YOU MAY BE FAMILIAR with Peter Lynch. In the 1970s and ‘80s, he was one of the most visible figures in the investment world. As manager of Fidelity Magellan Fund, he achieved the best track record, by far, among his peers. He shared his wisdom in a series of popular books for individual investors.
Among the ideas for which Lynch is best known is the notion of “diworsification.” As its name suggests, Lynch argued that diversification simply for the sake of diversification isn’t always a good thing.

I’M ALL IN FAVOR of striving. But I’ve also belatedly come to see the appeal of acceptance.
Should we strive for more, or should we accept what we currently have and what’s currently on offer? As I’ve noted in earlier articles, there’s great pleasure in striving. We love the feeling of making progress, even if our achievements don’t make us happy for long. It’s an instinct we no doubt inherited from our hunter-gatherer ancestors.

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.

OSCAR WILDE ONCE made this observation: “Education is an admirable thing, but it is well to remember from time to time that nothing that is worth knowing can be taught.” In other words, the only way to truly learn something is through experience.
When it comes to investing, this is easier said than done because learning through experience can be expensive. As Warren Buffett once quipped, “It is good to learn from your mistakes.

WE WANT OUR STOCKS to behave like bonds, and our bonds to behave like cash investments. That leads to all kinds of portfolio contortions—some of them damaging to our investment results.
Remember, risk is the price we pay to earn higher returns. Many folks want those higher returns, but they’re anxious to avoid risk. Chalk it up to loss aversion: We get far more pain from losses than pleasure from gains.
Result? Think about stock-market strategies like purchasing equity-indexed annuities and writing covered call options.

IN 1774, AMSTERDAM businessman Abraham van Ketwich created a new type of investment. After raising money from a group of individuals, van Ketwich built a portfolio of bonds. He deposited the bonds in a metal box in his office, which three people then secured using three different locks.
Van Ketwich’s fund could be considered the world’s first index fund. How so? For starters, the bonds purchased were broadly diversified across industries and geography. Second,

IN THE ANCIENT WORLD, before the invention of the printing press, a strategy for remembering information was to build a so-called memory palace. The idea was to associate words with images. Even today, this is how participants in memory competitions can achieve feats like reciting a thousand digits of pi.
Similarly, when it comes to personal finance, I’ve found that certain images can help illustrate important concepts. These are the ones I rely on the most:
1.

IN THE 1990s, Mark Cuban started one of the first internet companies, a video streaming service called Broadcast.com, and later sold it to Yahoo for several billion dollars. With some of the proceeds, he bought the Dallas Mavericks NBA franchise and sold that as well, taking home another several billion dollars.
And for 16 seasons, Cuban appeared on the reality TV show Shark Tank, in which entrepreneurs present ideas to a panel of prospective investors.

NINE MONTHS AGO, Jonathan Clements shared with readers that he’d been diagnosed with an incurable form of cancer. It was devastating news, especially for longtime readers, many of whom regard Jonathan not only as a journalist but also a friend. I count myself among them, so I was grateful that Jonathan agreed to sit for an interview to share more about his background, his early years and his current thinking. 
You’ve joked that,

THE U.S. STOCK MARKET has historically delivered similar returns under both Democrat and Republican administrations. For that reason, my view is that investors shouldn’t worry too much about who occupies the White House, and I tend to stay away from investment discussions that involve politics.
But sometimes, the news coming out of Washington dominates the headlines in a way that can’t be ignored. Such is the case today. Moreover, with the stock market faltering recently,

WHEN I STARTED writing about personal finance in the late 1980s, my focus was on giving “actionable” money advice. Here, at the end of my career, I’m more interested in offering thoughts that’ll help folks with all areas of their life, financial and otherwise.
I’m not sure how many articles I have left in me. Fingers crossed, it’ll be many more than my current diagnosis suggests. But whatever the case, here are four thoughts that I’d like readers to remember:
1.

ONE OF THE PERILS of being a HumbleDollar contributor is that you sometimes get hit up for advice that you aren’t necessarily qualified to give.
Such was the case recently when I was having breakfast with an old buddy. The topic turned to money and investments. Joe and I have been good friends since the days when we played on the high school basketball team. We try to get together every month or so to catch up and reminisce about old times.

MILESTONES MARK the growth of a child as she moves from infancy through school age. In similar fashion, we adults tend to measure our life’s progress with “firsts” or other significant events. Perhaps we remember the feeling of maturity that came with our first kiss or our first job. Milestones help us attach meaning to the course of a life that sometimes seems beyond our control.
Financial milestones often command special significance, like my first “real” job at age 15.

SOON AFTER GRADUATING college and starting work, I visited a dentist I found in the Yellow Pages for a long overdue teeth cleaning and exam. Although I had never had a cavity, the dentist informed me that I had multiple cavities that urgently needed to be filled. Naïve me allowed this dentist to fill the two supposed cavities of most concern.
Somewhat traumatized, I avoided dentists for a time. Finally, I queried several older coworkers,

THIS MONTH MARKS the five-year anniversary of the start of the pandemic. That makes this a good time to look back and ask what lessons we might learn.
In early 2020, when COVID-19 was first identified in the U.S., the stock market dropped 34% in the space of just five weeks. But later in the year—after the Federal Reserve stepped in with its bazooka—the market rebounded, ending the year in positive territory. For full-year 2020,