Home - HumbleDollar

Monopoly

D.J. | Oct 27, 2026

"Thanks, Dan. You'll have to let us know how your first game of Toledopoly goes. Are the Mud Hens one of the properties on the board?"

- D.J.

In Retirement

The pension conundrum and a solution

R Quinn | Oct 26, 2026

"Sounds very similar to my wife and me. Though we always considered our pensions as small, so we basically ignored them. So now we have healthy tax diversification: taxable, traditional, and Roth accounts (from maxing out IRA contributions every year plus conversions and mega back door). Who needs Social Security and pensions?"

- Randy Dobkin

Insurance

To Claim or Not to Claim, That Is the Question

Mark Crothers | Oct 28, 2026

"My understanding of our homeowners policy is that the policy provides a 5% back bonus on our renewal every year we go without filing a claim. We have been with the same insurance company over 10 years so I would prefer not to lose that discount. When we moved out of our previous home decades ago I was doing major DIY updates before selling. I contacted our insurance agent about proper coverage for a unoccupied home and we were rewarded with a 3X increase in the premium. I agree with with your thinking on not filing a claim. I also know that some policies take "depreciation" on some asset replacements when claims are actually filed. Sorry to hear you Bee Out O'Settin."

- William Perry

Family

The Advantage We Bring

Andrew Clements | Oct 28, 2026

"Bob, what a small world! We also visited the Homestead many times , and Woody was a familiar, welcoming presence in the dining room, greeting us warmly and showing us to our table. I can understand why returning without him was so emotional. People like Woody become part of what makes a place special. Thank you for bringing back that lovely memory."

- Andrew Clements

From HumbleDollar Founder Jonathan Clements

Careers

Late Shift

LIKE A SLOW-MOTION train wreck, we’ve spent recent decades inching toward a world where we have too few workers and too many retirees dependent…

Saving

Jonathan Clements Initiative at the Bogle Center for Financial Literacy

Sheila Roher | Aug 22, 2025

"We are giving much more than we ever have, but we still find it hard. In fact we have a couple DAF's (donor advised funds, essentially deferred giving) that have grown larger than most people's net worth. Why is it so hard to give money away? For us, having always been very frugal, a big barrier is the loss of control. Once we give away the keys, someone else will make the decisions about how to drive. I try to calm this fear by reminding myself that I am also an inadequate, imperfect, deficient manager, and that giving away control is just like diversification, which in the long run will lead to a greater and more stable return on investment. We'll try to keep working on it!"

- Steve Spinella

Markets

Doubling the Bear Market Low

Mark Crothers | Oct 22, 2026

"If the goal is to protect against a loss, perhaps it is better to cover that loss with past gains instead of withdrawal from the markets. For instance, my gain this last year is 25%. Doesn't that 25% gain protect me from a 25% correction? After all, I was content a year ago. To put it another way, I am in favor of meaningful diversification, but fail to see the value of withdrawing from the markets as a form of "safety." On the other hand, I can understand Mark's perspective that having already won, he is happy to quit playing. [I'm not quoting you, Mark, just trying to capture the retiring from the markets thinking I am projecting as I read. Perhaps you can correct me by saying it better. I know it's a valid perspective widely shared in our community.] Since I don't view it as a game, but rather a management challenge, I have personally voted in favor of staying fully invested. I do understand that staying fully invested means that a full collapse is also possible. That's why I treat diversification seriously. However, I assume if diversification doesn't protect me, neither will cash or bonds since they also require a functional economy."

- Steve Spinella

Retirement

Roth conversion cash flow

Severly Independent | Oct 24, 2026

"For what it is worth, I did a complete analysis with ChatGPT. Ran alternate conversion strategies, did sensitivity analysis and simulations that tweaked several parameters at the same time (had to specify some probabilities of various parameters). I cross-checked with a multi-page excel worksheet that i had coded. The answers were within spitting distance, and the overall strategy was clear cut. The AI prompt is the key -- you must tell it your goal and provide guidance (e.g., account for mortality risk). Finally, I only provided aggregate data to the AI (to nearest $100K to maintain some anonymity."

- ram bala

In Retirement

Widow’s IRA Choice

ArticleJohn Urban | Sep 12, 2026

WHEN A HUSBAND dies, his widow inherits his IRA. Somewhere in the paperwork of the months that follow there is a decision to make, and nobody presents it to her as one. She can take the account as her own, or she can leave it titled as inherited. Taking it as her own means filling something in. Leaving it means doing nothing, and the IRS tells custodians they may assume that is what she wants. So the account sits where it is, at the same firm, holding money the household always treated as joint, and the decision gets made by nobody. It is the more expensive of the two. Not by a little. Two Tables Every year, a required minimum distribution, or RMD, has to come out of the account. The amount is the balance divided by a number from an IRS table, and there are two tables in play here. Beneficiaries use the Single Life Expectancy table. Owners use the Uniform Lifetime table, which spreads the money over a longer period and therefore asks for less each year. That is the whole mechanism, and it is worth about a third of the annual bill. Take a widow of 76 with $480,000. Left titled as an inherited account, she must take $34,043 that year. Had she taken the same account into her own name, she would have to take $20,253. Same money, same woman, same birthday. The difference is which box got ticked in the months after the funeral. It Does Not Happen Once That gap is not a one-year event. Run both versions forward 10 years, same account, same growth, taking exactly what is required and nothing more. The inherited schedule forces out $374,306 over the decade. As owner, $246,281. She pays about $30,600 more in federal income tax getting there, and reaches 85 with roughly $171,000 less still inside the IRA. She has not lost that money. She has been made to take it out early, pay tax on it sooner, and hold it somewhere less sheltered for the rest of her life. That is a slower kind of damage than a penalty, and a larger one, because it renews every January for as long as she lives. A Floor, Not a Ceiling The usual objection to taking the account as your own is that it locks the money up. It does the opposite. A required distribution is a floor, not a ceiling. She can take more in any year she wants it, for any reason, and nobody asks why. What she leaves alone stays sheltered and keeps compounding. The lower figure buys her the choice. The higher one makes it for her, every year, whether the money is needed or not. One Case Runs the Other Way There is a real exception, and it matters enough to state plainly. Money paid out of an inherited IRA escapes the 10% early-withdrawal penalty at any age, because the IRS exempts what is paid to a beneficiary on account of the owner's death. Take the account as your own and you are back under the ordinary rules. So a survivor who is young enough that an early withdrawal would be penalized, and who expects to need the money, has a genuine reason to leave the account exactly where it is. That threshold is 59 and a half. For most couples already retired this will not apply, and the rest of the article governs. Where it does apply, it outranks everything above. Nobody Will Prompt You I wrote recently about the letter that never comes. A custodian has to tell an IRA owner what must be withdrawn each year, and owes an inherited account nothing at all. So the choice decides more than the size of the bill. Take the account as your own and the letter starts arriving, every January, for the rest of your life. Leave it as inherited and you are on your own to remember the RMD. The branch that requires no paperwork is therefore both the more expensive one and the quiet one, and those two facts feed each other. The option that costs more is also the one that removes the annual nudge that might have made you reconsider it. Decide It Before You Have To None of this is hard to work out. It is hard to work out in the eight weeks after a funeral, which is exactly when it gets decided, usually by default. If you are married and you both hold IRAs, settle it now, while it is hypothetical for both of you. Talk through which of you would be likely to need the money soon after the other died. That is what the 59-and-a-half question really asks, and it is a conversation about your circumstances rather than about tax tables. Then decide which way the survivor should go, write it down, and put it with your trust, your will and the beneficiary designations, where a survivor or an executor will actually come across it. Tell whoever else needs to know that it exists. Look at it again as either of you nears the age your own distributions must begin. That is 70 and a half if you were born before July 1949, 72 if you were born between then and the end of 1950, 73 if you were born between 1951 and 1959, and 75 if you were born in 1960 or later. It is the birthday that makes the whole question live. The paperwork will not choose for you. It will simply do nothing, which is a choice, and on these numbers it is the wrong one for most people who make it by accident. ________________________________________________________________________________ John Urban is the founder of RetireSmartIRA, a retirement tax-planning app. Earlier, he founded GT Nexus, a supply-chain software company acquired by Infor in 2015. He lives in Northern California with his wife, Kathy, and enjoys time with family, travel, reading, Bay Area sports, and the occasional deep dive into the fine print of the tax code.

In Retirement

Social Security “Haircuts”

achnk53 | Oct 25, 2026

"That is also the case with the national debt which a scarier issue than social security. Neither party wants to address anything that will affect people’s lives."

- Nick Politakis

In Retirement

Inherited IRA Trap

ArticleJohn Urban | Oct 24, 2026

EVERY JANUARY, if you own an IRA and money must come out of it that year, your custodian writes to you. The letter gives you the amount or offers to work it out. We barely read it, but it is doing more than we notice. Most people never miss a required distribution, and the reason is not diligence. It is that somebody tells them. Inherited IRAs are different. The IRS notice that creates the requirement says reporting is not required for the IRAs of deceased owners, and an inherited IRA is exactly that. No letter is owed to the person who inherits, and in many cases none arrives. When nobody tells us anything needs doing, we assume nothing does. Here that assumption is expensive. The question behind the question Everyone remembers the 10-year rule. It answers one question: when does the account have to be empty? It does not answer the one that costs money: does something have to come out this year? That turns on a fact about the person who died. Had they reached the age at which their own distributions had to begin? It is 72 for anyone born before 1951, 73 for those born between 1951 and 1959, and 75 for anyone born in 1960 or later. Take the common case, an adult child inheriting a traditional IRA. If the parent died before reaching that age, nothing has to come out until the account is emptied at the end of year 10. If the parent died on or after it, a required minimum distribution, or RMD, is due every year in the meantime, and the account still has to be empty at the end of year 10. That second case is the one people get wrong. The 10-year rule is widely remembered as permission to leave the money alone until year 10, and for a great many people who inherit, it is not. Other beneficiaries have their own timing, among them a disabled or chronically ill beneficiary, a minor child, and anyone less than 10 years younger than the person who died. Inherited Roth IRAs differ again, and a spouse has choices nobody else has. All of it sits in the SECURE Act and its 2022 successor, which is what to search. Take too little and the shortfall carries an excise tax of 25% of what should have come out, or 10% if you correct it promptly. That is on top of the income tax you owe when the money finally comes out. And there are two ways to trigger it. Taking too little in a year is one. The other is reaching the end of year 10 with money still in the account, because whatever is left on that date is treated as a shortfall too. What four quiet years cost A widow turns 76 the year after her husband dies. He was 78, well past the age his own distributions had to begin. She has Social Security of $36,000, a pension of $24,000, and his IRA, still titled as an inherited account, holding $480,000. She does not need the money, no reminder arrives from the custodian, and so she takes none of it for four years while the account grows at 5%. Because he had already passed that age, and because she left the account titled as inherited, she owes a distribution in every one of those years. At 76 she should have taken $34,043. At 77, $37,895. At 78, $42,000. At 79, $46,694, by which point the untouched balance has grown to $555,660. She has missed $160,631 of required distributions. At 25%, the excise tax on that is $40,158. Corrected in time it would be $16,063. Now the part I expected to be worse than it is. When she corrects, all four distributions come out in a single year, and I assumed that bunching would be the quiet disaster. Spread across four years, the distributions cost her $37,566 in federal income tax. Bunched into one, $38,783. The difference is $1,216. If you have been told the danger of a missed distribution is the bracket you land in when you fix it, check that against your own numbers before believing it. The bigger surprise came from Medicare. The surcharge nobody sees Take the distributions on time and her Medicare surcharge is zero in all four years. Bunch them into a single return and it is $6,355. That bill does not arrive with the tax. Medicare sets your Part B and Part D premiums from your income two years earlier, so the surcharge turns up long after the correction has been filed and forgotten, attached to something that does not look like a tax at all. Add it up. Four quiet years cost her about $47,700 she need not have spent: $40,158 of excise tax, $1,216 of extra income tax from the bunching, and $6,355 of Medicare surcharge. The $37,566 of income tax on the distributions themselves was never avoidable and was never the problem. In none of those four years did anyone write to her. The first letter came from the IRS, years late, and fixing it by then meant amended returns and a Form 5329 for every year. What actually prevents it Not vigilance. Nobody is vigilant about a rule they have not heard of, and the custodian was never obliged to tell you. If you have already inherited, two facts settle almost all of it. The year the person died, and whether by then they had reached the age their own distributions had to begin. Your custodian can tell you how the account is titled. Nobody but you is going to find that second date. And if you are reading this married, with both of you alive and nothing yet owed, you are in the only position from which this is easy. Work out the year each of you reaches that age. For whichever of you dies first, that is the year deciding whether the survivor owes a distribution the year after the death. Write both years down, with a line saying why they matter, and put them with your trust, your will and the beneficiary designations, where the survivor will actually come across them. The account will not remind anyone that a clock started. The only reliable reminder is the one you write down before you need it. A note of thanks The shape of this article came from William Perry, who spent his working years preparing returns and described in a comment thread how these cases reach a preparer. His account of the letter arriving to the widow years later convinced me the annual question deserved a piece of its own. ________________________________________________________________________________ John Urban is the founder of RetireSmartIRA, a retirement tax-planning app. Earlier, he founded GT Nexus, a supply-chain software company acquired by Infor in 2015. He lives in Northern California with his wife, Kathy, and enjoys time with family, travel, reading, Bay Area sports, and the occasional deep dive into the fine print of the tax code.

Investing

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

Bruce Roberts | Oct 26, 2026

"I agree Bruce. I am a longtime investor and currently own VEA, which is a broadly diversified ETF index of Euro countries. I have owned other mutual funds and ETFs focused on international markets. My experience and observation is that US markets are better performers and I agree with your logic of US based multi national companies."

- Jerry Pinkard

Behavior

Monopoly

D.J. | Oct 27, 2026

"Thanks, Dan. You'll have to let us know how your first game of Toledopoly goes. Are the Mud Hens one of the properties on the board?"

- D.J.

In Retirement

The pension conundrum and a solution

R Quinn | Oct 26, 2026

- Randy Dobkin

Insurance

To Claim or Not to Claim, That Is the Question

Mark Crothers | Oct 28, 2026

- William Perry

Family

The Advantage We Bring

Andrew Clements | Oct 28, 2026

- Andrew Clements

From HumbleDollar Founder Jonathan Clements

Careers

Late Shift

LIKE A SLOW-MOTION train wreck, we’ve spent recent decades inching toward a world where we have too few workers and too many retirees dependent…

Saving

Jonathan Clements Initiative at the Bogle Center for Financial Literacy

Sheila Roher | Aug 22, 2025

- Steve Spinella

Markets

Doubling the Bear Market Low

Mark Crothers | Oct 22, 2026

- Steve Spinella

Retirement

Roth conversion cash flow

Severly Independent | Oct 24, 2026

- ram bala

In Retirement

Widow’s IRA Choice

ArticleJohn Urban | Sep 12, 2026

Manifesto

Oct 28, 2026

NO. 68: AS INDIVIDUAL investors, we enjoy a key advantage: While money managers risk losing their job if their short-run results are lousy, we can invest for the truly long term.

think

Oct 29, 2026

TIME HORIZON. How long will your money be invested, before you need to convert back to cash to pay for your goals? The longer you have, the more risk you can take. Some goals, such as a house down payment, have hard deadlines, with all money needed on a particular day. Others, like retirement, involve softer deadlines, because you’ll use the money over many years.

act

Oct 28, 2026

MAKE SURE MUNIS make sense. High-income earners are often told to buy tax-free municipal bonds in their taxable account. But often, it's smarter to hold higher-yielding taxable bonds in a retirement account, while buying tax-efficient stock index funds in your taxable account. Even if munis make sense today, that may change if your income drops once you retire.

humans

Oct 27, 2026

NO. 18: SPENDING can give us a thrill. Just had a rough day? Others may cheer themselves up with comfort food or a beer. But for some, the antidote is to make a purchase or two, because this spending lifts their spirits. But thanks to hedonic adaptation, the thrill doesn’t last long and, taken to an extreme, such spending could cause financial problems.

Money Guide

Manifesto

Oct 28, 2026

NO. 68: AS INDIVIDUAL investors, we enjoy a key advantage: While money managers risk losing their job if their short-run results are lousy, we can invest for the truly long term.

Spotlight: In Retirement

Widow Tax

John Urban | Jul 25, 2026

THE WIDOW TAX is sold to the wrong households. It gets pitched to affluent couples as the reason to convert to a Roth or buy life insurance. The pitch says that when one spouse dies, the survivor files single, lands in a higher bracket, and…

Americans are rushing to collect Social Security. The reason is disturbing

R Quinn | Sep 12, 2026

I am incensed when I read nonsense posted on social media about social security - “Congress stole the SS funds and never paid it back,” “there would be plenty of money if we didn’t give it to people not eligible” and worse. All nonsense. Is…

For most retirees, the greatest fear is not death—it is running out of money before they die.

Matt Halperin | Aug 6, 2026

A recent Barron’s article notes, "for most retirees, the greatest fear is not death—it is running out of money before they die." As one survey they cite put it, "The prospect of running out of money in retirement is scarier to more people than death."…

The Number Is Not The Answer

John Goodell | Oct 10, 2026

YEARS AGO, while practicing law, I was a frequent contributor to Humble Dollar. I loved Jonathan Clements’s vision for the site - a corner of the financial universe built on clarity, frugality, and the quiet dignity of living within one’s means. Then my…

Taking It With You

Jeffrey K. Actor | Sep 5, 2026

DEEP DOWN INSIDE, I want to be the richest person in the graveyard. I retired at age 62, confident in our financial plan to survive market fluctuations. We saved over 25% of our income for nearly three decades. Perhaps a bit too much, but…

Risk and Taxes

Adam M. Grossman | Aug 8, 2026

AFTER YEARS OF heady gains in the stock market, many investors are facing the same question: To manage risk, they’d like to cut back on one or more of their holdings. But because of the potentially costly tax bill that might result, they aren’t sure…

My “Dark Side” of Generosity: How I’m Curbing it in Retirement.

Mark Crothers | Jul 14, 2025

I've always had a bit of a dark side, one I never really tried to control and certainly didn't think of as a problem. This was especially true when I ran my own business. Through sheer effort and hard work, that business threw off a lot of free cash flow. With all that cash sloshing around, I christened my peculiar…

From Public Housing to Early Retirement: A Path Forged in Adversity

Mark Crothers | Jul 18, 2025

In my childhood, I grew up in public housing. From the age of 11, I attended what in the UK is the rough equivalent of a public high school. This was during a very volatile and violent phase of societal change in my country, set against a backdrop of illegal paramilitary organisations. They effectively "hoovered up" a high portion of…

The High Cost of Financial Advice: A Tale of Two Portfolios

Mark Crothers | Jul 8, 2025

Suzie and I present a microcosm of the debate around financial advisors. I choose to use Vanguard and keep my costs low, whereas Suzie uses a former long-time colleague from her days in the banking sector who happens to be an independent wealth manager to operate her portfolio. To me, the portfolio seems unnecessarily complicated with an average fund fee…

The Auto Loan Compensation Scam

Mark Crothers | Nov 5, 2025

Here in the UK, there's an ongoing, large-scale auto loan scandal involving discretionary commission arrangements—where car dealers secretly earned higher commissions by steering customers into more expensive loans. A recent court ruling has ordered loan providers to potentially compensate millions of people who took out car finance over the last 18 years. The news has barely hit the headlines, but…

Country Club Venture Capital

Mark Crothers | May 17, 2026

I was in Barcelona today watching the world famous FC Barcelona win in front of their home fans. Being on my own, I headed back to the hotel after the game and caught the PGA Golf Championship on the screen in the hotel bar. With nothing better to occupy my mind, I started wondering how a golfer actually gets started…

When a Debt-Free Christmas Goes Wrong

Mark Crothers | Dec 23, 2025

I was talking to a friend this morning before pickleball. He's a retired teacher who stays in touch with former students, and right now he's trying to raise some money for one of them who's in a tough spot. Here's what happened: The guy is in his mid-thirties with two small children. A few weeks ago, he lost his job…

Monopoly

The pension conundrum and a solution

To Claim or Not to Claim, That Is the Question

The Advantage We Bring

Late Shift

Jonathan Clements Initiative at the Bogle Center for Financial Literacy

Doubling the Bear Market Low

Roth conversion cash flow

Widow’s IRA Choice

Social Security “Haircuts”

Inherited IRA Trap

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

Monopoly

The pension conundrum and a solution

To Claim or Not to Claim, That Is the Question

The Advantage We Bring

Late Shift

Jonathan Clements Initiative at the Bogle Center for Financial Literacy

Doubling the Bear Market Low

Roth conversion cash flow

Widow’s IRA Choice

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Manifesto

think

act

humans

Money Guide

Manifesto

Spotlight: In Retirement

Widow Tax

Americans are rushing to collect Social Security. The reason is disturbing

For most retirees, the greatest fear is not death—it is running out of money before they die.

The Number Is Not The Answer

Taking It With You

Risk and Taxes

Spotlight: Crothers

My “Dark Side” of Generosity: How I’m Curbing it in Retirement.

From Public Housing to Early Retirement: A Path Forged in Adversity

The High Cost of Financial Advice: A Tale of Two Portfolios

The Auto Loan Compensation Scam

Country Club Venture Capital

When a Debt-Free Christmas Goes Wrong