WHEN I WAS A TEENAGER, my father and I went to the local mall. I don’t recall why we went shopping together, but I do remember going into a Tandy craft store and buying a customizing kit for leather belts. Tandy Corp. would later become well known as the owner of RadioShack.
On the way home, my father and I were talking about the kit, and I made the comment, “It’ll be a good way to kill time.” My father shot back,

VOGUE RAN AN ARTICLE a decade ago about Marissa Mayer, then Yahoo’s CEO. The opening quote from Mayer grabbed my attention: “I really like even numbers, and I like heavily divisible numbers. Twelve is my lucky number—I just love how divisible it is. I don’t like odd numbers, and I really don’t like primes. When I turned 37, I put on a strong face, but I was not looking forward to 37.”
Mayer’s statement resonated with me.

WHAT’S THE BETTER choice? This is the perennial question for all of us, as we ponder how best to use our time, how to invest our savings and how to get the most out of the dollars we spend.
Want to lead a more thoughtful financial life? As I try to make better choices, here are five questions I find particularly useful.
1. Why would I stray from the global stock market’s weights?

WHEN I WAS IN MY 20s, I didn’t think much about money. My spending wasn’t lavish. I didn’t go to high-end restaurants or wear expensive clothes.
Still, if I wanted a book or a compact disc, I bought it. I wasted money on fast food instead of cooking at home. I blew money on electronics like a fancy CD player and bought a bigger, more expensive television than I needed. For somebody who considered himself reasonably bright,

BOXING CHAMPION Mike Tyson famously said, “Everybody has plans until they get hit for the first time.”
I’ve only been punched in the face once in my life. It occurred in sixth grade. I was alone in the boys’ bathroom when a bully came in. He said something to me and didn’t like my response, so he attempted to kick me.
I saw this happening out of the corner of my eye and I lifted his leg up,

WHEN I WAS YOUNG, my parents converted our basement into an indoor playground for the neighborhood kids.
My friends could listen to Elvis belt out Hound Dog or croon Love Me Tender on the Seeburg jukebox. Some chose instead to light up the Bally pinball machine. Others would challenge my father to a game of pool. Meanwhile, my mother would create mini-pizzas for everyone, with a slice of Swiss cheese drenched in tomato sauce on half an English muffin.

MY WIFE NEEDED KNEE replacement surgery a few years ago. Her health plan, which was provided through the school district where she worked, was a preferred provider organization with a large network of doctors. After some research, my wife decided she wanted her operation done at New York City’s Hospital for Special Surgery.
I love hearing about people’s lives. I’ve long read biographies to learn how others gained their fame or fortune, hoping for pointers that would help me with my own life.

IN MY ENGLISH CLASS in junior high school, we read a play called I Remember Mama. It was a story about a poor Norwegian immigrant family living in San Francisco in the early 1900s.
The mother ran the household while her husband went to work and the children went to school. The mother was in charge of the family’s finances. Any time a family member needed extra money, he or she would have to ask Mama for it.

MY FIRST DAY IN the investment industry was—unfortunately—not so great. On the morning of Sept. 15, 2008, the investment bank Lehman Brothers filed for bankruptcy, sending the stock market into a free fall. The rest of 2008 was equally ugly, with the S&P 500 losing 37% for the year. But that experience provided investors with a valuable lesson—about the power of recency bias.
Recency bias is the mind’s tendency to extrapolate. When things are terrible,

“I NEVER MEMORIZE anything I can look up.” Albert Einstein, it seems, said this or something similar. I first heard the quote in my freshman physics class. The teacher asked a student to recite a formula. The student’s response: “I never memorize anything I can look up.”
I’ve adopted the same philosophy. My wife loves to point out that I don’t remember the names of streets in our neighborhood. But I don’t need to know them.

MY SON AND I WALK the streets of our town, so my son can pick up trash and recyclables. He’s obsessive-compulsive about trash. He impulsively picks it up even if he isn’t wearing gloves or doesn’t have his grabber available. To reduce this behavior, he and I go out daily looking for trash, so he feels there’s less trash out there.
We do find trash, but we also find things that I wouldn’t classify as trash.

I KNOW FOLKS WHO consider their income to be the best measure of their wealth. Income, however, doesn’t gauge whether you’re making headway toward financial independence.
What does? My financial statement provides everything I need to measure my progress. At the end of each December, I gather the dollar amounts for my assets and liabilities, and assemble the details on a spreadsheet that compares my current standing with prior years. If you’re inspired to do the same,

“SO STEVE, WHAT BRINGS you to therapy?”
“I’ve been moody, sluggish and short-tempered lately. I think I’m depressed.”
“Any guesses what might be going on?”
“I do, but it’s so silly. My wife Alberta needs to make her first required minimum distribution in a few months. You know, when you reach that point in your 70s where they make you withdraw from your retirement accounts. I don’t think it’s about the tax liability. We’ve planned for that.”
“Then?”
“This is going to sound strange.

SOME FOLKS SEEM HAPPY to tell the world how much they earn, how much they have in the bank and what their portfolio is worth. Not me.

If I were to share my income and net worth, I’d expect some serious consequences, and not just from local thieves. In fact, I’m so cautious I have a plan not to tell anyone, except my wife Connie, if I win the lottery.

To be sure, overt sharing often isn’t necessary.

WHEN I WAS A KID, a popular expression was “same difference.” It meant that two choices were essentially interchangeable. It turns out the idea can be helpful in financial planning.
While some financial decisions are very important—and thus warrant careful analysis—others make far less of a difference. In those cases, additional analysis typically contributes little. According to one study, it can even be counterproductive. Below are several topics where extensive analysis is often less important than it might seem.