Retirement

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 life took a sharp pivot. I left legal practice to teach gifted-and-talented students and coach varsity athletics at a public magnet high school. Almost immediately, my submissions here dried up.

YOU MAY BE familiar with a concept known as Pascal’s wager. Named for Blaise Pascal, a devout seventeenth-century French mathematician, it was a thought experiment in which he tried to weigh, in logical terms, the costs and benefits of believing in God. His conclusion: The cost of not believing—a potential eternity of damnation—was so extreme that it far outweighed any other consideration.
I mention Pascal’s wager because a common question is whether similar logic might apply to financial decision-making.

RECENTLY, A READER—let’s call him Tom—posed this question: If stocks historically have delivered far better returns than bonds, then why should an investor own any bonds at all? Even with the stock market’s unpredictable ups and downs, wouldn’t you end up way ahead by betting only on stocks over the long term?
It’s a fair question. Over the past 100 years, stocks have delivered returns of roughly 10% per year, while bonds have returned just 5%.

On 9/29/2026 the US Senate passed the Claiming Age Clarity Act that the US House passed in December 2025 and the the legislation is now on the way to the President for his signature to become law.
In a nutshell the law changes the terminology about how the claiming ages are referred to by the Social Security Agency.
H. R. 5284 Section 2 of the pending bill as adopted by the Senate without amendment reads as follows –

This recent article in the WSJ got me thinking.
https://www.wsj.com/personal-finance/inflation-proofed-retirement-cd2a387a?st=cvZSf3&reflink=desktopwebshare_permalink
I read it and tried to relate to it. I wanted advice on how to invest with this inflation that is causing my nest egg to be worth less. I found the article telling me to stop spending.  I got that under control but what about investing?
so HD readers what are you doing to inflation proof your retirement?

I listened to an interview with a former Social Security deputy commissioner, and one point stuck with me: Social Security isn’t going to vanish, but Congress still needs to deal with its funding problem.
I’m getting close to retirement, so I’d like to know what to plan for. I can run the numbers with a smaller benefit. What I can’t do is guess which changes Congress might make—or whether they’ll wait until the trust fund is nearly depleted before making them.

WHAT’S THE MOST important idea in personal finance? It’s hard to single out just one, but over the years, I’ve found the following dozen ideas to be among the most useful.

Whether it’s on TV or online, there’s never any shortage of market prognosticators. Especially during a bull market, everyone seems to have an opinion on where things are headed. The reality, though, is that people can only guess about how the economy, the market or any individual investment will perform.

A RECENT post by achnk53 about the impact of a spouse’s death on the survivor’s taxes piqued my interest.  The post referenced an interesting Kiplinger article about the “Widow’s Penalty”, or the negative tax implications on a surviving spouse after the death of a spouse. A surviving spouse can file Married Filing Jointly (MFJ) in the year of their spouse’s death. In the full year following the spouse’s death you must file Single. 

Today marks the Autumnal Equinox, when the Sun crosses directly over the Earth’s equator, heading south. The equinox marks the official astronomical start of fall in the Northern Hemisphere and spring in the Southern Hemisphere. It occurs tonight at 8:05 PM EDT.  Days continue to grow shorter and the sun appears lower in the sky.
I wrote an article about the importance of four important astronomical days – the solstices and equinoxes – in my career as a spacecraft thermal engineer.

IT’S BEEN AN UNUSUAL week in the bond market, and not necessarily in a good way. This has many investors questioning the value of bonds, which is understandable. Bonds are supposed to be the “safe” side of a portfolio, but they’ve struggled in recent years.
Arguably, the drama we’re seeing in the bond market today began more than 50 years ago. To put today’s situation in perspective, I’ll briefly summarize that long history. Then we can look at what steps you might take to better protect your portfolio from here.

FOR MUCH OF THE seventeenth and eighteenth centuries, European monarchs used a financial instrument known as a tontine to help finance their governments. 
Tontines were first developed in the 1650s by an Italian government worker named Lorenzo Tonti and were similar to annuities: In exchange for a single, lump-sum purchase, tontines offered guaranteed payments for life. But tontines also offered some unique features.
Unlike an annuity, where payments end with the death of the owner,

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.

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 we lived well and always had sufficient funds to raise a family, maintain our household, and put our children through postgraduate education.
If anything, our retirement spending level is conservative,

This is from a survey of only 240 people from WalletHub August 2026, but still, the results are not optimistic. 
For example, 43% of those surveyed believe it is not realistic for the average American to expect to retire comfortably. “Not realistic?” How do HD readers feel about that?

Pension preference: 7 in 10 people believe a pension is better than a 401(k).  Understandable, but for most workers this is not practical because you need to be a participant in a pension plan (generally one employer) for decades to generate a significant retirement income and the average tenure with one employer is only 4-6 years +-
Americans worry about retirement: More than 1 in 3 Americans are not confident that they will have enough money to retire.

THE CHOICE BETWEEN a traditional retirement account or a Roth is a frequent topic on HumbleDollar. The choice is generally framed as a choice between paying taxes up front (a Roth), or deferring taxes until withdrawal (traditional). I thought it would be interesting to evaluate a real-life example of how this choice might work out.
In December of 2016 my wife and I had an opportunity to each open a Roth IRA. My wife took a partial sabbatical that year,