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Investment Versus Speculation

"Good question Andy. I have no idea."
- Jack Hannam
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Financial Planning

"You have been of great help here continuously, keeping us informed about HD and JC’s legacy. Thanks again!"
- Concerned
Read more »

Financial regrets about parenthood?

"Yes indeed. We look forward to spending as much as we can as long as we can on the grandchildren. My parents were unable and had no inclination to spend on us or our children even in modest ways, we are not going to repeat that."
- R Quinn
Read more »

Resist the Urge to Act

BEFORE WE GET into it, a brief word. We lost Jonathan last year, and those of us who followed his work felt it more than we perhaps expected.  He had a saying that I always liked - that there are really only twenty stories in personal finance, and the financial industry spends most of its time telling them on repeat in slightly different hats. He was right, of course. He usually was. It struck me that a fitting tribute might be to take his core principles and do something with them, not quote him at length, but wrestle with the ideas in our own words, from our own lives. I've chosen "Resist the Urge to Act," and had a go below. If the idea appeals to any readers posting on the forum, I'd love to see others pick a principle, whichever one speaks to you, and write about it in your own voice. No need to be an economist. Just be honest. I suspect Jonathan would have approved of that approach more than most. There's a strange truth lurking at the heart of personal finance that nobody tells you about, possibly because it would put a large number of people out of work. The more urgently you feel you ought to do something with your investments, the more damage you will probably do by doing it. I find this deeply satisfying, not because I'm wise, far from it, but because it seems my instinct to do very little was correct all along. Vindication, when it arrives, should be savored. Jonathan Clements spent decades writing about money for the Wall Street Journal before founding HumbleDollar, which if you're reading this you already know, and if you don't, welcome, you've somehow stumbled into excellent company by accident. One of his core messages, boiled down to its purest form, was this: The secret to successful investing is to be comprehensively, almost aggressively boring. He had a list of principles, and one of them was deceptively simple: Resist the Urge to Act. I have a suspicion he knew it was one of the hardest ones, which is perhaps why he saved it for near the end of his various lists. Telling people to do nothing runs headlong into every instinct the modern world has carefully cultivated in them. The financial news industry has a business model, and it is not, I would suggest, your long-term wealth they're hoping to help. Their holy grail is your attention span, and attention without action doesn't keep the lights on. So urgency is manufactured. Alarm is engineered. The moment a headline about Federal Reserve policy or market volatility lands on your phone screen, the correct and sophisticated response, according to Jonathan, is to put the phone face-down and go and make a cup of tea. This is not what the headline wants you to do. The headline wants you to feel that failure to react immediately constitutes negligence. It doesn't. The information has already been digested, debated, and priced in by people who got it considerably earlier than you did. Acting on it now isn't smart. It's like arriving late to a party that ended an hour ago and wondering why nobody's offering you a stiff drink. Jonathan was a firm believer in market efficiency, the rather humbling idea that you, me, and most professional fund managers with their impressive offices and Bloomberg terminals, cannot reliably outthink the combined judgment of millions of other investors. Once you genuinely accept this, something might shift for you. You'll probably stop checking your portfolio three times before lunch. Which matters more than it might sound, because there's a fairly direct relationship between how often you look at your balance and how likely you are to do something regrettable with it. He had a line I've shamelessly adopted as my own: Your portfolio is like a bar of soap, and the more you handle it, the smaller it gets. My wife Suzie heard me say this recently and pointed out that I've never shown this level of restraint with actual soap. She's not wrong. But then again, I liberate hotel soap. The other temptation Jonathan warned against was treating the market as a hobby. There's a certain thrill, I understand, in hunting for the next great stock, the overheard tip, the sector everyone's talking about. The feeling that you've spotted something the rest of us turkeys have missed is a powerful one. He was fairly blunt on this point. If you want that kind of excitement, go to the cinema. Go to a casino. These are perfectly respectable venues for the willing suspension of rational judgment. Your brokerage account is not. The urge to act, dressed up as diligence and research, is still the urge to act. The actual solution is somewhat anticlimactic. Broad index funds, bought automatically and regularly, regardless of what the television talking heads are shouting about. When the market drops and the headlines turn an alarming shade of red, the correct response, the disciplined, intelligent, sophisticated response, is to turn the television off, close the laptop, and take yourself for a walk. Jonathan was clear on this point: Doing nothing, at the right moment, is one of the harder things an investor can do. It only looks like laziness from the outside. From the inside, when every instinct is screaming at you to move, to switch, to sell, to “do something,” holding still takes genuine effort. I have found, in my own modest experience, that retirement makes this philosophy considerably easier to live by. Urgency has a way of evaporating when you no longer have somewhere to be. The news cycle hums along without me. The market does whatever it decides to do. And I go for my walk. By strange coincidence, the halfway point often coincides with a bar serving decent Guinness. I consider this a stroke of luck. It seems I was a follower of Jonathan's advice for many years before I stumbled upon his name and writing. There's something to be said for arriving at the right answer through a combination of temperament and mild indifference. I'm choosing to call it wisdom. This piece was never meant to be anything more than one person's attempt to retell one of Jonathan's principles in his own words, a tribute of sorts, filtered through lived experience rather than expertise. The voice is mine, for better or worse. The wisdom, unambiguously, was his. There are more principles still sitting there, waiting. Each of them deserves exactly this kind of treatment, personal, honest, and a little bit imperfect. So, who's next? Because if there are no takers I'll have a pretty big task ahead of me.
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 »

Taxes Season 3

"Thanks Rick and Dan for clarifying this. So I believe you are saying that most of your senior federal income tax filers were able to take advantage of the $6,000 Senior Deduction and most did not itemize deductions, but instead took the Standard Deduction because it was so large: "For the 2025 tax year (taxes filed in 2026), seniors over 65 can claim a total standard deduction of $23,750 for singles and $46,700 for married couples filing jointly (if both are over 65), combining the base deduction, the additional 65+ amount, and the new $6,000 per-person senior bonus." Only wealthier tax filers were unable to take advantage of ANY of the $6,000 Senior Deduction if their MAGI was over $175,000 single/$250,000 married filing jointly."
- David Rhoades
Read more »

My sister’s will and what it taught me.

"Thank you for sharing Mike. It just shows you never know when your time is up so it stresses the importance even more to plan your estate now."
- Andrew Clements
Read more »

Avoid the noise, buy the market and stay invested

"Glad to see you made it to the "two-comma club" as well. Welcome, new member, and Congratulations. It really is a simple process. NOT easy, but simple."
- Mike Lynch
Read more »

“We did everything right.” Maybe not. Retirement income should not be an unpleasant surprise.

"I was fortunate to work with five unions who supported me in our efforts to communicate to their members on how to obtain the most value from their employee benefits. They wanted appreciation from members for what they had negotiated and we both wanted value for the cost of the benefits, the unions well aware they gave up some pay to obtain those benefits. We were both frustrated at the high level of indifference by many workers."
- R Quinn
Read more »

Stock Tokens

RECENTLY, The Wall Street Journal ran a story about a new type of investment known as a digital stock token. For now, they aren’t available in the U.S., but they’re coming soon, so it’s worth taking a closer look. What are stock tokens? At the most basic level, they’re a technology designed to make stock market investing quicker and easier than it is today. With tokens, trading won’t be limited to traditional business hours. Instead, investors will be able to trade 24/7. And token trades will settle instantly, allowing investors to deposit or withdraw funds from an investment without the overnight delay imposed by traditional stock exchanges.  An additional benefit: Tokens will allow investors to purchase fractional shares. To see how this would work, consider Microsoft. Today, its share price is around $370. Through the token system, though, an investor with a modest budget could gain exposure to Microsoft with just $5 or $10. There will also be index-based tokens, so an investor could gain exposure to the S&P 500, for example. In many ways, stock tokens are the equivalent of cryptocurrencies but for stocks, allowing investors to trade more quickly and easily. That’s their key appeal, and it’s part of the broader trend toward digitizing the financial system. Along the same lines, a number of retailers are pursuing so-called stablecoins as an alternative to costly credit card networks. Stock tokens do carry risk, though. You may recall an episode that occurred in 2022, when a digital currency called TerraUSD, which was designed to maintain a fixed value of $1, suddenly lost most of its value. In that case, there was a breakdown in the algorithm that was supposed to prevent Terra from dipping below $1, and that caused the equivalent of a run on the bank. Supporters of stock tokens will tell you that Terra’s failure can be attributed to its primitive structure and that today’s technology wouldn’t be similarly vulnerable. That may be true, but stock tokens carry other potential vulnerabilities. For starters, they’re complex and rely on a significant amount of financial engineering. Unlike a share of stock which is simply an ownership stake in a business, tokens are more of a synthetic financial instrument. That’s why the recent Journal write-up referred to them as “digital avatars.” When you buy a token, you aren’t buying an actual share of stock. It’s more like a chip issued by a casino or a gift card issued by a retailer. It looks like real money, and under ordinary circumstances, it probably will function like real money. But in times of stress, they may not perform as expected. The financial firm Robinhood, which has already created a family of stock tokens for international investors, acknowledges another risk: Because tokens don’t represent actual shares of stock, they carry what’s known as counterparty risk. Under the hood, tokens are actually financial contracts, which means that the party on the other side of a given contract needs to remain solvent in order for a token to maintain its value. On its website, Robinhood includes this disclosure: “Investors may lose up to the full amount of their invested capital due to market conditions or the insolvency of Robinhood.” To be sure, counterparty failure is usually a low risk, but it isn’t zero, and actual shares of stock don’t need disclaimers like this.  Even under ordinary circumstances, stock tokens’ prices likely won’t move in lockstep with actual share prices. That’s for a few reasons.  First, because tokens aren’t real shares, they don’t pay dividends. While that might not seem like a significant factor, dividends do add up. Over the past 15 years, they’ve accounted for about 20% of the total return of U.S. stocks. Also, stock tokens don’t carry the voting rights associated with real shares. That might also seem insignificant to everyday investors, but because it is important to larger, institutional investors, it means that tokens will probably always trade at a bit of a discount to real shares. A final risk is one that is longer term but much more serious: Stock tokens are built on blockchain technology, and that means they’re vulnerable to hacking. Of most concern is the fact that blockchain technologies rely on cryptography to secure investors’ holdings. While blockchain encryption has never been cracked, advances in computing power—and specifically, a technology known as quantum computing—could one day compromise a blockchain. Most experts believe this is 10 or more years away, but companies including Google and IBM are actively working on it, so it’s worth bearing in mind. The bottom line: In thinking about this new innovation, I’d lean on a concept known as Lindy’s law. This is a rule of thumb which postulates that the future life expectancy of an idea is proportional to its current age. In other words, the longer an idea has stood the test of time, the more likely it is to continue to stand the test of time in the future. That’s how I’d look at stock tokens. They might or might not be a good idea, but it’s too soon to tell. And since the benefits they offer are more in the category of convenience rather than investment performance, I see no particular need to own them. For that reason, it might make sense to wait and watch until any bugs are worked out.   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 »

Carrying Humble Dollar Forward

"That's very true -- bigger problems. Recall that it took from 1929 to about 1945 for that come back. Sixteen years for someone retiring in '29 would usually have been a lifetime."
- John D.
Read more »

Investment Versus Speculation

"Good question Andy. I have no idea."
- Jack Hannam
Read more »

Financial Planning

"You have been of great help here continuously, keeping us informed about HD and JC’s legacy. Thanks again!"
- Concerned
Read more »

Financial regrets about parenthood?

"Yes indeed. We look forward to spending as much as we can as long as we can on the grandchildren. My parents were unable and had no inclination to spend on us or our children even in modest ways, we are not going to repeat that."
- R Quinn
Read more »

Resist the Urge to Act

BEFORE WE GET into it, a brief word. We lost Jonathan last year, and those of us who followed his work felt it more than we perhaps expected.  He had a saying that I always liked - that there are really only twenty stories in personal finance, and the financial industry spends most of its time telling them on repeat in slightly different hats. He was right, of course. He usually was. It struck me that a fitting tribute might be to take his core principles and do something with them, not quote him at length, but wrestle with the ideas in our own words, from our own lives. I've chosen "Resist the Urge to Act," and had a go below. If the idea appeals to any readers posting on the forum, I'd love to see others pick a principle, whichever one speaks to you, and write about it in your own voice. No need to be an economist. Just be honest. I suspect Jonathan would have approved of that approach more than most. There's a strange truth lurking at the heart of personal finance that nobody tells you about, possibly because it would put a large number of people out of work. The more urgently you feel you ought to do something with your investments, the more damage you will probably do by doing it. I find this deeply satisfying, not because I'm wise, far from it, but because it seems my instinct to do very little was correct all along. Vindication, when it arrives, should be savored. Jonathan Clements spent decades writing about money for the Wall Street Journal before founding HumbleDollar, which if you're reading this you already know, and if you don't, welcome, you've somehow stumbled into excellent company by accident. One of his core messages, boiled down to its purest form, was this: The secret to successful investing is to be comprehensively, almost aggressively boring. He had a list of principles, and one of them was deceptively simple: Resist the Urge to Act. I have a suspicion he knew it was one of the hardest ones, which is perhaps why he saved it for near the end of his various lists. Telling people to do nothing runs headlong into every instinct the modern world has carefully cultivated in them. The financial news industry has a business model, and it is not, I would suggest, your long-term wealth they're hoping to help. Their holy grail is your attention span, and attention without action doesn't keep the lights on. So urgency is manufactured. Alarm is engineered. The moment a headline about Federal Reserve policy or market volatility lands on your phone screen, the correct and sophisticated response, according to Jonathan, is to put the phone face-down and go and make a cup of tea. This is not what the headline wants you to do. The headline wants you to feel that failure to react immediately constitutes negligence. It doesn't. The information has already been digested, debated, and priced in by people who got it considerably earlier than you did. Acting on it now isn't smart. It's like arriving late to a party that ended an hour ago and wondering why nobody's offering you a stiff drink. Jonathan was a firm believer in market efficiency, the rather humbling idea that you, me, and most professional fund managers with their impressive offices and Bloomberg terminals, cannot reliably outthink the combined judgment of millions of other investors. Once you genuinely accept this, something might shift for you. You'll probably stop checking your portfolio three times before lunch. Which matters more than it might sound, because there's a fairly direct relationship between how often you look at your balance and how likely you are to do something regrettable with it. He had a line I've shamelessly adopted as my own: Your portfolio is like a bar of soap, and the more you handle it, the smaller it gets. My wife Suzie heard me say this recently and pointed out that I've never shown this level of restraint with actual soap. She's not wrong. But then again, I liberate hotel soap. The other temptation Jonathan warned against was treating the market as a hobby. There's a certain thrill, I understand, in hunting for the next great stock, the overheard tip, the sector everyone's talking about. The feeling that you've spotted something the rest of us turkeys have missed is a powerful one. He was fairly blunt on this point. If you want that kind of excitement, go to the cinema. Go to a casino. These are perfectly respectable venues for the willing suspension of rational judgment. Your brokerage account is not. The urge to act, dressed up as diligence and research, is still the urge to act. The actual solution is somewhat anticlimactic. Broad index funds, bought automatically and regularly, regardless of what the television talking heads are shouting about. When the market drops and the headlines turn an alarming shade of red, the correct response, the disciplined, intelligent, sophisticated response, is to turn the television off, close the laptop, and take yourself for a walk. Jonathan was clear on this point: Doing nothing, at the right moment, is one of the harder things an investor can do. It only looks like laziness from the outside. From the inside, when every instinct is screaming at you to move, to switch, to sell, to “do something,” holding still takes genuine effort. I have found, in my own modest experience, that retirement makes this philosophy considerably easier to live by. Urgency has a way of evaporating when you no longer have somewhere to be. The news cycle hums along without me. The market does whatever it decides to do. And I go for my walk. By strange coincidence, the halfway point often coincides with a bar serving decent Guinness. I consider this a stroke of luck. It seems I was a follower of Jonathan's advice for many years before I stumbled upon his name and writing. There's something to be said for arriving at the right answer through a combination of temperament and mild indifference. I'm choosing to call it wisdom. This piece was never meant to be anything more than one person's attempt to retell one of Jonathan's principles in his own words, a tribute of sorts, filtered through lived experience rather than expertise. The voice is mine, for better or worse. The wisdom, unambiguously, was his. There are more principles still sitting there, waiting. Each of them deserves exactly this kind of treatment, personal, honest, and a little bit imperfect. So, who's next? Because if there are no takers I'll have a pretty big task ahead of me.
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 »

Taxes Season 3

"Thanks Rick and Dan for clarifying this. So I believe you are saying that most of your senior federal income tax filers were able to take advantage of the $6,000 Senior Deduction and most did not itemize deductions, but instead took the Standard Deduction because it was so large: "For the 2025 tax year (taxes filed in 2026), seniors over 65 can claim a total standard deduction of $23,750 for singles and $46,700 for married couples filing jointly (if both are over 65), combining the base deduction, the additional 65+ amount, and the new $6,000 per-person senior bonus." Only wealthier tax filers were unable to take advantage of ANY of the $6,000 Senior Deduction if their MAGI was over $175,000 single/$250,000 married filing jointly."
- David Rhoades
Read more »

My sister’s will and what it taught me.

"Thank you for sharing Mike. It just shows you never know when your time is up so it stresses the importance even more to plan your estate now."
- Andrew Clements
Read more »

Avoid the noise, buy the market and stay invested

"Glad to see you made it to the "two-comma club" as well. Welcome, new member, and Congratulations. It really is a simple process. NOT easy, but simple."
- Mike Lynch
Read more »

Stock Tokens

RECENTLY, The Wall Street Journal ran a story about a new type of investment known as a digital stock token. For now, they aren’t available in the U.S., but they’re coming soon, so it’s worth taking a closer look. What are stock tokens? At the most basic level, they’re a technology designed to make stock market investing quicker and easier than it is today. With tokens, trading won’t be limited to traditional business hours. Instead, investors will be able to trade 24/7. And token trades will settle instantly, allowing investors to deposit or withdraw funds from an investment without the overnight delay imposed by traditional stock exchanges.  An additional benefit: Tokens will allow investors to purchase fractional shares. To see how this would work, consider Microsoft. Today, its share price is around $370. Through the token system, though, an investor with a modest budget could gain exposure to Microsoft with just $5 or $10. There will also be index-based tokens, so an investor could gain exposure to the S&P 500, for example. In many ways, stock tokens are the equivalent of cryptocurrencies but for stocks, allowing investors to trade more quickly and easily. That’s their key appeal, and it’s part of the broader trend toward digitizing the financial system. Along the same lines, a number of retailers are pursuing so-called stablecoins as an alternative to costly credit card networks. Stock tokens do carry risk, though. You may recall an episode that occurred in 2022, when a digital currency called TerraUSD, which was designed to maintain a fixed value of $1, suddenly lost most of its value. In that case, there was a breakdown in the algorithm that was supposed to prevent Terra from dipping below $1, and that caused the equivalent of a run on the bank. Supporters of stock tokens will tell you that Terra’s failure can be attributed to its primitive structure and that today’s technology wouldn’t be similarly vulnerable. That may be true, but stock tokens carry other potential vulnerabilities. For starters, they’re complex and rely on a significant amount of financial engineering. Unlike a share of stock which is simply an ownership stake in a business, tokens are more of a synthetic financial instrument. That’s why the recent Journal write-up referred to them as “digital avatars.” When you buy a token, you aren’t buying an actual share of stock. It’s more like a chip issued by a casino or a gift card issued by a retailer. It looks like real money, and under ordinary circumstances, it probably will function like real money. But in times of stress, they may not perform as expected. The financial firm Robinhood, which has already created a family of stock tokens for international investors, acknowledges another risk: Because tokens don’t represent actual shares of stock, they carry what’s known as counterparty risk. Under the hood, tokens are actually financial contracts, which means that the party on the other side of a given contract needs to remain solvent in order for a token to maintain its value. On its website, Robinhood includes this disclosure: “Investors may lose up to the full amount of their invested capital due to market conditions or the insolvency of Robinhood.” To be sure, counterparty failure is usually a low risk, but it isn’t zero, and actual shares of stock don’t need disclaimers like this.  Even under ordinary circumstances, stock tokens’ prices likely won’t move in lockstep with actual share prices. That’s for a few reasons.  First, because tokens aren’t real shares, they don’t pay dividends. While that might not seem like a significant factor, dividends do add up. Over the past 15 years, they’ve accounted for about 20% of the total return of U.S. stocks. Also, stock tokens don’t carry the voting rights associated with real shares. That might also seem insignificant to everyday investors, but because it is important to larger, institutional investors, it means that tokens will probably always trade at a bit of a discount to real shares. A final risk is one that is longer term but much more serious: Stock tokens are built on blockchain technology, and that means they’re vulnerable to hacking. Of most concern is the fact that blockchain technologies rely on cryptography to secure investors’ holdings. While blockchain encryption has never been cracked, advances in computing power—and specifically, a technology known as quantum computing—could one day compromise a blockchain. Most experts believe this is 10 or more years away, but companies including Google and IBM are actively working on it, so it’s worth bearing in mind. The bottom line: In thinking about this new innovation, I’d lean on a concept known as Lindy’s law. This is a rule of thumb which postulates that the future life expectancy of an idea is proportional to its current age. In other words, the longer an idea has stood the test of time, the more likely it is to continue to stand the test of time in the future. That’s how I’d look at stock tokens. They might or might not be a good idea, but it’s too soon to tell. And since the benefits they offer are more in the category of convenience rather than investment performance, I see no particular need to own them. For that reason, it might make sense to wait and watch until any bugs are worked out.   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

NO. 64: AS WE GROW wealthier, we should seize the chance to save on insurance—by raising deductibles, lengthening elimination periods and perhaps dropping some policies entirely.

think

CONFLICTS of interest. It’s hard to get unbiased financial advice. Insurance agents collect bigger commissions if we buy cash-value instead of term life insurance. Brokers make more if we trade frequently and buy high-commission products. Advisors who charge a percent of assets earn more if we keep money in our portfolios, rather than paying down debt.

humans

NO. 60: WE TEND to ignore low-probability events. But low risk isn’t the same as no risk, so it’s crucial to weigh the potential financial impact. For instance, it’s unlikely we’ll suffer an illness or disability that prevents us from working. But if that happened, the financial consequences could be devastating, which is why disability insurance can be a smart buy.

act

FREEZE YOUR CREDIT—which you can now do at no cost. This will prevent data thieves from taking out loans and credit cards using your identity. But it also means you’ll need to contact the three credit bureaus and unfreeze your credit temporarily whenever applying for credit. Sound like a hassle? As an alternative, consider setting up a fraud alert.

Basics

Manifesto

NO. 64: AS WE GROW wealthier, we should seize the chance to save on insurance—by raising deductibles, lengthening elimination periods and perhaps dropping some policies entirely.

Spotlight: Life Events

What Would You Take?

In 2020, the Silverado fire broke out near our city. At the time, I couldn’t imagine that fire would threaten our home because it would have to burn a large part of our town to get to us. Surely, the firefighters would have it under control before there was mass destruction. Then, the Palisades and Eaton fires this year destroyed thousands of structures fueled by low humidity and strong winds. I now realize we might not have been as safe as I thought we were.

Read more »

Feeling Lucky

How much of our success is due to luck?
As HumbleDollar’s U.S. readers have occasionally noted, we’ve all been lucky in one crucial way: We live in 2024 in what’s arguably the most economically successful nation ever. That’s meant large swaths of the population have enjoyed financial success, even if they weren’t the best students, or the hardest workers, or the most talented employees.
But our luck doesn’t end there. Before we persuade ourselves that our success was solely due to our own talents and efforts,

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From Public Housing to Early Retirement: A Path Forged in Adversity

In my childhood, I grew up in public housing. From the age of 11, I attended what in the UK is the rough equivalent of a public high school. This was during a very volatile and violent phase of societal change in my country, set against a backdrop of illegal paramilitary organisations. They effectively “hoovered up” a high portion of my childhood friends, regurgitating them as dead bodies or incarcerated prisoners with no future. This was the reality of my childhood and formative years.

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Financial Trauma

SOMETIMES WORLD events beyond your control create a hard reset point in your financial life. A before and after. For me, that point was the 2007 Great Financial Crisis (GFC). The psychological scars still reverberate into my current life.
 
Looking back, I was aware of something rumbling about in the financial landscape but didn’t take much notice due to being deeply involved in running my business. Little did I realize the impact heading my way.

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Random Thoughts on the Passing Scene (With Apologies to Thomas Sowell)

-During a dinner a year or so ago with some of my recently-retired but still working friends, talk turned to what toys the fellas were buying with their “bonus” income. Most of the guys had big-ticket items to report: expensive new trucks, recreational vehicles, motorcycles…things like that. I didn’t have a lot to add to that conversation, but when I was pointedly asked what I’d bought for fun, the most extravagant item I could come up with was a new Trek bicycle that cost me a little under a thousand dollars—far more than I’d ever paid for a bike previously.

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Back to the Future

The first movie I ever saw in a theater was 2001: A Space Odyssey. My sister Carol took me to it when I was six years old. She wasn’t sure I’d like it, but I really loved it—except for a bit of primitive violence in the opening scene that was too intense for my young eyes (and stomach). In particular, the future technology depicted in the film fired my imagination. People in 2001 casually used video telephone calling and iPad-like tablet computers.

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Spotlight: Spears

A Man With a Plan

YOU COULD CALL ME a 529 superfan. The college savings plans helped me put my two kids through college. Their state and federal tax advantages cut the exorbitant cost of college just enough so we didn’t have to borrow for our two kids’ education. Which makes it surprising that I knew the man who created the 529 plan—but I didn’t realize he’d fathered them. I covered Senator Bob Graham of Florida as a newspaper reporter in Washington in the 1990s, but left the beat the year before he introduced his 529 legislation. I only learned of his role in 529s shortly before he died on April 16 at age 87 in a retirement community in Gainesville, Florida. As a senator, Graham was tan and affable, but he spoke hesitatingly, choosing his words with care. He was what my old political science professor would have called a workhorse, not a show horse. A Harvard-educated lawyer, Graham concerned himself more with details than speech-making, and he worked well in a divided legislature. A Democrat, Graham worked across the aisle with Senator Mitch McConnell of Kentucky, a Republican, to write and pass the rules around 529 plans. About a dozen states, including Florida, had created state college savings plans by then, but the rules were inconsistent and limiting. In Florida, for example, parents could buy a tuition credit for a newborn at a fixed price that would pay for one credit hour of classes 20 years later. That was quite a bargain given the inflation rate in education, but it only worked if your child attended a state university in Florida. If your child went to an out-of-state institution or to a private college in Florida, you got a refund of your money paid, not college credits. Graham realized we needed one college…
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Raising Dough

The best financial advice I know is “live on less than you earn and save the difference.” But what if there’s no daylight between what you earn and what you spend? Many of us confront this problem because of four scary expenses: housing, healthcare, student loans and child care. Take housing alone. By my calculations, it would take a six-figure income to buy a $435,300 home, which is the median cost of a U.S. home today according to the National Association of Realtors.* The median U.S. household comes up well short of this, with $78,171 in 2025. With challenges like these, it’s time to add a new chapter to the financial planning textbook—how to make more money. What would you include in a “make money” playbook? I’ll pitch my ideas, but it honestly feels like I’m stating the obvious. You may have better ideas from your life. Please add them in comments—I look forward to reading them. Here are my thoughts: If you’re still in school, know what your college major pays before you—or your child—graduates. You can look up the average first-year earnings of many majors at specific colleges here. It’s a goldmine of nuggets like this: At Purdue, graduates in biology earn $33,500 a year, on average, versus $69,200 for mechanical engineers. If you’re already in the workforce, continue your education by earning a professional designation or advanced degree. This makes you a trusted authority with your employer. Extra credit: Many employers, like mine, will pay the freight on a job-related degree. Job hop for a big pay bump. I wrote about this once during the pandemic, when job seekers had the upper hand in salary negotiations. That may not be true now, except in specialty fields like AI. Back then, one commenter said that changing employers seemed…
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Powerful Savings

I BOUGHT AN EXPENSIVE new water heater last year for my house in Maine. The old heater had a ring of rust at the bottom, and I was spurred to act by an $800 rebate offered by the state of Maine, which was contingent on buying a heat pump water heater. The new water heater draws its heat from the surrounding air, and is two-to-three times more efficient than my earlier model. I filled out a rebate form at the appliance store counter. Months later, I got a curt email from the state of Maine saying I didn’t qualify for money back because the model I’d purchased wasn’t Energy Star rated. By then, the heater had already been installed and I didn’t want to unwind the purchase. Lesson learned: Read the fine print. That’s good advice if you want a share of the billions in energy-efficiency tax credits contained in 2022’s Inflation Reduction Act. From now until year-end 2032, homeowners can get money back after installing energy-efficient heaters, windows, doors, air-conditioners, furnaces, water heaters and more. Although these energy-efficiency incentives could return $28 billion to taxpayers, according to an estimate from the University of Pennsylvania’s Wharton School, most taxpayers haven’t heard of them. In past years, you may have used similar tax credits to snag a deduction for new windows and doors. In many cases, the new law is an extension of previous schemes, but with more generous allowances. Some are for energy savings, like insulation, and others are for energy creation, like solar panels. There’s fine print you’ll need to understand to make sure you qualify, which I’ll cover in a minute. To whet your appetite, here are 10 credits that may cut your utility bills—and your taxes, too. 1. Insulation. The government will pay 30% of an insulation…
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Runs in the Family

MY 28-YEAR-OLD wanted to know how much to contribute to her retirement plan at work. As a father, this was a text that I loved to get. In May 2020, we toasted Genevieve over Zoom when she graduated with a master’s degree in social work. Within a week, she’d landed a job helping children in foster care and their families. Now, nearly a year later, she was invited to join the retirement savings plan at work, a 403(b) at her nonprofit agency. “How much is the match?” I asked her over the telephone. She texted someone in human resources. “There’s a 100% match on the first 3% and a 50% match on the next 2%,” she said. “Well,” I said, “if you save 5%, you can give yourself a nice, big raise.” She decided to go one better, signing up to save 6% of pay, or 10% when you include her employer’s matching contributions. She also contributes annually to a Roth IRA, so her total retirement savings is approaching 20%. She’s also putting away money for a house purchase. Where does Genevieve come by this saving discipline? We give credit to Charlotte, my late mother. Her well-to-do father—my grandfather—lost everything in the Great Depression. My mother could never shake the fear that the bottom could drop out unexpectedly. She watched her pennies and saved religiously—even during the Blitz in London, when she was with the Red Cross and managed to put some pounds aside. My mother opened a savings account for me when I was two months old. I still have the passbook with every deposit recorded. Similarly, when Genevieve was young, we made an event of opening her savings account. We chose a bank with a grand marble lobby where a kindly banker welcomed their littlest customer. My mother’s…
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The Lobster Pinch

WE BUY LOBSTERS from the backdoor of a fisherman who we know here in Maine. On Tuesday, my wife texted him to say she’d left $35 in cash for the four lobsters he’d set aside for us in a cooler. He texted back to say $25 was more than enough. In a year of spiking inflation, I have a morsel of good news. The wholesale price of lobster has crashed since March, down 45% according to the Federal Reserve Bank of St. Louis. Lobstermen might get $4 or less a pound for lobsters delivered to the dock, about half what they earned last year. My fisherman neighbor said he’d received $3.60 a pound this summer. The price drop has left the bay quiet, as lobstermen make fewer trips to haul traps. The catch price might not cover their costs—diesel fuel plus bait. The latter is a fish that's known locally as pogies. Lobster prices are down partly because fine dining is still off. Expense account restaurants must be doing less business with so many workers at home. In China—traditionally a big market for Maine lobsters—the economy is spluttering as whole cities get locked down to combat the spread of COVID. A white truck that used to rumble through town every afternoon to pick up lobsters for the city has rarely appeared this summer. A second reason for the crash in lobster prices is environmental concerns. Seafood Watch recently “red-listed” Maine lobster, saying the lines suspended between the colorful buoys on the surface and the traps on the sea floor are a danger to the few right whales left in the world. Big buyers like Cheesecake Factory, Blue Apron and HelloFresh stopped ordering lobster, as they follow the Monterey, California-based organization’s recommendations. Maine’s politicians and lobstermen are livid over the red-listing, insisting there…
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Running on Empty

THE GOVERNMENT will be able to pay full Social Security benefits only until 2033, according to the latest trustees’ report on the Social Security and Medicare trust funds. After that, Social Security's trust fund will be depleted—and it could only cover 76% of scheduled benefits with the money it collects in payroll taxes. The timetable is even worse for Medicare Part A, which pays for inpatient hospital care. Its trust fund will be empty in 2026. Thereafter, tax collections would cover 91% of projected expenses. The best financed benefit programs are Medicare Part B—which pays primarily for doctor visits—and Part D, which covers prescription drugs. How do they escape insolvency? Simple. If their premiums don’t fully cover their costs, both are backed up by the federal government’s general tax revenue. Which raises an interesting question: Why can’t Social Security and Medicare Part A get the same backup funding from general tax revenue? Currently, Social Security and Medicare Part A are financed by payroll tax collections—and it won’t be enough. For a generation, Americans have been debating how to keep these programs going. On offer has been a distasteful stew of solutions: Raising the eligibility age for benefits, reducing promised benefits, and increasing taxes on workers and their employers. No wonder we haven’t made any progress. The counterargument: It would be costly to cover these programs’ deficits using general tax revenue. The unfunded obligation for Social Security alone is estimated at $19.8 trillion through 2095, according to the trustees. The other counterpoint: Using general tax revenue would tip Social Security and Medicare into the category of welfare programs, because they’d no longer be self-funding. That said, these programs are arguably already backed up by general tax revenue. After all, the trust funds are invested in special-issue government bonds. When the trust…
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