FREE NEWSLETTER

You could carry a credit card balance—or you could toss dollar bills out the window. Same thing.

Latest PostsAll Discussions »

Taxes

2026 Charitable Deductions

"Rick, very helpful and concise information. Thank you. Need to earmark this for tax preparation time."
- Jeff
Read more »

In Retirement

Momentarily Embarrassed by “Not Much”

"Jeff, I think the main takeaway is simple: stay active, stay social, and keep your mind sharp. Retirement shouldn’t mean retiring from life... although, we definitely deserve longer coffee breaks 😉"
- Mark Crothers
Read more »

Investing

Financial Lessons

WHAT'S THE MOST important idea in personal finance? It’s hard to single out just one, but over the years, I’ve found the following dozen ideas to be among the most useful.
  1. Whether it’s on TV or online, there’s never any shortage of market prognosticators. Especially during a bull market, everyone seems to have an opinion on where things are headed. The reality, though, is that people can only guess about how the economy, the market or any individual investment will perform. Convincing as they might sound, no one has a crystal ball. That’s why, when it comes to investing, I suggest taking an evidence-based approach, one that relies as much as possible on data and research rather than on the simple stories, anecdotes and sayings that are so prevalent among market commentators.
  2. What does the data tell us? Among the most significant research in recent years is the work of Hendrik Bessembinder. In looking at the historical returns of stocks, he found that just a tiny fraction—only 4%—have accounted for the vast majority of the market’s gains over and above what Treasury bills paid, and the median stock actually delivered a negative return. This is one of the key reasons I recommend index funds rather than picking individual stocks or investing in an actively-managed fund. Identifying that 4% is almost impossibly difficult. But if you invest in a broad-based index fund, you’ll have a high likelihood of owning the next Apple or Nvidia.
  3. Be careful not to miss the forest for the trees. The most important driver of investment risk and return for most people, most of the time, is asset allocation. In other words, the dollars you have in stocks vs. in bonds or in cash will almost always be the most consequential decision. It’s easy to lose sight of that, though, because so much of the investment commentary from day to day focuses on details like small differences in fund expenses or small differences in bond yields. To be sure, details can be important, but only after considering the big picture.
  4. Another challenge in investing is that certain rules of thumb gain so much popularity that they end up being seen as rules rather than just guidelines. For example, some say that the percentage of a portfolio allocated to bonds should be equal to an investor’s age. To me, that’s illogical. Consider Bill Gates. He’s 70 years old, but it stands to reason that he shouldn’t have the same asset allocation as any other 70-year-old. Rules of thumb are useful as points of reference, but we shouldn’t lose sight of the fact that everyone’s situation is different, and our investments should reflect that. More to the point, don’t worry if you’re doing something different from the next person.
  5. Buy insurance, but only to protect against losses you couldn’t absorb on your own. What does this mean in practice? In many cases, it’s possible to significantly cut insurance premiums by increasing deductibles. For example, if you have a seven-figure net worth, you might consider raising the deductible on your homeowner’s insurance to $5,000 or $10,000 or even more. Similarly, you might re-evaluate your life insurance as your net worth grows. You’ll likely become “self-insured” at some point, and then you could reduce or drop that coverage.
  6. Personal finance is quantitative, but we should never make decisions based only on the numbers. For example, a common question is how much cash to keep on hand. While we could work out an optimal number on a calculator, that shouldn’t be the final answer. You should also consider what would provide you with peace of mind. That is equally important.
  7. Be wary of the psychological pitfall known as recency bias. This is the tendency to extrapolate from recent experience and to downplay the possibility that things might change. The most famous example? In the late-1920s, when the stock market was booming, Yale University economist Irving Fisher declared that the stock market had reached a “permanently high plateau.” Just nine days later, the market crashed, ultimately dropping 89% from its peak.
  8. Avoid high fees. The research firm Morningstar once wrote, “If there’s anything in the whole world of mutual funds that you can take to the bank, it’s that expense ratios help you make better decisions. In every single time period and data point tested, low-cost funds beat high-cost funds.”
  9. Keep things simple. Most importantly, I would be wary of investments that aren’t easily understood. Not only can this help keep investment costs down, but it also makes it much easier to monitor your financial picture. Legendary fund manager Peter Lynch said it best: “Never invest in any idea you can't illustrate with a crayon.”
  10. Avoid “interesting” investments. So far this year, Wall Street has introduced more than 1,000 new exchange-traded funds (ETFs). How many of these are worth your attention? My guess is you could probably count them on one hand. More than 80% of these new funds are actively-managed, and more than 30% employ leverage. And there are more to come. Fund companies recently filed paperwork to create ETFs that will track the performance of major league sports teams. They won’t actually own shares in the teams; instead, they’re expected to rise and fall in response to each team’s wins and losses.
  11. For years, I’ve argued that bitcoin isn’t a valid investment. Even though it’s gone way up since I first made that argument, I still feel the same way, and for the same reason: because it lacks intrinsic value. Unlike stocks or bonds, it doesn’t generate any dividends or interest. Bitcoin’s price is not anchored to anything measurable or tangible, and that’s why, in my opinion, its price is so volatile.
  12. When it comes to investment risk, investors’ attention usually turns to the stock market. That makes sense, but as we’ve seen this year, bonds are not without risk. And unfortunately, the total-bond market index, which is often seen as the simplest, set-it-and-forget-it option, is one that carries quite a bit of risk. If you’re choosing bond investments, my recommendation is to pay attention to a metric known as duration. This tells you how sensitive a bond, or bond fund, will be to interest rate changes. In my view, investors should hold a sizable portion of their bond investments in a fund, or in individual bonds, with a duration of less than two years.
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 »

From HumbleDollar Founder Jonathan Clements

Investing

Behaving Badly

OTHERS MIGHT BE hoping to add to their wealth by picking the next hot stock. But here at HumbleDollar, we’re much more concerned about…
Read more »

Abuse

How do I scam thee? Let me count the ways

"It’s painfully fitting for Dan’s thread, but the last three comments here are all recovery scams. Whether they are promoting Telegram handles (Rebecca), fake reporting boards (Susan), or sneaky embedded websites like spirassp.com inside a list of warning signs (Micazuniga), they are all spambots trying to pull off advance-fee scams on previous victims. Dan’s polite reply to Micazuniga months ago just goes to show how clever these bots have become at blending in before slipping in their trap."
- Mark Crothers
Read more »

Update: Jonathan’s Getting Going on Saving Initative

"Thanks for the update, Elaine, it is great news. 👍"
- Chris (baldscreen)
Read more »

In Retirement

Strategic Retirement Income

"I see what you're saying and agree with you."
- Dan Smith
Read more »

Family

Room For Happiness

"William, thank you for commenting. Visiting every state, so many national parks and Europe: you’ve given yourselves wonderful memories to return to. I’m sorry cancer has been part of your journey, and appreciate your gratitude for the life you’re still enjoying. Your experience gives real weight to that woman’s advice in Naples. Thank you for sharing it, and I hope those trips closer to home continue to bring you pleasure."
- Andrew Clements
Read more »

Investing

Rich or Wealthy?

"“Not perfect, and no doubt someone will point out reasons why it isn’t, but it’s a reasonable ballpark.” 🙂"
- Michael1
Read more »

Happiness

The Number Is Not The Answer

YEARS AGO, while practicing law, I was a frequent contributor to Humble Dollar. I loved Jonathan Clements’s vision for the site - a corner of the financial universe built on clarity, frugality, and the quiet dignity of living within one’s means. Then my life took a sharp pivot. I left legal practice to teach gifted-and-talented students and coach varsity athletics at a public magnet high school. Almost immediately, my submissions here dried up. I was consuming entire days guiding brilliant teenagers through complex history, breaking down match film, and grading papers long past sunset and on weekends. I wrote to Jonathan with genuine regret, apologizing for going dark on such a wonderful enterprise. His reply was quintessential Jonathan: he explained to me with characteristic, succinct warmth that his own adult child was a teacher, adding that he wasn’t sure there was a higher calling on Earth. He was right about the calling. But what nobody warns you about a calling is its capacity to consume you whole if you let it. The Cliff Edge This past year, the math simply broke. Between high-load AP teaching, head coaching, and the relentless calendar of high school athletics, I was regularly clocking 17- to 18-hour days during soccer season. My central nervous system finally redlined badly. Worse, I realized with a gut punch that I had missed nearly the entire senior year of my oldest son while running on that treadmill. This realization hit me at his graduation when I felt physically exhausted and unable to enjoy what should have been one of the proudest moments of my life. I was determined to make it up to him in whatever way I could (for example, we are visiting him today at college, and we go often to see him in San Antonio - a 90-minute drive from Austin). Moreover, I will not repeat this mistake and will enjoy the years I have left with my two high-school-aged daughters. With teenagers preparing to leave the nest and a close family member facing severe illness, I stepped away. I took a sabbatical. Maybe it will delay our retirement slightly, but as I will express further below, I am not sure I will ever really retire. The Void Financial planners love to reduce retirement to a single milestone: "The Number." The spreadsheets run 10,000 Monte Carlo simulations, the house is paid off, the withdrawal rates are dialed in, and the industry assures you: You have arrived. You are safe. At 45, I had not retired in the traditional sense, but I had stepped off the cliff of full-time professional identity because my body told me I needed to. And what I discovered in the sudden, unanticipated quiet is something many retirees spend years agonizing over without having the vocabulary to describe: The number is not the answer. When you abruptly remove the machinery of a demanding daily routine, you don't instantly find nirvana. You find a void. In a recent discussion on non-financial retirement readiness, former financial adviser Tyler Gardner framed this dilemma in his video on non-financial retirement needs around Self-Determination Theory, pioneered by psychologists Edward Deci and Richard Ryan. Deci and Ryan posited that human well-being rests on three basic psychological nutrients: competence, relatedness, and autonomy. For all its stress and bureaucratic friction, a demanding career supplies all three automatically. When you walk away from work, those three nutrients can vanish before your celebratory cake is even eaten. If you don't deliberately rebuild them, the fallout can be physiological. The Trap of "Mental Retirement" In aging literature, researchers study a sobering phenomenon bluntly termed "mental retirement" - the cognitive softening that occurs when a person ceases to be intellectually stretched. A decade-long study from Binghamton University examining China’s rural pension expansion revealed that early retirement significantly accelerated cognitive decline. Crucially, the researchers noted that the negative impact of reduced social and mental engagement outweighed the physical benefits of improved nutrition and sleep that the pension provided. Work forced us to solve problems under pressure. Sabbaticals and retirements do not. To counteract that loss, I had to create self-imposed challenges. During my grueling years in the classroom, exercise was the first thing pushed off the ledge. On leave, I reclaimed the time. I started chasing benchmarks for physical competence. Recently, I set out to regain a grueling standard: 10 continuous minutes on the Jacob’s Ladder. It was a benchmark an elite special operator had given me when I served as an Army JAG supporting special operations in Afghanistan in my late twenties. My first time back on the ladder? I barely completed one minute and staggered off it trembling and nauseous. But every week, I kept working at it - sometimes adding a few seconds and other times several minutes until I got to 10 minutes again this week. Crossing that threshold didn't merely burn calories; it restored a measurable gradient of physical competence and, with it, confidence. Whether it is conquering a brutal conditioning standard, learning a language, or mastering an instrument, we need something where we can objectively say: I am better at this today than I was last month. I will now find a new physical benchmark to pursue, while coming back occasionally to that masochistic Jacob's Ladder. The 40 Invisible People The second nutrient, relatedness, is where most folks get ambushed. When people contemplate retirement, they assume their social health depends on their spouse or a handful of close friends. But work provides something entirely different: a vast scaffolding of "weak ties." In a landmark 2014 study published in Social Psychological and Personality Science, researchers Gillian Sandstrom and Elizabeth Dunn found that daily subjective happiness and feelings of belonging rose noticeably on days when people had more peripheral interactions - even something as fleeting as a 20-second genuine exchange with a coffee barista. Broader public health research reinforces this with astonishing gravity. A massive meta-analysis led by Julianne Holt-Lunstad spanning over 300,000 individuals found that strong social integration increased survival likelihood by 50%. Remarkably, the mortality benefit was strongest for complex, varied social networks (the diverse web of people you bump into) rather than simple binary measures like living with someone. When I taught, I had hundreds of involuntary interactions before lunch: hallway greetings, banter with the front desk, coaching video sessions, cafeteria check-ins. On my sabbatical, I plunged into writing a historical thriller called The Blood Money Ledger set during the Vietnam War - a passion project rooted in my love of history and informed by my own military service. I was thrilled to find that the fiction flowed with unexpected ease. In fact, I am now leaning toward turning my main character, Tom Calder, into a series of books about morality, the law, and institutional rot. But writing is, by definition, solitary confinement. Left entirely unmanaged, isolation is insidious. To survive it, I had to engineer artificial friction:
  • I go to the gym at the exact same hour every day to see the familiar faces of regulars.
  • Once a week, a close friend and I meet at a local coffee shop; he reads while I hammer out words for the book. It’s quiet, parallel work, but the ambient presence makes the solitary act of writing sustainable.
  • I signed up for an evening furniture-making class to work with my hands alongside people I wouldn't otherwise meet - a skill I am going to start out terrible at and eventually become... less terrible at.
  • I took on a volunteer docent shift at the Austin History Center, trading archival stories with curious strangers.
None of these people are lifelong confidants - except my close friend who joins me for coffee. But together, they rebuild the 40 casual touchpoints work used to gift me for free. Anticipation Over Accumulation The final hazard is structural: time without seams. When we dream of retirement, we picture unstructured calendars and checking off items on an expansive bucket list. But behavioral psychology shows we often misunderstand how human satisfaction works. In a well-known 2010 study by Dutch researcher Jeroen Nawijn tracking over 1,500 adults, vacationers exhibited significantly higher happiness before their trips than non-vacationers. The post-trip happiness bump, however, was negligible and evaporated rapidly. Even though I haven't written for Humble Dollar much in the past several years, I have been a frequent lurker, and know that this is a topic we all understand well. The engine of joy is almost entirely anticipation, not completion. A bucket list should never be treated like a grocery list where the goal is an empty page. If you clear out your list with no new ambitions behind it, life goes flat. The real art is maintaining a continuous horizon of things you are eagerly anticipating: an upcoming course, a seasonal trip, an archival project, or a fresh manuscript draft. We are in the midst of using high school and college graduation presents as family adventures we take. For my son's graduation gift - he loves soccer - I took him and his soccer-obsessed sister to the World Cup. My other daughter, who is very much not soccer-obsessed, and my wife visited a spa together for significantly less money. Win-win. The Real Ledger The Monday morning after your final Friday, your spreadsheet will not ask how you are doing, provide an intellectual hill to climb, or hand you an unexpected laugh across a desk. The number is just the admission ticket that we too often obsess over. The actual show begins when you decide what will make your days count.  John Goodell was a deputy director of policy and general counsel at the Texas Pension Review Board. Currently an Army Reservist, he previously served 14 years on active duty before leaving to become the general counsel at the Texas Veterans Commission. John has spent much of his career working with public sector employees on tax, investment, estate planning and retirement issues. His biggest passion is spending time with his wife and kids. Check out John's earlier articles.
Read more »

Saving

FINANCIAL MISTAKES

"My 2 greatest impacts, were my Father who bought and sold a few stocks to increase his wealth, we were very middle class. He always sent me for the newspaper, Red Streak with Final Markets for the day, 1950's. The next big impact was in Engineering School at IIT in Chicago, took a course called Engineering Economy by Grant Ireson. This course taught me a lot, present value of money, compounding, time value of money, rate-of-return analysis, depreciation, and cash-flow comparisons. This turned on the lights for me, and then later in life Bogle, Peter Lynch and Warren Buffett. At 80 I am following Buffett overall, with 85% stocks in the S&P and 15% cash. If I live to 100, I do not want inflation to take away what I have, Dad died at 101."
- William Dorner
Read more »

Investing

Market Risks

YOU MAY BE familiar with a concept known as Pascal’s wager. Named for Blaise Pascal, a devout seventeenth-century French mathematician, it was a thought experiment in which he tried to weigh, in logical terms, the costs and benefits of believing in God. His conclusion: The cost of not believing—a potential eternity of damnation—was so extreme that it far outweighed any other consideration. I mention Pascal’s wager because a common question is whether similar logic might apply to financial decision-making. While not perfectly analogous, I do think the central premise of Pascal’s wager is useful—that we should be attuned to situations where the relative outcomes may be lopsided. Consider the stock market, where two types of risk are, in my opinion, often underappreciated. The first of these risks is, counterintuitively, that market history can be unhelpful and misleading. Look back at the U.S. stock market over the past 100 years, and you’ll find that its average annual return has been right around 10%, thus doubling about every seven years. Through that lens, the stock market has been a powerful and reliable way to build wealth. The problem, though, is that this 10% figure is a long-term average return. Look at the market’s actual returns from year to year, and they’re anything but average. Some years are better than average, but some are much worse. As I noted last week, there have been a handful of years in which a worker entering retirement would have faced severe headwinds. These include 1929, of course, as well as 1969 and 2000. Most other years wouldn’t have posed as much of a challenge. But since there’s no way to know which sequence of returns any of us will encounter in our own retirements, we can’t rely on the market’s long-term average. In fact, we almost need to ignore that number and instead insulate our portfolios against those worst case scenarios. Long-term averages, unfortunately, don’t apply to any one individual. That’s the risk in looking at market history. The market’s current conditions can be equally misleading. That’s because, when the market is strong, as it is today, investors tend to draw one of two equally problematic conclusions. Some look at recent performance and conclude that it’s likely to continue. This is known as recency bias, but it’s a way of thinking that’s entirely understandable. After all, it’s totally rational to expect and assume that tomorrow won’t look dramatically different from today, because most of the time that’s the way things turn out. But from time to time, things do really change. Because those changes are the exception rather than the norm, though, and because they often arrive without warning, recency bias continues to be a powerful force that can lull investors into a false sense of security. Other investors look at a highflying market and draw an entirely different conclusion. They focus on metrics like the market’s price-to-earnings ratio (P/E)—which is undeniably elevated—and conclude that the market is skating on thin ice and thus likely to drop.  That seems rational. The problem with this conclusion, though, is that valuation tools like the P/E ratio aren’t perfectly predictive; they only look predictive. This has been known for a long time, but this week, a new paper by researcher Cullen Roche provided additional perspective to support this point. The paper is titled, “Valuations Matter. Just Not the Way Wall Street Says.” The central premise: The market’s P/E ratio has almost zero predictive power in the near term. Statistically, it tells us virtually nothing about returns over the coming 12-month period. When are valuation metrics helpful? In Roche’s research, he finds that metrics like the P/E are only roughly indicative of future returns and only over a 10-year period.  The bottom line: Whether one is an optimist or a pessimist, the data tell us that we should be careful to avoid bets that go too far out on a limb in any one direction. That presents a problem, though: If we shouldn’t look at market history and shouldn’t put too much stock in where the market is today, then how should we think about our finances? Here are three suggestions: 
  1. Set an asset allocation target for your portfolio and then manage to that target. In general, the result will be that you’ll sell stocks when they’re high and buy when they’re low, which is exactly the right result. And by taking this approach, you’ll avoid the generally unhelpful advice of market commentators claiming to be able to read the economic tea leaves.
  2. Put most of your focus on your own financial plan. I suggest tracking what I call the big four: your income and expenses, assets and liabilities. If you can get these numbers on one sheet of paper and track them over time, I see that as maybe the most productive financial exercise.
  3. Avoid “exciting” investments. It would be easy to look at a company like Nvidia, which has seen its stock gain 14,000% over the past 10 years, and feel motivated to search for the next market leader. Intuitively, we know this is harder than it looks, and the data confirm that stock-picking is extraordinarily difficult. But according to some studies, it’s even harder than that. Research by Hendrik Bessembinder has found that the median lifetime return of all of the stocks that have traded on U.S. exchanges historically is actually negative. Just 4% of all stocks have accounted for all of the market’s returns in excess of Treasury bills.
As Pascal might have suggested, look for ways to tilt the odds in your favor even when the future is, ultimately, unknowable. 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 »

Taxes

2026 Charitable Deductions

"Rick, very helpful and concise information. Thank you. Need to earmark this for tax preparation time."
- Jeff
Read more »

In Retirement

Momentarily Embarrassed by “Not Much”

"Jeff, I think the main takeaway is simple: stay active, stay social, and keep your mind sharp. Retirement shouldn’t mean retiring from life... although, we definitely deserve longer coffee breaks 😉"
- Mark Crothers
Read more »

Investing

Financial Lessons

WHAT'S THE MOST important idea in personal finance? It’s hard to single out just one, but over the years, I’ve found the following dozen ideas to be among the most useful.
  1. Whether it’s on TV or online, there’s never any shortage of market prognosticators. Especially during a bull market, everyone seems to have an opinion on where things are headed. The reality, though, is that people can only guess about how the economy, the market or any individual investment will perform. Convincing as they might sound, no one has a crystal ball. That’s why, when it comes to investing, I suggest taking an evidence-based approach, one that relies as much as possible on data and research rather than on the simple stories, anecdotes and sayings that are so prevalent among market commentators.
  2. What does the data tell us? Among the most significant research in recent years is the work of Hendrik Bessembinder. In looking at the historical returns of stocks, he found that just a tiny fraction—only 4%—have accounted for the vast majority of the market’s gains over and above what Treasury bills paid, and the median stock actually delivered a negative return. This is one of the key reasons I recommend index funds rather than picking individual stocks or investing in an actively-managed fund. Identifying that 4% is almost impossibly difficult. But if you invest in a broad-based index fund, you’ll have a high likelihood of owning the next Apple or Nvidia.
  3. Be careful not to miss the forest for the trees. The most important driver of investment risk and return for most people, most of the time, is asset allocation. In other words, the dollars you have in stocks vs. in bonds or in cash will almost always be the most consequential decision. It’s easy to lose sight of that, though, because so much of the investment commentary from day to day focuses on details like small differences in fund expenses or small differences in bond yields. To be sure, details can be important, but only after considering the big picture.
  4. Another challenge in investing is that certain rules of thumb gain so much popularity that they end up being seen as rules rather than just guidelines. For example, some say that the percentage of a portfolio allocated to bonds should be equal to an investor’s age. To me, that’s illogical. Consider Bill Gates. He’s 70 years old, but it stands to reason that he shouldn’t have the same asset allocation as any other 70-year-old. Rules of thumb are useful as points of reference, but we shouldn’t lose sight of the fact that everyone’s situation is different, and our investments should reflect that. More to the point, don’t worry if you’re doing something different from the next person.
  5. Buy insurance, but only to protect against losses you couldn’t absorb on your own. What does this mean in practice? In many cases, it’s possible to significantly cut insurance premiums by increasing deductibles. For example, if you have a seven-figure net worth, you might consider raising the deductible on your homeowner’s insurance to $5,000 or $10,000 or even more. Similarly, you might re-evaluate your life insurance as your net worth grows. You’ll likely become “self-insured” at some point, and then you could reduce or drop that coverage.
  6. Personal finance is quantitative, but we should never make decisions based only on the numbers. For example, a common question is how much cash to keep on hand. While we could work out an optimal number on a calculator, that shouldn’t be the final answer. You should also consider what would provide you with peace of mind. That is equally important.
  7. Be wary of the psychological pitfall known as recency bias. This is the tendency to extrapolate from recent experience and to downplay the possibility that things might change. The most famous example? In the late-1920s, when the stock market was booming, Yale University economist Irving Fisher declared that the stock market had reached a “permanently high plateau.” Just nine days later, the market crashed, ultimately dropping 89% from its peak.
  8. Avoid high fees. The research firm Morningstar once wrote, “If there’s anything in the whole world of mutual funds that you can take to the bank, it’s that expense ratios help you make better decisions. In every single time period and data point tested, low-cost funds beat high-cost funds.”
  9. Keep things simple. Most importantly, I would be wary of investments that aren’t easily understood. Not only can this help keep investment costs down, but it also makes it much easier to monitor your financial picture. Legendary fund manager Peter Lynch said it best: “Never invest in any idea you can't illustrate with a crayon.”
  10. Avoid “interesting” investments. So far this year, Wall Street has introduced more than 1,000 new exchange-traded funds (ETFs). How many of these are worth your attention? My guess is you could probably count them on one hand. More than 80% of these new funds are actively-managed, and more than 30% employ leverage. And there are more to come. Fund companies recently filed paperwork to create ETFs that will track the performance of major league sports teams. They won’t actually own shares in the teams; instead, they’re expected to rise and fall in response to each team’s wins and losses.
  11. For years, I’ve argued that bitcoin isn’t a valid investment. Even though it’s gone way up since I first made that argument, I still feel the same way, and for the same reason: because it lacks intrinsic value. Unlike stocks or bonds, it doesn’t generate any dividends or interest. Bitcoin’s price is not anchored to anything measurable or tangible, and that’s why, in my opinion, its price is so volatile.
  12. When it comes to investment risk, investors’ attention usually turns to the stock market. That makes sense, but as we’ve seen this year, bonds are not without risk. And unfortunately, the total-bond market index, which is often seen as the simplest, set-it-and-forget-it option, is one that carries quite a bit of risk. If you’re choosing bond investments, my recommendation is to pay attention to a metric known as duration. This tells you how sensitive a bond, or bond fund, will be to interest rate changes. In my view, investors should hold a sizable portion of their bond investments in a fund, or in individual bonds, with a duration of less than two years.
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 »

From HumbleDollar Founder Jonathan Clements

Investing

Behaving Badly

OTHERS MIGHT BE hoping to add to their wealth by picking the next hot stock. But here at HumbleDollar, we’re much more concerned about…
Read more »

Abuse

How do I scam thee? Let me count the ways

"It’s painfully fitting for Dan’s thread, but the last three comments here are all recovery scams. Whether they are promoting Telegram handles (Rebecca), fake reporting boards (Susan), or sneaky embedded websites like spirassp.com inside a list of warning signs (Micazuniga), they are all spambots trying to pull off advance-fee scams on previous victims. Dan’s polite reply to Micazuniga months ago just goes to show how clever these bots have become at blending in before slipping in their trap."
- Mark Crothers
Read more »

Update: Jonathan’s Getting Going on Saving Initative

"Thanks for the update, Elaine, it is great news. 👍"
- Chris (baldscreen)
Read more »

In Retirement

Strategic Retirement Income

"I see what you're saying and agree with you."
- Dan Smith
Read more »

Family

Room For Happiness

"William, thank you for commenting. Visiting every state, so many national parks and Europe: you’ve given yourselves wonderful memories to return to. I’m sorry cancer has been part of your journey, and appreciate your gratitude for the life you’re still enjoying. Your experience gives real weight to that woman’s advice in Naples. Thank you for sharing it, and I hope those trips closer to home continue to bring you pleasure."
- Andrew Clements
Read more »

Happiness

The Number Is Not The Answer

YEARS AGO, while practicing law, I was a frequent contributor to Humble Dollar. I loved Jonathan Clements’s vision for the site - a corner of the financial universe built on clarity, frugality, and the quiet dignity of living within one’s means. Then my life took a sharp pivot. I left legal practice to teach gifted-and-talented students and coach varsity athletics at a public magnet high school. Almost immediately, my submissions here dried up. I was consuming entire days guiding brilliant teenagers through complex history, breaking down match film, and grading papers long past sunset and on weekends. I wrote to Jonathan with genuine regret, apologizing for going dark on such a wonderful enterprise. His reply was quintessential Jonathan: he explained to me with characteristic, succinct warmth that his own adult child was a teacher, adding that he wasn’t sure there was a higher calling on Earth. He was right about the calling. But what nobody warns you about a calling is its capacity to consume you whole if you let it. The Cliff Edge This past year, the math simply broke. Between high-load AP teaching, head coaching, and the relentless calendar of high school athletics, I was regularly clocking 17- to 18-hour days during soccer season. My central nervous system finally redlined badly. Worse, I realized with a gut punch that I had missed nearly the entire senior year of my oldest son while running on that treadmill. This realization hit me at his graduation when I felt physically exhausted and unable to enjoy what should have been one of the proudest moments of my life. I was determined to make it up to him in whatever way I could (for example, we are visiting him today at college, and we go often to see him in San Antonio - a 90-minute drive from Austin). Moreover, I will not repeat this mistake and will enjoy the years I have left with my two high-school-aged daughters. With teenagers preparing to leave the nest and a close family member facing severe illness, I stepped away. I took a sabbatical. Maybe it will delay our retirement slightly, but as I will express further below, I am not sure I will ever really retire. The Void Financial planners love to reduce retirement to a single milestone: "The Number." The spreadsheets run 10,000 Monte Carlo simulations, the house is paid off, the withdrawal rates are dialed in, and the industry assures you: You have arrived. You are safe. At 45, I had not retired in the traditional sense, but I had stepped off the cliff of full-time professional identity because my body told me I needed to. And what I discovered in the sudden, unanticipated quiet is something many retirees spend years agonizing over without having the vocabulary to describe: The number is not the answer. When you abruptly remove the machinery of a demanding daily routine, you don't instantly find nirvana. You find a void. In a recent discussion on non-financial retirement readiness, former financial adviser Tyler Gardner framed this dilemma in his video on non-financial retirement needs around Self-Determination Theory, pioneered by psychologists Edward Deci and Richard Ryan. Deci and Ryan posited that human well-being rests on three basic psychological nutrients: competence, relatedness, and autonomy. For all its stress and bureaucratic friction, a demanding career supplies all three automatically. When you walk away from work, those three nutrients can vanish before your celebratory cake is even eaten. If you don't deliberately rebuild them, the fallout can be physiological. The Trap of "Mental Retirement" In aging literature, researchers study a sobering phenomenon bluntly termed "mental retirement" - the cognitive softening that occurs when a person ceases to be intellectually stretched. A decade-long study from Binghamton University examining China’s rural pension expansion revealed that early retirement significantly accelerated cognitive decline. Crucially, the researchers noted that the negative impact of reduced social and mental engagement outweighed the physical benefits of improved nutrition and sleep that the pension provided. Work forced us to solve problems under pressure. Sabbaticals and retirements do not. To counteract that loss, I had to create self-imposed challenges. During my grueling years in the classroom, exercise was the first thing pushed off the ledge. On leave, I reclaimed the time. I started chasing benchmarks for physical competence. Recently, I set out to regain a grueling standard: 10 continuous minutes on the Jacob’s Ladder. It was a benchmark an elite special operator had given me when I served as an Army JAG supporting special operations in Afghanistan in my late twenties. My first time back on the ladder? I barely completed one minute and staggered off it trembling and nauseous. But every week, I kept working at it - sometimes adding a few seconds and other times several minutes until I got to 10 minutes again this week. Crossing that threshold didn't merely burn calories; it restored a measurable gradient of physical competence and, with it, confidence. Whether it is conquering a brutal conditioning standard, learning a language, or mastering an instrument, we need something where we can objectively say: I am better at this today than I was last month. I will now find a new physical benchmark to pursue, while coming back occasionally to that masochistic Jacob's Ladder. The 40 Invisible People The second nutrient, relatedness, is where most folks get ambushed. When people contemplate retirement, they assume their social health depends on their spouse or a handful of close friends. But work provides something entirely different: a vast scaffolding of "weak ties." In a landmark 2014 study published in Social Psychological and Personality Science, researchers Gillian Sandstrom and Elizabeth Dunn found that daily subjective happiness and feelings of belonging rose noticeably on days when people had more peripheral interactions - even something as fleeting as a 20-second genuine exchange with a coffee barista. Broader public health research reinforces this with astonishing gravity. A massive meta-analysis led by Julianne Holt-Lunstad spanning over 300,000 individuals found that strong social integration increased survival likelihood by 50%. Remarkably, the mortality benefit was strongest for complex, varied social networks (the diverse web of people you bump into) rather than simple binary measures like living with someone. When I taught, I had hundreds of involuntary interactions before lunch: hallway greetings, banter with the front desk, coaching video sessions, cafeteria check-ins. On my sabbatical, I plunged into writing a historical thriller called The Blood Money Ledger set during the Vietnam War - a passion project rooted in my love of history and informed by my own military service. I was thrilled to find that the fiction flowed with unexpected ease. In fact, I am now leaning toward turning my main character, Tom Calder, into a series of books about morality, the law, and institutional rot. But writing is, by definition, solitary confinement. Left entirely unmanaged, isolation is insidious. To survive it, I had to engineer artificial friction:
  • I go to the gym at the exact same hour every day to see the familiar faces of regulars.
  • Once a week, a close friend and I meet at a local coffee shop; he reads while I hammer out words for the book. It’s quiet, parallel work, but the ambient presence makes the solitary act of writing sustainable.
  • I signed up for an evening furniture-making class to work with my hands alongside people I wouldn't otherwise meet - a skill I am going to start out terrible at and eventually become... less terrible at.
  • I took on a volunteer docent shift at the Austin History Center, trading archival stories with curious strangers.
None of these people are lifelong confidants - except my close friend who joins me for coffee. But together, they rebuild the 40 casual touchpoints work used to gift me for free. Anticipation Over Accumulation The final hazard is structural: time without seams. When we dream of retirement, we picture unstructured calendars and checking off items on an expansive bucket list. But behavioral psychology shows we often misunderstand how human satisfaction works. In a well-known 2010 study by Dutch researcher Jeroen Nawijn tracking over 1,500 adults, vacationers exhibited significantly higher happiness before their trips than non-vacationers. The post-trip happiness bump, however, was negligible and evaporated rapidly. Even though I haven't written for Humble Dollar much in the past several years, I have been a frequent lurker, and know that this is a topic we all understand well. The engine of joy is almost entirely anticipation, not completion. A bucket list should never be treated like a grocery list where the goal is an empty page. If you clear out your list with no new ambitions behind it, life goes flat. The real art is maintaining a continuous horizon of things you are eagerly anticipating: an upcoming course, a seasonal trip, an archival project, or a fresh manuscript draft. We are in the midst of using high school and college graduation presents as family adventures we take. For my son's graduation gift - he loves soccer - I took him and his soccer-obsessed sister to the World Cup. My other daughter, who is very much not soccer-obsessed, and my wife visited a spa together for significantly less money. Win-win. The Real Ledger The Monday morning after your final Friday, your spreadsheet will not ask how you are doing, provide an intellectual hill to climb, or hand you an unexpected laugh across a desk. The number is just the admission ticket that we too often obsess over. The actual show begins when you decide what will make your days count.  John Goodell was a deputy director of policy and general counsel at the Texas Pension Review Board. Currently an Army Reservist, he previously served 14 years on active duty before leaving to become the general counsel at the Texas Veterans Commission. John has spent much of his career working with public sector employees on tax, investment, estate planning and retirement issues. His biggest passion is spending time with his wife and kids. Check out John's earlier articles.
Read more »

Investing

Market Risks

YOU MAY BE familiar with a concept known as Pascal’s wager. Named for Blaise Pascal, a devout seventeenth-century French mathematician, it was a thought experiment in which he tried to weigh, in logical terms, the costs and benefits of believing in God. His conclusion: The cost of not believing—a potential eternity of damnation—was so extreme that it far outweighed any other consideration. I mention Pascal’s wager because a common question is whether similar logic might apply to financial decision-making. While not perfectly analogous, I do think the central premise of Pascal’s wager is useful—that we should be attuned to situations where the relative outcomes may be lopsided. Consider the stock market, where two types of risk are, in my opinion, often underappreciated. The first of these risks is, counterintuitively, that market history can be unhelpful and misleading. Look back at the U.S. stock market over the past 100 years, and you’ll find that its average annual return has been right around 10%, thus doubling about every seven years. Through that lens, the stock market has been a powerful and reliable way to build wealth. The problem, though, is that this 10% figure is a long-term average return. Look at the market’s actual returns from year to year, and they’re anything but average. Some years are better than average, but some are much worse. As I noted last week, there have been a handful of years in which a worker entering retirement would have faced severe headwinds. These include 1929, of course, as well as 1969 and 2000. Most other years wouldn’t have posed as much of a challenge. But since there’s no way to know which sequence of returns any of us will encounter in our own retirements, we can’t rely on the market’s long-term average. In fact, we almost need to ignore that number and instead insulate our portfolios against those worst case scenarios. Long-term averages, unfortunately, don’t apply to any one individual. That’s the risk in looking at market history. The market’s current conditions can be equally misleading. That’s because, when the market is strong, as it is today, investors tend to draw one of two equally problematic conclusions. Some look at recent performance and conclude that it’s likely to continue. This is known as recency bias, but it’s a way of thinking that’s entirely understandable. After all, it’s totally rational to expect and assume that tomorrow won’t look dramatically different from today, because most of the time that’s the way things turn out. But from time to time, things do really change. Because those changes are the exception rather than the norm, though, and because they often arrive without warning, recency bias continues to be a powerful force that can lull investors into a false sense of security. Other investors look at a highflying market and draw an entirely different conclusion. They focus on metrics like the market’s price-to-earnings ratio (P/E)—which is undeniably elevated—and conclude that the market is skating on thin ice and thus likely to drop.  That seems rational. The problem with this conclusion, though, is that valuation tools like the P/E ratio aren’t perfectly predictive; they only look predictive. This has been known for a long time, but this week, a new paper by researcher Cullen Roche provided additional perspective to support this point. The paper is titled, “Valuations Matter. Just Not the Way Wall Street Says.” The central premise: The market’s P/E ratio has almost zero predictive power in the near term. Statistically, it tells us virtually nothing about returns over the coming 12-month period. When are valuation metrics helpful? In Roche’s research, he finds that metrics like the P/E are only roughly indicative of future returns and only over a 10-year period.  The bottom line: Whether one is an optimist or a pessimist, the data tell us that we should be careful to avoid bets that go too far out on a limb in any one direction. That presents a problem, though: If we shouldn’t look at market history and shouldn’t put too much stock in where the market is today, then how should we think about our finances? Here are three suggestions: 
  1. Set an asset allocation target for your portfolio and then manage to that target. In general, the result will be that you’ll sell stocks when they’re high and buy when they’re low, which is exactly the right result. And by taking this approach, you’ll avoid the generally unhelpful advice of market commentators claiming to be able to read the economic tea leaves.
  2. Put most of your focus on your own financial plan. I suggest tracking what I call the big four: your income and expenses, assets and liabilities. If you can get these numbers on one sheet of paper and track them over time, I see that as maybe the most productive financial exercise.
  3. Avoid “exciting” investments. It would be easy to look at a company like Nvidia, which has seen its stock gain 14,000% over the past 10 years, and feel motivated to search for the next market leader. Intuitively, we know this is harder than it looks, and the data confirm that stock-picking is extraordinarily difficult. But according to some studies, it’s even harder than that. Research by Hendrik Bessembinder has found that the median lifetime return of all of the stocks that have traded on U.S. exchanges historically is actually negative. Just 4% of all stocks have accounted for all of the market’s returns in excess of Treasury bills.
As Pascal might have suggested, look for ways to tilt the odds in your favor even when the future is, ultimately, unknowable. 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 »

Free Newsletter

Get Educated

Manifesto

NO. 6: OUR FINANCIAL life involves endless tradeoffs. We usually have a good idea of what our dollars are buying us. But to be good stewards of our wealth, we should also ponder what we’re giving up.

humans

NO. 46: DIVERSIFICATION has been described as Wall Street’s only free lunch—but some folks take the notion too far. They’ll spread their money across multiple financial advisors, multiple funds that invest in the same market sector and far too many financial firms. The result can be high investment costs and an overly complicated financial life.

think

MARSHMALLOW TEST. Researchers found that children’s ability to delay gratification at ages four to six—as reflected in their ability to resist a treat in return for a larger treat later—was predictive of future success. But later studies questioned the results. That doesn’t mean delaying gratification isn’t an important skill; it just takes some children longer to learn.

Truths

NO. 115: HOMES aren’t as safe an investment as they feel. A house is a big, undiversified and often leveraged investment bet. Yet owning a home seems less unnerving than owning stocks—because we don’t get constant price updates. The same illusion holds for other infrequently valued investments, like hedge funds, timber and private equity.

Great debates

Manifesto

NO. 6: OUR FINANCIAL life involves endless tradeoffs. We usually have a good idea of what our dollars are buying us. But to be good stewards of our wealth, we should also ponder what we’re giving up.

Spotlight: Markets

Federal debt

The national debt just hit $40 trillion and rising. Seems like possible dire consequences for the markets perhaps the economy as more borrowing may raise interest rates. ’What is the general consensus on the risks we may be facing. Time to go into bonds?
Read more »

AI, Bubbles, and Markets

IN AN INTERVIEW a little while back, the technology investor Peter Thiel drew an uncomfortable comparison. Today’s frenzy around artificial intelligence, he said, parallels the tech stock bubble of the 1990s. To illustrate his point, Thiel pointed to Amazon. By any measure, it’s been an…
Read more »

Managing Investment Risk

BEFORE ITS FAILURE in 2008, Lehman Brothers had been one of the most prominent investment firms in the United States. After 158 years in business, what caused it to collapse so suddenly? In a word: complexity. Lehman had been involved in the securitization of mortgages,…
Read more »

Endowment Lessons

LAST YEAR, an unusual story made the news: The University of Chicago was reportedly looking to sell an entity known as the Center for Research in Security Prices (CRSP). The story came and went quietly, but it’s worth pausing to understand it. CRSP’s origins date…
Read more »

Risk Management

BY NOW, YOU'VE probably heard the story of the 25-year-old wunderkind Leopold Aschenbrenner. After graduating as valedictorian from Columbia University at age 19, he worked for FTX, the crypto trading firm, then found his way to OpenAI, where he worked as a researcher for about…
Read more »

Investment Wisdom

THE INVESTMENT WORLD is full of storytellers. And while these folks might be entertaining, they generally aren’t very helpful. There’s one category of stories, however, that I do think is useful: They’re what I might call investment fables. They’re apocryphal stories that likely aren’t real.…
Read more »

Spotlight: Marsh

Doin’ the Charleston

I WROTE RECENTLY about my wife’s lifelong love of traveling, and of my resolve to get in step with her as she resumes her rambles. To that end, earlier this summer, I drove our family to Charleston, South Carolina, to attend the retirement ceremony for my cousin Chris, and to see a bit of the city, to boot. As our…
Read more »

Reverse Hospitality

IN THE SOUTH, it’s common for a restaurant server or store clerk to refer to me as “sweetie” or “honey.” I’ll often respond by asking, “How did you know my name is Sweetie?” This will usually bring a smile to the face of even a harried worker. Our friendly banter is the worker practicing some of the charm and hospitality…
Read more »

Peace Premium

TWO YEARS AGO, at age 59½, I thought I was on the verge of taking a major step toward retirement. At the time, my usual zest for my work as a physical therapist was waning. Though I don’t think the quality of my patient care suffered, I found it took more effort to maintain the energy needed to complete a…
Read more »

Getting Old

I COULD BE KIND TO my home and say it has rustic charm, but that would be pretentious. The truth is, it’s an old house, built in 1930 by my maternal grandparents. It sits on a remnant of the farm my family once owned. It’s a place I love, and where I’d like to grow old, and therein lies the…
Read more »

Adios, America

OVER EIGHT MILLION Americans have said “so long” to the U.S., heading overseas to work or retire. These expats—short for expatriates—most likely have eight million different reasons to leave our shores for life in another country. My wife’s cousin Chuck and her brother John are among them. John had his eye on living abroad when he took his first engineering…
Read more »

Just Say Noël

MY FAMILY IS FRUGAL all year long, even during the Christmas season. We’re modest with our gifts and sparing with our decorations. Each year, our sprucing up consists of one cut-your-own Christmas tree trimmed with the same ornaments we used the year before. I can’t say the same for our neighbors. They pull out all the stops to create a…
Read more »
HumbleDollar · https://humbledollar.com/ · printed Oct 12, 2026

Log in