Home - HumbleDollar

The pension conundrum and a solution

R Quinn | Oct 26, 2026

"That was my point about that value of a pension. There is very limited value without longevity with the employer sponsor. So, people who see their career among different jobs with or without a pension should maximize any defined contribution plan they can get."

- R Quinn

Monopoly

D.J. | Oct 27, 2026

"Given the nature of the game was originally to warn of the dangers of capitalism is scarcely a surprise that the biggest risk taker won by sailing close to the wind. What would have been interesting in the context of a family game is if you'd truly forced the developer into facing the moral hazard of bankruptcy and forced disposal of properties at an undervalue or let him off the hook with loans and subsidies. Clear parallels in the real world there too."

- bbbobbins

Social Security “Haircuts”

achnk53 | Oct 25, 2026

"My comment is simple. The current administration has no interest in taking action to fix SS. And given the timing, it can avoid doing so and leave office with 3-4 years left for someone else to make the fix and take the heat and blame for the changes necessary at that point."

- R Quinn

From HumbleDollar Founder Jonathan Clements

Ignore Valuations?

Make no mistake: Stocks are expensive, with the companies in the S&P 500-index currently at 28 times trailing 12-month reported earnings, offering a dividend…

Investing

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

Bruce Roberts | Oct 26, 2026

"For a long time I have followed the logic that major US companies in S&P derive significant revenues from their international operations. But recently, I have started moving towards a still more diversified portfolio. Rather than VTI, based solely on US stocks, I have moved towards VT. Both are ETFs offered by Vanguard. Yes, the wisdom here comes from JL Collins."

- V Saraf

Retirement

Roth conversion cash flow

Severly Independent | Oct 24, 2026

"I’ve used Boldin and it gives you a lot of options on how you want to model it, by tax rate, highest ending estate balance, IRMMA cliffs,etc"

- Joe

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.

Priced as Marked

D.J. | Oct 22, 2026

"Sometimes a deal just feels right. Enjoy the new printer!"

- D.J.

Estate Plan

Exit Strategy

ArticleDavid Gartland | Jul 9, 2024

IF YOU’RE LIKE ME, you aren’t eager to spend down your investments. What fun is that? Aren’t you curious to see how big your portfolio could grow? Of course, you are.

After my wife and I are gone, my son will have dibs on the money we’ve amassed. We’ve set up a special needs trust to provide him with income when we’re no longer around. My son has no siblings, so we needed the trust to make sure he’s taken care of.

But until then, I view our portfolio as a beautiful garden that I need to nurture. I believe many investors are like me, and don’t really enjoy spending. Instead, they cultivate their wealth with an eye to passing it on to their heirs or their favorite causes.

But what about those investors who don’t have anybody lined up to take over their money after they’re gone? We’ve had wealthy celebrities, like Prince and Aretha Franklin, who died without clear instructions for how their estate should be handled.

I don’t understand such neglect. You’ve been caring for your portfolio with the goal of seeing how big it can get before you “kick the bucket.” That’s great. But you also have a responsibility to make sure your efforts don’t go to waste. You should have a plan in place for this thing you’ve enjoyed owning for so long.

Some investors say, “Oh, I don’t care what happens after I’m gone.” That’s the wrong attitude. You owe it to your wealth to see that it’s put to good use after your death. Just find someone or some cause that you feel would benefit from all your hard work.

Maybe your beneficiaries will fritter away your money. Maybe they’ll show respect for what you’ve done and keep your wealth growing. Maybe they’ll put it to good use and help many others with this gift you’ve given.

But no matter how your beneficiaries behave, the important thing is that you do your part—and have a plan for what happens after you’re gone. Once you’ve done that, you can go back to tending to your investment garden and making sure you don’t mess it up for the next owner.

Investing

The Trouble With Being Different

Mark Gardner | Oct 24, 2026

"Financial websites and cable channels try to manipulate us into reacting to short-term fluctuations that are essentially meaningless noise. I’ve stopped tracking 1/3, and 5-year returns and now focus solely on 10-year investments (approximately 3-5 rebalancing events per my plan) and beyond. It’s incredibly challenging to do so, considering how sophisticated the media algorithms have become!"

- Mark Gardner

Advisors

The Time Value of Money

Dan Smith | Oct 23, 2026

"I think it may be innate, but still may require a learning process. Like a newborn baby has the innate ability to speak, it takes a long time to fully develop the skill. And some of us talk gooder than others!"

- Dan Smith

Beyond Predictions

ArticleAdam M. Grossman | Oct 24, 2026

NATURE ABHORS a vacuum. That’s well known, but when it comes to investing, this poses a particular problem. Why? In the absence of anyone having the ability to predict the future, commentators and prognosticators are happy to step in with stories of their own. The reality, though, is that no matter how rigorous anyone’s analysis might be, no one can know for sure what the future holds, for the economy, for the stock market or for any individual investment. Rationally, we know this, but still it’s an uphill battle, because market commentators have at their disposal an endless library of smart-sounding anecdotes and aphorisms to support their views. And they can be convincing. To see how this works, we can look at some of today’s most frequently debated questions through the lens of these storytellers. The first question on many investors’ minds: Is the stock market skating on thin ice? For some, this question isn’t difficult to answer. They point to the Cyclically-Adjusted Price-to-Earnings ratio (CAPE). Developed by Robert Shiller, a Nobel laureate, the CAPE ratio is a respected measure of market valuation. Today, it’s at its highest level since the market peak in 2000 and much higher even than it was in 1929, just before the crash. Compounding these concerns, there’s worry that traditional valuation methods like the CAPE may even be underestimating market risk. Companies in the AI ecosystem are of particular concern because of the ways in which they’re doing business with each other. Nvidia, for example, has announced an investment of as much as $100 billion into OpenAI at the same time that OpenAI is spending billions on Nvidia’s chips. Nvidia has invested in dozens of other AI-related companies, helping further drive demand for its own chips. This calls into question many companies’ earnings. If they’re passing the same dollars around, to some extent, should those dollars be counted as sustainable revenue, or is it a game of financial musical chairs that may come to an end? It’s an open question, but the optics of these deals buttress the argument that the market is out over its skis. Market bears also like to point to a famous Wall Street anecdote: According to lore, someone once asked J.P. Morgan to share the secret of his success. His reply: “I made all my money selling too early.” Caution, in other words, may be rewarded. Especially in light of the CAPE ratio and other concerns, it sounds like it might be wise advice to take a more conservative tack with one’s investments. But this is where the anecdotes run headlong into the data. According to a 2023 study titled “Selling Fast and Buying Slow,” a key driver of mutual fund underperformance is that fund managers tend to make errors in timing their sales. Perhaps J.P. Morgan did benefit by shrewdly selling before market downturns, but according to the data, that’s not the experience of most professional investors. Who’s right in this debate? My view is that proponents of each argument have a legitimate point. The problem, though, is that what happens in the future can’t be decided on any given set of data. Instead, where things ultimately go will depend on a more complicated interplay among all of the factors out there, from AI to interest rates to elections, geopolitics, and innumerable other factors we may not even be thinking about. For that reason, we shouldn’t put too much stock in definitive-sounding predictions. A similar debate is swirling around U.S. Treasury bonds. In finance textbooks, U.S. government bonds are referred to as the “riskless asset,” owing to the U.S. economy’s status as the largest and most productive in the world. Because of that, the Treasury has historically been able to borrow as much as it needed each year. Indeed, the government’s debt load topped $40 trillion a few months ago, and its nearly flawless credit rating has allowed Congress to continue financing multi-trillion dollar deficits each year. It’s for these reasons that some commentators see it as irrational to worry about the U.S. government’s financial position. One recent book titled The Deficit Myth argued that the government could, more or less, print as much money as it wished. That’s one line of argument. But here too, the stories seem to be in conflict with the data. In the first eight months of this year, the Federal Reserve held rates steady, but despite that, market interest rates rose almost continuously over that period, defying the Fed. Why would market interest rates rise when the Fed hadn’t made any moves at all? One explanation is that bond investors are growing more concerned about the federal government’s fiscal health. In round numbers, the government now spends about $7.5 trillion per year but is only taking in about $5.5 trillion in revenue, and Congress doesn’t seem to be focusing in any serious way on addressing that gap. Taken together, these data points suggest that concerns about deficits are definitely not a myth, and that the notion of a “riskless” asset carries with it no guarantees. As an individual investor, how should you respond to these sorts of debates? This is the simple formula I suggest: First, don’t make changes to your finances in response to any given commentator, since, as we’ve seen here, there often exists an equally articulate, but opposite, point of view on any given question. At the same time, I wouldn’t entirely tune out the prognosticators. Instead, I would take the time to closely examine your own finances and run stress tests to see how your plan might be affected under each of the various scenarios they predict. Then see if there’s a way to diversify your holdings to protect against those potential outcomes. Diversification is probably the simplest rule in personal finance but may be the most valuable. 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.

Family

Jonathan, How I Wish You Were Here

Andrew Clements | Oct 25, 2026

- Mark Crothers

The pension conundrum and a solution

R Quinn | Oct 26, 2026

- R Quinn

Monopoly

D.J. | Oct 27, 2026

- bbbobbins

Social Security “Haircuts”

achnk53 | Oct 25, 2026

- R Quinn

From HumbleDollar Founder Jonathan Clements

Ignore Valuations?

Make no mistake: Stocks are expensive, with the companies in the S&P 500-index currently at 28 times trailing 12-month reported earnings, offering a dividend…

Investing

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

Bruce Roberts | Oct 26, 2026

- V Saraf

Retirement

Roth conversion cash flow

Severly Independent | Oct 24, 2026

"I’ve used Boldin and it gives you a lot of options on how you want to model it, by tax rate, highest ending estate balance, IRMMA cliffs,etc"

- Joe

Inherited IRA Trap

ArticleJohn Urban | Oct 24, 2026

Priced as Marked

D.J. | Oct 22, 2026

"Sometimes a deal just feels right. Enjoy the new printer!"

- D.J.