FREE NEWSLETTER

Financial danger sign: Your broker saves you money by only recommending funds with “no initial sales commission.”

Latest PostsAll Discussions »

Better Questions

"Mark, all this talk of spreadsheets is going to blow RDQ’s brain apart!  Seriously, knowing the right questions to ask is important in all aspects of life. Being honest with yourself when answering the questions is important as well. Sounds like AI provided good direction for you. I often use AI when researching a topic. It’s a bit unnerving when AI engages me in a conversation, as if I were talking to a real person. AI even makes references to my HumbleDollar posts, (at least someone is reading them).  Thanks for a thought provoking post. "
- 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 »

So Maybe That’s What It’s All About

"Mark, my choir and I will be singing our way around Ireland next June. We'll be performing in cathedrals and meetinghouses (and no doubt a pub or two), not cow fields, but hey, anywhere you can find an audience, right?"
- Mike Gaynes
Read more »

Haunted Head

"I'd love to donate more of my time, but I don't want anything close to a mandated schedule or a place I need to be on time. The non-profits in my area mostly don't impress me. I keep looking around, but I'm not going to jump into something unless I deeply feel the merit."
- Martin McCue
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 »

A taxing situation, but is it reality?

"That gets us back to your main point (here and in other articles). The US has a progressive tax and health care system - mostly. Tax rates increase with income. Medicare costs increase with income / wealth withdrawals from retirement accounts. We don't have great healthcare options for younger people who aren't covered by work-sponsored insurance or who qualify for an assistance program of some sort. If this was the result of a reasoned policy debate or election results, we'd say that's our choice v. Europe's choice. Sadly, the general sense from HD readers is that our tax / health system has been cobbled together over years without much thought. We just deal with the results."
- Mike inLA
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 »

Don’t Let a Roth Conversion Trigger a Penalty

"For the past several years I have made quarterly withdrawls for slightly more than our tax liability from an inherited IRA, for more than the RMD of the deceased, and 100% going to the IRS. This account will run dry this year so will have to consider a new tactic next year. PS a comment from Michael1 I read after posting this is to use 100% of my small pension to cover the bulk of my tax liability. THIS IS WHY HUMBLE DOLLAR IS SO GREAT!"
- DavidHLancaster
Read more »

About that inflation in retirement

"I follow this issue very closely and the only thing I see is growing talk about raising or eliminating the taxable wage cap which does not actually fix the problem and is just a popular way to push the burden onto about 6% of worker who earn above the current cap. Because of the anti-tax sentiment and the false narrative that eliminating “fraud” will be a fix, you can’t expect anything to be done in the next three years. My greatest fear are fixes that cause us to deviate from the original design of the program such as using general revenue or capping the benefit or taxing earnings that are not counted in the benefit calculation. Nobody seems to have the guts to tell Americans the truth. I read every day where people are convinced all would be well if Congress had not “stolen” the funds, not paid interest and didn’t give the money back- all of which is rubbish. SS has been funded the same with the accounting trust way since 1939. Here is a good example on what people believe https://quinnscommentary.net/2026/07/12/do-the-math/ I hear people say they paid taxes all their working lives and now want to know where the money went not having a clue how the system works or that their taxes paid the previous generations benefits."
- R Quinn
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 »

Every Writer Has a Beginning: Organ Transplant Fails

"Thanks Andrew for these wonderful tidbits about Jonathan. We treasure your brother, and all his wonderful wisdom."
- William Dorner
Read more »

Better Questions

"Mark, all this talk of spreadsheets is going to blow RDQ’s brain apart!  Seriously, knowing the right questions to ask is important in all aspects of life. Being honest with yourself when answering the questions is important as well. Sounds like AI provided good direction for you. I often use AI when researching a topic. It’s a bit unnerving when AI engages me in a conversation, as if I were talking to a real person. AI even makes references to my HumbleDollar posts, (at least someone is reading them).  Thanks for a thought provoking post. "
- 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 »

So Maybe That’s What It’s All About

"Mark, my choir and I will be singing our way around Ireland next June. We'll be performing in cathedrals and meetinghouses (and no doubt a pub or two), not cow fields, but hey, anywhere you can find an audience, right?"
- Mike Gaynes
Read more »

Haunted Head

"I'd love to donate more of my time, but I don't want anything close to a mandated schedule or a place I need to be on time. The non-profits in my area mostly don't impress me. I keep looking around, but I'm not going to jump into something unless I deeply feel the merit."
- Martin McCue
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 »

A taxing situation, but is it reality?

"That gets us back to your main point (here and in other articles). The US has a progressive tax and health care system - mostly. Tax rates increase with income. Medicare costs increase with income / wealth withdrawals from retirement accounts. We don't have great healthcare options for younger people who aren't covered by work-sponsored insurance or who qualify for an assistance program of some sort. If this was the result of a reasoned policy debate or election results, we'd say that's our choice v. Europe's choice. Sadly, the general sense from HD readers is that our tax / health system has been cobbled together over years without much thought. We just deal with the results."
- Mike inLA
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 »

Don’t Let a Roth Conversion Trigger a Penalty

"For the past several years I have made quarterly withdrawls for slightly more than our tax liability from an inherited IRA, for more than the RMD of the deceased, and 100% going to the IRS. This account will run dry this year so will have to consider a new tactic next year. PS a comment from Michael1 I read after posting this is to use 100% of my small pension to cover the bulk of my tax liability. THIS IS WHY HUMBLE DOLLAR IS SO GREAT!"
- DavidHLancaster
Read more »

Free Newsletter

Get Educated

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

Falling Short

I SERVED ON a scholarship committee for a local foundation. We offered awards to college students entering their sophomore year. Our coordinator had the unhappy job of explaining to some students and parents that, even though their students had a full freshman schedule and passed all their classes, they didn’t actually have sophomore standing. How can this be? The answer is remediation.
Almost 24% of entering college freshmen at Ohio universities required remediation in English or math and 6% needed both.

Read more »

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).

Read more »

Ranking Colleges

I’VE TAUGHT BEHAVIORAL economics, which holds that even our most important decisions are influenced by unrecognized biases. For my students, there’s no better example than the choice of where they went to college.
Although the cost is enormous, the decision of where to go hinges on the smallest things. A teenager who says, “I want to be close to my boyfriend,” will zero in on a nearby college, even if her high school romance is fading.

Read more »

An Educated Choice

WHEN I WAS YOUNG and unschooled about money, I borrowed thousands of dollars to attend Northwestern University. As I recall, tuition was around $12,000 a year in 1980, and I had only $3,000 to my name. How could I pay?
The dean sent me a letter explaining that the college would lend me the money for my master’s degree in journalism. It would also extend me a work-study job, which would help pay for my spartan off-campus room.

Read more »

A+ for Effort

WE HAVE A PROBLEM: We may have saved too much for our daughter’s college education.
My wife and I started contributing aggressively to our daughter’s 529 college savings account as soon as she was born. For the first two years, we invested the full amount of the annual gift-tax exclusion, which was then $14,000. Now, the exclusion is at $16,000, but lately we haven’t been saving as much as we used to. The reason: Our early aggressive saving,

Read more »

Are top private colleges worth the cost?

Read more »

Spotlight: Kondrack

A Tax Filing Conundrum

https://www.wsj.com/articles/beware-of-e-filing-your-tax-return-legal-trouble-for-error-privacy-risk-cyberattack-96d31111?mod=e2tw I am not advocating for either method of filing your taxes but everyone who files their own taxes should be aware of the information contained in the above referenced article.
Read more »

The Envelope Returns

HAVE YOU HEARD of the latest budgeting technique? It’s called cash stuffing. No, it’s not shoving money into your mattress. It’s the new name for an old budgeting method, where you divide your weekly pay into envelopes earmarked for various spending categories, such as food, gas, rent, vacations, clothing and so on. For each expense, you spend only from that envelope and, when it’s empty, that’s it. No cheating. No dipping into other envelopes. I’m sure you get the idea. After all, this isn’t a new phenomenon. I remember my parents sitting around the kitchen table, apportioning the family salary into various envelopes that they’d carefully budgeted money for. My father had one marked “house money”—a catch-all for food and miscellaneous small expenditures related to running our household. This time around, cash stuffing has sprouted into a popular industry. You can buy all manner of envelope sets, such as envelopes of different colors for different categories. There’s a budget planner binder and even a genuine leather all-in-one deluxe version for $89. The more you spend on these organizers, the more sophisticated and supposedly inclusive the binder, with all manner of compartments and zippered pouches. You can get them personalized, glamorized and customized. We’re now offered cash-stuffing budget sheet planners, stickers and even tear-resistant envelopes—on and on, ad infinitum. You can purchase a plethora of these must-haves on the Amazon and Walmart websites. The market for products relating to cash stuffing seems to still be in its infancy. Soon, an even more amazing variety of items will no doubt be available. You get it, don’t you? You have to spend money to budget money. Oh—and some sellers have renamed the cash envelopes “currency envelopes.” Fancy schmancy. Before long, we’ll need a new budget envelope to pay for all our cash-stuffing supplies.…
Read more »

Other People’s Stuff

MOST OF US HAVE TOO much stuff, and we’re apt to joke about it. But clutter, if allowed to spiral out of control, can turn into hoarding. Hoarders are people who acquire an excessive number of items, some with little or no value, and yet they continue to add to their chaotic overflow. Unable to manage the clutter but unwilling to let any of it go, they become upset and anxious when others offer to help clear it up. The result is debilitating clutter. It’s estimated that there are some 19 million people in the U.S. who are hoarders. The majority are age 55 and up. It’s hard to arrive at an accurate figure, however, because hoarders are secretive about their habits, usually live alone and don’t invite people into their homes. The exact cause of hoarding is unknown. While hoarding can be triggered by a traumatic event, not everyone who experiences trauma becomes a hoarder. Family history can also be a factor. Initially, it was thought to be connected to OCD—obsessive-compulsive disorder. But recent studies reveal that it may be a disorder all its own, and possibly linked to a form of dementia. I think that, as we age, we experience loss in many ways—diminished hearing, eyesight, loss of teeth, hair, mobility, cognitive abilities and so on. Maybe we react by trying to hold on to as much as we can for as long as we can. Throughout history, there have been extreme hoarders. Perhaps the two most infamous examples are the Collyer brothers, Homer and Langley, of New York City. Born into a wealthy family, they were graduates of Columbia University. Homer was a lawyer, while Langley studied engineering and was a concert pianist. They lived in a four-story brownstone mansion in Manhattan. But they devolved into hermits and…
Read more »

Not What We Planned

MY HUSBAND WAS STILL working at age 65 when he went into heart failure. After heart surgery, he wanted to return to his job as the warranty administrator at a large New Jersey auto dealership. But we worried that the commute would be too taxing. He traveled 55 miles each way to and from his job, and it could take hours and be treacherous when the weather was bad. When additional complications ensued from the surgery, we decided it was time. As many others can attest, we don’t always get to choose when we retire. Sometimes, the time is decided for us by circumstances over which we have no control. My husband and I didn’t have everything in place for the retirement we wanted. Still, our nest egg was sufficient. We knew we’d be fine because of prudent planning throughout our marriage. I had already retired five years earlier to care for my mother, and was receiving Social Security benefits. When my husband reached his full retirement age, he filed for Social Security spousal benefits based on my earnings record, taking advantage of a now-disallowed strategy known as “file and suspend.” Later, at age 70, he filed for benefits based on his own earnings record—a benefit that was larger thanks to the delayed retirement credits he’d earned in the meantime. I was covered under my husband’s health insurance while he was working. But with his sudden retirement, we both needed to get coverage through Medicare, including purchasing Medigap insurance. Don’t skimp on this. Good health care coverage—along with sufficient savings—are essential to your peace of mind and well-being in retirement. One wrinkle in our plan: What would be our primary source of income? There were no large balances in either our Roth or traditional IRAs. At the time, there was…
Read more »

The Ties That Bind

This post explores another aspect of Dr. Lefty’s exceptional article of July 10, 2025, “Estrangements and Estates”.  Specifically that of Reconciliation. People are just beginning to talk about estrangement even though one out of four families —or 30% of American families have an estranged member, as cited in Dr. Lefty’s article.  That’s a pretty big number. When someone severs ties, it’s not about a day that went wrong, or even one event that happened. It’s an accumulation of things that  pile up and fester, and some trivial misunderstanding that no one even remembers can trigger an estrangement. There are many reasons for an estrangement.  I think we can agree that toxic relationships might include drug abuse, violence, mental health issues, involvement in unlawful activities and so on.  But there are other intolerable situations such as certain personality disorders that can drive a person to put an end to the relationship. Difficult childhood histories, abusive parenting—These get carried over into adulthood. Now, unfortunately, we also have polarizing political views. Business deals gone wrong or loans un-repaid are also archetypal.  The list goes on. If reconciliation is your goal, both parties may have to settle for a different relationship. You can go home again but it may well be a different home.. The other person may never live up to your values or your standards.  The question you need to ask yourself is do I really want this person in my life.  If the answer is yes, remember It takes two to reconcile. There has to be enough love on both sides for the reconciliation to work. Love is fundamental to reconciliation. You may not forget but you can forgive.  Love is a word that is bandied about.  Too many people have a skewed idea of what love is—a misunderstanding of the…
Read more »

SCOTUS AND THE ODD COUPLE

At a time when American society has become increasingly polarized, I can’t think of a more propitious time to look at an example of how respect, civility and friendship  can flourish and overcome dissenting factious opinions. There is no finer example of this than the friendship that existed between former Supreme Court Justices Antonin Scalia and Ruth Bader Ginsburg,  who eventually became to represent two branches of the Supreme Court.  Affectionately known as R.B.G by her supporters, Ginsburg was known to have anchored the liberals.  Scalia, “The Lion of the Law” led the conservatives. These two became the best of friends based on their devotion to the Constitution; although built on different interpretations—bonding over a shared love of opera, love of country,  good food and wine, and their childhoods in New York. This  enduring friendship helped them form a mutual respect that extended far beyond the courtroom.  Their families became friends too—the soft spoken but powerful Ginsburg—and the gregarious, witty  Scalia.  In remembrance of these two titans of the law, it might inspire  us to Look at this remarkable and yes, cordial, relationship. Ginsburg’s most famous quote is  “Fight for the things that are important to you, but do it in a way that will lead others to follow you.” Scalia  is noted for remarking, “Call us the odd couple.  She’s a very nice person. What’s not to like? Except for her views on the law.” Because they were ideological opposites, their relationship was considered improbable.  They didn’t compromise those beliefs for each other,  but they didn’t let it cause animosity or disrupt their friendship.
Read more »