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Lessons on the Ground

ArticleDennis Friedman  |  Jul 18, 2026

THE OTHER DAY, WHILE walking to my mailbox, I noticed a summer class schedule for a private gifted youth academy lying on the ground. I assumed it belonged to one of my neighbors, who has elementary-aged children. Their interest in extra academics didn't surprise me. Many families move to this area because of its excellent schools. Parents here clearly value education. On any given day, it's common to hear children practicing the piano or violin as you walk through the neighborhood. I admire parents who encourage their children to excel in school. But as I looked over that schedule, I found myself wondering about the lessons that aren't taught in a classroom. Coincidentally, another neighbor's son had just graduated from college and was preparing to begin his career. If he were my son, what advice would I give him as he stepped into adulthood? After some thought, I settled on five ideas. Invest to Build Wealth. The most reliable way for ordinary people to build wealth is to become owners instead of just consumers. Buying shares of businesses allows you to participate in the growth of the global economy rather than relying solely on a paycheck. The good news is that you don't need much money to begin. What matters most is time. Starting early allows compounding to work its magic, with investment returns generating returns of their own over many years. Be a Long-Term Investor. If I could offer only one piece of investing advice, it would be to keep things simple. Invest regularly in low-cost index funds and stay invested. Trying to pick winning stocks or predict market swings is tempting, but history suggests that patience usually beats prediction. I recently read a New York Times column by Jeff Sommer that made this point well. Long-term market returns are driven by a surprisingly small number of extraordinary companies. The problem, of course, is knowing in advance which companies those will be. Broad diversification through index funds allows investors to own tomorrow's winners without having to guess who they are. Even if you think you're smart enough to spot those superstar companies, holding onto them for the long haul is a rollercoaster. They can be incredibly volatile. I've learned that lesson firsthand. A few years ago, my wife and I bought a small position in Nvidia (NVDA). It represented only a tiny fraction of our portfolio, but the stock's wild price swings made us uncomfortable. We eventually sold our shares too early for about $112, and the last time I checked, it was trading at $204.  Do I regret selling? Not really. The vast majority of our stock holdings remain in Vanguard's Total Stock Market Index Fund (VTI), which owns Nvidia along with thousands of other companies. That approach has allowed us to sleep well at night while still benefiting from the market's long-term growth. Cultivate Friendships. Money matters, but people matter even more. Looking back, some of the biggest turning points in my life came because of friends. One college friend, Chuck, helped me get my foot in the door at an aerospace company when I was a history graduate struggling to find work. That opportunity led to a rewarding career. Another friend, Steve, introduced me to the woman who became my wife. That single introduction changed the course of my life far more than any investment decision ever could. But those special bonds don’t happen by accident; they require making time for them despite a busy career. Good friends encourage us, open doors we never expected, and help us through life's inevitable setbacks. Those relationships are among the greatest investments anyone can make. Give Every Job Your Best. I learned the value of hard work from my parents. When I was growing up, my father routinely left for work before sunrise and often didn't return until evening, six days a week. At the same time, he and my mother managed a 36-unit apartment building. My mother prepared dinner for our family before leaving for her own job each morning, returning home in the evening with just enough time to spend a few quiet hours with my father before doing it all again. Watching them taught me that meaningful accomplishments usually require persistence more than brilliance. There will be phases in your life when long hours are unavoidable. During those times, give your work your best effort. A reputation for reliability and diligence has a way of creating opportunities that talent alone cannot. Protect Your Greatest Asset. For someone just beginning a career, the greatest financial asset isn't an investment account. It's the ability to earn a living. Poor health can quietly undermine that ability. Regular exercise may not seem like a financial strategy, but it helps protect the income that makes every other financial goal possible. I recently came across a quote from a doctor in the comment section of an article in The New York Times that captured this idea perfectly: "Exercise, by its effect on skeletal muscle, can in part preserve cognition, prevent depression, prevent cardiovascular disease, prevent diabetes, prevent some cancers, prevent osteoporosis, and preserve independence. And the list goes on. There isn't a single pill on earth that delivers all of those benefits." Taking care of your health isn't simply about living longer. It's about preserving your independence and giving yourself the opportunity to enjoy the life you've worked so hard to build. As I walked back from the mailbox, I hoped the child whose summer schedule I'd found would do well in every class. Academic success opens many doors. But I also hope someone teaches lessons like these along the way. Years from now, I doubt anyone will remember a report card or a test score. They'll remember the habits that shaped a life: investing patiently, working hard, nurturing friendships, and taking care of their health. Those lessons may never appear on a syllabus, but they can make all the difference.   Dennis Friedman retired from Boeing Satellite Systems after a 30-year career in manufacturing. Born in Ohio, Dennis is a California transplant with a bachelor’s degree in history and an MBA. A self-described “humble investor,” he likes reading historical novels and about personal finance. Follow Dennis on X @DMFrie and check out his earlier articles
Read more »

Will Your Death Double Your Spouse’s Tax Bill?

achnk53  |  Jul 15, 2026

"It's been seven years since my spouse died unexpectedly. I would agree that there is a time when a widow(er) is most "financially vulnerable", and it can last much longer than one might imagine. The first (and only) hard discussion for us came a decade earlier, as we each anticipated the ever-rarer workplace pension. To establish a 100% survivor's benefit required a notable reduction in benefit, with smaller hits for a 75% or 50% survivor's benefit. We agreed to each offer the other a half pension. My spouse retired early and took the hit for a 50% survivor's benefit. When I started my pension, I took a similar hit. So, when he died, instead of our family losing his whole pension, we lost half. Having half has helped, since the expenses for our family barely budged (house costs the same plus inflation, college for kids costs the same plus inflation, etc.) My Social Security benefit based on my own earnings record exceeded what I would have got as a spousal benefit (not always the case) so becoming a widow made no change to that beyond no "who files first" decision to let my calculated benefit ride and build 8% a year to age 70 while still collecting something off his record (he collected Railroad Retirement not Social Security, complicating matters around survivor's annuities and distinctions between these two retirement systems.) To me, a 50% survivor's benefit is more valuable than any lump-sum term life insurance policy, as one's thinking can be muddled in early widowhood. A lump sum can be misspent easily, while an annuity/pension trickles along and mistakes can be made and corrected without derailing one's financial future. To the degree that younger workers contribute to Roth IRAs instead of traditional IRAs, more women are collecting off their own employment history, and traditional pensions cover a decreasing segment of the workforce, some elements of the so-called widow's penalty vanish. IRMAA bracket compression is still tricky, as cliff brackets mean a single extra MAGI dollar at the margin can bump the premium up $120 a month. But that only happens if one is retiring with more income than three-quarters of the population, so plenty okay enough already in most people's thinking. The Bernstein piece Michael1 linked also includes this great line: "the actual U.S. income tax structure is a hot mess". There isn't one-size-fits-all advice for those worried about the possible future life of their widow(er). Best to make the most of each day you are a couple, and be grateful for the chance to share this moment with someone you love and who loves you. The fourth to do in the Kiplinger article is not advice to widow(er)s per se. Everyone needs to "keep the portfolio working", that is, recognize that some people live longer. In fact, once widowed, the planning horizon decreases. One of two people will more likely live past 90 than any particular person. This can be seen in the IRS's own Life Tables I and II: 19.6 more years for a single 69 year old, but 24.3 more years for one of two persons, both aged 69 today. https://www.irs.gov/publications/p590b#en_US_2025_publink100090290 Some might decide we therefore need more TIPS, a higher allocation to equities, more money in total, there are so many suggested strategies for this dilemma, less necessary for the shorter retirement horizon of the widow(er)."
- Catherine
Read more »

One Person’s Luxury, Another’s Necessity

Mark Crothers  |  Jul 21, 2026

"I see a lot of value in "essential" activities. For my wife and I it is two YMCA branches, a community center and a senior center (twice) every week in search of boot camps, yoga classes, cardios, pilates and zumba (even though we don't share all of them) and weight training. Each morning is as busy as it used to be as when I was working. Prior to this I try to do six mile bike and a three mile walk each morning before the day gets started. I used to visit a hematologist /professor at one time who recently passed away. After looking at what I do he said, "you know, when I came to work at Baylor my supervisor used to tell me to be careful, as we are blessed with only so many heartbeats." In my experience what is essential is purely subjective and purely personal."
- V Saraf
Read more »

FIFA Financials

R Quinn  |  Jul 19, 2026

"I now feel inadequate with my 65 inch screen. Time to go shopping."
- Mike Gaynes
Read more »

A Can of Worms

Dan Smith  |  Jul 17, 2026

"David, I sure think that's true most of the time, still, I've seen some exceptions that just leave me scratching my head."
- DAN SMITH
Read more »

Buying a car in retirement

Julie C  |  Jul 11, 2026

"I brought through USAA several times, but unfortunately they ended the program a few years ago."
- S Phillips
Read more »

K-shaped Economy

ArticleAdam M. Grossman  |  Jul 18, 2026

A TOPIC THAT'S been in the news recently is the so-called K-shaped economy.  Imagine a chart plotting the relative standing over time of those with higher incomes and those with lower incomes. Owing to a strong stock market and rising home values, the shape of the chart for those with higher incomes would extend up and to the right and has been moving increasingly in that direction since Covid. Folks with lower incomes, on the other hand, haven’t benefited as much from rising markets. Instead, they’ve had to contend with higher prices on key budget items, including housing, tuition and healthcare. For this group, unfortunately, a chart of their financial progress would extend down and to the right. Put these two charts together, and they form a K—hence, the K-shaped economy. Because this divide has been especially pronounced for young people, more parents are asking how they can help their children. But they aren’t always sure of the best way to approach this. You may have heard the story about the late Charlie Munger. Some years ago, a friend asked Charlie if he planned to leave his considerable fortune to his children. Specifically, his friend wondered whether too much wealth would impact his children’s work ethic. “Of course it will,” Munger replied. “But you still have to do it.” “Why?” his friend asked. “Because if you don’t give them the money, they’ll hate you.” On the one hand, this is funny, but it also gets at why this topic can be so difficult. In fact, I’ve often referred to it as the hardest question in personal finance. But it isn’t impossible. If you’d like to help your children—either today or as part of your estate—here are four questions I suggest considering as you develop your plan. 1. What problem are you most trying to solve? Some families are clear that they just want to help their children as much as they can today, to combat the challenges of the K-shaped economy. Other families are focused on the long term and just want to see their assets pass to their children tax-efficiently at the end of their lives. Both are reasonable objectives, but it’s important to have clarity on what’s most important to you as the first step. 2. To what degree do you value simplicity over tax savings? With the federal estate tax at 40%—and many states levying their own taxes on top of that—folks with assets above the lifetime exclusion often conclude that it’s worth spending virtually any amount on legal fees in an effort to defray that tax.  But not everyone agrees. Other families see it this way: While estate planning strategies can be effective in reducing taxes, they can be costly to set up and to maintain. For that reason, other families decide to spend little or nothing on estate tax strategies. They accept that their estates might—and likely will—end up facing a larger tab at the end of the day. But, they argue, if their estate is large enough for the estate tax to apply, then by definition, their heirs will nonetheless still receive a significant sum. 3. Do you worry about the problem Munger’s friend highlighted? If you’re worried about impacting your children’s work ethic, then counterintuitively, it may make sense to start making gifts sooner rather than later. The key is to make modest gifts and to make them incrementally. When you start making gifts like this sooner, it can serve two purposes. As a parent, it gives you the opportunity to see how your children handle these smaller sums. Do they immediately head to Bora Bora, or do they save and invest the dollars they receive? Making gifts incrementally can also help the recipient. To the extent that the first—or the second—gift is spent frivolously, modest gifts provide children the opportunity to acclimate and hopefully to adjust. 4. To what degree would you like to control your children’s use of assets down the road? If you go the route of an irrevocable trust and plan to leave assets to your children as a bequest, you won’t have the opportunity to iterate in the way I described above. That said, you may still prefer to leave assets to your children in this way. The key challenge with trusts is how to structure the distribution provisions. Put too many restrictions in place, and you risk causing your children a lifetime of stress or, worse yet, resentment. But put too few restrictions in, and the trust assets could be spent unwisely and deplete too quickly. How can you thread the needle? There’s no single right approach, but here are four distribution strategies you might consider. Based on age or stage: You might stipulate, for example, that a child reach age 30 before receiving any funds. Or you might require that a child have finished college or be married before receiving funds. The benefit of this approach is that it doesn’t leave room for debate between your children and the trustee. The downside is that this sort of structure can be too rigid, because children’s needs don’t always align with specific ages or stages. The reality is that everyone takes different paths through life in ways that no formula can fully contemplate. I often reference the movie The Bachelor, which is a comedy but illustrates how an overly rigid structure can have unintended consequences. Annual percentage with no discretion: This structure also has the benefit of being straightforward, with no room for debate between beneficiaries and the trustee. In addition, a fixed percentage can help preserve a trust’s assets for many years. The downside is that children’s needs typically vary from year to year. They’ll want to buy homes and may have tuition expenses for their own children. For those reasons, a fixed percentage, while attractive in theory, runs the risk of being an obstacle to your children’s most important goals. Annual percentage with an override for specific needs: The benefit of this structure is that it provides flexibility if a child wants to buy a home or has other higher-than-normal expenses in a particular year. The downside is that it opens the door to debate between beneficiary and trustee. The trustee might deem a proposed home purchase too expensive, for example.  Trustee’s discretion: A final approach is to leave distributions entirely up to the trustee. That’s the most flexible but also the most potentially fraught. If a trustee and a beneficiary don’t get along, this setup would give the trustee wide latitude to make the beneficiary’s life miserable for decades. No distribution structure is perfect, but it’s for this reason that I tend to recommend against this approach, common as it is.   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 »

Many seniors think we paid for our Social Security benefits based on the FICA taxes we paid. Let’s dispel that myth- we didn’t

R Quinn  |  Jun 15, 2026

"It wouldn’t even have to be eliminated. Given data analytics today, it would be possible to track via tax returns spouses, young children, disabled children household income etc. SS tax could be modified to account for various life circumstances. There’s no need for one size fits all these days."
- Marilyn Lavin
Read more »

Danger, Junk Mail

Sonja Haggert  |  Jul 16, 2026

"I hope you'll be as pleased with the shredder as I have been with mine: When I retired and thus no longer had free access to a shredder at work, one of the best purchases I made as soon as I moved to my CCRC was an Aurora compact micro-cut shredder. Convenient, small, easy to use, and no way could someone piece together the shreds. With simplicity and security being my priority in retirement, this is one less thing to worry about."
- 1PF
Read more »

The Paradox of Wealth

Mark Crothers  |  Jul 15, 2026

"Mark, with time being our most valuable resource, it's unfortunate that most people don't put as much effort into managing it as they do their financial portfolio."
- Mark Crothers
Read more »

A Letter 40 Years Later: What Mrs. Dolezal Remembered

Andrew Clements  |  Jul 1, 2026

"Jeff, thank you so much. I couldn’t agree more. Kindness has a remarkable ripple effect, often reaching far beyond the moment itself. Mrs. Dolezdal’s kindness touched my family all those years ago, and through her letter, it continues to touch others today. I think that’s a wonderful reminder of the difference even the smallest acts can make."
- Andrew Clements
Read more »

IRMAA & late filing of tax returns

Danbo  |  Jul 15, 2026

"you are correct, Luigi."
- DAN SMITH
Read more »

Lessons on the Ground

ArticleDennis Friedman  |  Jul 18, 2026

THE OTHER DAY, WHILE walking to my mailbox, I noticed a summer class schedule for a private gifted youth academy lying on the ground. I assumed it belonged to one of my neighbors, who has elementary-aged children. Their interest in extra academics didn't surprise me. Many families move to this area because of its excellent schools. Parents here clearly value education. On any given day, it's common to hear children practicing the piano or violin as you walk through the neighborhood. I admire parents who encourage their children to excel in school. But as I looked over that schedule, I found myself wondering about the lessons that aren't taught in a classroom. Coincidentally, another neighbor's son had just graduated from college and was preparing to begin his career. If he were my son, what advice would I give him as he stepped into adulthood? After some thought, I settled on five ideas. Invest to Build Wealth. The most reliable way for ordinary people to build wealth is to become owners instead of just consumers. Buying shares of businesses allows you to participate in the growth of the global economy rather than relying solely on a paycheck. The good news is that you don't need much money to begin. What matters most is time. Starting early allows compounding to work its magic, with investment returns generating returns of their own over many years. Be a Long-Term Investor. If I could offer only one piece of investing advice, it would be to keep things simple. Invest regularly in low-cost index funds and stay invested. Trying to pick winning stocks or predict market swings is tempting, but history suggests that patience usually beats prediction. I recently read a New York Times column by Jeff Sommer that made this point well. Long-term market returns are driven by a surprisingly small number of extraordinary companies. The problem, of course, is knowing in advance which companies those will be. Broad diversification through index funds allows investors to own tomorrow's winners without having to guess who they are. Even if you think you're smart enough to spot those superstar companies, holding onto them for the long haul is a rollercoaster. They can be incredibly volatile. I've learned that lesson firsthand. A few years ago, my wife and I bought a small position in Nvidia (NVDA). It represented only a tiny fraction of our portfolio, but the stock's wild price swings made us uncomfortable. We eventually sold our shares too early for about $112, and the last time I checked, it was trading at $204.  Do I regret selling? Not really. The vast majority of our stock holdings remain in Vanguard's Total Stock Market Index Fund (VTI), which owns Nvidia along with thousands of other companies. That approach has allowed us to sleep well at night while still benefiting from the market's long-term growth. Cultivate Friendships. Money matters, but people matter even more. Looking back, some of the biggest turning points in my life came because of friends. One college friend, Chuck, helped me get my foot in the door at an aerospace company when I was a history graduate struggling to find work. That opportunity led to a rewarding career. Another friend, Steve, introduced me to the woman who became my wife. That single introduction changed the course of my life far more than any investment decision ever could. But those special bonds don’t happen by accident; they require making time for them despite a busy career. Good friends encourage us, open doors we never expected, and help us through life's inevitable setbacks. Those relationships are among the greatest investments anyone can make. Give Every Job Your Best. I learned the value of hard work from my parents. When I was growing up, my father routinely left for work before sunrise and often didn't return until evening, six days a week. At the same time, he and my mother managed a 36-unit apartment building. My mother prepared dinner for our family before leaving for her own job each morning, returning home in the evening with just enough time to spend a few quiet hours with my father before doing it all again. Watching them taught me that meaningful accomplishments usually require persistence more than brilliance. There will be phases in your life when long hours are unavoidable. During those times, give your work your best effort. A reputation for reliability and diligence has a way of creating opportunities that talent alone cannot. Protect Your Greatest Asset. For someone just beginning a career, the greatest financial asset isn't an investment account. It's the ability to earn a living. Poor health can quietly undermine that ability. Regular exercise may not seem like a financial strategy, but it helps protect the income that makes every other financial goal possible. I recently came across a quote from a doctor in the comment section of an article in The New York Times that captured this idea perfectly: "Exercise, by its effect on skeletal muscle, can in part preserve cognition, prevent depression, prevent cardiovascular disease, prevent diabetes, prevent some cancers, prevent osteoporosis, and preserve independence. And the list goes on. There isn't a single pill on earth that delivers all of those benefits." Taking care of your health isn't simply about living longer. It's about preserving your independence and giving yourself the opportunity to enjoy the life you've worked so hard to build. As I walked back from the mailbox, I hoped the child whose summer schedule I'd found would do well in every class. Academic success opens many doors. But I also hope someone teaches lessons like these along the way. Years from now, I doubt anyone will remember a report card or a test score. They'll remember the habits that shaped a life: investing patiently, working hard, nurturing friendships, and taking care of their health. Those lessons may never appear on a syllabus, but they can make all the difference.   Dennis Friedman retired from Boeing Satellite Systems after a 30-year career in manufacturing. Born in Ohio, Dennis is a California transplant with a bachelor’s degree in history and an MBA. A self-described “humble investor,” he likes reading historical novels and about personal finance. Follow Dennis on X @DMFrie and check out his earlier articles
Read more »

Will Your Death Double Your Spouse’s Tax Bill?

achnk53  |  Jul 15, 2026

"It's been seven years since my spouse died unexpectedly. I would agree that there is a time when a widow(er) is most "financially vulnerable", and it can last much longer than one might imagine. The first (and only) hard discussion for us came a decade earlier, as we each anticipated the ever-rarer workplace pension. To establish a 100% survivor's benefit required a notable reduction in benefit, with smaller hits for a 75% or 50% survivor's benefit. We agreed to each offer the other a half pension. My spouse retired early and took the hit for a 50% survivor's benefit. When I started my pension, I took a similar hit. So, when he died, instead of our family losing his whole pension, we lost half. Having half has helped, since the expenses for our family barely budged (house costs the same plus inflation, college for kids costs the same plus inflation, etc.) My Social Security benefit based on my own earnings record exceeded what I would have got as a spousal benefit (not always the case) so becoming a widow made no change to that beyond no "who files first" decision to let my calculated benefit ride and build 8% a year to age 70 while still collecting something off his record (he collected Railroad Retirement not Social Security, complicating matters around survivor's annuities and distinctions between these two retirement systems.) To me, a 50% survivor's benefit is more valuable than any lump-sum term life insurance policy, as one's thinking can be muddled in early widowhood. A lump sum can be misspent easily, while an annuity/pension trickles along and mistakes can be made and corrected without derailing one's financial future. To the degree that younger workers contribute to Roth IRAs instead of traditional IRAs, more women are collecting off their own employment history, and traditional pensions cover a decreasing segment of the workforce, some elements of the so-called widow's penalty vanish. IRMAA bracket compression is still tricky, as cliff brackets mean a single extra MAGI dollar at the margin can bump the premium up $120 a month. But that only happens if one is retiring with more income than three-quarters of the population, so plenty okay enough already in most people's thinking. The Bernstein piece Michael1 linked also includes this great line: "the actual U.S. income tax structure is a hot mess". There isn't one-size-fits-all advice for those worried about the possible future life of their widow(er). Best to make the most of each day you are a couple, and be grateful for the chance to share this moment with someone you love and who loves you. The fourth to do in the Kiplinger article is not advice to widow(er)s per se. Everyone needs to "keep the portfolio working", that is, recognize that some people live longer. In fact, once widowed, the planning horizon decreases. One of two people will more likely live past 90 than any particular person. This can be seen in the IRS's own Life Tables I and II: 19.6 more years for a single 69 year old, but 24.3 more years for one of two persons, both aged 69 today. https://www.irs.gov/publications/p590b#en_US_2025_publink100090290 Some might decide we therefore need more TIPS, a higher allocation to equities, more money in total, there are so many suggested strategies for this dilemma, less necessary for the shorter retirement horizon of the widow(er)."
- Catherine
Read more »

One Person’s Luxury, Another’s Necessity

Mark Crothers  |  Jul 21, 2026

"I see a lot of value in "essential" activities. For my wife and I it is two YMCA branches, a community center and a senior center (twice) every week in search of boot camps, yoga classes, cardios, pilates and zumba (even though we don't share all of them) and weight training. Each morning is as busy as it used to be as when I was working. Prior to this I try to do six mile bike and a three mile walk each morning before the day gets started. I used to visit a hematologist /professor at one time who recently passed away. After looking at what I do he said, "you know, when I came to work at Baylor my supervisor used to tell me to be careful, as we are blessed with only so many heartbeats." In my experience what is essential is purely subjective and purely personal."
- V Saraf
Read more »

FIFA Financials

R Quinn  |  Jul 19, 2026

"I now feel inadequate with my 65 inch screen. Time to go shopping."
- Mike Gaynes
Read more »

A Can of Worms

Dan Smith  |  Jul 17, 2026

"David, I sure think that's true most of the time, still, I've seen some exceptions that just leave me scratching my head."
- DAN SMITH
Read more »

Buying a car in retirement

Julie C  |  Jul 11, 2026

"I brought through USAA several times, but unfortunately they ended the program a few years ago."
- S Phillips
Read more »

K-shaped Economy

ArticleAdam M. Grossman  |  Jul 18, 2026

A TOPIC THAT'S been in the news recently is the so-called K-shaped economy.  Imagine a chart plotting the relative standing over time of those with higher incomes and those with lower incomes. Owing to a strong stock market and rising home values, the shape of the chart for those with higher incomes would extend up and to the right and has been moving increasingly in that direction since Covid. Folks with lower incomes, on the other hand, haven’t benefited as much from rising markets. Instead, they’ve had to contend with higher prices on key budget items, including housing, tuition and healthcare. For this group, unfortunately, a chart of their financial progress would extend down and to the right. Put these two charts together, and they form a K—hence, the K-shaped economy. Because this divide has been especially pronounced for young people, more parents are asking how they can help their children. But they aren’t always sure of the best way to approach this. You may have heard the story about the late Charlie Munger. Some years ago, a friend asked Charlie if he planned to leave his considerable fortune to his children. Specifically, his friend wondered whether too much wealth would impact his children’s work ethic. “Of course it will,” Munger replied. “But you still have to do it.” “Why?” his friend asked. “Because if you don’t give them the money, they’ll hate you.” On the one hand, this is funny, but it also gets at why this topic can be so difficult. In fact, I’ve often referred to it as the hardest question in personal finance. But it isn’t impossible. If you’d like to help your children—either today or as part of your estate—here are four questions I suggest considering as you develop your plan. 1. What problem are you most trying to solve? Some families are clear that they just want to help their children as much as they can today, to combat the challenges of the K-shaped economy. Other families are focused on the long term and just want to see their assets pass to their children tax-efficiently at the end of their lives. Both are reasonable objectives, but it’s important to have clarity on what’s most important to you as the first step. 2. To what degree do you value simplicity over tax savings? With the federal estate tax at 40%—and many states levying their own taxes on top of that—folks with assets above the lifetime exclusion often conclude that it’s worth spending virtually any amount on legal fees in an effort to defray that tax.  But not everyone agrees. Other families see it this way: While estate planning strategies can be effective in reducing taxes, they can be costly to set up and to maintain. For that reason, other families decide to spend little or nothing on estate tax strategies. They accept that their estates might—and likely will—end up facing a larger tab at the end of the day. But, they argue, if their estate is large enough for the estate tax to apply, then by definition, their heirs will nonetheless still receive a significant sum. 3. Do you worry about the problem Munger’s friend highlighted? If you’re worried about impacting your children’s work ethic, then counterintuitively, it may make sense to start making gifts sooner rather than later. The key is to make modest gifts and to make them incrementally. When you start making gifts like this sooner, it can serve two purposes. As a parent, it gives you the opportunity to see how your children handle these smaller sums. Do they immediately head to Bora Bora, or do they save and invest the dollars they receive? Making gifts incrementally can also help the recipient. To the extent that the first—or the second—gift is spent frivolously, modest gifts provide children the opportunity to acclimate and hopefully to adjust. 4. To what degree would you like to control your children’s use of assets down the road? If you go the route of an irrevocable trust and plan to leave assets to your children as a bequest, you won’t have the opportunity to iterate in the way I described above. That said, you may still prefer to leave assets to your children in this way. The key challenge with trusts is how to structure the distribution provisions. Put too many restrictions in place, and you risk causing your children a lifetime of stress or, worse yet, resentment. But put too few restrictions in, and the trust assets could be spent unwisely and deplete too quickly. How can you thread the needle? There’s no single right approach, but here are four distribution strategies you might consider. Based on age or stage: You might stipulate, for example, that a child reach age 30 before receiving any funds. Or you might require that a child have finished college or be married before receiving funds. The benefit of this approach is that it doesn’t leave room for debate between your children and the trustee. The downside is that this sort of structure can be too rigid, because children’s needs don’t always align with specific ages or stages. The reality is that everyone takes different paths through life in ways that no formula can fully contemplate. I often reference the movie The Bachelor, which is a comedy but illustrates how an overly rigid structure can have unintended consequences. Annual percentage with no discretion: This structure also has the benefit of being straightforward, with no room for debate between beneficiaries and the trustee. In addition, a fixed percentage can help preserve a trust’s assets for many years. The downside is that children’s needs typically vary from year to year. They’ll want to buy homes and may have tuition expenses for their own children. For those reasons, a fixed percentage, while attractive in theory, runs the risk of being an obstacle to your children’s most important goals. Annual percentage with an override for specific needs: The benefit of this structure is that it provides flexibility if a child wants to buy a home or has other higher-than-normal expenses in a particular year. The downside is that it opens the door to debate between beneficiary and trustee. The trustee might deem a proposed home purchase too expensive, for example.  Trustee’s discretion: A final approach is to leave distributions entirely up to the trustee. That’s the most flexible but also the most potentially fraught. If a trustee and a beneficiary don’t get along, this setup would give the trustee wide latitude to make the beneficiary’s life miserable for decades. No distribution structure is perfect, but it’s for this reason that I tend to recommend against this approach, common as it is.   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.  
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Many seniors think we paid for our Social Security benefits based on the FICA taxes we paid. Let’s dispel that myth- we didn’t

R Quinn  |  Jun 15, 2026

"It wouldn’t even have to be eliminated. Given data analytics today, it would be possible to track via tax returns spouses, young children, disabled children household income etc. SS tax could be modified to account for various life circumstances. There’s no need for one size fits all these days."
- Marilyn Lavin
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Danger, Junk Mail

Sonja Haggert  |  Jul 16, 2026

"I hope you'll be as pleased with the shredder as I have been with mine: When I retired and thus no longer had free access to a shredder at work, one of the best purchases I made as soon as I moved to my CCRC was an Aurora compact micro-cut shredder. Convenient, small, easy to use, and no way could someone piece together the shreds. With simplicity and security being my priority in retirement, this is one less thing to worry about."
- 1PF
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Manifesto

Jul 19, 2026

NO. 30: INVESTING is best when it is simplest. If we own costly, complicated products, we’re filling Wall Street’s coffers—at our own expense. Don’t understand an investment? Don’t buy it.

Truths

Jul 21, 2026

NO. 9: BIG SALARY increases, especially late in your career, can make it harder to retire. As your paycheck grows, you’ll likely raise your standard of living. That means you now need a larger nest egg to sustain that lifestyle in retirement. The problem: You were likely previously saving as though you were looking to replicate a more modest lifestyle.

humans

Jul 20, 2026

NO. 72: WE ENJOY working hard. We tell ourselves, “I just want time to relax,” and yet relaxation doesn’t satisfy us for long and we quickly grow restless. We should keep this in mind as we ponder retirement. Contrary to what we imagine, we get great pleasure from working, especially work we’re passionate about and that gives us a sense of purpose.

think

Jul 20, 2026

HYPERBOLIC discounting. Suppose we’re choosing between a smaller reward today and a larger reward at some future date. To get us to wait, the later reward typically has to be far bigger, perhaps giving us a 100% return for delaying just a few days or weeks. Such hyperbolic discounting highlights how we favor today and shortchange our future self.

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Manifesto

Jul 19, 2026

NO. 30: INVESTING is best when it is simplest. If we own costly, complicated products, we’re filling Wall Street’s coffers—at our own expense. Don’t understand an investment? Don’t buy it.

Spotlight: Cars

Scared Debtless

Richard Quinn   |  Jun 17, 2020

MONEY IS ONE OF THE most emotional issues we deal with. It can create both immense stress and moments of pleasure. I’m guessing the way each of us view money, and how we handle it, is as unique as our fingerprints.
My wife’s car of 14 years was kaput and headed for the junkyard. Fixing the wiring and computer on her 2006 Jaguar would have cost $5,000—far more than the car was worth, even though it was otherwise in very good shape.

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Another HD Post About Cars

Jeff Bond   |  May 27, 2025

Here’s another car-themed Forum post. Last June I wrote a Humble Dollar article about vehicle ownership and longevity. I ended that article with a description of the most recent major repair required for my 2011 Subaru Forester when the clutch assembly failed and required replacement. Those of you wishing to revisit that article can view it here.
I mentioned at the end of that article it might be time to search for another Subaru. At the end of 2024 I read about the introduction of a Subaru Forester option in the new model year –

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Ageing and the Open Road

Mark Crothers   |  May 2, 2026

RECENTLY I TOOK a free ride on a driverless bus trialling its proposed route, part of my local administration’s ten-year rollout plan for self-driving public transport and taxis. I see real potential in this technology, and I’m hoping the infrastructure and implementation stay on schedule. That hope is mostly selfish, I’ll admit.
In fifteen years I’ll be in my mid-seventies, and I’d love to ditch my car and rely on cheap, dependable robo-taxis instead.

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Mercedes and Me

Richard Quinn   |  Sep 11, 2019

MY FATHER WAS A CAR salesman. For the last 20 years of his career, he sold Mercedes and he was good at it. He even won a sales contest that included a trip to Germany to tour the factory.
Unfortunately, selling Mercedes does not mean you can afford one. But he did get to drive them. As a kid, I was also hooked. When I was 17, I was allowed to drive a 190SL in the local July 4th parade.

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What’s the best strategy for getting a good deal on a car?

Jonathan Clements   |  May 14, 2021

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Car Trouble

Ron Wayne   |  May 12, 2023

I WAS HAPPY TO receive this year’s boost to my Social Security benefit—but I’m regularly reminded that it doesn’t match the endless inflation.
A case in point: The same oil change at the same gas station for my 2020 Honda Fit cost me 28% more last week than it did nine months earlier. With detailed invoices, I could compare the reasons for the jump. Surprisingly, it wasn’t the cost of four quarts of full synthetic oil,

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Spotlight: Fourneau

My First Retirement

Juan Fourneau   |  Jan 3, 2023

I LOST A MATCH ON Nov. 12 against my former tag-team partner, Kevin Gutierrez, who wrestles under the colorful name “Corn Boi.” It was a classic Lucha Libre stipulation match. I put my mask on the line, and Kevin would cut his shoulder-length hair if he lost. Mask versus hair—or, as they say in Mexico, mascara versus cabellera. We had many tried-and-true plot lines going for us. Teacher versus student. Old friends and tag partners who were now fighting furiously against each other. Older, bitter, crotchety veteran wrestler—that’s me—frustrated with this not-so-serious newer generation. It was a good story. All the while, I knew how it would end—with me losing my mask and announcing my retirement from wrestling. I’ll wrestle a goodbye match or two next summer, but essentially, I was done. When I put on the mask at age 40, I remembered a line from the great wrestling journalist Dave Meltzer. He wrote the obituary for Junkyard Dog, the African-American grappler who was a Main Event star and drew tons of money in the New Orleans area and later in the World Wrestling Federation. “If he had kept his weight under control and continued training, he could have been a star into his 50s like Ric Flair, The Crusher or Dick the Bruiser.” [caption id="attachment_1536026" align="alignright" width="400"] Juan's final wrestling match. Photo by Clint Dye of Tag Team Photography.[/caption] Right there, Meltzer had given me the formula for longevity in the sport. Ric Flair also said in his podcast that the enemy of any professional wrestler was inactivity. So, for the past nine years, I’ve tried to keep a regular wrestling schedule. If I didn’t have a match, I headed up to the Black & Brave wrestling school in nearby Davenport, Iowa, and worked out in that hard ring.…
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Wrestling for Money

Juan Fourneau   |  Nov 13, 2021

IN THE FALL OF 1994, when I was 21, I made the trip south from Iowa down I-35 to Texas. I was starting my wrestling training on Commerce Street in downtown Dallas at Doug’s Gym. What I wasn’t expecting were the financial lessons I picked up from some of the colorful professional wrestlers of that era. Doug’s Gym wasn’t air-conditioned. It had a classic collection of weights and machines. I felt transported back in time, using the same equipment that Jack LaLanne and Steve Reeves would have used decades before. Doug Eidd still owned and ran the old-school gym, which he opened in 1962. The building was across the street from the police station where Jack Ruby shot Lee Harvey Oswald days after President Kennedy’s assassination. I was there to meet Doug’s cousin, Skandor Akbar or, as we called him, Ak. His real name was Jim Wehba, and he was 60. He had the brawn, broken-down knees and walk of a retired professional wrestler. As I began to train and spend time at Doug’s Gym, we would get visitors. They all came to hear Ak’s stories. It became clear that Ak was good with his money. He was not wealthy. But over the years, he had made a good income working in some of the major wrestling territories. He’d spent time in New York working for Vince McMahon Sr. He’d made a good living there, despite missing out on the chance to have a Main Event program with the Italian-born strongman and champion Bruno Sammartino. Fellow Texan Stan Hansen broke Sammartino’s neck in Madison Square Garden, costing Ak his big payday. Instead of New York glory, Ak had extended stays in Georgia, Australia and the Dallas office of a promoter who had wrestled under the name Fritz Von Erich. But…
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My Side Hustle

Juan Fourneau   |  Oct 12, 2022

WHEN I BEGAN MY journey to becoming a professional wrestler in 1994, I didn’t give much thought to the money aspect of the business. Wrestling was a secret organization similar to magicians or, frankly, the Mafia. Information wasn’t readily available on the industry’s economics. I simply had a burning desire to be a part of this crazy circus that I’d always loved as a fan. As I began training to be a wrestler under Skandor Akbar in Dallas, information came in trickles. In my class, there was a huge wrestler who got booked before me, even though I’d trained for longer. It didn’t bother me. He was a legit six foot 10 inches tall and weighed a solid 400-plus pounds. He was a nice guy and I was happy for him. At the time, even World Wrestling Entertainment (WWE) was losing money and struggling to draw crowds. When my fellow newbie debuted, he said the crowd was fewer than 100 people, and full of former Texas wrestling stars and veterans. He shared that he didn’t get paid for his first match. After several delays and setbacks, I had my first match in 1996. There were some veteran wrestlers on the card. The business was becoming hot again, the start of a boom that peaked in 1999. I debuted at the Sportatorium in Dallas in front of a healthy crowd of more than 800 fans. My first match was one of my worst. I sucked up my disappointment and headed back to thank promoter Grizzly Smith and the rest of the office crew for the opportunity. I wasn’t sure if I’d get paid. As I walked in, they handed me an envelope and asked me to sign my name to confirm I’d received my earnings for the night. It was $40.…
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Born to Sell

Juan Fourneau   |  Apr 28, 2023

I ONCE DABBLED IN the world of sales. I wasn't very good at it. In 1997, I got a job at Schwan’s, driving one of those yellow trucks you see in neighborhoods all over the U.S. selling frozen treats, ice cream and a variety of food. I thought it would be a delivery and service job. But I found out during the orientation and training that there was an element of sales. I read the books of motivational speaker Zig Ziglar in my free time and got some basic training in sales from the company. But as I began my route in the railroad town of Fort Madison, Iowa, I could see I needed help. A natural sales guy I was not. At a party one weekend, I ran into my dad’s old friend, Pablo. My dad was godfather, or padrino, to Pablo’s youngest son. I was interested in talking to him because he was a successful car salesman. As we talked about my struggles in sales, Pablo gave me a few tips. He also shared with me how he began his career. Pablo was from San Antonio. He spoke good English, but like many Hispanic men in my hometown of that era, he had a limited education. He dropped out of school in sixth grade to work because his family didn’t have a lot of money. He met his wife when they were both working as migrant laborers, following the crops. My Midwestern town is home to a Heinz manufacturing plant where, in the old days, migrant workers picked tomatoes from the fields and transported them to the plant. After one season in the mid-1960s, Pablo and his wife never went back to Texas. Instead, they decided to make a home here in Iowa. He met my dad at…
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Playing Ball

Juan Fourneau   |  Jan 8, 2025

MY SON IS A FRESHMAN in high school, and I’m beginning to be more purposeful about his baseball aspirations. But after dropping $85 on a one-hour pitching lesson, I was wondering, was my money well spent? My search for an answer began with the Netflix series Receiver. I tuned in to see football player George Kittle, a former University of Iowa Hawkeye and bigtime professional wrestling fan. Kittle was kind enough to send autographed memorabilia for a softball fundraiser we had a few years ago. He’s now a star for the San Francisco 49ers. I learned about Kittle through a mutual friend, Steve Manders, who was a walk-on for the Hawkeyes for three years before he began professional wrestling. During my wrestling career, I tagged with Steve for a period of time, and learned a lot about hard work, grit and perseverance from being around him. While I watched Receiver to learn more about Kittle, the Netflix series was also my introduction to Detroit Lions wide receiver Amon-Ra St. Brown. What caught my eye was his dad, John Brown, a former Mr. Universe. I subsequently listened to the father’s podcast and interviews. It became clear he had strong opinions about parenting, including how parents need to take charge of the direction of their children's lives. It was eye-opening. I always like to have my beliefs questioned. And when someone has results, I’ll listen with an open mind. And oh my, does the older Brown have opinions: “If your kid’s not doing something, it’s the parents’ fault, it’s not the kid’s fault.” “I raised my boys to dominate. We’re not having fun. We’re not competing. We're here to dominate.” “No coach can prepare you to be the top in the world. They don't have the time. They have 30 kids, 40 kids on the…
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When Bubbles Burst

Juan Fourneau   |  Feb 17, 2023

ABOUT HALF THE RENTALS that my wife and I own were foreclosures we bought around the time of the Great Recession. In fact, I closed on the first one on my wedding day—a fact my wife isn’t anxious to let me forget. In 2000, a family had bought the house for $70,000. In 2006, JPMorgan Chase foreclosed on the house. In 2007, the bank unloaded the property for $93,000 to the Department of Housing and Urban Development (HUD), which had guaranteed the mortgage. I bought the place in 2007 for $50,000. I overpaid. It was the start of a tidal wave of foreclosures that would hit my hometown and the rest of the country. The pattern I saw with my first foreclosure was one I’d see again several times over the next eight years. A family would buy a home in the early to mid-2000s as interest rates dropped and property prices rose. They got a mortgage backed by a government agency. Next, a new loan was secured for more than the original purchase price, or home equity was borrowed to pay for renovations and improvements. Then the economy slowed and eventually hit a brick wall. The family would lose the home and the government would get the property back. The place would sit on the market for months, maybe a year. A local investor or landlord would pick it up for a fraction of the price that the family had paid. October 2010 was Lucas Street, another foreclosure. In January 2007, a couple bought it for $72,000. The Federal Home Loan Mortgage Corporation foreclosed on it during summer 2010. I bought it in October for $35,000. The front of the house was a striking stone structure that increased its curb appeal. When I had to cut the stone to…
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