IT WAS A WARM MAY night in 1977. I was 19 years old and the manager of a fast-food restaurant. I was also in the middle of a five-year addiction to compulsive gambling that would eventually lead me to the brink of spiritual and financial bankruptcy. It was about 10:30 p.m. and I was cleaning up the store after closing. I was planning on going to the racetrack to catch the last race when I was done.

IF I’M HONEST WITH myself, I’ve been financially comfortable for so long that I’ve lost the ability to truly relate to those living paycheck to paycheck. But over a lifetime of working with people and their money, I’ve learned to be aware of signs that someone may be on the brink of breakdown—and could use some help.
I was only 22 years old when I had my first shocking experience with the power of money to cause a life to self-destruct.

A FEW MONTHS AGO, I decided to join a neighborhood golf club. Although I started playing when I was a teenager, I’ve never been that good. Since the group invited players of all handicaps, I thought it would be a fun way to get some exercise and meet new people.
I realized on the first day that I was probably the youngest player. Despite my rustiness, I was putting for birdies on both of the first two holes.

MY MOM AND DAD split up when I was seven years old. Money was an issue for the rest of my childhood. Mom was rarely able to work fulltime and, according to her, child support and alimony were never enough.

When I started working a newspaper stand at age 12, I was expected to give 25% of my daily take for rent. Mom also demanded that I save at least 10%. Depending on the headlines,

AT A RECENT FAMILY event, some of the younger adults were asking their uncle what investments they ought to buy. The uncle is a veteran finance professional with a background in alternative investments.
The young men, all in their early 20s, were just starting their careers. They wanted his opinion on hot stocks, cryptocurrencies and nonfungible tokens (NFTs). One of them had recently made several hundred dollars buying and selling an NFT of an NBA image.

I’VE WORKED AS a financial advisor for 25 years and yet I’m still struck by how many people fall for one of the oldest cons in the book: keeping up with the Joneses.
Being ostentatious is no longer seen as déclassé, at least in America. Instead, it’s a requirement for reality TV, the currency of Instagram Influencers and a proxy for achievement on Facebook. Why be rich when we can appear rich?
We’re hardwired to act this way.

WHAT DOES IT TAKE to manage money prudently? Yes, we should save diligently, favor stocks, diversify broadly, hold down investment costs, buy the right insurance and so on. But all these smart financial moves stem from key assumptions we make about our lives and the world around us.
What assumptions? I believe prudent money management starts with five core notions—which, as you’ll discover below, sometimes contradict one another:
1. We’ll live a long life.

ON NEW YEAR’S DAY 1994, life was looking pretty good. I was age 35 and, despite not having a college degree, was slowly climbing the corporate ladder. I’d just finished the most lucrative year of my career, and a semi-promotion promised to increase my income by 50% to 100%. My wife Kathleen was happily home-schooling our six- and 13-year-old boys, and we were thinking about buying a bigger house.

Then life happened.

On Jan.

WHEN PEOPLE MENTION Eastern philosophy, Westerners often have images of mystic monks in saffron robes, surrounded by clouds of incense and speaking in cryptic riddles like, “What is the sound of one hand clapping?”
In fact, Asian philosophy can be very pragmatic in addressing everyday decisions, from family matters to investment choices—and many Westerners welcome the different approach to facing life’s challenges.
Daoism (also called Taoism) is one of the world’s oldest philosophies. It’s believed to have emerged more than 2,000 years ago during a period of dissolution,

WE ALL HAVE LIMITED time and limited money. How can we make the most of these two scarce resources?
More than anything, the answer lies in getting the big picture right. That means thinking through the tradeoffs involved, so we don’t allocate too much time and money to some parts of our financial life, while neglecting others.
On that score, it’s hard to offer hard-and-fast rules because personal preferences play a key role. Still,

I THOUGHT SAYING goodbye to my coworkers, and walking out my office door for the last time, would be the most memorable moment from the beginning of my retirement. But, no, that moment didn’t come until the next day.
I woke up, got out of bed and walked into the living room. Staring out the front window, I felt this sense of calm and peacefulness that I can’t remember ever feeling before. I felt so relaxed that I could swear I was weightless.

HERE AT HUMBLEDOLLAR and in many other places, this point has been made: The best investment portfolio isn’t the one that’s theoretically or empirically superior. Rather, it’s the one that lets you sleep at night.
What I’ve found, as far as my portfolio goes, is that the necessary prerequisite for a good night’s sleep is one thing above all else: an oversized cash reserve. By that, I mean a cash hoard that can handle not only the most likely contingencies,

I’VE LATELY BEEN having a hard time sleeping—and I have a pretty good idea why. It has to do with two words that keep bouncing around inside my head. If you let them, those two words will also keep you up at night. They’re powerful because there’s no end to them. You ask, “What are the two terrible words?” The answer: what if.
What ifs are about what could happen in the future and,

WARREN BUFFETT doesn’t have the best investment record over the past three decades. That accolade apparently belongs to Jim Simons. Buffett also isn’t the world’s richest person. In fact, he hasn’t held that title for the past dozen years and currently ranks No. 6, with barely half the wealth of today’s richest person, Jeff Bezos.
I doubt Buffett feels bad about this. Is your surname neither Simons nor Bezos? I don’t think you should feel bad,

AS A BANKER, I GOT a ringside seat from which to watch the many ways that people are separated from their hard-earned money. Some are illegal. Some are legal, but unethical. And many, while legal and ethical, would be unnecessary with a little more knowledge about managing money.
For me, the most disturbing experiences were when scammers extracted money from the naïve and innocent. I’ve seen the pain of customers who found out that their elderly mother had given her life savings to a manipulative TV preacher.