
Surprising Advice From a Wealthy Man
It just might change your life.
My father was an administrative law judge. Monday through Friday, he’d rise at 5AM and drive to the train station. From there, he’d travel to San Francisco, catch a bus and arrive at his office.
Dad would repeat the journey at the end of each work day. He typically arrived back home around 6PM, except for those times when he fell asleep on the train and missed his stop.
We lived in a three bedroom home in the hills of Los Gatos, California. We had a view of silicon valley. When I was a boy, the dot com era hadn’t begun yet.
Dad made a good living as an administrative law judge, and while we weren’t financially wealthy, we were comfortable. As the years passed, Santa Clara County evolved into the tech hub it is today. More and more “McMansion” homes started popping up around us, as the newfound wealth of Silicon Valley grew.
It wasn’t long before our quiet town of Los Gatos changed. BMW’s, Mercedes Ferrari’s and other expensive cars zipped around town. Michelin rated restaurants emerged to cater to the new glitterati of Silicon Valley.
Meanwhile, Dad continued to drive around town in his old, beat up Ford Ranger truck. “There’s nothing wrong with wealth,” Dad used to tell me, “But for many, they lose themselves in the process. It’s not wealth that defines you…it’s character.”
Of course, as a cocky teenager, my retort was, “Well, I’d rather be a wealthy guy with character than a poor guy with character.” Dad smiled and said, “Sure, but the funny thing is, the most content people I meet are often not wealthy.”
For example, one of my Dad’s favorite people was Corey, the local paver who repaired the neighborhood roadways. Dad used to hire him for odd jobs and invite him over for lunch and iced tea.

They’d talk about history and life. “Corey is more down to earth and authentic than most of the people he works for,” Dad used to say. Dad’s other favorite person was his barber, Pat, who I’ve written about here:
My mother and father sometimes attended parties in our neighborhood, although Dad’s preference was to stay home with a good history book. He went to these soirées mostly for my Mom, who enjoyed socializing.
Dad often observed that many of our wealthy neighbors didn’t seem very happy. Yes, they had huge homes and expensive cars, but some also had marital problems, alcohol issues, stress related health challenges, and more. Others, despite making a lot of money, spent it foolishly. “Half these folks are mortgaged to the hilt,” Dad would say.
My father retired from the bench at the age of 79. He retired later in life because he enjoyed his work and the intellectual engagement it provided. When he retired, he owned his home and cars. He had a good pension, medical benefits, and even invested in excellent, long-term care policies for my mother and himself (policies we’d end up needing later in life).
What I learned from my Dad is that money is helpful, but it doesn’t guarantee happiness.
It’s never enough
There’s a Sufi saying that says:
“You can never get enough of what you don’t really need.”
Maybe that’s what the actor Jim Carrey was referring to when he said:
“I think everybody should get rich and famous and do everything they ever dreamed of so they can see that it’s not the answer.”
The reality is that a focus on materiality, fame and fortunes doesn’t seem to bring lasting happiness. Just look at all the dysfunction associated with Hollywood celebrities. The divorces, drug and alcohol abuse, mental breakdowns and more.
An article in the MessyMinimalist.com had this to say about happiness:
“Let me explain: when every day — every thought — is centered around what you THINK will bring happiness, you’ll quickly find that it’s never enough. This is because after having a happy moment, our brains must come back down to our homeostasis (our natural state of being). If we trick our brains over and over that these temporary ‘happy moments’ (such as eating at a restaurant, getting new furniture or clothes, or vacationing), are how we’re always supposed to feel, then coming back to our homeostasis may begin to feel like a loss… Thus triggering us to pursue MORE feelings of happiness.
The pursuit of happiness is expensive, time-consuming, and exhausting.”
Happiness is fleeting. Sooner or later, the vacation ends. The expensive dinner out is over. We return to the quotidian rhythms of life.
So, if the endless pursuit of money, possessions and fame doesn’t make us happy for long, what should we do?
This is where contentment comes in. Happiness may come and go, but contentment can be more consistently achieved.
Again, from the Messyminimalist.com article:
“If we are content with ourselves and able to accept who we are while in our natural state of being, we will have more time, money, and energy to live and experience life, in both its delightful and inglorious moments. It doesn’t mean we can’t have goals for a better or different lifestyle, but it’s important to find acceptance and contentment no matter your situation. Even if you have nothing, you can enjoy a sunrise. Even if you have no one, you can partake in conversation with a stranger.”
Chasing a mechanical rabbit
Racing dogs run their hearts out around a track chasing a mechanical rabbit. The problem is, they never get to catch the rabbit. In a way, our pursuit of happiness feels like this. What’s worse, even if we catch the “rabbit” of our ambitions, the happiness is fleeting.

We get the promotion, or achieve that degree. We celebrate. But then, the sun sets, and the next day we have to soldier on to the next thing.
Andrew Weil, M.D. argues that we should pursue contentment rather than happiness. Contentment is an inner feeling of satisfaction. It’s not dependent on external things, like a promotion or winning the lottery. By all means, there’s nothing wrong with ambition and achievement. It’s just that we shouldn’t put all our emotional eggs in that basket.
Here’s Dr. Weil briefly explaining:









