THIRTY YEARS AGO, I took a course on sales and entrepreneurship. We had to buy a few books, subscribe to The Economist and The New York Times, and buy an HP 12C calculator. This was not your usual sales class. I felt like I was piloting the space shuttle as I learned how to use that HP calculator.
I’ll never forget the first time the instructor had us calculate how much money we’d need when we retired.

I SAW MY MOTHER walking through the neighborhood the other day. She was wearing this big floppy hat hiding her face from the sun. But I knew it was her because I can tell by the way she walked. I see her from afar quite often. She drove by me just yesterday when I was coming out of the grocery store. I wonder why she didn’t wave to me. I knew she saw me.

MY WIFE AND I DO a mid-year and year-end financial review. This includes an updated family balance sheet, cashflow analysis, portfolio review and a review of retirement projections.
I’m semi-retired and do some consulting when work is available. This income isn’t guaranteed, so I keep a spreadsheet that estimates our income and tax burden for the year. I usually update this quarterly to see if we need to submit any estimated state or federal tax payments.

IF YOU THINK BITCOIN or any other cryptocurrency will one day be used as readily as dollars and cents, give some thought to this year’s volatility. Suppose you were using your bitcoin stash to pay your $2,000 monthly mortgage payment. Between April and today, the effective cost of your mortgage would have doubled—because bitcoin’s value has been pretty much cut in half.
Now, if you were paid in bitcoin and your mortgage payment was fixed at some value specified in bitcoin,

ARE THERE TIMES when a near 100% international stock allocation makes sense? I believe there are—and that today is just such a moment.
Never in my life have I had such a low allocation to U.S. stocks. My overall portfolio is 60% stocks and 40% bonds. But the stock portion is comprised of just 15% U.S., with the remainder held in international stocks, split evenly between emerging and developed markets.
I realize that’s unorthodox.

IF YOU WANT TO SEE your fellow citizens at their least appealing, look no further than online discussion forums. All too often, they’re a repugnant cesspool of anger, bullying and boastfulness. The comments posted on HumbleDollar are typically fairly civil, though even they occasionally veer toward the unnecessary nastiness that’s rampant everywhere else.
But here’s what these virulent commenters miss: Their postings reveal far more about themselves than about the subject they’re opining upon.

I JUST REVIEWED MY Social Security earnings record. It brings back memories. For instance, it shows I earned $105 in 1959 when I was age 16 and working after school in the city library for 75 cents an hour. I’ve paid Social Security taxes every year since, though in 2020 they were based on earnings of just $2,333 and I was counted as self-employed. That darn blogging money.

Here’s something to put matters in perspective: Over 64 years,

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,