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So Maybe That’s What It’s All About

"Dunn, it's always great to hear my amateur efforts give someone a smile 😁"
- Mark Crothers
Read more »

Reluctantly Saving Money

"William, I would definitely have been on your wife's team... working on a roof in your seventies? Definitely a hard no!"
- Mark Crothers
Read more »

Better Questions

"Mark, in the run-up to retiring, I didn't just look at my retirement spreadsheets every day—I practically lived in them. I was opening them multiple times a day, obsessively tweaking variables and micro-managing scenario tabs like a man possessed. Yet, since finally stepping away in March 2025, I can count on one hand the number of times I’ve actually launched Excel. Once I finally crossed the finish line, the urge to stress-test my life every twenty minutes completely evaporated. These days, Claudia AI has basically replaced Google as my go-to query engine for whatever random topic pops into my head. In fact, I occasionally suffer a wave of modern guilt, wondering just how much grid energy I’m burning through just to get an instant, deeply detailed answer to some of the most beautifully inane questions imaginable."
- Mark Crothers
Read more »

About that inflation in retirement

"Jack (and the original recommender), thanks for the link to Advisor Perspectives and the Bernstein/McQuarrie article. Another one I enjoyed by the same two gents is this one: The Many Utilities of Retirement - Articles - Advisor Perspectives"
- Andrew Forsythe
Read more »

Don’t Let a Roth Conversion Trigger a Penalty

"Grant - Thanks for the reply. If I understand your process correctly, my observation would be: The Step 2 distribution came out of a Traditional IRA. Roll it back into a Traditional within 60 days with brokerage cash and it's a tax-free wash. Roll it into the Roth instead and it's a Roth conversion, fully taxable, because you've moved Traditional money into a Roth. So the "tax money" doesn't pay the tax. It becomes an extra conversion equal to the tax, which means a $100,000 conversion you thought you did is actually $130,000. And that overshoot is the whole risk: if you sized the $100k to stay under a bracket or IRMAA threshold, the real $130k blows through it."
- John Urban
Read more »

A taxing situation, but is it reality?

"I would have to agree that in my experience with Medicare some years ago on my parent's behalf, I found it surprisingly easy to deal with. On a more limited basis same with Social Security for them. That does not automatically make them efficient by default however in order to provide that level of service. All that said, your article is not about Social Security or Medicare, it is about taxes and only one (federal) portion of the broader tax load picture at that. When you focus an article on taxes, all aspects of government efficiency with the public's funds are fair game when contemplating more taxes. S.S. and Medicare are but two pixels in a much broader picture of morbid mediocrity. Reference corporations: you highlight two positives: 1) the ability to right size private sector organizations to changing business conditions or enhanced technology or LEAN based efficiencies (or maybe correct inefficiency that set in through poor management and needs to be cleaned up) ....without having to go to the Supreme Court to do it. 2) For businesses that fail due to inefficiency or not evolving fast enough, natural selection culls the herd- healthy for the overall economy. Not so with government agencies.....unfortunately- unhealthy for the overall economy."
- Dunn Werking
Read more »

Haunted Head

"Martin, that about sums it up for me as well. I do find preparing taxes for AARP to be deserving of my time. Chrissy volunteers at a cat rescue, which helps in getting cats spayed or neutered, and off the streets. I’m sure I could find other worthy assignments, but I’m pretty happy with my level of involvement. "
- Dan Smith
Read more »

Trump Accounts

INNOVATION IN THE world of retirement plans is decidedly slow moving. But as of July 4th, investors now have a new savings option known as a Trump account. In short, these are retirement accounts designed specifically for children. Trump accounts share some similarities with traditional individual retirement accounts (IRAs), but there are also key differences. If you have children, grandchildren, nieces or nephews, this new option may be worth exploring. Who is eligible for a Trump account? An account can be opened for any child who will be under 18 as of December 31 in the year that the account is opened. How are Trump accounts different from traditional IRAs? The primary goal of these accounts is to allow children to begin to accumulate retirement funds much earlier than has been possible in the past. For that reason, and in contrast to traditional IRAs, Trump accounts don’t require a child to have any earned income. Contributions could begin as soon as a baby is born.  What is the process for opening an account? To get started, head to the new government website at trumpaccounts.gov. From there, you can download a mobile app to start the account opening process. I tried it myself, opening an account for one of my sons, and found the process quite easy. One nice feature is that the funds are invested automatically in low-cost index funds. What are the contribution limits? Trump accounts have their own unique contribution caps, which are a little complicated. Individuals and employers can contribute up to a total of $5,000 per child per year, though the employer portion is limited to $2,500 of that $5,000. This limit will grow in future years. In addition, the government and a group of philanthropists have established a pilot program and are making contributions to certain new Trump accounts. Children born between January 1, 2025 and December 31, 2028 are eligible to receive a $1,000 contribution from the government upon opening a new account. In addition to this $1,000 contribution from the government, a group of philanthropists, including Michael Dell, Ray Dalio and others, are contributing $250 to Trump accounts for children up to 10 years old who live in particular Zip codes. These additional contributions don’t count toward the $5,000 annual contribution limit. Do Trump account contributions affect IRA contribution limits? If your child has earned income, he or she can contribute the maximum to a Trump account and still also contribute to a regular IRA or Roth IRA up to the annual IRA contribution limit. There’s no tradeoff. How are withdrawals treated? Withdrawals from Trump accounts aren’t permitted during the initial “growth period,” which begins at birth and ends on December 31 of the year before the child turns 18.  After the growth period, withdrawals from Trump accounts will be treated in much the same way as traditional IRAs. Specifically, withdrawals prior to age 59½ are subject to a 10% tax penalty. Trump accounts do, however, allow for penalty-free withdrawals before 59½ under certain circumstances, including a first-time home purchase, higher education and a few other, less common situations. The tax treatment of withdrawals differs by donor: Contributions by individuals are made on an after-tax basis, so those dollars come out tax-free. Investment gains on those contributions, however, are subject to ordinary income tax. Any dollars received from the government or other donors under the pilot program will also be subject to ordinary income tax. Should you contribute to a Trump account? The answer, as with most financial questions, is that it depends. Here’s a framework you might consider: Step 1: If your child was born between 2025 and 2028 and is thus eligible for the government contribution of $1,000, that is the easiest decision. I would head over to the new website today to get started. Step 2: Should you make contributions beyond the government’s initial $1,000? I would pause at this point to assess where your college savings stand. Since education is such a significant expense and since 529 accounts have the benefit of growing tax-free, I would prioritize college savings over a Trump account contribution. Step 3: The next account to consider is a custodial Roth IRA. If your children have any income, they can contribute to a Roth IRA. And since Roth balances grow tax-free too, I would also prioritize Roth contributions over Trump account contributions, where the growth will be taxable. Step 4: After addressing potential 529 and Roth IRA contributions, ordinarily the next savings option to consider would be a custodial taxable account—often referred to as an UTMA. But it’s at this point that you might consider a Trump account.  How should you think about this decision? While there are tax differences between UTMA accounts and Trump accounts, and there are differences in contribution limits, neither of those, in my view, should be the primary consideration. Instead, the question I’d ask is how you’d like the funds to be used, and on that point, there’s a big difference between an UTMA and a Trump account. Depending on the state, children can generally access funds in an UTMA at either age 18 or 21. If you feel your child would benefit from having some funds to help get established in the early years after college, then an UTMA might be the better choice. In contrast, Trump accounts are really designed to be retirement accounts, with only the handful of early withdrawal provisions referenced earlier. If you’d prefer to see your child’s savings grow for decades, then the Trump account might be the better choice. If you aren’t sure how to decide between a contribution to an UTMA and a Trump account, you could always split the difference. One reason to do that is because Trump accounts present an interesting tax planning opportunity. After the growth period, if a child has a Trump account balance, that balance would be eligible for a Roth conversion, whereby it would transfer over to a Roth IRA to grow tax-free. Of course, Roth conversions are taxable, but if a child is in a low tax bracket in the early years after college, the tax might be modest. I see that as a compelling reason to consider making at least some contributions to a Trump account.   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 »

Frittering away Frugality 

"I understand the skepticism, but there are reasons Costco works for some. Like any subscription arrangement, you have to balance the cost against savings every year for Costco (as you need to do for Amazon Prime and similar things). I have a small numbers of things I particularly like at Costco, and buy over and over for the savings - like Advil, certain breakfast cereals, Keurig pods and gas for my car. There are a handful of others. I first went there for eyeglasses - great service and much lower prices. Periodically, I buy individual things for better prices, like lawn fertilizer, printer ink, canned olives, dried mango and in the spring, plants. I don't buy much else. The eyeglasses alone saved me much more than the annual fee. Cheaper gas is always about 15-20 cents a gallon better than local stations. My gut calculations tell me I am better off each year, since I don't load up on things unnecessarily. But the Costco advantage is not a giant advantage. One thing I do notice is that Costco is also a destination for many non-profits that serve the poor. I often see people with three and four loaded carts at a time, all with essentials and no impulse item. I think that when those people load up their carts with food essentials, they should be applauded for using their contributions wisely."
- Martin McCue
Read more »

The Making of Jonathan Clements

WHEN READERS THINK of my younger brother Jonathan Clements, they often picture the longtime Wall Street Journal columnist or the founder of HumbleDollar. They remember the clear financial advice, the thoughtful essays and the quiet wisdom that helped millions make better decisions with their money. But every writer has a beginning. As I've been researching Jonathan's life over the past several weeks, I've found myself drawn less to the career everyone knows and more to the people who helped shape it. Before the books, the columns and the countless readers, there was a curious teenager discovering that he loved to write. Jonathan's journey began long before Wall Street, long before Forbes and long before HumbleDollar. It began with a school magazine at Bryanston School in Dorset, England. As a teenager, Jonathan joined the staff of Saga, the school magazine. There he wrote an article criticizing Bryanston's decision to spend money on a new pipe organ while other parts of the school needed attention. Years later, Jonathan looked back on that article with characteristic humor, saying it earned him "the enmity of a host of people." But he also said something far more revealing. That article, he believed, "was my entrée to becoming a journalist." More importantly, Jonathan had discovered not just that he enjoyed writing, but that he enjoyed asking difficult questions. Reading those early Saga articles today, what strikes me isn't simply Jonathan's talent. It's how familiar his voice already sounds. Even as a teenager, he questioned accepted wisdom with humor rather than hostility, weighed competing arguments fairly and cared deeply about priorities. Years later, readers would come to know him for helping them decide what mattered most in their financial lives. Looking back, those instincts were already there. Journalism also ran in the family. Our father began his career as a journalist before becoming an economist, and Jonathan often said his example inspired him to pursue financial journalism. After leaving Bryanston, Jonathan had almost a year before beginning his studies at Cambridge, our father's alma mater. During that time, a family friend, Mrs. Dolezal, helped him secure a reporting job at the Potomac Almanac, a small community newspaper in suburban Washington. For the next eight months, Jonathan did what young reporters often do. One day he covered education. The next, sports. Then police, then business. It wasn't glamorous work, but it taught him the fundamentals of reporting. Years later, Jonathan would describe those eight months as "the most fun and the most educational experience I had in journalism." It wasn't a large newspaper, but it gave a young reporter the opportunity to learn every aspect of the profession. Even more importantly, it introduced him to the paper's editor, Leslie Leven. Decades later, after writing for Forbes, The Wall Street Journal and founding HumbleDollar, Jonathan was asked about the people who had influenced his career. His answer surprised me. Of everyone he had worked with, he singled out Leslie, describing her as "probably the most important mentor I had." Those words say as much about Jonathan as they do about Leslie. No matter how successful he became, Jonathan never forgot the people who had believed in him before anyone else did. Cambridge came next, but by then journalism was no longer simply an interest. Jonathan later admitted that during one term he attended only four lectures because he was so immersed in editing the student newspaper, Varsity. Somewhere along the way, writing had stopped being a hobby and had become the work he wanted to spend his life doing. After Cambridge, Jonathan joined Euromoney in London, his first full-time journalism position. It was another stepping stone that eventually led him to New York and Forbes, where he discovered the world of personal finance writing. The years that followed are well known. After Forbes came nearly two decades at The Wall Street Journal, where Jonathan became one of the country's most respected personal finance columnists. He later spent six years at Citigroup as Director of Financial Education, helping investors better understand their financial lives. But the entrepreneurial spirit never left him. In 2016, he founded HumbleDollar, creating not simply another financial website, but a community built on thoughtful conversation, generosity and the belief that money is ultimately a means to a richer life, not an end in itself. Millions of readers came to trust his judgment and his remarkable ability to explain complicated ideas with clarity, humanity and compassion. Growing up, I don't think any of us could have imagined where Jonathan's curiosity and love of writing would eventually lead. He was simply my younger brother; curious, thoughtful and always eager to learn. Looking back now, the path seems almost inevitable. At the time, it was anything but. But as I've pieced together Jonathan's early years, I've come away with a different appreciation of his career. I always knew where Jonathan finished. Only recently have I begun to appreciate where, and with whom, it all began. Long before Jonathan became a mentor to countless writers and readers, someone had mentored him. A family friend opened a door. An editor patiently taught him his craft. A small community newspaper gave him a chance. We often celebrate the finished product. The successful journalist, the respected author, the trusted voice. Yet behind almost every accomplished life are people whose names are seldom remembered, people who quietly open doors, encourage talent and believe in someone long before the rest of the world notices. Jonathan never forgot them. Perhaps that's why, years later, so many aspiring writers would tell similar stories about him. He answered emails, encouraged new voices, edited with kindness and opened doors for others just as doors had once been opened for him. In the end, Jonathan's story isn't simply about becoming one of the world's most respected financial journalists. It's also about the people who quietly shaped that journey. Mrs. Dolezal opened the first door and Leslie Leven helped Jonathan find his footing as a young reporter. Those early opportunities gave him the confidence to pursue the career that followed. Every accomplished life begins somewhere. Jonathan's began with people who saw potential in a young man long before the rest of the world did.   After spending more than two decades building a successful landscaping business with his twin brother Nicholas, Andrew Clements retired in 2015 with a new appreciation for what matters most. Born in England, his essays draw on a life that has included growing up in England and Bangladesh, entrepreneurship, caregiving, family loss and travel. A regular HumbleDollar contributor, he enjoys tellingstories that remind readers life’s richest lessons often have little to do with money. Andrew is the older brother of HumbleDollar founder Jonathan Clements, whose life and legacy have inspired some of his most personal writing. He lives in Florida with his husband, Joey.
Read more »

Thinking of a possible reason to tap Roth earlier then planned

"One idea that maybe won’t work for you but might work for others is what’s called a box spread— four options trades that together result in effectively a loan against the market at close to treasury rates. I don’t think you can trade options against an IRA though, so you would need assets in a taxable account. You wouldn’t have to sell the assets in the taxable account, but you would need assets in a taxable account."
- cheitzig
Read more »

Happy 250th Birthday America

"Most of us are very thankful immigrants and Proud to be an American. Thanks for the reminder."
- William Dorner
Read more »

So Maybe That’s What It’s All About

"Dunn, it's always great to hear my amateur efforts give someone a smile 😁"
- Mark Crothers
Read more »

Reluctantly Saving Money

"William, I would definitely have been on your wife's team... working on a roof in your seventies? Definitely a hard no!"
- Mark Crothers
Read more »

Better Questions

"Mark, in the run-up to retiring, I didn't just look at my retirement spreadsheets every day—I practically lived in them. I was opening them multiple times a day, obsessively tweaking variables and micro-managing scenario tabs like a man possessed. Yet, since finally stepping away in March 2025, I can count on one hand the number of times I’ve actually launched Excel. Once I finally crossed the finish line, the urge to stress-test my life every twenty minutes completely evaporated. These days, Claudia AI has basically replaced Google as my go-to query engine for whatever random topic pops into my head. In fact, I occasionally suffer a wave of modern guilt, wondering just how much grid energy I’m burning through just to get an instant, deeply detailed answer to some of the most beautifully inane questions imaginable."
- Mark Crothers
Read more »

About that inflation in retirement

"Jack (and the original recommender), thanks for the link to Advisor Perspectives and the Bernstein/McQuarrie article. Another one I enjoyed by the same two gents is this one: The Many Utilities of Retirement - Articles - Advisor Perspectives"
- Andrew Forsythe
Read more »

Don’t Let a Roth Conversion Trigger a Penalty

"Grant - Thanks for the reply. If I understand your process correctly, my observation would be: The Step 2 distribution came out of a Traditional IRA. Roll it back into a Traditional within 60 days with brokerage cash and it's a tax-free wash. Roll it into the Roth instead and it's a Roth conversion, fully taxable, because you've moved Traditional money into a Roth. So the "tax money" doesn't pay the tax. It becomes an extra conversion equal to the tax, which means a $100,000 conversion you thought you did is actually $130,000. And that overshoot is the whole risk: if you sized the $100k to stay under a bracket or IRMAA threshold, the real $130k blows through it."
- John Urban
Read more »

A taxing situation, but is it reality?

"I would have to agree that in my experience with Medicare some years ago on my parent's behalf, I found it surprisingly easy to deal with. On a more limited basis same with Social Security for them. That does not automatically make them efficient by default however in order to provide that level of service. All that said, your article is not about Social Security or Medicare, it is about taxes and only one (federal) portion of the broader tax load picture at that. When you focus an article on taxes, all aspects of government efficiency with the public's funds are fair game when contemplating more taxes. S.S. and Medicare are but two pixels in a much broader picture of morbid mediocrity. Reference corporations: you highlight two positives: 1) the ability to right size private sector organizations to changing business conditions or enhanced technology or LEAN based efficiencies (or maybe correct inefficiency that set in through poor management and needs to be cleaned up) ....without having to go to the Supreme Court to do it. 2) For businesses that fail due to inefficiency or not evolving fast enough, natural selection culls the herd- healthy for the overall economy. Not so with government agencies.....unfortunately- unhealthy for the overall economy."
- Dunn Werking
Read more »

Haunted Head

"Martin, that about sums it up for me as well. I do find preparing taxes for AARP to be deserving of my time. Chrissy volunteers at a cat rescue, which helps in getting cats spayed or neutered, and off the streets. I’m sure I could find other worthy assignments, but I’m pretty happy with my level of involvement. "
- Dan Smith
Read more »

Trump Accounts

INNOVATION IN THE world of retirement plans is decidedly slow moving. But as of July 4th, investors now have a new savings option known as a Trump account. In short, these are retirement accounts designed specifically for children. Trump accounts share some similarities with traditional individual retirement accounts (IRAs), but there are also key differences. If you have children, grandchildren, nieces or nephews, this new option may be worth exploring. Who is eligible for a Trump account? An account can be opened for any child who will be under 18 as of December 31 in the year that the account is opened. How are Trump accounts different from traditional IRAs? The primary goal of these accounts is to allow children to begin to accumulate retirement funds much earlier than has been possible in the past. For that reason, and in contrast to traditional IRAs, Trump accounts don’t require a child to have any earned income. Contributions could begin as soon as a baby is born.  What is the process for opening an account? To get started, head to the new government website at trumpaccounts.gov. From there, you can download a mobile app to start the account opening process. I tried it myself, opening an account for one of my sons, and found the process quite easy. One nice feature is that the funds are invested automatically in low-cost index funds. What are the contribution limits? Trump accounts have their own unique contribution caps, which are a little complicated. Individuals and employers can contribute up to a total of $5,000 per child per year, though the employer portion is limited to $2,500 of that $5,000. This limit will grow in future years. In addition, the government and a group of philanthropists have established a pilot program and are making contributions to certain new Trump accounts. Children born between January 1, 2025 and December 31, 2028 are eligible to receive a $1,000 contribution from the government upon opening a new account. In addition to this $1,000 contribution from the government, a group of philanthropists, including Michael Dell, Ray Dalio and others, are contributing $250 to Trump accounts for children up to 10 years old who live in particular Zip codes. These additional contributions don’t count toward the $5,000 annual contribution limit. Do Trump account contributions affect IRA contribution limits? If your child has earned income, he or she can contribute the maximum to a Trump account and still also contribute to a regular IRA or Roth IRA up to the annual IRA contribution limit. There’s no tradeoff. How are withdrawals treated? Withdrawals from Trump accounts aren’t permitted during the initial “growth period,” which begins at birth and ends on December 31 of the year before the child turns 18.  After the growth period, withdrawals from Trump accounts will be treated in much the same way as traditional IRAs. Specifically, withdrawals prior to age 59½ are subject to a 10% tax penalty. Trump accounts do, however, allow for penalty-free withdrawals before 59½ under certain circumstances, including a first-time home purchase, higher education and a few other, less common situations. The tax treatment of withdrawals differs by donor: Contributions by individuals are made on an after-tax basis, so those dollars come out tax-free. Investment gains on those contributions, however, are subject to ordinary income tax. Any dollars received from the government or other donors under the pilot program will also be subject to ordinary income tax. Should you contribute to a Trump account? The answer, as with most financial questions, is that it depends. Here’s a framework you might consider: Step 1: If your child was born between 2025 and 2028 and is thus eligible for the government contribution of $1,000, that is the easiest decision. I would head over to the new website today to get started. Step 2: Should you make contributions beyond the government’s initial $1,000? I would pause at this point to assess where your college savings stand. Since education is such a significant expense and since 529 accounts have the benefit of growing tax-free, I would prioritize college savings over a Trump account contribution. Step 3: The next account to consider is a custodial Roth IRA. If your children have any income, they can contribute to a Roth IRA. And since Roth balances grow tax-free too, I would also prioritize Roth contributions over Trump account contributions, where the growth will be taxable. Step 4: After addressing potential 529 and Roth IRA contributions, ordinarily the next savings option to consider would be a custodial taxable account—often referred to as an UTMA. But it’s at this point that you might consider a Trump account.  How should you think about this decision? While there are tax differences between UTMA accounts and Trump accounts, and there are differences in contribution limits, neither of those, in my view, should be the primary consideration. Instead, the question I’d ask is how you’d like the funds to be used, and on that point, there’s a big difference between an UTMA and a Trump account. Depending on the state, children can generally access funds in an UTMA at either age 18 or 21. If you feel your child would benefit from having some funds to help get established in the early years after college, then an UTMA might be the better choice. In contrast, Trump accounts are really designed to be retirement accounts, with only the handful of early withdrawal provisions referenced earlier. If you’d prefer to see your child’s savings grow for decades, then the Trump account might be the better choice. If you aren’t sure how to decide between a contribution to an UTMA and a Trump account, you could always split the difference. One reason to do that is because Trump accounts present an interesting tax planning opportunity. After the growth period, if a child has a Trump account balance, that balance would be eligible for a Roth conversion, whereby it would transfer over to a Roth IRA to grow tax-free. Of course, Roth conversions are taxable, but if a child is in a low tax bracket in the early years after college, the tax might be modest. I see that as a compelling reason to consider making at least some contributions to a Trump account.   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 »

Frittering away Frugality 

"I understand the skepticism, but there are reasons Costco works for some. Like any subscription arrangement, you have to balance the cost against savings every year for Costco (as you need to do for Amazon Prime and similar things). I have a small numbers of things I particularly like at Costco, and buy over and over for the savings - like Advil, certain breakfast cereals, Keurig pods and gas for my car. There are a handful of others. I first went there for eyeglasses - great service and much lower prices. Periodically, I buy individual things for better prices, like lawn fertilizer, printer ink, canned olives, dried mango and in the spring, plants. I don't buy much else. The eyeglasses alone saved me much more than the annual fee. Cheaper gas is always about 15-20 cents a gallon better than local stations. My gut calculations tell me I am better off each year, since I don't load up on things unnecessarily. But the Costco advantage is not a giant advantage. One thing I do notice is that Costco is also a destination for many non-profits that serve the poor. I often see people with three and four loaded carts at a time, all with essentials and no impulse item. I think that when those people load up their carts with food essentials, they should be applauded for using their contributions wisely."
- Martin McCue
Read more »

The Making of Jonathan Clements

WHEN READERS THINK of my younger brother Jonathan Clements, they often picture the longtime Wall Street Journal columnist or the founder of HumbleDollar. They remember the clear financial advice, the thoughtful essays and the quiet wisdom that helped millions make better decisions with their money. But every writer has a beginning. As I've been researching Jonathan's life over the past several weeks, I've found myself drawn less to the career everyone knows and more to the people who helped shape it. Before the books, the columns and the countless readers, there was a curious teenager discovering that he loved to write. Jonathan's journey began long before Wall Street, long before Forbes and long before HumbleDollar. It began with a school magazine at Bryanston School in Dorset, England. As a teenager, Jonathan joined the staff of Saga, the school magazine. There he wrote an article criticizing Bryanston's decision to spend money on a new pipe organ while other parts of the school needed attention. Years later, Jonathan looked back on that article with characteristic humor, saying it earned him "the enmity of a host of people." But he also said something far more revealing. That article, he believed, "was my entrée to becoming a journalist." More importantly, Jonathan had discovered not just that he enjoyed writing, but that he enjoyed asking difficult questions. Reading those early Saga articles today, what strikes me isn't simply Jonathan's talent. It's how familiar his voice already sounds. Even as a teenager, he questioned accepted wisdom with humor rather than hostility, weighed competing arguments fairly and cared deeply about priorities. Years later, readers would come to know him for helping them decide what mattered most in their financial lives. Looking back, those instincts were already there. Journalism also ran in the family. Our father began his career as a journalist before becoming an economist, and Jonathan often said his example inspired him to pursue financial journalism. After leaving Bryanston, Jonathan had almost a year before beginning his studies at Cambridge, our father's alma mater. During that time, a family friend, Mrs. Dolezal, helped him secure a reporting job at the Potomac Almanac, a small community newspaper in suburban Washington. For the next eight months, Jonathan did what young reporters often do. One day he covered education. The next, sports. Then police, then business. It wasn't glamorous work, but it taught him the fundamentals of reporting. Years later, Jonathan would describe those eight months as "the most fun and the most educational experience I had in journalism." It wasn't a large newspaper, but it gave a young reporter the opportunity to learn every aspect of the profession. Even more importantly, it introduced him to the paper's editor, Leslie Leven. Decades later, after writing for Forbes, The Wall Street Journal and founding HumbleDollar, Jonathan was asked about the people who had influenced his career. His answer surprised me. Of everyone he had worked with, he singled out Leslie, describing her as "probably the most important mentor I had." Those words say as much about Jonathan as they do about Leslie. No matter how successful he became, Jonathan never forgot the people who had believed in him before anyone else did. Cambridge came next, but by then journalism was no longer simply an interest. Jonathan later admitted that during one term he attended only four lectures because he was so immersed in editing the student newspaper, Varsity. Somewhere along the way, writing had stopped being a hobby and had become the work he wanted to spend his life doing. After Cambridge, Jonathan joined Euromoney in London, his first full-time journalism position. It was another stepping stone that eventually led him to New York and Forbes, where he discovered the world of personal finance writing. The years that followed are well known. After Forbes came nearly two decades at The Wall Street Journal, where Jonathan became one of the country's most respected personal finance columnists. He later spent six years at Citigroup as Director of Financial Education, helping investors better understand their financial lives. But the entrepreneurial spirit never left him. In 2016, he founded HumbleDollar, creating not simply another financial website, but a community built on thoughtful conversation, generosity and the belief that money is ultimately a means to a richer life, not an end in itself. Millions of readers came to trust his judgment and his remarkable ability to explain complicated ideas with clarity, humanity and compassion. Growing up, I don't think any of us could have imagined where Jonathan's curiosity and love of writing would eventually lead. He was simply my younger brother; curious, thoughtful and always eager to learn. Looking back now, the path seems almost inevitable. At the time, it was anything but. But as I've pieced together Jonathan's early years, I've come away with a different appreciation of his career. I always knew where Jonathan finished. Only recently have I begun to appreciate where, and with whom, it all began. Long before Jonathan became a mentor to countless writers and readers, someone had mentored him. A family friend opened a door. An editor patiently taught him his craft. A small community newspaper gave him a chance. We often celebrate the finished product. The successful journalist, the respected author, the trusted voice. Yet behind almost every accomplished life are people whose names are seldom remembered, people who quietly open doors, encourage talent and believe in someone long before the rest of the world notices. Jonathan never forgot them. Perhaps that's why, years later, so many aspiring writers would tell similar stories about him. He answered emails, encouraged new voices, edited with kindness and opened doors for others just as doors had once been opened for him. In the end, Jonathan's story isn't simply about becoming one of the world's most respected financial journalists. It's also about the people who quietly shaped that journey. Mrs. Dolezal opened the first door and Leslie Leven helped Jonathan find his footing as a young reporter. Those early opportunities gave him the confidence to pursue the career that followed. Every accomplished life begins somewhere. Jonathan's began with people who saw potential in a young man long before the rest of the world did.   After spending more than two decades building a successful landscaping business with his twin brother Nicholas, Andrew Clements retired in 2015 with a new appreciation for what matters most. Born in England, his essays draw on a life that has included growing up in England and Bangladesh, entrepreneurship, caregiving, family loss and travel. A regular HumbleDollar contributor, he enjoys tellingstories that remind readers life’s richest lessons often have little to do with money. Andrew is the older brother of HumbleDollar founder Jonathan Clements, whose life and legacy have inspired some of his most personal writing. He lives in Florida with his husband, Joey.
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Manifesto

NO. 5: WE CAN’T stop misfortune from befalling us—but we can limit the fallout by keeping emergency money, living below our means, taking on debt cautiously and buying the right insurance.

Truths

NO. 113: ACADEMICS talk about the risk-free rate—the investment return you can earn without taking any risk—and they usually point to Treasury bonds. But for you, the risk-free rate may be the sum charged by the highest-cost debt you have. Got credit card debt that's costing you 20%? That’s the risk-free rate you can earn by paying down that debt.

act

VISUALIZE YOUR goals. Daydream about the vacation cottage, new car, remodeled kitchen and what you’ll do in retirement. Why? It will make you more motivated to save and you’ll enjoy the pleasure of anticipation. It’ll also give you a chance to ponder your goals in greater detail—and you might discover, on second thought, that some aren’t so enticing.

Truths

NO. 66: TWENTY STOCKS aren’t enough. One rule says you need 20 individual stocks to be diversified. With that many, your portfolio's volatility won't be much greater than the broad market's. Problem is, you might still earn returns that differ radically from the market averages. To avoid this tracking error, you need to own hundreds of stocks.

Our favorite investment: index funds

Manifesto

NO. 5: WE CAN’T stop misfortune from befalling us—but we can limit the fallout by keeping emergency money, living below our means, taking on debt cautiously and buying the right insurance.

Spotlight: College

The Places You’ll Go

MY TWIN DAUGHTERS just finished sorting through college offers and making their decision ahead of the May 1 acceptance deadline. With nearly 3,000 four-year colleges to choose from, how did they decide?
It wasn’t easy. The pandemic didn’t just close our local public schools. It also ended visits from universities and limited school-based college counseling. Counselors compensated with lunchtime workshops, links to webinars, and lots of robocalls and emails urging students to fill out and submit the Free Application for Federal Student Aid (FAFSA).

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A 529 for Sophia

OVER CHRISTMAS, I got the sort of question I love to answer. My daughter’s thoughtful boyfriend had set aside some money for his niece’s college education. What was the best way to invest it?
I said that we’d paid for much of our children’s education with money invested in 529 college savings plans. The investment gains went untaxed because we’d spent the money on tuition, room and board. On top of that, our 529 contributions were deductible against our state-income tax in Pennsylvania,

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Think of the Children

WE PUT OUR TWO KIDS through college using 529 plans—and I estimate the accounts easily added 10% to the value of our college savings, compared to what we would have accumulated if we’d invested through a regular taxable account. Yet only 37% of families use 529s to help pay for college, according to a 2021 survey by Sallie Mae.
Like an IRA, a 529 plan gives you a tax break for saving for a specific goal—but,

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What’s the Price?

DRIVE TO HOSPITAL. Cut the umbilical cord. Figure out names. Open a 529.
While the primary focus upon our two babies’ births was bonding, I had another item to check off: I opened a 529 college savings account for each one within a month of their births.
It’s paid off handsomely. Through automatic monthly contributions—plus stellar market performance over the past decade—they’ve amassed sizable balances for higher education. One child now is in high school,

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The Student Trap

NOT ALL DEBT IS created equal—and that’s especially true when it comes to student loans.
For the vast majority of debt, we can calculate the ongoing monthly payment if we know the interest rate, number of payment periods, current balance and if the payment is due at the beginning or end of the period. But for federal student loans, we may need to know one more variable: the borrower’s discretionary income.
With federal student loans,

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College Crapshoot

A LIFE OF FRUGALITY might mean your children graduate college debt-free, which is a major accomplishment. But what about your happy-go-lucky neighbors, who spent every dime they earned and never saved for college?
At issue here is the Free Application for Federal Student Aid (FAFSA), which is the basis for the all-important expected family contribution (EFC). The whole thing can seem like one big crapshoot, as I can now attest.
The EFC may determine that your spendthrift neighbors’ kids also get to graduate debt-free.

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Spotlight: Gartland

Mind Games

IN MY ENGLISH CLASS in junior high school, we read a play called I Remember Mama. It was a story about a poor Norwegian immigrant family living in San Francisco in the early 1900s. The mother ran the household while her husband went to work and the children went to school. The mother was in charge of the family’s finances. Any time a family member needed extra money, he or she would have to ask Mama for it. She’d listen to the request and, if it was critical, she’d get the money from the petty cash fund. If there wasn’t enough petty cash, she’d ask the person if it was important enough to justify withdrawing money from the bank. Upon further review, the person would say it wasn’t. The big surprise: As we learn at the end of the play, there was no bank account. Instead of saying, “we can’t afford it,” Mama wanted family members to decide on their own that the item wasn’t important. This would allow them to save face and not feel poor. They squelched the desire themselves and moved on. My mother-in-law would tell me of her upbringing in New York City. Her parents were Chilean immigrants who didn’t have a lot of money. They raised their six kids on her father’s salary. They were poor, but so was everybody else in the neighborhood, so they never thought of themselves as poor. My mother-in-law’s life was just like the characters in the play. With money so tight, she constantly had to decide that some purchases just weren’t important. A digression: Two famous actors came from the neighborhood. When they were kids, Lauren Bacall and Burt Lancaster were friends with my mother-in-law’s siblings. What I found most interesting about I Remember Mama: Because family members believed…
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It’s Only Money

MY FATHER DIED WHEN I was 15 years old. My mother didn’t work outside the house, so we now had no money coming in. She eventually got a job as a receptionist in the local hospital’s X-ray department, but she only worked weekends and holidays. Meanwhile, by then, my older brother was married and out of the house, so he wasn’t affected by this change in our family’s financial circumstances. As I saw it, no money coming in—or relatively little—meant poverty, and I considered us poor. I didn’t want to live in poverty, so wealth became my overriding goal. But my view of our family’s financial circumstances wasn’t shared by my mother or brother. While my mother often used the phrase “we can’t afford that,” she didn’t mean that we had no money and she didn’t behave as though we were poor. Rather, she just didn’t want to spend money on the item in question. It wasn’t until years later that I found out why my mother and brother didn’t consider us poor. As it turns out, my father had purchased a group life insurance policy with a $500,000 death benefit. Why was this kept from me? I don’t know, but it was. Through my teenage and early adult years, I felt I needed to help out as best I could. I got part-time jobs in high school and college. My goal was to never be a financial burden to my mother. Fast forward to 2007. My mother died. My brother and I were co-executors and co-beneficiaries of my mother’s estate. My status as executor was only established two years earlier, when my brother had my mother’s will rewritten while she was in the hospital. At the time of my mother’s death, my 64-year-old brother, his 63-year-old wife and his…
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Back to Life

SOME PEOPLE CAN LOOK at a blank page and imagine a new creation—perhaps a new business or a new house. I can’t. What I seem to be pretty good at is taking something that’s broken and coming up with creative solutions for fixing it. It's like a game or a puzzle. The goal: Bring this broken object back to life as cheaply as possible. When, say, a washing machine or a dishwasher breaks, the repair person will look up the manufacturer and order the necessary replacement part. The repair person will install the part, and charge you for labor, plus a marked-up price for the part. Most folks are accustomed to this, and view the expense as the cost of doing business. I see it differently. The manufacturer’s parts are designed to fit the original product, but that fit comes at a premium price. Suppose a part breaks on your Ford SUV or pickup truck. Yes, you could go to a Ford dealership. But what most people don’t understand is the dealership makes its largest profit not on the sale of a vehicle, but from servicing it. When something needs repairing, the dealership only installs original equipment manufacturer (OEM) parts and it charges high hourly labor rates. Folks who go this route soon start complaining about how expensive it is to keep their vehicle running, so they elect to buy a new one. That means not only a new auto loan, but also an incentive to get the new vehicle serviced at the dealership, so they don’t void the warranty. It’s a nice racket for the dealer. Instead of OEM parts, there are aftermarket parts sold at places like Advance Auto Parts, AutoZone, NAPA and O’Reilly. Typically, they’re much cheaper than OEM parts and, in most cases, the aftermarket part…
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The Simple Life

WHEN I STARTED learning about investing, I stumbled upon a book at my library that immediately grabbed my attention: The Lazy Person’s Guide to Investing by Paul B. Farrell. A portfolio championed by the book consisted of just two mutual funds—one stock index fund and one bond index fund, with 50% of your portfolio invested in each. With only two choices to make, decision-making becomes far more straightforward. Farrell's suggested 50-50 split simplifies the process even further. The strategy underscores the beauty of simplicity—a lesson I took to heart. Why complicate matters with additional funds if just two could suffice? Diversification is a popular investment strategy. But how many funds do you truly need? Do you need exposure to private equity, gold, real estate? The options seem endless. But perhaps less is more. For some investors, constantly tweaking their portfolio is comforting. The activity gives them peace of mind. For them, tweaking and touching and buying and selling is a wonderful way to live. Doing something feels better than doing nothing. Yet a landmark paper, based on Schwab trading data, suggests the more people trade, the lower their investment returns. Often, the stocks they sell perform better than the new ones they buy. That’s why Vanguard Group founder Jack Bogle used to advise investors, “Don’t just do something—stand there.” All this strongly suggests that investors could benefit by doing less. Frequent trading may reflect overconfidence in our investment expertise. It reminds me of the scene in The Wizard of Oz when Judy Garland and crew drew back the curtain to reveal the Wizard. He’s just an ordinary man, busily pulling on different levers to make impressive sound effects. My “simplicity is best” approach applies to more than just my investments. My wife and I approach retirement differently. She fills her…
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Special Care Needed

FATHERHOOD WASN'T one of my life goals. I didn’t feel like I had a wonderful childhood, so I didn’t think I had much to offer my offspring that would help them to lead a wonderful life. If children happened, okay, but it was never a goal. My first marriage ended because I placed money over fatherhood. I thought not having kids would speed my path to wealth. My wife disagreed—and walked out. When I met my current wife, I thought about the whole kids thing again. This time, I decided a life without children might not be so great. Unfortunately, having a family was easier said than done. My wife suffered numerous miscarriages. Finally, we found a fertility specialist who got the job done. My son was born and we were off to the races—or so we thought. Our pediatrician noted that our son wasn’t walking as soon as he should. She suggested a neurologist. A neurologist? What’s his brain got to do with his feet?  The neurologist discovered the first of many issues with our son. The good news: This was early on. As more issues arose, we were mentally prepared. I handled the financial end of things. My wife became the primary caregiver. My goal for my son was for him eventually to have a job. I saw that as the first step on the road to independence. His public school education was in self-contained classes, not mainstream with all the “typical” students. Typical is the term used, not normal. Do you know what a normal teenager is? I don’t. They’re all weird. During his high school years, which continued until he was 21, my son spent time "job shadowing" at local businesses. I assumed one of his employers would recognize his brilliance and give my son a…
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Aiming High

MY WIFE NEEDED KNEE replacement surgery a few years ago. Her health plan, which was provided through the school district where she worked, was a preferred provider organization with a large network of doctors. After some research, my wife decided she wanted her operation done at New York City’s Hospital for Special Surgery. I love hearing about people's lives. I’ve long read biographies to learn how others gained their fame or fortune, hoping for pointers that would help me with my own life. I also pepper people with questions about their background. When we met my wife’s surgeon, I knew he’d graduated from Princeton University, which is near where we live. But I wanted to know more. I asked him what his major was. When I found out, I was surprised. “Art history? That’s a big leap to orthopedic surgery.” “My father knew that I’d have to work hard in medical school, so he wanted me to enjoy my undergraduate years.” “Did you know where you were going to med school?” I asked. The surgeon’s response: His father had graduated from Columbia University’s medical school, and he’d make sure his son got in. Early in my career, a manager once told me that “rank has privileges.” The rich have always enjoyed benefits that elude others. Clearly, my wife’s surgeon was part of the 1%, getting the benefit of an Ivy League education, plus guaranteed entrance to medical school. It must be nice. Knowing what the 1% have can either inspire us or defeat us. In his book The Magic of Thinking Big, David J. Schwartz makes the argument that the higher you aim, the higher your final landing spot will be. I’ve always wanted to be rich. Did I get it all? No. But my lofty goal meant I probably…
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