PEOPLE TEND TO attribute their investment gains to skill and their losses to bad luck. To these two categories, I’d like to suggest a third: making a fortune—thanks to good luck. Let me give you an example.
I’m a member of the National Press Club in Washington, D.C. It’s a downtown club where reporters went for a drink and a bite to eat after they filed their stories. As you might expect, business was rocky during the pandemic.

ARE WE HAVING FUN yet? I take no pleasure in seeing my portfolio shrink, but I love buying stock index funds at discount prices and I’m always amused by the hand-wringing in the financial media.
Two years ago, we were hiding out in our homes, fretting over a global pandemic and worrying about an economic collapse. Today, COVID is still spreading like wildfire, but vaccines have helped slash the number of hospitalizations and deaths,

AN OLD WALL STREET adage tells investors to “sell in May and go away.” If you’ve been around long enough to remember that phrase—and you heeded it this year—you’re probably feeling pretty smug, having sidestepped the ugly, unforgiving bear that’s lately been roaming Wall Street.
But such pearls of investment wisdom often make better cocktail chatter than they do an investment strategy, and for good reason: The advice can’t always be counted on. Then again,

MORE WEALTH HAS been lost in this year’s stock and bond market decline than in any previous downturn, according to research firm Bespoke Investments. And, no, that doesn’t include the $2 trillion of crypto value that’s gone up in smoke.
A counterpoint to this jarring reality: Folks today are wealthier than during previous bear markets. Goldman Sachs reports that U.S. household net worth as a percentage of disposable personal income remains sharply above pre-pandemic levels.

SINCE THE START of the year, the stock market has dropped almost 24%. That’s significant, but it pales next to the losses suffered by cryptocurrency investors, with the shellacking continuing into this weekend.
Dogecoin is down more than 90%, and smaller currencies like terra have lost essentially all their value. Even bitcoin and ethereum, which are much more established, have suffered big losses. Ethereum is down around 75% year-to-date, and bitcoin has fallen some 60%.

WHEN WE AIM for financial independence, what we’re usually trying to do is to convert our current work time into future free time. We exchange our time and labor for money today. The wealth we accumulate then buys us a future that’s free from labor.
Given this exchange of labor for future freedom, what’s the most efficient way to speed our progress? According to a research paper, “Capitalists in the 21st Century,” the best strategy is to own a business.

I WAS PLEASANTLY surprised recently when a lump-sum dividend payment showed up in my brokerage account. It was from a preferred stock I bought a few years ago to boost my investment income. The windfall reminded me of the three criteria I’d used to screen preferred shares:

Taxation. Unlike bond payments, which are taxed as ordinary income, the income payments from most—but not all—preferred stocks enjoy the favorable tax treatment given to qualified dividends.

YOU MIGHT WANT to check your mailbox. Mr. Market has been sending around a book of discount coupons on some great index funds and individual stocks.
Twenty-two percent off the S&P 500’s closing high set earlier this year. Seventeen percent off the Dow Jones Industrial Average. How about a whopping 33% off the Nasdaq Composite?
Still kicking yourself for not scooping up Amazon’s stock (symbol: AMZN) in early 2020 when it was—adjusted for the recent stock split—below $100?

FOR THE FIRST TIME, retail investors have more money in index funds than actively managed funds. This is based on March 31 figures compiled by Morningstar and reported by columnist Allan Sloan.
Twenty-five years ago, Vanguard Group founder Jack Bogle published his remembrance of the 1970s launch of the first index fund geared to main street investors. As I page through the book again, I’m reminded of how close indexing came to failing.
Bogle recounts going on a 12-city roadshow,

THE INVESTMENT consulting firm Callan publishes its periodic table of investment returns each year. It shows the results of key asset classes on a year-by-year basis. Each asset class is color-coded and ranked from best to worst. This makes it easy to see not just annual performance, but also relative results.

The periodic table is valuable because it illustrates that there’s rarely a consistent pattern to relative returns from one year to the next.

THIS IS ABOUT my crypto journey. Spoiler alert: I still don’t own any.
My journey began in 2013, when I was serving as an assistant principal in Philadelphia. Since I was always giving advice on our 403(b) plan based on my voracious reading of personal finance blogs, a colleague asked what I thought about bitcoin and whether she should invest. Back then, the price was well under $100—close to $30, I think. I dismissively told her to avoid it.

“WHO DOESN’T KNOW that already?” That’s the question we should ask when making an investment decision.
Take Tesla. It builds wonderful cars. It’s an innovative company led by a visionary CEO. Its sales are growing by leaps and bounds. Question: Who doesn’t know that already?
If the attributes of a company are widely known, more than likely its stock price reflects that. The question for investors isn’t whether Tesla is a great company. Rather,

TARGET-DATE FUNDS are riding a wave of popularity. Morningstar reports that investors placed $170 billion into these funds in 2021, more than double their 2020 inflow. Morningstar also reports that, as of 2019, 58% of all 401(k) participants were invested in a target-date fund. That percentage is likely higher today.
It’s clear why the funds have become so popular. They can be an excellent solution for retirement savers who prefer a hands-off approach. To this end,

MIKE ZACCARDI recently wrote about his favorite podcasts. His list was excellent, but it didn’t include my own favorite, which is Focus on Facts by Eric Sussman. One of the most popular professors at the University of California at Los Angeles’s Anderson School of Management, Sussman delivered a series of riveting podcasts in the first half of 2021.
Given its short run, it’s no surprise that Mike missed the series. But I recommend that Mike—along with other HumbleDollar readers—go to Sussman’s podcast archives to hear his witty insights on the financial markets.

IN BEN CARLSON’S wonderful book, A Wealth of Common Sense, there’s a vignette about Bob, the world’s worst market timer.
Bob is a diligent saver. But unfortunately, he’s cursed with horrible market-timing skills, plowing money into the stock market just before every major decline. For you market history buffs, Bob buys into an S&P 500 index fund on the following dates: December 1972, August 1987, December 1999 and October 2007. The subsequent plunges from these highs were 48%,