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,

LET’S START WITH TWO definitions:
Specʹtrum, n. a trade name of Charter Communications used to market avaricious cable television, internet, telephone and wireless services.  
Vig’or•ish, n.[via Yid., from R. výigryš, lit., gain, winnings.] interest owed a loan shark in consideration for credit. Abbrev: vig.
I bought a home a few months back and, besides trying to meet the neighbors, I had the pleasure of trying to arrange internet service.

WE OFTEN WRITE at HumbleDollar that saving and investing aren’t everything. Spending money on the right things—such as fulfilling experiences—can also be a great investment, especially if the dollars bring ample happiness.
Nearly seven years ago, I thought I’d wasted $4,000 on a foreign trip. But the law of unintended consequences has since worked in my favor.
The 2015 trip was supposed to be an investment in my career. I thought I could make a difference in the world and become a freelance foreign correspondent.

CLUTTER IS DEFINED as “things lying in heaps or crowded confusion.” Its origin as a word dates to the 1570s. More than four centuries later, you might imagine we would have got the problem under control, but it seems not.
I had a friend in high school who lived like a monk. He had nothing on his bedroom dressers except lamps and a record player. I wish I could achieve such a pristine state in my condo.

I DEVOTE A GOOD amount of time to learning, not because I worry about cognitive decline—though that’s a worthy reason—but because I enjoy sampling a host of subjects, everything from meditation to music theories.
Before online courses became popular, my self-directed learning involved watching lecture DVDs. I later discovered many free online offerings from reputed universities, including Stanford, Harvard, Yale, MIT and Princeton.
When the pandemic forced me to spend more time at home,

COULD I BE WRONG about indexing?
Every investor soon learns that being wrong is a frequent malady, particularly on the day-to-day decisions of when to buy. Those minor errors are, as we also learn, part of the “game” of investing and are best ignored. But what if there’s evidence that conflicts with your longer-term thinking and expectations? What if evidence conflicts with your central beliefs?
I suspect it could happen to me.
After 60 years of experience and study of investing,

SELLING COVERED calls can sound like a winning investment strategy, especially to yield-hungry investors frustrated by today’s low interest rates. Wouldn’t you know it? There are exchange-traded funds (ETFs) designed to mimic the strategy.
For background, covered calls are a yield-enhancement play that involve selling call options against stocks that you own. The call option gives you extra income, but—during the life of the option—your gains are capped at the call option’s strike price.

IF YOU FIND YOURSELF with a loved one in hospital who can’t make medical decisions, it can be overwhelming, intimidating and emotionally charged. Decisions are needed and each family member is conflicted: What would I want? What would the patient want? What do I want for the patient? The result can be sharp family disagreements.
Death, the prospect of death or even thinking about death is so loaded with emotion that it can hinder our willingness to prepare.

PREPARING FOR infirmity is one of the most important—and least popular—parts of financial planning. A neighbor’s recent stroke provides a stark example of this challenge. He’s in his mid-80s and has some underlying health problems.
Our neighbor lives in a second-story condominium, with external stairs as access. The stairs end at a narrow deck, with a right-hand turn into the home. An overhang blocks the screen door from opening fully.
When he had a stroke,

MY FIRST RESOLUTION for 2022 is to clean up my investment portfolio. While my garage and my closets are in good order, I shudder when I review my brokerage account.
Over the years, I’ve accumulated close to 20 mutual funds and exchange-traded funds. Overall, I’ve done well with these investments—most of which are based on stock market indexes—but it’s an unnecessary hodge-podge. By the end of the year, I plan to sell a majority of these positions and consolidate the proceeds in a target-date fund.

MINUTES FROM the latest Federal Open Market Committee (FOMC) meeting, which were released last Wednesday, roiled financial markets. Stocks fell sharply, with both the Nasdaq Composite and Russell 2000 falling more than 3% that day. On the week, the Nasdaq was down 4.5%, the S&P 500 down 1.9% and the Dow Jones Industrial Average 0.3% lower. What did investors read in the minutes that gave them such pause?
For background, FOMC minutes are released three weeks after the meeting itself.

ARE LONG-SUFFERING value investors and those with a large allocation to foreign stocks finally about to get some relief? The new year has seen significant relative strength by both areas of the market. Meanwhile, after peaking in the first half of 2021, highflying small- and mid-cap growth companies continue to get hammered. Mega-cap tech shares have also lately succumbed to selling pressure.
What’s worked thus far in 2022 are the boring old large-cap blue chip names.

I WROTE PREVIOUSLY about my parents being victims of financial abuse by one of my brothers. Recently, I returned to Bangkok, which gave me a chance to discuss this situation at length with the entire family, including my other brothers and my uncle.

When the financial abuse of an elderly person is committed by a stranger, the rest of the family often has no chance to see warning signs. But 90% of abusers are family members or trusted individuals.

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.

TOO MUCH FREE TIME, coupled with easy access to the internet, create a problem for this retiree. I obsessively check my IRA at least once—and often several times—each day.
I retired two years early with an above-average Social Security payment and a decent state pension, but not a whole lot in my IRA, which is my only retirement savings. Experts say I need much more, but a job loss in my late 50s, and the inability to find an equivalent position in my field and at the same pay level,