FREE NEWSLETTER

Topic

Estate Plan

Financial Choices

Adam M. Grossman  |  Sep 12, 2026

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,

Read More

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 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,

Read More

K-shaped Economy

Adam M. Grossman  |  Jul 18, 2026

A TOPIC THAT’S been in the news recently is the so-called K-shaped economy. 
Imagine a chart plotting the relative standing over time of those with higher incomes and those with lower incomes. Owing to a strong stock market and rising home values, the shape of the chart for those with higher incomes would extend up and to the right and has been moving increasingly in that direction since Covid.
Folks with lower incomes, on the other hand,

Read More

Close to Everything I Need

Dennis Friedman  |  Jun 20, 2026

I DON’T HAVE MANY regrets in life. But there is one conversation with my mother that I wish I had never had. It was about moving her into an assisted living facility. She was in her 90s, and I thought it would be best for both of us.
My mother would receive better care, and I could take much-needed breaks. She could even keep her house and spend time there when I was with her.
It seemed like a middle-of-the-road approach to providing care.

Read More

Giving Advice

Adam M. Grossman  |  Apr 5, 2025

WHEN STEWART MOTT graduated college in 1961, he received $6 million from his father, an auto industry entrepreneur who was one of the founders of General Motors. On top of the $6 million, a family trust began paying Mott an annual stipend of $850,000.
That allowed Mott to spend his adult life pursuing a variety of eccentric endeavors. He funded research on extrasensory perception. Inside his Manhattan apartment, he built a 10,000-square-foot garden, along with a chicken coop.

Read More

Share the Power

Dennis Friedman  |  Jan 2, 2025

LIKE OTHER FOLLOWERS of HumbleDollar, I look forward to Jonathan’s Saturday articles. I have to admit that my interest has been heightened by his cancer diagnosis. Not many folks would have the courage to write about what’s going through their mind when they’re fighting for their life. We don’t often get this kind of insight into someone’s life.
Jonathan has probably received a lot of advice about treatment plans and the doctors he should see.

Read More

That Final Payment

Brian White  |  Oct 30, 2024

IT’S IMPORTANT TO BE familiar with what happens with Social Security benefits when someone dies. Otherwise, you may find yourself in a long, painstaking battle to get the payment to which your loved one was entitled. I found this out the hard way.
My father-in-law Bernard died in September 2015. My wife was his executor and the agent under his power of attorney (POA). But I’d earlier served as POA and executor for my mother,

Read More

Death Benefits

Jonathan Clements  |  Oct 19, 2024

I TURN AGE 62 IN January—which means I could claim Social Security retirement benefits and perhaps collect at least a few monthly checks before I succumb to cancer.
But is that the smartest strategy? One of my top priorities is ensuring Elaine is financially comfortable after I’m gone, so I want to make sure she gets as much from Social Security as possible.
We got married in late May, a few days after I was told I had lung cancer that had metastasized to my brain and elsewhere.

Read More

Having the Last Word

Dan Smith  |  Oct 9, 2024

IT WAS 1982 OR thereabouts. After attempting to be a landlord for several years, I decided it wasn’t for me. I sold the house and the four-family apartment building I’d been managing.
The final task in closing out this adventure would come at tax time. Keeping the books was the one aspect of being a landlord that I didn’t mind. I understood how accumulated appreciation would be recaptured and how capital gains tax would affect that year’s taxes.

Read More

Misplaced Trust

Dana Ferris  |  Oct 3, 2024

WHEN I WAS A YOUNG adult, my parents sat me down and explained that I might at some point inherit money from my grandfather’s trust, which had also helped put me through college. My grandfather passed away in 1984, and his wife—my father’s stepmother—became the trust’s beneficiary.
My father was an only child. The trust stipulated that, if his stepmother died before him, he would receive two-thirds of the trust, while my two siblings and I would share the other third.

Read More

No Slowing Down

Jonathan Clements  |  Jul 27, 2024

WHO HAS TIME TO die? I never realized death would be so busy.
I thought I had my financial affairs in good order. But in the two months since my cancer diagnosis, I’ve made countless financial tweaks, mostly with a view to making things easier after my death for my wife Elaine and my two children.
Here are just some of the steps I’ve taken:

I took my two checking accounts—my personal account and the business account for HumbleDollar—and made Elaine the joint account holder with rights of survivorship.

Read More

Exit Strategy

David 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.

Read More

Not So Simple

Jeffrey K. Actor  |  Jun 11, 2024

MY WIFE AND I HAVE divided household duties over our 36 years of marriage. I’m responsible for the upkeep of anything mechanical. Lori has the last word on almost everything else. In essence, my wife presides over functions that make the household a “home,” while I take credit and blame for keeping the nuts and bolts operational.
I also hold primary responsibility for trafficking the family’s money. I pay bills, ensure accounts are reconciled,

Read More

One Life to Live

Sundar Mohan Rao  |  Jun 10, 2024

DURING A GATHERING of retired friends, the topic of wills came up. Many had completed their wills and had their finances in order, while others were working on updating their wills. But there were several who hadn’t even started thinking about it. One of them said, “As a retiree, I’m just starting to enjoy my freedom and have some fun. It’s too stressful to think about death. I’ll get to it someday.”
As you might imagine,

Read More

Getting Along

Tom Sedoric  |  Jun 7, 2024

ONE OUT OF SIX of our nation’s children lives in a blended family, with 40% of today’s marriages defined as blended, meaning that one or both spouses had been previously married. I live in one of those blended households.
Three decades ago, the data on children from “broken families” weren’t encouraging. I can happily debunk that early data, which didn’t give our family much hope. My two exceptional stepchildren, and our biological daughter, are all productive and contributing adults.

Read More
SHARE