A NEIGHBOR WAS recently telling me about the increasing amount of care he and his wife have to provide to his 90-year-old mother-in-law, and the challenges and expenses he expects in the near future.
I was able to offer some advice—because this is an area where my wife and I have significant experience. Together, we took care of her parents and mine, both medically and financially. If this is something you’re experiencing, or may soon,

IF THERE’S ONE STORY that seems to have captured the investing public’s imagination this summer, it’s the revelation that venture capitalist Peter Thiel has managed to accumulate more than $5 billion in his Roth IRA—where it will be entirely tax-free to him.

In its reporting, ProPublica, the news outlet that carried the story, focused mostly on the tax aspects—the fact that Thiel was able to use his Roth IRA in such unusual ways. In my opinion,

THERE’S NOTHING THAT deters financial planning like a scarily large price tag.
We should ask ourselves all kinds of tough financial questions. But many of the toughest never get asked—because we know answering them will involve agonizing choices, difficult conversations and unthinkable amounts of dollars. Consider these four:
1. How would you cope if you were out of work for six months? As I’ve noted in earlier articles, the big financial emergency isn’t replacing the roof or the air-conditioning system,

MY HUSBAND AND I have been selecting investments together for years—and we’re still married. How have we gotten along for decades without killing each other?
Our investment discussions revolve mostly around individual stocks and bonds. They constitute the bulk of our investments and take up the bulk of our time. We own everything from small amounts of risky stocks like Immutep (symbol: IMMP) to blue chips like Johnson & Johnson (JNJ) and 3M (MMM).

ONCE IT LOOKED SAFE to travel again, I didn’t waste any time. I jumped on a plane and spent three weeks in the Carolinas. It was a great vacation.
Staying in an Airbnb on Hilton Head Island gave me a much-needed chance to recharge while enjoying the beach. Renting a place on Lake Norman, the largest man-made lake in North Carolina, gave me quality time with two of my grandchildren. It was like breathing freedom again after the long COVID-19 lockdown.

IT WAS A WARM MAY night in 1977. I was 19 years old and the manager of a fast-food restaurant. I was also in the middle of a five-year addiction to compulsive gambling that would eventually lead me to the brink of spiritual and financial bankruptcy. It was about 10:30 p.m. and I was cleaning up the store after closing. I was planning on going to the racetrack to catch the last race when I was done.

MY RELATIONSHIP WITH money is complicated. I want to get the best value for our dollars, so I spend a lot of time comparison shopping. Other people hunt for bargains. I go on long safaris.
My frugality and comparison shopping have served Jim and me well. In our double-income household, we managed to save 50% of our combined pay—basically living on one income and saving the rest. That, coupled with some lucky breaks, propelled us to early retirement.

EVERYTHING I KNOW about estate planning I learned in court.
As part of my litigation practice, I represent parties—often warring family members—involved in disputes over wills, trusts and family businesses. These disputes have common themes that teach important lessons about financial planning in general and estate planning in particular.
Driving these disputes is the enormous transfer of wealth—trillions of dollars—from the Greatest Generation to their children, grandchildren and great-grandchildren. Couple that wealth transfer with other demographic trends,

A FEW WEEKS BACK, I discussed some of the challenges with traditional long-term-care (LTC) insurance: In addition to steep and rising premiums, these policies are complex. Many policyholders have to contend with an annual renewal letter that presents a mind-numbing matrix of options.
But there’s more to it than that. Long-term care is also an emotional topic. There’s the expression that personal finance is more personal than it is finance. I’ve been reminded of that over the past few weeks,

WHAT WORRIES ME? It isn’t the stock market, but rather stock market investors.
Despite all the hand-wringing, this doesn’t strike me as an especially dangerous time to own stocks. Corporate earnings are rapidly recovering from last year’s economic shutdown—not exactly a scenario where you’d expect a big stock market decline. Meanwhile, bonds and cash investments are offering scant competition for investors’ dollars, which is another reason to be bullish on stocks.
But even if the overall market appears no riskier than usual,

IF I’M HONEST WITH myself, I’ve been financially comfortable for so long that I’ve lost the ability to truly relate to those living paycheck to paycheck. But over a lifetime of working with people and their money, I’ve learned to be aware of signs that someone may be on the brink of breakdown—and could use some help.
I was only 22 years old when I had my first shocking experience with the power of money to cause a life to self-destruct.

I HAVE TO ADMIT IT, I’m one of those guys who likes to hide money. I have cash hidden in a couple of places in my house and even in the garage. And I’m not talking about a few dollars. I probably have more than $3,000 in denominations large and small tucked in envelopes. I also have a jar of coins.
You might ask, “Why in the world would someone have so much cash lying around the house?” I keep it on hand in case of an emergency.

A 156-YEAR-OLD newspaper company filed for reorganization in bankruptcy court last year. The company said it just couldn’t come up with the millions it owed to its pension plan. Some 24,000 current and future retirees were promised payments from that plan—and I’m one of them.
This is the story of what happened to our benefits after the pension plan failed.
For 10 years, I was lucky enough to cover Washington, DC, as a newspaper reporter.

MANY PEOPLE TELL ME they need, say, $1 million or $2 million to retire, effectively equating retirement with a dollar amount. But there’s more to retirement than just the financial side. It’s a major turning point that will alter virtually all of our priorities—how we spend our days, how we interact with loved ones, what we care about and what we hope to achieve.

Even if we focus only on the financial side, we can’t sum up retirement with a single number.

OVER A PRODUCTIVE 30-year career that ended in 1950, Willie Sutton robbed as many as 100 banks for gains worth $40 million today—without ever firing a shot. That sort of bank robbery is rare now and, when it happens, customers don’t lose a dime, thanks to FDIC insurance.
Today, Sutton—the Babe Ruth of robbers—wouldn’t waste time knocking over banks. Trillions of dollars held in millions of internet-accessible retirement and brokerage accounts are much softer and more lucrative targets.