to market such an inferior product? Henderson’s hypothesis was that the fund companies designed them to be intentionally as complex as possible in order to exploit individual investors. The bottom line: To a great degree, Wall Street is upside down. But as an individual investor, you don’t have to be. My rule of thumb: In building a portfolio, investors should do more or less the opposite of what Wall Street recommends. That, I believe, is a reliable formula for success.   Adam M. Grossman is the founder of Mayport, a fixed-fee wealth management firm. Sign up for Adam's Daily Ideas email, follow him on X @AdamMGrossman and check out his earlier articles.
Read more »

Retirement Toys

Mark Crothers  |  May 4, 2026

"What? Everyone can’t relate to the tough issues and the dark and depressing side of financial life? 😱"
- R Quinn
Read more »

The reality of Social Security and Medicare- My real life experience.

R Quinn  |  May 4, 2026

"I’m a bit surprised. I thought this post would generate more discussion. Maybe the HD folks are too knowledgeable on the subject. A know the Threads and Facebook crowd sure aren’t though. 🤷🏻‍♂️"
- R Quinn
Read more »

Ageing and the Open Road

ArticleMark Crothers  |  May 2, 2026

RECENTLY I TOOK a free ride on a driverless bus trialling its proposed route, part of my local administration's ten-year rollout plan for self-driving public transport and taxis. I see real potential in this technology, and I'm hoping the infrastructure and implementation stay on schedule. That hope is mostly selfish, I'll admit. In fifteen years I'll be in my mid-seventies, and I'd love to ditch my car and rely on cheap, dependable robo-taxis instead. It would give me freedom precisely in that decade of life when driving starts to become genuinely problematic. I'm planning to change my car in 2027 for a modern hybrid, but in the back of my mind is the thought that it could be my last. If the self-driving rollout hits its targets, I can see the case for never buying another. The advantages for someone in my demographic at that stage of life would be hard to argue with. Think about what car ownership actually costs. There's the purchase price, insurance, road tax, fuel, servicing, tyres, and the occasional bill that arrives like a punch to the stomach. For most people, a car is the second most expensive thing they own after their home. In retirement, when income typically drops and budgets tighten, that ongoing drain becomes harder to justify. This is especially true when the car spends the vast majority of its time sitting on a driveway looking pretty. A robo-taxi model, where you pay only for the journeys you actually take, could represent a dramatic shift in how much personal transport really costs. The numbers, I suspect, will be compelling — with current estimates from real world operations suggesting an 80% reduction in the cost of fares being achievable. Then there's the question of independence. This is the one that matters most to me personally, and I'd imagine it resonates with anyone approaching or already in their later years. Giving up your car keys is one of those milestones that nobody really talks about, but everyone in that demographic understands. It represents a loss of spontaneity and self-sufficiency that can genuinely affect quality of life. The difference with autonomous vehicles is that surrendering the wheel doesn't have to mean surrendering the freedom. A reliable, affordable self-driving taxi available on demand restores something that previous generations simply had to go without once driving became difficult. This could be a trip to the supermarket on a weekday morning or a late evening visit to family. The safety dimension is also worth considering. Reaction times slow as we age. Night vision deteriorates. Concentration over long distances becomes harder. Most older drivers are aware of this and manage it carefully, but there comes a point for everyone where the road becomes a source of anxiety rather than freedom. Autonomous vehicles remove that calculation entirely. You get in, state your destination, and arrive, without the cognitive load of navigating, anticipating other drivers, or worrying whether your responses are still sharp enough. That peace of mind shouldn't be underestimated. There are wider social benefits too. Older people who can no longer drive are disproportionately affected by isolation. Poor rural transport links, infrequent bus services, and the general assumption that everyone has access to a car all contribute to a situation where many retired people find their world gradually shrinking. Autonomous vehicles, particularly if integrated intelligently with existing public transport, have the potential to reverse that. A robo-taxi that can be summoned by a smartphone, or even a simple voice command, could keep people connected to their communities, their families, and their routines far longer than is currently possible. There are, of course, reasons to be cautious. Technology rollouts rarely go entirely to plan. The ten-year schedule my local administration is working to is ambitious, and a lot can change in funding priorities, in public appetite, and in the regulatory environment. The early trials are promising, but promising trials and full-scale dependable infrastructure are very different things. It's worth keeping in mind, with a groan inducing pun: your mileage will vary — literally. Dense urban and suburban areas will almost certainly see reliable services first, and I'm fortunate that describes my situation. For those in more rural communities, the very people for whom isolation is already the sharpest problem, the wait could be considerably longer. I'm hopeful, but I'm not banking on it entirely. Which is why the 2027 hybrid still makes sense. It's a practical hedge, a good, modern, efficient car that will serve me well through the transition years, whatever pace that transition takes. But the fact that I'm already thinking of it as potentially my last car feels significant. A decade ago that thought wouldn't have crossed my mind. The technology has moved from science fiction to credible near-future fast enough to genuinely reshape how I'm thinking about retirement planning. If it delivers, the generation hitting their seventies in the late 2030s could be the first in history for whom ageing and mobility don't have to be in conflict. That's not a small thing. That might turn out to be one of the most personally transformative shifts of the entire autonomous vehicle revolution. It is not about the flashy early adopters or the logistics industry efficiencies. Instead, it is the simple dignity of an older person getting where they need to go, independently, on their own terms. I'm hopeful I'll be taking that ride and certain my children and grandchildren definitely will.
Mark Crothers is a retired small business owner from the UK with a keen interest in personal finance and simple living. Married to his high school sweetheart, with daughters and grandchildren, he knows the importance of building a secure financial future. With an aversion to social media, he prefers to spend his time on his main passions: reading, scratch cooking, racket sports, and hiking.
Read more »

Tax Free Income Trap, Dealing With MAGI

DAN SMITH  |  Apr 21, 2026

"Agree! When it comes to Roth conversions, tax arbitrage is usually the focus of discussion, but “portfolio return“ arbitrage (if that’s a proper term?) is usually less mentioned."
- Andy Morrison
Read more »

A Life You Build

Jeff Peck  |  Apr 19, 2026

"Jeff, That is an incredible article. One of if not the best HD articles I’ve ever read.That moved me. As I was reading I was thinking to mention a couple of the most inspiring takeaways you included but there were so many. Thank you so much for taking the time to write and share this piece with the HD community. Ideally, I hope this reaches way beyond HD. Well done on your life’s journey and well done capturing it here!"
- Andy Morrison
Read more »

How much to provide a college student monthly?

Chris  |  Apr 25, 2026

"I have one child who didn't ask for a lot. We were always like, do you need any money, do you need any money? Decades ago when I was in school, I tracked necessary expenses and then would ask my dad to reimburse me for those. So, then, what is "necessary?" Books, groceries, anything school-related, anything needed to live. Beyond that, I paid for it. I never overbilled him. I hated asking for money. I would have rather had a certain amount sent to me."
- David J. Kupstas
Read more »

Blood Money

Michael Flack  |  Mar 28, 2026

"On April 30 (with WTI closing at $105.07/bbl.) I sold another 10% of my XOM shares @ $154.413 (up nicely from it mid-month low of $146.44). Plan is to continue selling next month."
- mflack
Read more »

New Face, old scam

Jim Wasserman  |  May 2, 2026

"Thanks. Good to see you contributing again."
- Jeff Bond
Read more »

Is saving really that hard? Nope, not for the great majority of Americans. 

R Quinn  |  Apr 28, 2026

"It’s also easy to rationalize. Disney has an estimate on multiple visits, but that’s why I said “many.” In any case, the point is not Disney, but non-necessary spending before the financial house is in order and a plan for the future is in place."
- R Quinn
Read more »

Wall Street Trap

ArticleAdam M. Grossman  |  May 2, 2026

IN THE INVESTMENT world, May 1st is a notable day. It was on May 1, 1975 that the Securities and Exchange Commission deregulated the brokerage industry. For the 183 years prior to that, trading commissions on the New York Stock Exchange had been fixed at uniformly high rates. But when deregulation arrived, competition got going. That’s when discount brokers like Charles Schwab got rolling, and over time, May Day, as it’s now referred to, has delivered enormous savings to consumers. More than 50 years later, though, Wall Street still operates in ways that are often at odds with consumer interests. As an individual investor, what are the obstacles to be aware of? At the top of the list is Wall Street’s fixation with individual stocks. For almost 100 years, the data has been clear that stock-picking is counterproductive. Probably the first to uncover this was a fellow named Alfred Cowles. Cowles came from a wealthy family and wondered whether the investment advice his family had been receiving was worthwhile. He set about answering that question and in 1933, published a paper titled “Can Stock Market Forecasters Forecast?” Cowles’s conclusion: They can’t. More recently, research by finance professors Brad Barber and Terrance Odean came to a similar conclusion. The title of their most well known paper is self-explanatory: “Trading Is Hazardous to Your Wealth.”  Along the same lines, Standard & Poor’s regularly examines actively-managed mutual funds to see how many are able to outperform the overall market. The most recent finding: Over the past 10 years, fewer than 15% of funds benchmarked to the S&P 500 managed to beat the index. Research by Jeff Ptak at Morningstar has found that the more active a fund is, the worse it performs. So-called tactical funds, which shift among different asset classes in response to economic forecasts have, in Ptak’s words, “incinerated” shareholder dollars. This data is fairly well known. The problem, though, is that trading activity generates revenue for the brokerage industry, so it has an interest in keeping investors engaged with the market. That’s why brokerage analysts are on TV every day, offering their forecasts for individual stocks, for the overall market and for the broader economy. To be sure, this makes for interesting television. The problem, though, is that it’s been shown to carry almost no value. According to research by Joachim Klement, the accuracy of Wall Street prognosticators is approximately zero. Why are they so poor at forecasting? For starters, there’s the simple fact that no one has a crystal ball. No one can know what a company—or its competitors—will do a month or a year from now, and how that will translate into stock price gains or losses. Sociologist Ezra Zuckerman Sivan uncovered a more subtle explanation. In research published after the technology selloff in 2000, Sivan found that Wall Street analysts are constrained by two obstacles. The first is that they’re dependent on access to companies’ management teams to help in their research. For that reason, it’s in their interest to maintain positive relationships with the companies that they follow. Investment banks that take a positive view on a company may also be rewarded with profitable mergers or acquisitions work when the need arises. Those factors bias stock recommendations overwhelmingly in the direction of “buy” ratings. Another reason analysts tend to avoid negative comments about the companies they cover: Sivan found that there is a community effect that tends to form among the analysts assigned to a given company, and thus an incentive develops to not “rock the boat” in saying anything too critical. People generally want to get along, and that results in a sort of self-censorship. This research is well understood, and yet Wall Street continues to generate forecasts day after day, year after year. Why? There are two explanations, I believe. The first is that it’s entertaining. I’ll be the first to acknowledge that index funds aren’t terribly interesting to talk about. It’s far more interesting to talk about smartphones or AI and the companies behind them. That makes Wall Street analysts invaluable to the media, who need to fill airtime.  And as long as they’re granted that airtime, forecasters are of great value to the brokerage industry. Since trading activity is profitable for Wall Street, it’s in brokers’ interest to generate continued interest in stocks. That brings in commission dollars for brokers. And even though commissions have shrunk in recent years, brokers benefit in other ways from active trading, including the “bid-ask spread” on each trade. That’s the difference between what buyers pay and what sellers receive, and though these spreads are tiny, they add up for the brokers who collect them. For good reason, then, Wall Street continues to promote stock-picking. At the same time, the investment industry is always busy developing new funds. In the first half of last year, for example, fund companies rolled out more than 640 new funds. Among them: funds that hold single stocks with varying degrees of leverage and other seemingly unnecessary new formulations. The result: There are now many more funds than there are stocks trading on U.S. exchanges.  Many of these new funds follow ever more esoteric strategies. They’re often opaque. And almost invariably, they carry higher fees. In a 2011 study titled “The Dark Side of Financial Innovation,” finance professor Brian Henderson and a colleague looked at one popular category of fund known as a structured product. Their conclusion: These funds were overpriced to the point that their expected return was actually a bit below zero. How were they able to market such an inferior product? Henderson’s hypothesis was that the fund companies designed them to be intentionally as complex as possible in order to exploit individual investors. The bottom line: To a great degree, Wall Street is upside down. But as an individual investor, you don’t have to be. My rule of thumb: In building a portfolio, investors should do more or less the opposite of what Wall Street recommends. That, I believe, is a reliable formula for success.   Adam M. Grossman is the founder of Mayport, a fixed-fee wealth management firm. Sign up for Adam's Daily Ideas email, follow him on X @AdamMGrossman and check out his earlier articles.
Read more »

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Get Educated

Manifesto

May 3, 2026

NO. 52: WE SHOULD aim to become homeowners—not because homes deliver handsome capital gains, but because owning locks in our housing costs and, with every mortgage payment, forces us to save.

act

May 4, 2026

GO TO THE LIBRARY. You can borrow DVDs, rather than paying to stream movies and TV shows. You can cancel your magazine and newspaper subscriptions, and peruse the library’s periodicals instead. You can borrow the latest books, rather than ordering from Amazon. All this will get you out of the house, meeting your neighbors and reading more—at no cost.

think

May 4, 2026

EVOLUTIONARY psychology. Why are we so fearful of losses, so bad at saving money and always hankering for more material goods? Evolutionary psychology explains such behavior by identifying the traits that helped our nomadic ancestors to survive. These hardwired instincts often hurt us in today’s world—and it can take great mental effort to overcome them.

humans

May 3, 2026

NO. 29: WE SUFFER from recency bias, meaning we’re overly influenced by current events. Today’s investment dramas loom large, triggering fear or greed and prompting foolish portfolio changes. Meanwhile, we lose sight of market history—the crises that were overcome, the hot stocks that turned cold, and the broad market’s impressive march higher.

Money Guide

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Manifesto

May 3, 2026

NO. 52: WE SHOULD aim to become homeowners—not because homes deliver handsome capital gains, but because owning locks in our housing costs and, with every mortgage payment, forces us to save.

Spotlight: Life Events

A Diamond Wedding Anniversary

Marjorie Kondrack   |  Apr 9, 2025

I wore a gown of Chantilly lace—the sun caught the sparkles in my bridal headdress. My husband was resplendent in his tuxedo—the sun was shining on a beautiful April morning —Our wedding day, 60 years ago, April, 1965.
While The choice of a spouse is among the most important decisions most people ever make,  it’s a choice that comes with no guarantees of long term happiness.  That said, we all have an ideal vision of the person we would like to marry. 

Read more »

Sad news about T. V. Narayanan, a writer for HD

smr1082   |  May 22, 2025

I want to share the sad news that Mr. T. V. Narayanan passed away in India, two days ago, of a brief illness. He is survived by his wife, son, daughter-in-law, and 3 grandchildren. We will miss him dearly.
Here is an article he wrote for HD: https://humbledollar.com/2023/07/come-a-long-way/
He says in this article that he must have read just about every column that Jonathan Clements wrote as a personal finance columnist for the Journal and learned much from them.

Read more »

Did we do this all wrong?

polamalu2009   |  Aug 27, 2024

Looking up at the ceiling recovering from major surgery has this 70+ boomer rethinking life. Everyone on here has an intense interest in personal finance. Most of us are boomers.  Our parents were the Greatest Generation who lived the Depression and fought the war then shared their stories of sacrifice. We’ve read the Wall Street Journal, especially when Jonathan was there, financial papers, magazines and websites galore. My guess is that our playbook is pretty much the same:  get an education,

Read more »

Tributes to Jonathan Clements

Adam M. Grossman   |  Sep 27, 2025

HUMBLEDOLLAR FOUNDER and longtime Wall Street Journal columnist Jonathan Clements passed away earlier this week. He was 62.
I reached out to several of Jonathan’s close friends and colleagues to ask for their remembrances. Taken together, they paint a picture of someone who was as beloved by his peers as he was by his readers.
As Jason Zweig put it, “I have just lost a friend, and so have you.”
Christine Benz,

Read more »

A Gift Worth Reading

Dennis Friedman   |  Jul 2, 2025

When I was in third grade, my mom worked at a small diner near our house. Every morning before school, I’d walk there for breakfast and read the sports section of the Canton Repository. That habit stuck with me, and soon I was arriving early to school just to read the newspaper in the library.
I wasn’t the best student, but if they had quizzed me on what was going on in the world,

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The Wedding Extravaganza: A Pre-Mortum for Future Parents of the Bride

Mark Crothers   |  Jun 24, 2025

Today, I have the not-so-joyful task of collecting my suit from the dry cleaners. This instrument of torture is, of course, for a wedding I’m attending in a few weeks. Suzie and I are close friends with the bride’s family, and for the past 18 months, we’ve been “in the loop” on all the drama and discussions surrounding the planning. It seems every visit to a bridal show adds a new “must-have” addition to what’s become quite the circus,

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Spotlight: Perry

Free to Roam

Michael Perry   |  Oct 6, 2023

LIKE MANY WHO THINK about where they’d like to retire, we’ve always had a vague list of wants: comfortable climate, walkability, good health care, access to cultural events and outdoor activities, friendly tax regime, reasonable cost of living, that sort of thing. I wrote previously about feeling stuck for many years in a place where we didn’t want to stay, but also not really having one place where we felt drawn to settle, whether for a few years or permanently. Spending three months in England has influenced our thinking about what we want. Unfortunately, it may have also made that place harder to find. One of the things we’ve really enjoyed here is having the countryside on our doorstep and being able to walk it easily, including between towns. We’ve had days when we leave our charming town, walk across a few gently rolling pastures to have coffee or lunch in the next charming town, and walk through others for a different route back home. We’ve hit 10,000 steps by midday more times than I care to count. Sometimes, we meet another friendly walker along the way, and other times it’s just us. In England and Wales, people have the legal right to use designated public footpaths or bridleways. Some of these are prehistoric routes that have been trod since ancient times. Others are of more recent vintage. In either case, once they’re so designated, they must be respected, and they form a vast network. To my understanding, Scotland goes even further, with a generally accepted “right to roam” in the countryside, footpath or not. An interesting thing about these paths is that they often cross private land. We’ve walked one that crossed a field of vegetables, another that crossed through someone’s lawn, and many that crossed pastures of cattle…
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Too Heavy a Load

Michael Perry   |  Oct 16, 2021

I’M A MORNINGSTAR subscriber. I find that the site provides investing and personal finance information that’s sensible and useful for the average person, and that it promotes good investing and planning behaviors. Still, I was taken aback by a recent article, which discussed four funds that investors have been buying. In terms of deciding what I buy, I don’t really care what others have been purchasing. Still, it’s interesting to see, so I checked it out. My surprise: Three of the four funds mentioned are A share funds, which means buyers have to pay a front-end commission, or load. For instance, one of the funds is Columbia Dividend Income, a Morningstar medalist that “really emphasizes quality” and “has put in some nice defensive qualities,” according to the Morningstar analyst. That sounds good. But not mentioned in the article is that, for regular retail investors, the Columbia fund’s A shares have a 5.75% front-end load. You can avoid that sales commission—but only if, say, you buy through an advisory account, which will then charge you a fee, or it’s offered in your 401(k). As of May 31, the front-end load A shares held $4.2 billon, second only to one of the institutional share classes. Besides my surprise that Morningstar has given a silver rating to a front-end load fund, I’m also surprised that investors have apparently been piling into it, such that the fund’s about to close. I realize not everyone has gotten the message from HumbleDollar and elsewhere that costs matter, but Morningstar usually promotes the concept. It’s one thing to pay an above-average expense ratio. But to me, a front-end load is something else entirely, because it can take years to recoup that cost—and it may never happen. Maybe that’s my own mental accounting at work, and a cost…
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Too Much Cash?

Michael Perry   |  Nov 17, 2022

I'VE SPENT THE PAST seven or eight years lamenting our cash position, both the interest it was earning and the size of it. The former was too little, the latter too much. Some years ago, we sold an investment property with the idea of buying another somewhere we might potentially retire. But as I noted in a recent article, we’ve never been able to settle on where that would be. We were also constantly thinking we were going to move or be moved away from the Houston area, where my job had deposited us, and that we might want the cash for a house in our new location. Of course, despite repeatedly raising the possibility of a relocation to my higher-ups, this never happened. The result: Hundreds of thousands of dollars have languished in cash, with me grousing about it—at least until last year, when I retired. But with the volatility in the stock and bond markets that soon followed, this large cash position has probably contributed to the quality of our sleep. Still, I know high inflation is eating away at it. True, a majority of this money is in a 401(k) stable value fund, which provides higher rates than are available in most other options. Our stock position is now three percentage points off our target, and is politely asking for a rebalance. Add the coming proceeds from the house we just sold, and the voice becomes more insistent: Shouldn’t we be buying stocks? Well, maybe, except we may still want to purchase a property. We’ve decided to store everything and travel, but for how long? We could tire of living out of suitcases and decide to pick a place from our U.S. short list, or we might pull the trigger on a part of Italy that we like.…
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Free in the World

Michael Perry   |  Nov 1, 2022

YESTERDAY EVENING we went under contract to sell our home of the past 10 years, by far the longest I’ve ever lived in one place. In our neighborhood, the average time on the market is currently 33 days. We’d been on the market for one day and the offer was over asking. We credit this to taking good care of our home, and having a sharp listing agent and staging consultant. This experience, and what we learned from it, could be its own article. But this one isn’t about real estate. As we’ve seen retirement approaching over the past few years, a constant topic of conversation between my wife and me is where we want to live. Our Houston-area home has a lot going for it. It’s small, efficient, well-maintained, with good neighbors, in a low-cost-of-living area with no personal income tax, great medical facilities and a major airport. Until recently, we’d thought about keeping it as a base while we travel—as travel was always a major part of our retirement plans. While we like our house, it just isn’t located where we’d choose to spend a lot of time, with our biggest complaint being the climate. We’d talked for years about buying something else but could never settle on one location. We’ve thought about lots of places—starting, of course, with places we like. We’ve considered the weather, cost of living and taxation. I’ve become conversant with various state tax regimes and the resident visa requirements for a few foreign countries. At one point, my wife lamented that we couldn’t even settle on a continent. My response was there are only seven, and Antarctica is basically uninhabitable, so we can almost count our choices on one hand. I’m a glass-half-full kind of guy. What made choosing so hard is that…
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An Appreciated Gift

Michael Perry   |  Jul 28, 2021

MY NEPHEW GRADUATED from high school this past spring and starts college in the fall. Alex is fortunate to have received a full scholarship from his college of choice. Wait, scratch that. Alex isn’t fortunate. Rather, his diligence and academic success in high school have been rewarded. While Alex needs no help paying for college, his notable accomplishment should still be recognized. We’d write him a check, but where’s the fun in that? How about a financial gift that’ll allow some one-on-one time that might spark an interest in sensible investing? For instance, we could gift him some appreciated stock, which would also absolve ourselves of a future capital-gains tax burden. Or we could make a contribution to a Roth IRA up to the amount of his earned income and start him on a lifetime of tax-free growth. Problem is, we can’t put appreciated assets in an IRA, only cash. That means we can’t unload our appreciated assets and help Alex start a Roth. Or can we? It turns out we can, but there will be a few steps involved. Here are the steps and considerations we need to keep in mind: We’ll have Alex set up a taxable brokerage account in which to receive the gift, as well as a Roth IRA to be funded later. There are several firms that would be suitable, but since we’re at Fidelity Investments and understand its website and customer service, we’ll have him set up Fidelity accounts. Being at the same institution should make it easier to navigate the various steps. Once Alex has his brokerage account open, we’ll instruct Fidelity to make the transfer of an appreciated holding from my wife’s taxable brokerage account to Alex’s. This can be done in a few days. Once Alex has received the shares, he…
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Working My Losses

Michael Perry   |  Aug 24, 2021

AT THE START OF THE pandemic, we picked up a nice chunk of capital losses. I say “nice” because these were intentional. When the market dropped significantly, we realized losses and immediately reinvested the proceeds in other fallen stocks. What about capital gains? In 2020, some of our mutual funds distributed capital gains, but we didn’t intentionally realize any other gains. Some of our realized losses offset the distributed fund gains. Another $3,000 was applied against ordinary income. But our remaining capital losses were carried over for future years. We intend to put some of these losses to use in 2021, allowing us to harvest more tax-free gains. Our taxable accounts have a combination of index funds, actively managed funds and individual stocks. Where should we realize gains? One approach would be to simplify our portfolio by selling individual stocks, which include some rather small positions. As we get closer to retirement, having fewer holdings would make managing our investment income and taxes simpler. It would also make the portfolio easier for my wife to manage should I not be around to help. But I’m not 100% convinced this is the right strategy. Besides being tax-efficient and very low cost, some of the individual stocks are nice dividend payers. As I near retirement, I wonder if this is the right time to remove a source of income. Finally, some of our holdings are undervalued, according to Morningstar. Why sell these now if they may have room to run? Another approach would be to realize gains in one or more of our actively managed funds. That would slightly improve our overall portfolio’s tax efficiency and slightly reduce our overall fees. None of these funds is highly tax-inefficient, judging by the tax cost ratio provided by Morningstar. But there’s undoubtedly room for…
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