Home - HumbleDollar

The Decaying Curve vs. the Time Value of Money

Mark Crothers | Nov 13, 2026

"Mark, your reference to "Die With Zero" sent me to a book review I had published about 3 years ago. The book promotes a concept called "time buckets", which aligns closely with your "shelf life" idea. I thought it was one of the best parts of the book. It also aligns with the "go go - slow go - no go" framework in retirement. Lots of good stuff to think about in this post. Well done."

- Rick Connor

Life Events

A Gift, Not A Given

Andrew Clements | Nov 11, 2026

"Dave, I’m sorry that settling your mother’s estate was followed by such a painful family rift. It’s sad when an inheritance becomes tied to hurt and mistrust, especially while everyone is grieving. Your experience shows how deeply expectations can affect relationships. Thank you for sharing something so personal, and for your thoughtful words about the article."

- Andrew Clements

Investing

Financial literacy is not the problem nor the solution.

R Quinn | Nov 9, 2026

"Basic knowledge of both investing fundamentals and the emotional aspects of decision making are key. Buffett said the investing game is not "won" by those with the highest IQs, but rather those with emotional discipline."

- Jack Hannam

Insurance

Umbrella insurance

Donald Nix | Nov 11, 2026

"My umbrella policy jumped $200 this year. Insurer said they only analyze umbrella prices about every 5 years, hence the big jump in one year. I still believe the cost is reasonable and necessary, although the likelihood of me ever using it is remote. I feel its greatest benefit is that the insurance lawyers are involved for me if I ever do need it."

- Jerry Pinkard

From HumbleDollar Founder Jonathan Clements

Investing

Not Exactly True

THERE ARE FINANCIAL issues on which reasonable people can disagree. This article is not about those issues. Instead, it’s about issues where people disagree—because…

Investing

Bond Lookalikes

Rick Connor | Nov 12, 2026

"Rick, interesting exercise. I agree that Social Security and pensions give us the freedom to take more risk with our investments. But I'm not sure I'd count them as bonds. Bonds also provide liquidity, help cushion market declines, and give us something to rebalance from when stocks fall. Guaranteed income can't do those things. And there's another question worth considering. Once our retirement spending is comfortably funded, aren't we effectively investing much of the remaining portfolio for our children or charities? If so, perhaps we should be thinking about their investment horizon rather than our own. Perhaps the real question isn't how much of our guaranteed income we should count as bonds, but why we need to hold bonds in the first place."

- Mark Gardner

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.

Taxes

IRS Inflation Updates

Bogdan Sheremeta | Nov 12, 2026

"Thanks Bogdan. It's always interesting to see what is indexed to inflation, and what isn't."

- Rick Connor

Investing

Does my bond strategy make sense?

R Quinn | Nov 11, 2026

"👍"

- R Quinn

Investing

2026 Bogleheads Conference

William Perry | Nov 12, 2026

"Bill, Thanks for the reminder. I'm really happy Adam is getting the recognition and look forward to watching his presentation. Jim Dahle's appearance on Christine Benz's podcast last week was well worth a listen. best, Rick"

- Rick Connor

Investing

Is Direct Indexing Useful?

Paul Ward | Nov 8, 2026

"A waste of time. Just read from Dalbar Study 4% of the stocks are responsible for all gains over last 100 years Your odds are slim if you are a LT stock picker"

- Kenneth Tobin

Family

Pirates, Pieces of Eight, and the $ in Your Pocket

Mark Crothers | Nov 11, 2026

"David, I appreciate the positive feedback!"

- Mark Crothers

Spending

The Decaying Curve vs. the Time Value of Money

Mark Crothers | Nov 13, 2026

- Rick Connor

Life Events

A Gift, Not A Given

Andrew Clements | Nov 11, 2026

- Andrew Clements

Investing

Financial literacy is not the problem nor the solution.

R Quinn | Nov 9, 2026

- Jack Hannam

Insurance

Umbrella insurance

Donald Nix | Nov 11, 2026

- Jerry Pinkard

From HumbleDollar Founder Jonathan Clements

Investing

Not Exactly True

THERE ARE FINANCIAL issues on which reasonable people can disagree. This article is not about those issues. Instead, it’s about issues where people disagree—because…

Investing