I OUTLINED 10 REASONS everybody should have an estate plan in a 2018 article—and what was true then remains true today, especially for those whose assets could be subject to estate taxes.
Under today’s rules, the federal estate tax applies to individuals with assets over $12.9 million. That might sound like a high number. But in 2026, the limit is set to be cut in half. In addition, many states impose their own estate tax,

I’VE WRITTEN BEFORE about harvesting tax losses and using them to offset the gains from selling other investments. We have a bit of a sprawling portfolio, with numerous small positions and lots of embedded capital gains.
Gradually harvesting gains would simplify the portfolio and make it more tax-efficient. And if we do so during these early retirement years, while our income is low, and if we can partially offset those gains with realized losses,

WANT TO DONATE TO charity? It usually makes sense to give now rather than upon death. You’ll get the pleasure of helping a cause you care about, and your generosity may also earn you an immediate tax deduction.
But what about giving money to your children or other heirs? This is a much trickier question, one I’ve thought about a lot ever since my first child was born almost 35 years ago.
Giving now.

I SAT IN THE LAWYER’S office in Erie, Pennsylvania, in the summer of 2011. He was handling the high six-figure inheritance I was about to receive. I should have been overjoyed, but I was exhausted.
In fall 2004, my mother, a 70-year-old former elementary school teacher, had suffered a massive stroke and developed vascular dementia. My father, a 76-year-old former elementary school principal, had tried to take care of her by himself. He fell ill in summer 2006 and died that fall.

WE BOUGHT A FARM earlier this year. We already have a greenhouse business, where we grow flowers, as well as several small tracts of land. The purchase was part of our farming plan, which involves expanding our crop business as opportunities arise.
But buying a farm is also part of our estate plan—and our fishing hopes. We now have two ponds with fish. True, they’re very small fish, as far as we can tell from three afternoons of fishing,

“LOOK RIGHT HERE, Charlie. If you click on the background of Windows Vista in just the right place, the script that I developed will launch and give you access to all my online passwords. You will need to know that if something were to happen to me.”
Dad was a self-taught computer nerd and paranoid about securing passwords. The year was 2007.
Dad died in 2018. I didn’t remember where to click to get his passwords.

MY FATHER-IN-LAW Carson was a stereotypical engineer—organized and precise. All four of his children know the motto “measure twice, cut once.” Carson applied these traits to his finances, which he managed on behalf of himself and Mary Jean, his wife. Mary Jean depended on this.
As they aged, Carson maintained his mental acuity, but he was the first of the two to deteriorate physically. Mary Jean was strong physically but slowly surrendered to Alzheimer’s.

MY HUSBAND AND I WERE late bloomers when it came to estate planning. Though we took care of the basics when we became parents, such as purchasing term life insurance and naming a guardian, we never had a professionally executed will and trust until 2016, when we were in our late 50s.
Observing my in-laws, now in their 80s, made us realize how important it was to get our own estate-planning house in order.

EVERYTHING I KNOW about managing money I learned in court. As part of my legal practice, I represent people involved in disputes over money or property. These can include claims against financial advisors for alleged misconduct, contested wills and trust disputes, and family members at odds over a family business.
These disputes can teach us important personal finance lessons. Here are four lessons—learned the hard way—from four cases my firm handled. All are based on an actual case,

HIGHLY INTELLIGENT people sometimes don’t know much about investing. Still, they can have a misplaced confidence in their own abilities and feel certain they require no help. In the end, it’s often their adult children who sort things out—which, in this particular case, meant me.
Five years ago, my 84-year-old mother and 85-year-old stepfather moved from the mountains of Colorado to Georgia to live closer to my wife and me. For more than 20 years,

THIS PAST SPRING, my brother Phil made the six-hour trip from our hometown in North Carolina to northern Virginia to visit our 95-year-old aunt, whom we know as Aunt Ina Lou. We hadn’t heard from her in a while, which was unusual.
Since we were children, she’d always sent us Christmas and birthday cards, and she’d missed some recently. Phil tried calling several times, but she hadn’t been answering her phone. This wasn’t particularly surprising since our aunt is almost deaf.

I CALL IT MY “BIG BOOK.” I got the name from a Washington Post article about compiling all the information your family will need to navigate your life, should you become incapacitated or after you die. It can include your will, insurance information, investments, real estate deeds, car titles—even who gets the family china handed down from Grandma.
I started my big book in Dropbox, the cloud filing service I can access from home or away.

I’M TOO EMBARRASSED to reveal how long it took my wife and me to prepare our wills. We knew this important task was near the top of almost every financial “to do” list—a list that, it seems, we’ve spent our adult lives slowly working our way through.
We’d discussed the details of our wills, including the crucial decision of who would care for our minor child in the event both of us died. Despite this,

I AM NOW AGE 78—the same age at which my father died 34 years ago. I’m starting to think about dying, though I have no immediate plans to do so.

Of course, my father effectively smoked himself to death, unleashing a combination of heart disease and emphysema. I’ve been a no-smoking zone my entire life. No, I’m not depressed and I’m not being maudlin. But if Queen Elizabeth can’t go on forever, what hope is there for us commoners?

THE WILLS, POWERS of attorney and advance directives drawn up for my wife and me were drafted according to the laws of another state—and were badly out-of-date.
For example, these various documents included guardianships for our then-young children, with a trust to make gradual payouts until they turned age 35. Both our children have since graduated college, become professionally employed and demonstrated they’re financially responsible.
Despite all that, I’m embarrassed to admit that we procrastinated over getting new wills.