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 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.

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,

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.

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,

THERE’S A CHANGE coming in the way many of us invest. But for background, it’s important first to look at a related—though seemingly mundane—investment concept known as tax-loss harvesting.
To understand how tax-loss harvesting works, consider a simple example. Suppose you purchased a stock in your taxable account for $10, and it subsequently dropped to $8. That would be unfortunate, but there’d be a silver lining: You could sell the stock to capture the $2 loss for tax purposes and then reinvest the proceeds in another stock.

FIFTY YEARS AGO, when the first index funds were getting started, critics wasted no time attacking the idea. They called it “un-American” and a “sure path to mediocrity.”
But over time, indexing has grown to the point where it now accounts for more than half of all U.S. mutual fund assets. Last year, research firm Morningstar declared that “index funds have officially won.” But this victory seems to have only increased the level of criticism.

MARVIN STEINBERG was a psychologist who founded the Connecticut Council on Problem Gambling. During his career, he made some uncomfortable observations about the behavior of stock market investors. In many cases, he felt, investors’ behavior veered awfully close to gambling.
This is the sort of observation that seems like it could be true, but it also seems difficult to quantify. That’s why a recent study by Morningstar analyst Jeffrey Ptak caught my eye.
Ptak wanted to examine investors’ experience with so-called thematic funds.

MICHAEL BURRY IS a hedge fund manager who gained fame betting against the housing market in 2008. When that market collapsed, Burry made a fortune, and that cemented his reputation as a market seer. Burry was later portrayed as the central character in Michael Lewis’s The Big Short.
But in the years since, Burry’s predictions haven’t turned out as well. Five years ago, he spooked index-fund investors when he argued that they might have trouble accessing their funds.

EARLY LAST WEEK, The Wall Street Journal ran an article with the headline “Why This Frothy Market Has Me Scared.” The author cited a number of indicators that have him worried, including a survey of investor optimism that’s at a 35-year high. Investors, the Journal said, are feeling “euphoric,” and that’s often a bad sign.
So, as we head into year-end, it’s worth taking stock of where things stand. The stock market has returned nearly 25% so far this year.

AT LEAST ONCE A YEAR, I watch the hilarious short YouTube clip by personal-finance author JL Collins. If you aren’t around small children and can handle liberal use of America’s favorite four-letter word, check it out. Some may recognize it as a parody of actor John Goodman’s soliloquy from the film The Gambler starring Mark Wahlberg.
The clip, however, is more than just entertaining. Its content is what keeps me and, judging from the half-million views,

WHEN I STARTED learning about investing, I stumbled upon a book at my library that immediately grabbed my attention: The Lazy Person’s Guide to Investing by Paul B. Farrell. A portfolio championed by the book consisted of just two mutual funds—one stock index fund and one bond index fund, with 50% of your portfolio invested in each.
With only two choices to make, decision-making becomes far more straightforward. Farrell’s suggested 50-50 split simplifies the process even further.

LOOKING TO CONDUCT a review of your investments? Below is a five-point end-of-year housekeeping checklist.
Suitability. When it comes to the world of investments, the most common types of assets are stocks and bonds—but they aren’t the only ones. There are alternatives like real estate and commodities and, of course, there’s bitcoin, which has more than doubled this year. Which of these is right for you? Since everyone is different, the first litmus test is to assess the suitability of the types of assets you own.