FREE NEWSLETTER

If you think today’s purchase will make you happy forever, you need to spend more time looking through your closets.

Latest PostsAll Discussions »

Taxes

Roth Conversions

ArticleAdam M. Grossman  |  Nov 7, 2026

AMONG THE MOST COMMON debates in personal finance is whether Roth conversions are a wise strategy. Especially as the end of the year approaches, it’s worth looking at both sides of this question. If you aren’t familiar with it, the idea behind a Roth conversion is that individuals can choose, at any time, and at any income level, to move money out of a pre-tax traditional IRA into a Roth IRA. There’s a catch, though: In the year that you complete a conversion, you must pay income tax on the amount that you convert. So, the bet you are making with a conversion is that your tax rate today will be lower than it will be in the future, when you otherwise would have taken those dollars out of your IRA. For example, if you could pay a tax of just 22% today to convert dollars from your pre-tax IRA to your Roth IRA, you would happily do that if you expected your tax rate down the road to be much higher—say, 32%.  This seems straightforward, but not everyone agrees. For starters, Roth conversions’ detractors point to the uncertainty inherent in the exercise. Predicting future tax rates is an imperfect science, and if rates end up going lower in the future, that could turn the benefit of a conversion upside down. You could end up paying a higher rate today than you would’ve in the future. Given the state of federal finances, it might seem unlikely to expect tax rates to go down, but no one can say that with certainty. Congress often changes the rules, and as recently as the late-1980s, the highest ordinary income tax rate was nine percentage points lower than it is today (28% vs. 37%). In addition, it can be difficult to predict our own future income with precision. Consider required minimum distributions (RMDs) from retirement accounts. They’re a key component of most retirees’ income, but because they’re dependent on future investment returns, the best any of us can do is to estimate this figure. Roth conversions, in other words, involve uncertainty along multiple dimensions. This is a point even supporters acknowledge. That’s why, to help manage this uncertainty, I look at Roth conversion candidates as falling into one of three categories. The first category: When a taxpayer’s marginal tax rate is currently in one of the two lowest brackets, either 10% or 12%, I see it as an easy decision to complete a conversion. That’s because it’s hard to imagine that their future tax rate would be any lower. At worst, in that case, a Roth conversion in one of these two lowest brackets might just be a wash. The second category: When a taxpayer’s marginal rate is over 30%, I see that as an easy decision as well, but for the opposite reason. Roth conversions rarely make sense at that level because it’s hard to make the argument that a taxpayer in a very high bracket might end up in a bracket that’s even higher. To be sure, it can happen—and I’ll describe one clear case below—but it’s hard to have confidence in that expectation. For that reason, a conversion at a rate over 30% typically doesn’t make sense. The third category: If your marginal rate is in one of the middle brackets—either 22% or 24%—that’s when the conversion decision doesn’t have an easy “yes” or “no” answer, and it’s worth examining other factors. When would a conversion in this middle range make sense? If the composition of your assets is such that you have significant balances in pre-tax accounts and you haven’t yet hit RMD age (either age 73 or 75), that’s when you’d want to sharpen your pencil. If your RMD based on your current pre-tax balances would push your income into a much higher tax bracket, then it would be safe to assume that, with some additional investment growth, your tax bracket will almost certainly be higher down the road. That’s a clear case for a Roth conversion. Similarly, if you have other income sources, such as a pension, that are guaranteed, that too would make the conversion decision easier. What if the comparison between your current and projected future tax rates isn’t conclusive? Suppose, for example, your taxable ordinary income today is $210,000. For someone married and filing jointly, that would translate to the 22% marginal tax bracket. Even if your income rose sharply in future years with required minimum distributions, up to $300,000, for example, the tax impact would be modest. Income of $300,000 would translate to a marginal bracket of just 24%. So a Roth conversion might not seem like an urgent priority. In that case, there’s another factor that might be a tie-breaker. If one spouse passed away, the surviving spouse would be subject to the tax brackets for single taxpayers. Continuing with this same example, $300,000 of income would result in a substantially higher marginal bracket of 35%. If that were the case, then a conversion today at 22% might make good sense. The upshot: If you’re doing Roth conversion math, and the results look inconclusive, consider what might tip the scales. Another potential tie-breaking factor to consider, if the math isn’t conclusive, would be the estate tax. At the federal level, a tax of 40% applies to assets over $15 million, or $30 million for a married couple. For someone with a balance sheet at that level, Roth conversions can make a lot of sense because they have the result of reducing the size of an estate without reducing the after-tax value of the assets. Consider a simple example: If you complete a conversion of $200,000 that results in $40,000 in taxes, that $40,000 is no longer in your estate, and thus no longer subject to estate tax. This is the only case in which I see an argument for conversions at rates over 30%, because any tax below 40% would still be less costly than the future estate tax levy. 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 »

Estate Plan

Protecting What We Built

ArticleDennis Friedman  |  Nov 7, 2026

SINCE RETIRING, WE’VE done a lot of traveling. One thing that continually stands out is just how crowded airports have become—even top-tier airline lounges are sometimes packed to capacity. Watching the endless stream of travelers, my wife often turns to me and asks, “Where do all these people get their money?” I suspect some of them, especially the older travelers, are “middle-class millionaires.” They didn’t build their wealth through massive salaries. Instead, they accumulated it gradually through home appreciation, retirement savings, disciplined investing, and decades of compound growth. That’s how my wife and I built our net worth. We grew our savings slowly over the course of our careers through patience and discipline. Now that we’ve reached a point where we feel we have enough, our focus has shifted from growing our wealth to protecting it. Here are three ways we are protecting our hard-earned savings while continuing to enjoy our retirement. Fortifying Our Liability Coverage Ever since a friend told me that his own son-in-law sued him after falling down his stairs, I’ve been concerned about our own liability exposure. I don’t consider us to live a lifestyle that would expose us to a particularly high risk of being sued. We don’t have a dog, swimming pool, rental property, or boat. Even though I consider our risk relatively low, I’ve become more conscious of how much we have to lose from an unexpected liability claim, such as a severe auto accident. I’m not an attorney or insurance professional, so I’m not suggesting that our approach is appropriate for everyone. But it did lead me to take a closer look at how our assets might be protected if we were ever sued and a judgment entered against us. In recent years, our modest California home has appreciated significantly alongside real estate values across the state. When I considered our home equity together with our taxable savings and other assets, we eventually concluded that our existing umbrella coverage was no longer sufficient for the amount of wealth we had accumulated. I also learned that California’s homestead exemption provides a certain amount of protection for equity in a primary residence, although the rules are more complicated than I had previously realized. The amount of protection depends on the circumstances and is subject to statutory limits and adjustments. For our home, I didn’t want to assume that all of our home equity would be protected from a judgment. Our IRAs also have statutory protection under California Code of Civil Procedure §704.115 based on what is deemed reasonably necessary for retirement support. Learning this gave me some comfort, but it also reinforced the fact that different types of assets can have different levels of protection. Our taxable brokerage account, however, does not have the same type of statutory protection. It remains exposed to potential legal claims. We ultimately purchased additional umbrella coverage through a specialty insurer. Securing that extra layer of protection provides us an invaluable peace of mind. Adopting a Moderately Conservative Asset Allocation  Now that we’re in our 70s, we feel we can afford to be less aggressive in the stock market. Our portfolio is currently allocated 45% to stocks, 45% to bonds, and 10% to cash.  This asset allocation gives us enough exposure to growth to help combat inflation while providing some protection against a severe bear market. Consider a difficult scenario in which the stock market falls 40% and the bond market declines 10%. Under those conditions, our portfolio would lose roughly 22.5%. Alternatively, if our 55% allocation to bonds and cash holds its value while stocks absorb the full 40% decline, we would still have 82% of our portfolio’s value intact. This allocation gives us a larger cushion against a severe stock-market downturn. It would allow us to rebalance into stocks after a major decline, rather than being forced to sell stocks when prices are depressed. More importantly, this asset allocation has so far allowed us to maintain a comfortable lifestyle without worrying about market swings. Hiring a Financial Advisor I don’t recommend a financial advisor for everyone. In fact, if we were younger, we probably wouldn’t have one. But at age 75, I have to concede that I’m not as sharp as I used to be, and I can get emotional at times. Those aren’t ideal qualities to have in a world where scammers are becoming increasingly sophisticated. What I like about having a financial advisor manage our money is that I have to go through my advisor to access our funds. That extra layer of protection helps protect our portfolio from scams—and from ourselves. It gives us a chance to pause and think things through rather than make an emotional decision in the moment. At this stage of our lives, we’re paying for more than investment management. We’re paying for another layer of discipline and protection—and for the peace of mind that comes with knowing someone else is looking out for us. Focusing on Making It Last Now that we're retired and have accumulated enough to support the life we want, our priorities have changed. We don't need to squeeze every last dollar of growth from our portfolio. Instead, we're trying to make what we've built lasting—protecting it from lawsuits, market declines, scams, and, perhaps most importantly, our own mistakes.  Dennis Friedman retired from Boeing Satellite Systems after a 30-year career in manufacturing. Born in Ohio, Dennis is a California transplant with a bachelor’s degree in history and an MBA. A self-described “humble investor,” he likes reading historical novels and about personal finance. Follow Dennis on X @DMFrie and check out his earlier articles
Read more »

Retirement

The Leap of Faith

Mark Crothers  |  Nov 3, 2026

"Great article Mark. Retirement is based upon a whole series of assumptions including income, expenses, longevity, your health, unexpected events such as storms/flooding (which seem to be on the news in the U.S. every night), and so on. I think the person that can anticipate all those variables and make conservative projections and assumptions has the best chance. I never did this, but using an advisor might be very helpful at this point in life because they'll probably have many points of view that others would never think to consider. And then, of course, we could all use the luck of the Irish in retirement! ☘️🇮🇪"
- Patrick Brennan
Read more »

Lists

Jonathan’s Parting Thoughts: No. 5

Jonathan Clements  |  Nov 6, 2026

"In life, Jonathan was a steady voice for rational investing and money management. I appreciate his "Parting Thoughts" series, where he leaves us with the core principles for getting the most from our money."
- Edmund Marsh
Read more »

From HumbleDollar Founder Jonathan Clements

Behavior

Knowing Me

DOES OUR PERSONALITY help determine our financial success? It seems it does, or so says academic research. Psychologists have zeroed in on five key…
Read more »

Spending

Is an 18% Service Charge a TIP?

James McGlynn CFA RICP®  |  Oct 13, 2026

"It’s a pity that restaurant owners have turned their staff into professional beggars in order to pay their rent. Why not pay your employees fairly? A tip should really be a gratuity to buy a cup of coffee, not a means of survival."
- Mary Gizzie
Read more »

Estate Plan

Tax Planning After the Election

Paul Ward  |  Nov 5, 2026

"Thanks"
- Michael1
Read more »

Taxes

Tax Planning Challenge

Randy Dobkin  |  Oct 20, 2026

"All you tax nerds who didn't attend missed out! It was interesting to graphically see all the sneaky marginal tax rates our ridiculously complicated tax system has created. I came away with a good plan for my Roth conversion this year. Looking forward to another tax planning challenge next year."
- Randy Dobkin
Read more »

Spending

Dickies simplistic view of personal finances

R Quinn  |  Nov 3, 2026

"I’m curious what good tax planning means and if your effective tax rate is that low why you are even concerned about taxes? Aren’t the expenses you mentioned among the most stable we have recurring month after month? Just don’t understand what tracking them does to add value for your money management."
- R Quinn
Read more »

Investing

Do I really need International funds in my portfolio? I say no.

Bruce Roberts  |  Oct 26, 2026

"You bring up some good points. The argument that I'm excluding some excellent companies headquartered overseas is compelling. Question is - what fund should I buy to get that exposure? Regarding the exclusion of sector tilt - I don't know that I'm smart enough to know what percent of my portfolio should be in industrials, vs metals, vs tech, etc."
- Bruce Roberts
Read more »

Houses

Full Asking Price

D.J.  |  Nov 5, 2026

"That's quite a story, Mike. Enjoy that view!"
- D.J.
Read more »

Saving

The Repair I Didn’t Need

Andrew Clements  |  Nov 4, 2026

"Commission-based pay can create a conflict of interest, but I wouldn’t say that means every service advisor isn’t on the customer’s side. I liked our dealership advisor and appreciated her communication. My experience simply reinforced the value of asking questions and getting a second opinion before approving an expensive repair."
- Andrew Clements
Read more »

Taxes

Roth Conversions

ArticleAdam M. Grossman  |  Nov 7, 2026

AMONG THE MOST COMMON debates in personal finance is whether Roth conversions are a wise strategy. Especially as the end of the year approaches, it’s worth looking at both sides of this question. If you aren’t familiar with it, the idea behind a Roth conversion is that individuals can choose, at any time, and at any income level, to move money out of a pre-tax traditional IRA into a Roth IRA. There’s a catch, though: In the year that you complete a conversion, you must pay income tax on the amount that you convert. So, the bet you are making with a conversion is that your tax rate today will be lower than it will be in the future, when you otherwise would have taken those dollars out of your IRA. For example, if you could pay a tax of just 22% today to convert dollars from your pre-tax IRA to your Roth IRA, you would happily do that if you expected your tax rate down the road to be much higher—say, 32%.  This seems straightforward, but not everyone agrees. For starters, Roth conversions’ detractors point to the uncertainty inherent in the exercise. Predicting future tax rates is an imperfect science, and if rates end up going lower in the future, that could turn the benefit of a conversion upside down. You could end up paying a higher rate today than you would’ve in the future. Given the state of federal finances, it might seem unlikely to expect tax rates to go down, but no one can say that with certainty. Congress often changes the rules, and as recently as the late-1980s, the highest ordinary income tax rate was nine percentage points lower than it is today (28% vs. 37%). In addition, it can be difficult to predict our own future income with precision. Consider required minimum distributions (RMDs) from retirement accounts. They’re a key component of most retirees’ income, but because they’re dependent on future investment returns, the best any of us can do is to estimate this figure. Roth conversions, in other words, involve uncertainty along multiple dimensions. This is a point even supporters acknowledge. That’s why, to help manage this uncertainty, I look at Roth conversion candidates as falling into one of three categories. The first category: When a taxpayer’s marginal tax rate is currently in one of the two lowest brackets, either 10% or 12%, I see it as an easy decision to complete a conversion. That’s because it’s hard to imagine that their future tax rate would be any lower. At worst, in that case, a Roth conversion in one of these two lowest brackets might just be a wash. The second category: When a taxpayer’s marginal rate is over 30%, I see that as an easy decision as well, but for the opposite reason. Roth conversions rarely make sense at that level because it’s hard to make the argument that a taxpayer in a very high bracket might end up in a bracket that’s even higher. To be sure, it can happen—and I’ll describe one clear case below—but it’s hard to have confidence in that expectation. For that reason, a conversion at a rate over 30% typically doesn’t make sense. The third category: If your marginal rate is in one of the middle brackets—either 22% or 24%—that’s when the conversion decision doesn’t have an easy “yes” or “no” answer, and it’s worth examining other factors. When would a conversion in this middle range make sense? If the composition of your assets is such that you have significant balances in pre-tax accounts and you haven’t yet hit RMD age (either age 73 or 75), that’s when you’d want to sharpen your pencil. If your RMD based on your current pre-tax balances would push your income into a much higher tax bracket, then it would be safe to assume that, with some additional investment growth, your tax bracket will almost certainly be higher down the road. That’s a clear case for a Roth conversion. Similarly, if you have other income sources, such as a pension, that are guaranteed, that too would make the conversion decision easier. What if the comparison between your current and projected future tax rates isn’t conclusive? Suppose, for example, your taxable ordinary income today is $210,000. For someone married and filing jointly, that would translate to the 22% marginal tax bracket. Even if your income rose sharply in future years with required minimum distributions, up to $300,000, for example, the tax impact would be modest. Income of $300,000 would translate to a marginal bracket of just 24%. So a Roth conversion might not seem like an urgent priority. In that case, there’s another factor that might be a tie-breaker. If one spouse passed away, the surviving spouse would be subject to the tax brackets for single taxpayers. Continuing with this same example, $300,000 of income would result in a substantially higher marginal bracket of 35%. If that were the case, then a conversion today at 22% might make good sense. The upshot: If you’re doing Roth conversion math, and the results look inconclusive, consider what might tip the scales. Another potential tie-breaking factor to consider, if the math isn’t conclusive, would be the estate tax. At the federal level, a tax of 40% applies to assets over $15 million, or $30 million for a married couple. For someone with a balance sheet at that level, Roth conversions can make a lot of sense because they have the result of reducing the size of an estate without reducing the after-tax value of the assets. Consider a simple example: If you complete a conversion of $200,000 that results in $40,000 in taxes, that $40,000 is no longer in your estate, and thus no longer subject to estate tax. This is the only case in which I see an argument for conversions at rates over 30%, because any tax below 40% would still be less costly than the future estate tax levy. 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 »

Estate Plan

Protecting What We Built

ArticleDennis Friedman  |  Nov 7, 2026

SINCE RETIRING, WE’VE done a lot of traveling. One thing that continually stands out is just how crowded airports have become—even top-tier airline lounges are sometimes packed to capacity. Watching the endless stream of travelers, my wife often turns to me and asks, “Where do all these people get their money?” I suspect some of them, especially the older travelers, are “middle-class millionaires.” They didn’t build their wealth through massive salaries. Instead, they accumulated it gradually through home appreciation, retirement savings, disciplined investing, and decades of compound growth. That’s how my wife and I built our net worth. We grew our savings slowly over the course of our careers through patience and discipline. Now that we’ve reached a point where we feel we have enough, our focus has shifted from growing our wealth to protecting it. Here are three ways we are protecting our hard-earned savings while continuing to enjoy our retirement. Fortifying Our Liability Coverage Ever since a friend told me that his own son-in-law sued him after falling down his stairs, I’ve been concerned about our own liability exposure. I don’t consider us to live a lifestyle that would expose us to a particularly high risk of being sued. We don’t have a dog, swimming pool, rental property, or boat. Even though I consider our risk relatively low, I’ve become more conscious of how much we have to lose from an unexpected liability claim, such as a severe auto accident. I’m not an attorney or insurance professional, so I’m not suggesting that our approach is appropriate for everyone. But it did lead me to take a closer look at how our assets might be protected if we were ever sued and a judgment entered against us. In recent years, our modest California home has appreciated significantly alongside real estate values across the state. When I considered our home equity together with our taxable savings and other assets, we eventually concluded that our existing umbrella coverage was no longer sufficient for the amount of wealth we had accumulated. I also learned that California’s homestead exemption provides a certain amount of protection for equity in a primary residence, although the rules are more complicated than I had previously realized. The amount of protection depends on the circumstances and is subject to statutory limits and adjustments. For our home, I didn’t want to assume that all of our home equity would be protected from a judgment. Our IRAs also have statutory protection under California Code of Civil Procedure §704.115 based on what is deemed reasonably necessary for retirement support. Learning this gave me some comfort, but it also reinforced the fact that different types of assets can have different levels of protection. Our taxable brokerage account, however, does not have the same type of statutory protection. It remains exposed to potential legal claims. We ultimately purchased additional umbrella coverage through a specialty insurer. Securing that extra layer of protection provides us an invaluable peace of mind. Adopting a Moderately Conservative Asset Allocation  Now that we’re in our 70s, we feel we can afford to be less aggressive in the stock market. Our portfolio is currently allocated 45% to stocks, 45% to bonds, and 10% to cash.  This asset allocation gives us enough exposure to growth to help combat inflation while providing some protection against a severe bear market. Consider a difficult scenario in which the stock market falls 40% and the bond market declines 10%. Under those conditions, our portfolio would lose roughly 22.5%. Alternatively, if our 55% allocation to bonds and cash holds its value while stocks absorb the full 40% decline, we would still have 82% of our portfolio’s value intact. This allocation gives us a larger cushion against a severe stock-market downturn. It would allow us to rebalance into stocks after a major decline, rather than being forced to sell stocks when prices are depressed. More importantly, this asset allocation has so far allowed us to maintain a comfortable lifestyle without worrying about market swings. Hiring a Financial Advisor I don’t recommend a financial advisor for everyone. In fact, if we were younger, we probably wouldn’t have one. But at age 75, I have to concede that I’m not as sharp as I used to be, and I can get emotional at times. Those aren’t ideal qualities to have in a world where scammers are becoming increasingly sophisticated. What I like about having a financial advisor manage our money is that I have to go through my advisor to access our funds. That extra layer of protection helps protect our portfolio from scams—and from ourselves. It gives us a chance to pause and think things through rather than make an emotional decision in the moment. At this stage of our lives, we’re paying for more than investment management. We’re paying for another layer of discipline and protection—and for the peace of mind that comes with knowing someone else is looking out for us. Focusing on Making It Last Now that we're retired and have accumulated enough to support the life we want, our priorities have changed. We don't need to squeeze every last dollar of growth from our portfolio. Instead, we're trying to make what we've built lasting—protecting it from lawsuits, market declines, scams, and, perhaps most importantly, our own mistakes.  Dennis Friedman retired from Boeing Satellite Systems after a 30-year career in manufacturing. Born in Ohio, Dennis is a California transplant with a bachelor’s degree in history and an MBA. A self-described “humble investor,” he likes reading historical novels and about personal finance. Follow Dennis on X @DMFrie and check out his earlier articles
Read more »

Retirement

The Leap of Faith

Mark Crothers  |  Nov 3, 2026

"Great article Mark. Retirement is based upon a whole series of assumptions including income, expenses, longevity, your health, unexpected events such as storms/flooding (which seem to be on the news in the U.S. every night), and so on. I think the person that can anticipate all those variables and make conservative projections and assumptions has the best chance. I never did this, but using an advisor might be very helpful at this point in life because they'll probably have many points of view that others would never think to consider. And then, of course, we could all use the luck of the Irish in retirement! ☘️🇮🇪"
- Patrick Brennan
Read more »

Lists

Jonathan’s Parting Thoughts: No. 5

Jonathan Clements  |  Nov 6, 2026

"In life, Jonathan was a steady voice for rational investing and money management. I appreciate his "Parting Thoughts" series, where he leaves us with the core principles for getting the most from our money."
- Edmund Marsh
Read more »

From HumbleDollar Founder Jonathan Clements

Behavior

Knowing Me

DOES OUR PERSONALITY help determine our financial success? It seems it does, or so says academic research. Psychologists have zeroed in on five key…
Read more »

Spending

Is an 18% Service Charge a TIP?

James McGlynn CFA RICP®  |  Oct 13, 2026

"It’s a pity that restaurant owners have turned their staff into professional beggars in order to pay their rent. Why not pay your employees fairly? A tip should really be a gratuity to buy a cup of coffee, not a means of survival."
- Mary Gizzie
Read more »

Estate Plan

Tax Planning After the Election

Paul Ward  |  Nov 5, 2026

"Thanks"
- Michael1
Read more »

Taxes

Tax Planning Challenge

Randy Dobkin  |  Oct 20, 2026

"All you tax nerds who didn't attend missed out! It was interesting to graphically see all the sneaky marginal tax rates our ridiculously complicated tax system has created. I came away with a good plan for my Roth conversion this year. Looking forward to another tax planning challenge next year."
- Randy Dobkin
Read more »

Spending

Dickies simplistic view of personal finances

R Quinn  |  Nov 3, 2026

"I’m curious what good tax planning means and if your effective tax rate is that low why you are even concerned about taxes? Aren’t the expenses you mentioned among the most stable we have recurring month after month? Just don’t understand what tracking them does to add value for your money management."
- R Quinn
Read more »

Free Newsletter

Get Educated

Manifesto

Nov 6, 2026

NO. 2: WE GET one shot at making the financial journey from here to retirement—and failure is not an option, so we should save like crazy, avoid big investment bets and insure against major risks.

humans

Nov 7, 2026

NO. 23: MANY FOLKS loathe paying taxes, but sometimes that’s the prudent choice. In our taxable account, suppose we have a hefty position in one stock with big unrealized capital gains. Selling and paying the tax bill may be painful. But that tax loss is modest compared to the potential investment loss—and often the wise move is to reduce risk by selling.

act

Nov 7, 2026

REVIEW AUTOMATIC payments. Do you pay for magazines, the health club, cable TV, streaming services and other items through monthly or annual automatic debits? It’s easy to overlook these regular charges to your checking account and credit cards, so take a moment to go through them—and make sure you aren't paying for services you no longer need.

Truths

Nov 6, 2026

NO. 74: THE TAX deduction for traditional 401(k) and IRA contributions can pay the eventual tax bill. Imagine you invested those tax savings in the account. If you’re in the same tax bracket when you draw down your 401(k) or IRA as when you funded it, the initial tax savings will grow to cover the final tax bill, leaving you with tax-free growth for the rest of the account.

Money Guide

Start Here
Planner
Portfolio
Retire
Invest
Best of Jonathan Clements

Manifesto

Nov 6, 2026

NO. 2: WE GET one shot at making the financial journey from here to retirement—and failure is not an option, so we should save like crazy, avoid big investment bets and insure against major risks.

Spotlight: Advisors

Financial Planning

Concerned   |  Apr 11, 2026

I suspect like me, most HD members are against paying large yearly fees to investment advisors. I have made all of our investment decisions and have done pretty well. I also do our taxes. While I have no immediate plans to stop, because my wife…
Read more »

The Silent Compounding Cost of a 1% Fee

W.D. Housley   |  May 13, 2025

We often hear about the power of compounding returns—how investments grow exponentially over time. But there’s a lesser-known side to compounding: the cost of ongoing financial advisor fees. Consider a $1,000,000 portfolio growing at 7% annually. Over 10 years, that could grow to about $1,967,151—if…
Read more »

My Mistakes

Dana Rusinak   |  Feb 21, 2025

Thank you Jonathan for as always, for your willingness to tell your story, the good and the bad. I have one big mistake to get out there. About 10 years before my wife and I retired, I started getting interested in money. I educated myself…
Read more »

Too Heavy a Load

Michael Perry   |  Oct 16, 2021

I’M A MORNINGSTAR subscriber. I find that the site provides investing and personal finance information that’s sensible and useful for the average person, and that it promotes good investing and planning behaviors. Still, I was taken aback by a recent article, which discussed four funds…
Read more »

Dinner Is Served

Mike Zaccardi   |  Sep 15, 2021

HOW LUCKY I WAS to be the recipient of a dinner invitation to Ruth’s Chris. I love a sizzling ribeye, so I booked my seat at the event. Those nearing and in retirement have a good idea of what I’m referring to—the good old annuity…
Read more »

Advice at a Price

Richard Connor   |  Dec 8, 2021

THE PREDOMINANT WAY financial planners get paid is by charging a fee based on the amount of money they’re managing. The typical industry fee I’ve seen is 1%, and it’s been that way for years. Under this model, a financial planner managing a client’s $1 million…
Read more »

Spotlight: Smith

Studying for the Bar

Dan Smith   |  May 9, 2024

HOW DO SOME INVESTORS end up in places they don’t belong? Where do they turn for information and guidance? Who do they talk to before making important financial decisions? What follows are the results of my unscientific research, which was conducted in some of the finest and most respected centers of advanced learning anywhere. Barroom seminars, your window on the…
Read more »

No Such Thing as Easy Money

Dan Smith   |  Jan 8, 2026

I enjoy tasting new beers, and today there are some very good ones on the shelves. Still, it hasn’t always been this way.  Some time in the nascent days of the micro-brewery craze, I recall my boss, the owner of the beer distributor, commenting that it was as if the tiny brewers were having a contest to see who could…
Read more »

Get Your Stuff Together (For Taxes)

Dan Smith   |  Jan 3, 2025

The following is from one of the newsletters I used to send to my clients each year. It is not meant to be comprehensive but it may help the organized challenged people (OCP) among us. Most of you are probably sick of reading this paragraph because I include it every year. If you are one of my organized peeps you…
Read more »

Sleep Disorder

Dan Smith   |  Oct 17, 2024

This may be a stretch for the forum but I’m going to throw it out there and hope it helps someone. When my first wife told me that I held my breath while sleeping I didn’t think much about it. Then Chris (new wife) told me that I stop breathing and probably have apnea, and should do a sleep study.…
Read more »

Punched in  the Mouth

Dan Smith   |  Feb 13, 2026

I don’t have the right stuff to be an engineer, as the math involved boggles my mind. But that didn’t stop my infatuation with spreadsheets in the nascent days of computer ownership. That was around 1990, roughly the same time-frame as the implementation of my employer's 401k.  Oh boy, enabled by my new love of Excel, my life was planned…
Read more »

Your Results May Vary

Dan Smith   |  Jun 12, 2024

"SELL THE SIZZLE, BOYS." With those words from the sales manager at a big insurance company, the 2003 class of newly minted registered representatives were off to the races, extolling the virtues of the firm’s products to family, friends and anyone else who would listen. I still vividly remember that moment. Yes, I was there. To become registered reps, the…
Read more »
FREE NEWSLETTER
How To
Follow Us
HumbleDollar · https://humbledollar.com/ · printed Nov 7, 2026

Log in