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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 »

A taxing situation, but is it reality?

"When you say "there is no more inefficiency in government than in any large organization" that clarifies where you are coming from. We'll just have to disagree. If the average corporation in America was run like a government entity, we'd all be in the poor house and have no appreciable wealth from the capital markets. It comes down not to the workers being any different, they are all human. The fault rests where it always does: bad management. There is not enough energy, intellect or integrity being put into efficiency or accountability in government. Low government management standards (all levels) to prevent waste and fraud etc. are NOT widely accepted in the private sector, full stop. There is more natural economic accountability for poorly run corporations and their executives over time. Some state level incompetence may arguably rival the Federal level these days. That waste adds up for average citizens bearing the tax burdens in aggregate. The government (at any level) can't tax its way out of this morass."
- Dunn Werking
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 »

So Maybe That’s What It’s All About

"Mark, I can find dairy cows at a dairy farm just a mile up the road, but alas I’m pretty sure they have no interest in my singing Bruce Springsteen tunes to them, so I shall pass. PS: That is unless they are interested in producing buttermilk or cottage cheese."
- 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 »

Frittering away Frugality 

"I think you may have proved my point with that cartload. Costco intentionally uses oversized carts as part of their business model. The main reasons: Accommodates bulk purchases: Their products come in large packages, multi-packs, and oversized items (e.g., giant TP packs, cases of water,). Regular carts wouldn’t fit enough, creating friction and limiting what people buy. Psychology of shopping—more space in the cart subconsciously leads people to fill it up and spend more. It’s a deliberate design choice to boost sales volume. While you get a bargain on A, B and C, you are also buying D, E, F and G that you may otherwise would not buy except for the motivation created by the shopping model. So you saved on an item basis, but you spent more in total. For some people that doesn’t matter, for others who shop at a COSTCO more out of necessity, it may matter. They are encouraged to spend more than they should."
- R Quinn
Read more »

Haunted Head

"I loved this short, but thought-provoking article. I am 2.5 years into retirement. During my first year (2024), my wife and I traveled to 5 states, doing the Airbnb thing, driving. Flying is too stressful and BS-laden for me today. We visited our two kids (one in TX and one in MD) and flew them and their spouses to us in NC. No grandkids, unfortunately. I did fly to a couple of events in 2024... the NRA Coinvention and the Berkshire Hathaway Annual Shareholder's Meeting. I have been to several NRA conventions, but it was my first & only time attending the Berkshire Hathaway Annual Shareholders' Meeting. It was an event unlike any other I have attended. The odd thing I am experiencing is the overwhelming desire to consider "opportunities." Examples are college teaching opportunities, professional training positions, and even chaplaincy opportunities in Hospitals, workplaces, and Hospices. I need to slap myself and remind myself that just because I can doesn't mean I should. I think it is the result of being a lifetime of overachievement, overambition, and success orientation, with a strong desire to serve. In 2025, I focused on earning my chaplaincy credentials and pursuing and completing seminary studies, culminating in my Doctor of Ministry Degree. Because of my age (I am 75), I wasn't eligible to become a permanent deacon in my church or a military chaplain, so I pursued the D. Min. as an alternative route to service. My dissertation was focused on Strengthening Christian Marriages, and today I am involved in premarital counseling within my parish. I am certified as a PREPARE/ENRICH facilitator and a Ramset Financial Master Coach. I will be putting on my first Online "Financial Peace University" for my parish later this fall. In addition, I am completing coursework to facilitate the "Faith & Money Matters" and "God, Marriage and Money" courses for Compass Catholic. Marriage. These are all part of the ministry and are all offered pro bono. I found my way to use my 58 years of financial services education and experience, along with my ministry education and over 35 years of serving various parishes in 9 different states throughout my working lifetime. My wife and I are blessed financially, and it is a wonderful feeling to be able to help people without needing to generate income to provide that help. I hope all HD readers are able to "matter" in their retirement, and feel they still have "purpose!""
- Mike Lynch
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 »

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 »

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 »

Reluctantly Saving Money

"Please look harder and find a local handyman your neighbors been using for a reasonable price. If I could do that so can you."
- William Dorner
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 »

A taxing situation, but is it reality?

"When you say "there is no more inefficiency in government than in any large organization" that clarifies where you are coming from. We'll just have to disagree. If the average corporation in America was run like a government entity, we'd all be in the poor house and have no appreciable wealth from the capital markets. It comes down not to the workers being any different, they are all human. The fault rests where it always does: bad management. There is not enough energy, intellect or integrity being put into efficiency or accountability in government. Low government management standards (all levels) to prevent waste and fraud etc. are NOT widely accepted in the private sector, full stop. There is more natural economic accountability for poorly run corporations and their executives over time. Some state level incompetence may arguably rival the Federal level these days. That waste adds up for average citizens bearing the tax burdens in aggregate. The government (at any level) can't tax its way out of this morass."
- Dunn Werking
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 »

So Maybe That’s What It’s All About

"Mark, I can find dairy cows at a dairy farm just a mile up the road, but alas I’m pretty sure they have no interest in my singing Bruce Springsteen tunes to them, so I shall pass. PS: That is unless they are interested in producing buttermilk or cottage cheese."
- 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 »

Frittering away Frugality 

"I think you may have proved my point with that cartload. Costco intentionally uses oversized carts as part of their business model. The main reasons: Accommodates bulk purchases: Their products come in large packages, multi-packs, and oversized items (e.g., giant TP packs, cases of water,). Regular carts wouldn’t fit enough, creating friction and limiting what people buy. Psychology of shopping—more space in the cart subconsciously leads people to fill it up and spend more. It’s a deliberate design choice to boost sales volume. While you get a bargain on A, B and C, you are also buying D, E, F and G that you may otherwise would not buy except for the motivation created by the shopping model. So you saved on an item basis, but you spent more in total. For some people that doesn’t matter, for others who shop at a COSTCO more out of necessity, it may matter. They are encouraged to spend more than they should."
- R Quinn
Read more »

Haunted Head

"I loved this short, but thought-provoking article. I am 2.5 years into retirement. During my first year (2024), my wife and I traveled to 5 states, doing the Airbnb thing, driving. Flying is too stressful and BS-laden for me today. We visited our two kids (one in TX and one in MD) and flew them and their spouses to us in NC. No grandkids, unfortunately. I did fly to a couple of events in 2024... the NRA Coinvention and the Berkshire Hathaway Annual Shareholder's Meeting. I have been to several NRA conventions, but it was my first & only time attending the Berkshire Hathaway Annual Shareholders' Meeting. It was an event unlike any other I have attended. The odd thing I am experiencing is the overwhelming desire to consider "opportunities." Examples are college teaching opportunities, professional training positions, and even chaplaincy opportunities in Hospitals, workplaces, and Hospices. I need to slap myself and remind myself that just because I can doesn't mean I should. I think it is the result of being a lifetime of overachievement, overambition, and success orientation, with a strong desire to serve. In 2025, I focused on earning my chaplaincy credentials and pursuing and completing seminary studies, culminating in my Doctor of Ministry Degree. Because of my age (I am 75), I wasn't eligible to become a permanent deacon in my church or a military chaplain, so I pursued the D. Min. as an alternative route to service. My dissertation was focused on Strengthening Christian Marriages, and today I am involved in premarital counseling within my parish. I am certified as a PREPARE/ENRICH facilitator and a Ramset Financial Master Coach. I will be putting on my first Online "Financial Peace University" for my parish later this fall. In addition, I am completing coursework to facilitate the "Faith & Money Matters" and "God, Marriage and Money" courses for Compass Catholic. Marriage. These are all part of the ministry and are all offered pro bono. I found my way to use my 58 years of financial services education and experience, along with my ministry education and over 35 years of serving various parishes in 9 different states throughout my working lifetime. My wife and I are blessed financially, and it is a wonderful feeling to be able to help people without needing to generate income to provide that help. I hope all HD readers are able to "matter" in their retirement, and feel they still have "purpose!""
- Mike Lynch
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 »

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: Borrowing

This Old House

WHEN WE MOVED to Pennsylvania in 1996, I wanted to buy an old house. After months of looking, we found a stone farmhouse close to my new job and in a good school district. There was just one problem: We didn’t know if we could afford it.
We hadn’t been able to sell our home in Maryland, so we didn’t have any home equity to bring to the table. When our real estate agent saw the asking price,

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Pay It Down

DECIDING WHETHER to buy bonds or pay down the mortgage used to be a tricky decision. Not anymore: Paying extra on your home loan will almost always be the right choice.
This takes some explaining—because it involves wrapping your head around the standard vs. itemized deduction, investment taxes, and a mortgage’s shifting mix of principal and interest.
First, let’s dispense with the obvious objection: Yes, if you’re inclined to buy stocks rather than pay down the mortgage,

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No Interest

THE HOUSE I GREW UP in was built in 1950 by my father, with some assistance from his best friend Joe, who was a master homebuilder by profession. After his work day as an accountant for a local hardware and lumber chain, my dad would head over to the job site and labor into the night.
My mom also provided some sweat equity, painting and even swinging a hammer at times. I was born in 1962,

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Debtor’s Dozen

THE GREAT RECESSION highlighted the frightening amount of debt—especially mortgage debt—that had been taken on by many American families.
A decade later, the picture is far brighter, with one exception: student loans. Since 2008’s third quarter, education debt has ballooned 144%, according to data just released by the Federal Reserve Bank of New York. But the total of all other debt—mortgages, car loans and credit card balances—is up less than 1% over the same period.

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Credit Where It’s Due

THE BEST FINANCIAL advice I could give to a Gen Z or millennial is this: Join a credit union. But they probably wouldn’t listen.
A GOBankingRates survey earlier this year found that fewer adults under age 40 are banking with credit unions, instead preferring national or online banks by as much as a two-to-one margin. I’ve done all my banking with a local credit union for almost 18 years, and it’s provided me with a degree of personal customer service that’s likely less common with banks.

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Best Investment 2018

THE ABOVE HEADLINE overpromises, I readily admit. Still, three considerations—taxes, risk and the economic cycle—point to one conclusion: Paying down debt in 2018 looks like an awfully smart move.
Debtors’ prison. Ridding yourself of debt, even mortgage debt, has long been a savvy alternative to buying bonds and certificates of deposit. But thanks to the new tax law, it looks especially savvy right now—and especially if you’re married.
How come? The new tax law took away personal exemptions but compensated by roughly doubling the size of the standard deduction.

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Spotlight: Rohleder

Rx for Medicare

RONALD REAGAN SAID “the nine most terrifying words in the English language are ‘I’m from the government and I’m here to help’.” Government programs are put in place to address real concerns. But they often come with unintended consequences. When created in 1965, Medicare addressed the real need of senior citizens who couldn’t afford health care, just as Social Security was established in 1935 to help seniors in poverty. Both have become pillars of American retirement, but not without cost. At the start, Medicare copied the insurance industry’s prevailing “fee for service” model for paying physicians, while hospitals were paid on a “cost-plus” basis. “Costs” were Medicare’s portion of hospital operating costs. The “plus” was meant to provide hospitals with some margin to reinvest in their plant and equipment. We’re all economic animals and respond quickly to financial incentives. Physicians found that providing more services, and hospitals found that spending more money, resulted in more income. Rewarded for growth, our health care system suddenly supported many more doctors, facilities, personnel, technology and drugs. The benefits to seniors were great: improved access to health care and steadily lengthening lifespans. But so was the unintended consequence: Medicare contributed to a health care cost explosion. Health care expenditures rose from 5% of GDP in 1960 to 8.9% by 1980. As Medicare’s costs mushroomed, regulators began a long tug of war with providers to bend down the cost curve while still delivering promised medical care. Over the next four decades, there were waves of reform attempts: Studies showed more care didn’t necessarily mean better care, so some controls on utilization were added. Hospital charges varied widely from one area to another, or even within the same city, so standardized payments were imposed by region. Medicare found it was paying to fix medical errors, so…
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Share This Message

In my years working in Hospital Administration, I routinely had staff telling me about patients or families caught in a medical crisis caused by a fall or major surgery or simple aging.  They were “surprised” to find that when they were told they could no longer live safely in their home, that Medicare was not going to pay for their needed long term care living arrangements. I’m assuming that this information will not be a surprise to Humble Dollar readers.  But I found this post on Linked In from a Senior Care Educator and Advocate named Katie Monahan Brooks, CDP, DCS.  I don’t know her and I don’t know the Humble Dollar policy about reposting what she posted on Linked In. But she has expressed this more clearly and bluntly than I could have.  And, it is apparent from her writing that she wants this message broadcast far and wide.  My hope is that Humble Dollar readers can be part of this education process.  Here is what Ms. Brooks wrote, unedited by me: “I’m done pretending this confusion is acceptable. If I have to explain one more time that Medicare does NOT pay for senior living, I might actually lose what’s left of my sanity. Let’s be painfully clear: Medicare pays for your medical care. It does NOT pay for your housing, daily care, or supervision. Assisted Living, Memory Care, and Independent Living are NOT medical benefits. They are housing with support. And yet—every. single. week.—I sit across from families who are shocked. Angry. Betrayed. “Why doesn’t Medicare pay for this?” “Isn’t this healthcare?” “No one ever told us this.” And that’s exactly the problem. This isn’t just a misunderstanding. This is a massive, nationwide education failure that leaves families blindsided in the middle of a crisis—when emotions, guilt, fear,…
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Gaining Perspective

ON MONDAY, OCT. 19, 1987, stocks plunged more than 20%. I was relatively new to investing—and the crash shocked me. I realize now that, when you’re starting out, no matter how much you study, the trait you’re most lacking is perspective. When I began investing, I approached a successful investor and asked for tips to learn about the market. Part of his advice was to watch Wall Street Week with Louis Rukeyser on PBS. That Friday in 1987, Lou started the show with a monologue explaining that the world was not coming to an end. Over the next few weeks, bolstered by his words, I added to my stock funds. Prior to 1987, I had been scared out of some of my stock funds by normal market fluctuations, not realizing that drops in price were often the best time to buy more. Over the years, I learned that dollar-cost averaging and rebalancing help take the emotion out of investing. Looking back, I see that this was all part of a normal learning curve. As a new investor, you can gain perspective by talking to trusted mentors, listening to experts and reading up on market history. But there’s no substitute for actually living through multiple up and down markets, and learning from your own successes and failures. This highlights the value of starting to invest in early adulthood. A strategy of dollar-cost averaging into index funds may sound dull to your 20-something self. At that juncture, you might believe you can beat the market averages by picking stocks or timing the market. But as is often the case, the negative sting of lousy results will be your most valuable feedback. The good news: The earlier you get through your period of trial and error—and develop some perspective—the more time you’ll have…
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Getting in Line

WE RECENTLY MADE a down payment on our next home. After several months of research, we joined the waiting list for a continuing care retirement community, or CCRC. We’re in our late 60s and only relocated to our current home four years ago. It’s in a metropolitan area two hours’ drive from our daughter and her young family. We know that perhaps 10 years or so from now, we’ll want to be closer to her, so we looked at CCRCs near where she lives. We have some familiarity with the CCRC concept. Both of our parents lived in CCRCs and had positive experiences. I serve on the board of directors of a CCRC where we live now. I previously shared thoughts on choosing a CCRC in a HumbleDollar article. We solicited ideas for which CCRC campuses to visit from some of my contacts. Ultimately, we visited three. There were things to like about each. Our preference was to find a type A community—those that lock in the monthly fee, regardless of the level of care you need. We only found type C communities, where you pay for each level of care at market rates. Type C communities are far more common due to the financial risk that type A communities assume. All three facilities we visited had acceptable accommodations and amenities. They all appear to have the financial strength for the long haul. We screened for those things before we visited and we weren’t disappointed. In joining the waiting list, one of our intentions is to monitor the organization. Does it continue to maintain its facilities? Does it maintain its financial strength? As the real estate cliché goes, our final selection was based on three things: location, location, location. Of the three we visited, our choice is closest to my…
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Taxes Season 3

This was my third season as an AARP volunteer tax aide…and my third post about my experiences. I volunteer two days a week from February 1 to tax day at two different senior centers which draw from different socioeconomic strata: one is definitely middle class; the other has many clients living on very little. I began the season wondering how the Big Beautiful Bill would impact our clients. Since most are over 65, I expected the new $6000 senior deduction to have a big, across-the-board impact. Many came in asking about it: They had either heard about the “$6000 deduction” or “no tax on Social Security.”  The impact was not as much as I expected. I quickly realized that the income of many clients is so low that they are already paying little or no taxes… another deduction doesn’t matter. I did see the advantage of a flat deduction versus eliminating tax on Social Security. We have government or railroad pensioners who receive other government retirement, but no Social Security. They were able to benefit. With the phase-out for higher incomes, the BBB hit its target: my middle-income seniors were the beneficiaries. Since we see few working people, I only saw few examples of “no tax on tips” or “no tax on overtime.”  I had one young married couple where she was a waitress, he was a firefighter, and they had a new baby in 2025. They hit the trifecta: her tips were excluded, as was his overtime. And, the baby was eligible for a $1000 deposit into a Trump account. The new emphasis by the IRS to eliminate paper checks caused some consternation. We have clients who do not trust the IRS to have their banking information. We try to explain that if they receive Social Security, the government…
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Managing to Profit

THE GAMBLING TRUISM says you can’t beat the house. That brings me to a recent HumbleDollar article that discussed choosing either a Medicare Advantage plan or traditional Medicare with an accompanying Medigap policy. Almost two dozen readers weighed in with comments. My two cents: Never forget that the managed-care companies offering Advantage plans are mostly for-profit companies that are publicly traded. The government’s purpose is to transfer its insurance risk to those companies. These managed-care companies must then manage that risk through rationing, limiting choice and negotiating provider payments, as well as encouraging healthy behavior among their customers. To the extent they’re allowed, they deny coverage or charge higher rates to those with preexisting conditions. Although Medicare Advantage was first offered in the late 1990s, enrollment really took off about 10 years ago. That was when Congress made the program more palatable to insurance companies. Advantage plans became their growth driver and industry marketing got more aggressive. Enrollment has doubled over the past decade. I looked at the major national managed-care companies in the Medicare Advantage market over that time period. Here are their stock returns for the past 10 years, without dividends reinvested, as of Oct. 18: Aetna (AET) +499% Anthem (ANTM) +537% Humana (HUM) +514% UnitedHealth Group (UNH) +873% S&P 500 (SPX) +271% Over the long haul, the stock market recognizes value. Don’t imagine that managed-care companies are charitable ventures. This factors into how they “manage” your care. Rather than choosing one of their Advantage plans, your best bet might be to become a stockholder. That way, you can smile at your brokerage statement because you’ll be betting with the house. I spent years in hospital administration sitting across the table from insurance companies. When it came time to decide, I opted for traditional Medicare plus a Medigap policy. It…
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