Adam M. Grossman

I’LL ACKNOWLEDGE THAT today’s topic isn’t the most upbeat. I want to talk about risk—and, specifically, some of the underappreciated risks related to retirement.

In thinking about risk, the hardest part—in my view—is that it defies a single definition. Because of that, there’s no uniform yardstick for measuring it and thus no single strategy for managing it. As Howard Marks states in his book The Most Important Thing, “Much of risk is subjective,

JUST HOURS INTO the new year, I received an email from a concerned investor. His worry: the state of the market—the S&P 500, in particular. With hundreds of constituent companies, the S&P index has the veneer of broad diversification. But scratch the surface, and it seems to carry more risk than investors might like. The issue: It’s top heavy.

As a group, the top 10 companies in the S&P 500 account for more than 30% of its overall value.

LOOKING BACK OVER the past two years, one word comes to mind: extreme. It’s been a period of extremes in the market and the economy. Many have benefitted, but we’ve also seen excesses that aren’t necessarily healthy—from the rise in NFTs to the craze in SPACs to the boom in day trading. That’s why, as you look ahead to the coming year, the theme I recommend is moderation.

LAST WEEK, I REFERRED to the stock market as a hall of mirrors. That was perhaps too kind. With its erratic and often illogical movements, the market also has elements of a pinball machine, a rollercoaster and maybe a clown car. This has always been the case, but it feels especially true this year. There’s one silver lining, though. The market’s recent behavior highlights many of the behavioral biases we read about in textbooks.

LAST WEDNESDAY, the Federal Reserve’s policymaking committee concluded its quarterly meeting with two big announcements. First, the Fed is going to scale back its monthly purchases of Treasury securities. Because these multi-billion-dollar purchases have helped keep interest rates low, the Fed’s objective here is to let interest rates begin to rise. That was the first announcement.

The second is that the committee expects to raise its benchmark rate by nearly a full percentage point next year.

GOT CHARITABLE giving on your mind? Join the crowd. Many folks donate at this time of year, with their charitable giving driven by the charities themselves.

As solicitations arrive, people decide on a case-by-case basis whether to pull out their checkbooks. But some folks follow a more structured process, and that’s the approach I favor. It includes asking these three questions:

1. How much ideally would you like to give? As a starting point,

THE STOCK MARKET’S recent wrenching price swings offer a valuable investment lesson. Let’s start by reviewing the facts:

On the day after Thanksgiving, the S&P 500 suffered its worst day in months and the Dow had its worst day in more than a year. The proximate cause: news about Omicron, a new coronavirus variant. Overnight, investors seemed to revive their playbook from the early 2020 recession. Airline stocks dropped precipitously. Oil plunged 13%. Meanwhile,

RON LIEBER, in his book The Opposite of Spoiled, describes a 2012 conversation between Chris Rock and Jon Stewart. In an interview on Stewart’s show, they got around to discussing the challenges both faced in raising children who could remain grounded amid wealthy surroundings.

Rock described how his own modest upbringing differed from the comfortable life his children enjoy. “My kids are rich,” he said. “I have nothing in common with them.”

Stewart agreed.

A FRIEND DESCRIBED his recent experience trying to buy a new car. “I had two choices,” he said. “One dealer wanted full sticker price. The other wanted even more. It wasn’t much of a choice.”

The inflation situation in the car market is well understood. A shortage of components is limiting car makers’ output, driving up prices. But inflationary pressures aren’t limited to cars. The most recent reading for the Consumer Price Index was higher than it’s been in 30 years.

LIFE IS EXPENSIVE—especially for young adults contending with budget busters like housing and tuition. If you have adult children facing these expenses and want to help them financially, you may be wondering what’s the best approach. While every family is different, below are three principles that I’ve seen work well.

1. Transparency. This applies in several ways. First, you should let your children know your objectives for these gifts. Do you want to see them spend it on something specific—such as a home down payment—or are they free to use it as they see fit?

WALL STREET JOURNAL personal finance columnist Jason Zweig recently made this observation: Getting rich isn’t the hard part, he said. “Staying rich is the hard part.”

On the surface, staying rich might seem easy. After all, you simply need to build a balanced portfolio and then withdraw from it at a reasonable rate. Sure, there are stories about lottery winners and professional athletes going broke. But you might assume that phenomenon—having a hard time staying rich—is limited to such extreme cases.

A FEW WEEKS BACK, I talked about the good-is-better-than-perfect principle. A close corollary: Approach financial decisions incrementally. What do I mean by that? An example is dollar-cost averaging, where you invest a sum of money in regular increments, rather than all at once.

Does dollar-cost averaging guarantee a better outcome? No. But it takes what would be one big decision and breaks it into several smaller ones. The benefit: Each of those smaller decisions ends up carrying lower stakes.

BACK IN THE 1950s, economists Franco Modigliani and Merton Miller developed a theory that, even today, is taught in virtually every finance class.

To understand the theory, suppose you’re running a company and want to build a new factory. To raise money for the project, you generally have two options: You can sell shares to investors or you can borrow money. No one disputes that basic framework, but Modigliani and Miller added a twist: They argued that,

I RECENTLY STARTED reading Think Again, the new book by Adam Grant. Subtitled The Power of Knowing What You Don’t Know, Grant’s book got me thinking about all the ways that, over the years, conversations with clients have led me to look at things through different lenses. Below are eight such topics:

1. There’s one important financial question that stumps most everyone—for good reason. In building a financial plan,

EARLIER THIS MONTH, The Wall Street Journal carried a seemingly innocuous article by Derek Horstmeyer, a finance professor at George Mason University. Horstmeyer described an analysis he and his research assistant had recently conducted. The question they sought to answer: Could investors achieve better results in their 401(k)s by avoiding target-date funds and instead constructing their own portfolios?

If you aren’t familiar with them, target-date funds are intended as all-in-one solutions for investors.