INVESTING MAY BE simple, but it’s far from easy. Our mettle is tested during market extremes, whether it’s bubbles or bear markets. Today, both U.S. and international stocks are close to bear market territory. Amazingly, even major bond market segments are sporting double-digit losses, with Vanguard Total Bond Market ETF (symbol: BND) down almost 10% in 2022.
What makes years like this one so difficult is our deep aversion to losses. Successful investing is about balancing risk and reward.

THE HIGHEST expression of complexity is thoughtful simplicity. It’s like standing on a mountaintop after navigating the ascent.
The work of the mountain’s trailblazer is arduous. He or she must focus intently on the task at hand, glancing left and right, guessing what will come around each new bend. But from the pinnacle looking down, the perspective puts the most efficient path in clear view. It becomes possible to make a map to aid those who will come next.

WHAT ARE THE MOST important financial notions? For me, the answers are “compounding” and “financial independence.”
Albert Einstein purportedly called compounding the eighth wonder of the world. Warren Buffett has said that the power of compound interest played an important role in his success. But what I’ve learned is that compounding doesn’t just apply to our finances. It can also be used to improve our health, our relationships and our mastery of whatever topic we choose.

EVERY LEGITIMATE short list of history’s greatest basketball coaches includes Pat Summitt and John Wooden. I’m not even going to attempt to recount their myriad successes. Instead, I want to discuss why they were successful.

Many of the best to ever play basketball went to the University of Tennessee and to the University of California, Los Angeles, to work with these legendary coaches. When players like Candace Parker and Kareem Abdul-Jabbar (then Lew Alcindor) stepped onto the floor,

WHILE VISITING MY mother, I walked along my old paper route. It made me wonder: Which customer am I?
It helps to have a little background on these long-ago entrepreneurs. Paper carriers were independent contractors with the local newspaper. We were given a territory—the route. We purchased the papers from the newspaper company and then delivered them to our customers. Every other week, we would also go around to our customers and ask for payment for the preceding two weeks.

THERE ARE MANY virtues, but one of the rarest is persistence in following through. In our complicated world, often you can’t get something done on the first go. Instead, you have to revisit the task, sometimes more than once. This is true not just of financial decisions but also many other aspects of our lives.
In fact, if you’re trying to get folks to do something, often their first defense is to stall—because they know that,

I RECENTLY HAD a chance to go back in time. An alumnus from my high school is spending his retirement documenting the school’s football program. He’s done an amazing job. He created a YouTube channel populated with an extensive library of game films dating back to the 1950s.
I recently stumbled across the channel, and scrolled to my senior year, which was 1974-75. I played tight end on arguably the worst team in my high school’s long and storied history.

PARKINSON’S LAW states that work expands to fill the time available for its completion. This law is a pervasive reality—and misguided practice—in much of the working world. But I recall first encountering it before I joined the ranks of the employed.
During the summer before my senior year of college, I spent several weeks in Fort Lewis, Washington, for the ROTC training required for a commission in the Army. On the day when it was my turn to lead my peers,

WE ALL HAVE microphones—be it our social media accounts, our podcast or our blog posts. We all have something we want to say, and we want the world to hear it.
Our venting can be shrill and insufferable at times. Who among us hasn’t grown tired of never-ending political arguments and culture wars? Other times our sharing is just inane: If you’ve ever posted a selfie while looking in a bathroom mirror, you’re guilty.

LOOKING TO IMPROVE your physical and financial health? You might have heard similar sounding advice: All you have to do is burn more calories than you consume—and to spend less than you make.

While there’s an element of truth to both platitudes, I don’t find either helpful. There’s a psychological canyon between such abstract ideas and putting them into practice.
One thing experience has taught me: If I’m authentically stirred to want to do something,

WHEN I WAS IN THE Navy, the checklist was a way of life. Everything from a radiation leak to starting an air compressor required one. In emergency situations like flooding, you were expected to take memorized “immediate actions,” and then use a checklist to ensure all the actions were accomplished. For more routine procedures, you would follow the checklist line by line—deviations were not allowed.
While this wasn’t conducive to a creative working environment,

I ENJOY WATCHING superhero shows. It feels good to see the hero swoop in and save the day. Truth is, however, I also get a bit annoyed, as there are always some citizens who seem to ignore imminent danger. They sometimes just stare at it coming, doing nothing to get out of harm’s way.
It’s almost like they just count on the hero saving the day, and that’s a bad strategy. Strangely, many people in real life adopt the same strategy,

I WAS SURPRISED to realize the other day that, despite the varied topics HumbleDollar has addressed, I couldn’t recall a single mention of Sun-Tzu, the 6th century B.C. military commander who purportedly wrote The Art of War. The book is a favorite read of business schools. Even a cursory search on Amazon shows how often Sun-Tzu and The Art of War are invoked regarding business, finance and investing.

DOES IT MAKE SENSE to heed the advice of experts? This doesn’t seem like a hard question. I certainly listen to my doctor and to many others with specialized expertise. As a society, we all rely on experts—from civil engineers to airline pilots to firefighters—for our health and safety.
At the same time, however, human judgment seems to be riddled with flaws. Consider these examples:

After reading his senior thesis, Michael Lewis’s advisor at Princeton University gave him this advice: Whatever you do,