THERE’S AN IRONY IN the world of personal finance: The activity that’s the most entertaining—picking stocks—is also, according to the data, one of the most counterproductive. Meanwhile, making asset allocation decisions is more akin to watching paint dry, and yet—according to the data—that’s one of the most important decisions an investor can make.
Asset allocation refers to the split among your investments—how much you hold in stocks, for example, versus bonds or real estate.

WHEN I WAS IN COLLEGE, I thought I had investing all figured out. I’d taken a handful of finance and portfolio management courses, I’d allocated real money for the University of North Florida’s student-managed fund, and I’d researched individual stocks, mutual funds, exchange-traded funds and even options.
But my confidence was crushed by a year of unsuccessful options trading when I was age 20. Nonetheless, through my 20s and into my 30s, I remained optimistic that I could earn handsome long-run returns by overweighting a few investment factors—such as smaller companies and value stocks—and by having plenty of foreign stock exposure.

WHAT DRIVES THE PRICE of individual company stocks, and why do some soar while others sink? It comes down to five factors, I believe.
The first two factors are a company’s observable strengths and weaknesses. Consider Apple. Its strengths are easily quantifiable. In the U.S., it’s captured more than half the smartphone market. When you take into account the company’s premium prices, it collects a disproportionate share of the industry’s revenue. Last year, Apple’s profits hit nearly $100 billion,

I HAVE LONG ADMIRED my grandfather, John H. Watson, for chronicling the contributions to criminology made by his close friend, Sherlock Holmes, Esq. Since retiring from my psychiatry practice, I have similarly had the pleasure, if not the duty, to record the efforts of his grandson Sherwood to expose wrongdoing in the financial industry.
The more informed among you are no doubt familiar with my latest study, The Disappearance of the Load Fund.

STEIN’S LAW STATES that, “If something cannot go on forever, it will stop.” It’s named for Herbert Stein, an economist who was influential in the 1970s and served as chair of the president’s Council of Economic Advisors.
Stein first made this comment when he saw government debt growing to what he felt was an unsustainable level. While half-joking in the way he put it, Stein was making a serious observation: Trends rarely last forever.

I RECENTLY FINISHED reading the second edition of William Bernstein’s The Four Pillars of Investing—twice. This new edition is a significant rewrite of the first edition that was published in 2002. Even if you’ve read the first edition, reading the second edition is worth your time.
Though I’ve read most of the books written by well-known investment luminaries familiar to HumbleDollar readers, there were still pearls of wisdom I gathered from this second edition.

HOW DO YOU COMPETE in an investment contest when you’re a firm believer that investors can’t consistently beat the market averages? That was my dilemma several years ago.
A school not far from where I taught was given money by an alumnus to endow the St. Louis Area Collegiate Investment Contest. All colleges and universities in the area are invited to participate in the competition, which is held regularly. Each is given a hypothetical $1 million and asked to select 20 value stocks.

WHEN I WAS NINE years old, I managed a diversified portfolio—and yet I knew nothing of stocks and bonds. My primary asset classes matched those of my peers: coins, baseball cards and stamps.
Rather than a brokerage firm, we had the Koin Korner, a fairly large store in our nearby shopping mall that sold coins, stamps and a few other collectibles. And instead of following the gyrations of the stock market in The Wall Street Journal,

A KEY CONUNDRUM FOR investors: On the one hand, the data on tactical trading are clear. Frequent portfolio shifts are a bad idea and can damage returns. On the other hand, we shouldn’t be so wedded to the status quo that we’re unwilling to ever make a change.
With this conundrum in mind, it was notable when investor and author Howard Marks declared a “sea change” in the investment landscape and recommended that investors revamp their portfolios.

DO YOU EXPECT IT TO be warmer this winter in Minneapolis or in Miami? This isn’t meant to be a trick question. We’d probably all agree that it’ll be warmer in Miami. But what if I asked you to predict the precise temperature in either city on Jan. 1. This is a much more difficult question.
In his book Mastering the Market Cycle, investor Howard Marks uses illustrations like this to make an important point.

WHEN I TOOK OVER responsibility for my developmentally disabled uncle’s finances, following my father’s death in 2001, I inherited the stock broker that my dad was using. The broker was associated with a well-known financial company. I’d never used a broker before. Any investments I personally owned were held in my employer’s 401(k) plan.
The first time I met the broker, whose name was Jim, I took notice of the large and finely appointed office he had.

WHAT’S THE BIGGEST threat to your retirement?

For young adults, we know a key pitfall is failing to invest in stocks because they’re so afraid of the market’s short-term ups and downs, thus unwittingly risking impoverishment later in life.

But for those of us nearing retirement, the market’s ups and downs can start to matter more than stocks’ long-term inflation-beating performance. An ill-timed market crash or a run of bad annual returns could ruin our retirement plans.

AS THE SAYING GOES, a picture is worth a thousand words. Over the years, I’ve found certain images and illustrations to be immensely helpful in discussing investment concepts. These are the ones I’ve relied on the most:
Only in Australia. A key challenge for investors—if not the key challenge—is that none of us has a crystal ball. It’s impossible to know what markets will do next month or next year.

ACCORDING TO THE consensus of HumbleDollar’s thoughtful and learned readers and contributors, I’m making a mistake by actively managing my investments instead of passively investing in index funds. In an earlier piece, I touched briefly on my reasons for doing so. It’s simple. I do it because I like to do it.
After the past few months, when my investments have definitely lagged the averages, I’ve decided to revisit my decision. What I write here is in no way intended to influence anyone else’s decision.

FROM AN EARLY AGE, whenever I heard the word “stock,” it was said with a derisive tone. My father hadn’t owned any shares, but the 1929 stock market crash and Great Depression still hit him hard. He wasn’t able to find steady work until after the 1941 attack on Pearl Harbor.
Given its effect on our family, my father had a pathological disdain for the market that was, inadvertently, passed on to me. Without being aware of it,