Dan’s recent post about the risk of cuts in Social Security benefits only seven or so years away got me thinking.

This title isn’t serious,  but I wonder if my unconventional SS strategy has once again helped me fall on greener grass? Actually I hope not because 60 million people would be harmed.
I took and saved SS at FRA while still working, my benefit wasn’t reduced and our combined benefits were invested in tax free bond funds for several years.

I’ve been reading HumbleDollar for the past few years, and I wanted to share a brief reflection and invite discussion.
Like many here, my thinking about money has been shaped by a mix of books, websites, and experience. One thing I’ve appreciated about HumbleDollar—and Jonathan Clements’ writing more broadly—is the consistent emphasis on simplicity, behavior, and long-term thinking. The idea that saving rate, costs, and consistency matter more than complexity or clever strategies has stayed with me.

BEFORE THE YEAR ENDS, I wanted to cover a great concept – tax-loss harvesting. It’s a strategy to lower your tax liability by selling investments and repurchasing a similar one. The loss can be used to cancel out gains from other investments, which helps reduce the taxes you owe. Or you can use up to $3,000 of those losses each year to lower your taxable income if you don’t have any gains.
Here’s the key goal of the tax-loss harvesting strategy:
Swap assets into similar,

IN THE WORLD of personal finance, some topics are serious—and others less so. Since it’s the holiday season, it seems appropriate to look back at some of the year’s less weighty stories.
Early delivery. The year started off on a positive note for an Alabama couple. Sha’Nya Bennett was in labor and on her way to the hospital when a snow squall rolled in, forcing her to pull over. The expecting mom ended up delivering in her car,

It’s in the news, and since I don’t know much about lotteries, I figured I’d look into this one.
I’ve never purchased a ticket and expect I never will. It’s not just the nearly impossible odds (1 in 292,201,338 in this case); I consider it a government-sponsored blood sport. In addition to being a tax on the poor and ignorant, the likelihood of an improvement in the lives of winners turns out to be about as probable as winning the lottery itself.

What a difference a year makes. Time, it seems, doesn’t merely pass, it can transform us, reshaping the ordinary rhythms of our days into something we scarcely recognize as our own life.
I spent this afternoon at the season highlight of the local soccer league year, an annual clash between the two biggest teams with around 20,000 other spectators cheering them on. My wife Suzie and I had a grand time with my grandson, caught up in the spectacle and the shared excitement.

Recently I wrote that the potential for long term care (LTC) expenses was my main financial concern. There’s another concern in hot pursuit. 
Not many years ago, I was certain that funding to maintain current Social Security (SS) benefits would be secured. After all, no politician concerned with their job security would let the trust fund run dry. Right? I don’t know about you, but I’m losing hope. There are bills in each chamber regarding SS,

A married couple, both aged 82, have a portfolio of $10M, some in brokerage and some in tax deferred accounts (IRA). They have $70K a year in Social Security.
In addition to the Social Security, they want an additional $150K/year in pre-tax income for a total of $220K/year in pretax income.
What is the standard advice for how to get this additional income in a way that is “guaranteed”?

Occasionally, I read a newspaper article or web posting where the author prophesies that digital payment systems will eventually dominate the economy, and cash (currency and coinage) will become obsolete.
Not so fast.
While the use of digital payment technology is widespread and growing, cash will remain an important backstop in times when digital payment systems fail. And they do fail. Unfortunately, power grids and communication networks aren’t as robust as we’d like to believe.
We know that severe weather events can knock out power grids,

For those of us nearing retirement, you may be interested in this research published in September 2025 in the Financial Analysts Journal, a publication of the respected CFA Institute. Although audaciously titled The Only Other Spending Rule Article You Will Ever Need, the thesis is very simple:

use a TIPS ladder to cover all essential expenses (that are not otherwise covered by Social Security, pensions, existing annuities, etc.);
invest the remainder 100% in stock/equities;

I know we’re all dedicated index investors, but I’ve been given a real hot tip that I’m going to give serious consideration to investing in if it ever comes on the open market. Since it’s Christmas, I thought I’d let you all in on the possible opportunity. At the moment it’s a massive private manufacturing and just-in-time integrated distribution concern with deep history and a worldwide market.
Let me walk you through the fundamentals because they’re genuinely extraordinary.

I wrote this in my wife’s nail salon. On the way there today I was informed she had also made an appointment for me to have a pedicure and manicure.
Yup, a first. It was pointless to resist, besides I was curious. On the other hand,  it would be difficult to get more into unnecessary spending. 
I recall in Copenhagen there was a shop where you put your feet in a tub of water filled with little fish who nibbled dead skin off your feet.

Rachel and I live comfortably now, but it didn’t happen by accident. For most of my adult life, I lived simply—sometimes inconveniently so—and saved steadily. At the time, it felt normal. Only looking back do I see how much those quiet choices shaped the life we have today.
We married in our 60s, in a house I had inherited and was still fixing up. I remember hugging her upstairs and whispering, “If you marry me, we can have a wonderful life together.” I believed it because we were already aligned.

You’re Warren Buffett’s second coming. You’re almost 6 (kids don’t tell you how old they are—only how old they’re about to be), and you’ve just helped a neighbor clean out his garage. Now you have a shiny $10 bill in your pocket.
Good start, but you’re WB2 and aiming for the stars. New neighbor, new mark: another $10, and you’ve doubled your fractional shares in VOO at Fidelity! Soon you’re covering multiple neighborhoods and employing a crew of kids to multiply your profits.

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 but, thankfully, found new work within a week.
Then the timing fell apart. His old employer was supposed to pay his final wages last Friday,