“IT DOESN’T MATTER IF our planned trips might jeopardize our retirement savings.” The word “jeopardize” was spoken with a sarcastic tone.
It was clear my two financial-planning clients didn’t appreciate my message. They were adamant. Their 10 pricey National Geographic trips, which would span the globe, must remain on their bucket list.
So began a challenging chat. Based on their excitement about their retirement wish list, it would have been easier to simply applaud their exotic plans.

I SPOKE RECENTLY with a fellow who had climbed Mount Everest. The first question I asked: What was it like at the top?
What I expected him to say was that the view was dramatic. Instead, he said, his time at the summit turned out to be less than he’d expected. For starters, it was 4:45 a.m., so there wasn’t a lot of visibility. In addition, it was minus 45 degrees. Because of that,

AS A TEENAGER, I wanted to be an architect. I took six years of mechanical drawing during junior and senior high school, and I was good at it, earning nearly all As.

At another time, in my 30s, I thought about becoming a lawyer. People told me I’d make a good one. A lawyer’s opinion seemed to carry more weight, even when the subject was unrelated to legal matters.

I also wanted to play a musical instrument.

MY AFFINITY FOR spreadsheets began in the late 1960s when I was a paperboy in Virginia Beach. I had a morning route for The Virginian-Pilot and an afternoon route for the now-defunct Ledger-Star. I used my Huffy bicycle with huge baskets front and back.
The business model was straightforward. I paid wholesale for the papers, and customers paid the retail price of 35 cents per week, or 55 cents if they also got the Sunday paper.

I SPENT NINE YEARS at English boarding schools. The food was beyond disgusting. The buildings were cold and drafty. I was constantly bullied. I would go as long as 14 weeks at a time without seeing my parents, who were based first in Bangladesh and then Washington, D.C.
But I also knew I was getting a good education, and I opted to stay when I had the chance to return home and go to the local U.S.

EVEN IN OUR consumer-driven society, some things are looked down upon if bought. One of those things is companionship.
I’ll leave the topic of sexual intimacy for another day. What I’m talking about here is paying—directly or indirectly—for social interaction. We might buy a younger colleague lunch simply to have somebody to dine with. We might continue therapy long after we’ve finished exploring the issues that prompted us to sign up. We all have a need to connect with others and thereby have our own existence validated.

IN OLD ENGLISH, to be “ready” for something meant to be well counseled. The English King Aethelred the Unready earned his nickname because he was ill-advised. His tumultuous reign ended with invasions and revolts, including one by his son.
When we feel we have “extra” money or even just a hankering to spend, there’s a host of outside voices to counsel us. Most try to influence our actions out of self-interest—for their commercial benefit.

HOW WE SPEND DEPENDS on how we feel about money.
To be sure, we’re supposed to spend according to our financial situation and needs. But life experiences can so badly distort our attitude toward money that our financial decisions end up being ruled by fear and insecurity rather than questions of affordability. Such is the case with an acquaintance—let’s call her Satee—whose money habits are at odds with her financial standing.
Satee grew up in a typical Indian family of four.

IN JANUARY 1987, I was an unmarried junior Coast Guard officer just beginning the flight stage of U.S. Navy flying training. I decided to see a financial advisor who’d been recommended by friends.
This wasn’t just any advisor, but rather a retired Air Force lieutenant colonel and fighter pilot. He worked for a firm whose advisors were comprised mostly of retired military officers, and they marketed their services primarily to military officers. If there was anyone I could trust,

I ONLY WOKE UP TO the notion of financial independence at age 50. I’d been asleep at the financial wheel and almost crashed. It had been a 20-year Rip Van Winkle slumber. I realized suddenly that I had an irresponsible, unconscious and unintentional money mindset.
I could offer plenty of excuses, but they don’t make me feel better. Shame, grief and disbelief overcame me initially. At times, regret still haunts me. We had lost so much time without taking care of our future.

I LIKE CHALLENGING myself to do hard things. I guess it’s just the way I’m wired.
Recently, I started thinking about the hardest things I’ve done. Convincing my wife to marry me was hard. She was a tough sell. But eventually I wore her down and got the deal done—one of my best deals, by the way.
Attempting Ironman Cozumel at age 68 was hard and, even though I failed, it’s one of my most cherished memories.

WHILE HANGING OUT at the local Charles Schwab office, you meet a high-octane trader named Hal. He paces up and down like the Energizer bunny and talks so fast you can’t get a word in. Incessantly checking his phone, he abruptly gestures to the door and insists you join him for lunch. Apparently, Apple is up three points, his options are in-the-money and he wants to celebrate.
Hal speeds to a nearby Subway, where he proceeds to order the Spicy Italian for both of you.

JUST BEFORE CHRISTMAS, I had a call scheduled with a financial planning client to discuss investment and tax strategies, with an eye to making sure everything was squared away before year-end.
This client is a retired executive who was successful because of her attention to detail. Her retirement is no different. She’s savvy and loves to get into the weeds of financial planning. As a financial nerd, that’s fine with me.
Naturally, given her personality,

PRESIDENT BARACK OBAMA told Vanity Fair, “You’ll see I wear only gray or blue suits. I’m trying to pare down decisions. I don’t want to make decisions about what I’m eating or wearing. Because I have too many other decisions to make.”
He believed that spending mental energy to make an inconsequential decision about clothes early in the day might lead to a bad decision on a consequential matter for the country later in the day.