AS I WATCH MY daughter gleefully play with her toes and stare in wonder as she turns the pages of a new book, I’ve never felt more fulfilled. The day she entered the world, I knew I’d finally found my true purpose.
I’ve always believed that money buys us choices, and I wanted a lot of choices and flexibility once I became a mom. My daughter, who is my firstborn, arrived eight months ago,

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,

AS ALWAYS, DR. SEUSS said it best: “Oh, the places you’ll go and the people you’ll meet.”
In making this statement, the good doctor could have been talking about the benefits of volunteering. Since inheriting some money in 2011, I haven’t had to work multiple jobs, as I did in graduate school and during the three years that followed. From 2012 on, I’ve had mostly full-time work, leaving me with time to volunteer for causes I care about.

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.

WHEN I WAS YOUNG, I felt immortal. We all did. It’s natural and likely hardwired into our brains. Such feelings of immortality have an evolutionary advantage, encouraging us to take the risks necessary to succeed.
When I planned for retirement, the notion of immortality was front and center. I consider myself in excellent health. I eat right. I’m not overweight. I stay active. I have a close circle of friends and an active social community from which to draw strength.

I HAD A REVELATION while shoveling snow earlier this year. When I was age 40 or so, digging out after a snowstorm was always an ordeal for me, even with the aid of a snowblower. I’d need to take frequent breaks and would be wiped out for the rest of the day. Multiple body aches would appear over the next 24 hours, and full recovery might take a few days.
But in January, at age 61,

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,

THE SECOND HALF of life isn’t just a continuation of the first. Rather, it’s an opportunity for transformation, new adventures and deepening wisdom. As we navigate these years, understanding the five key stages of this journey can help us live more joyfully and meaningfully. What five stages? Here’s a look at each:
Phase 1: Pre-Rapture. This stage, typically between ages 45 and 60, is marked by a feeling of newfound freedom and independence.

FIDDLER ON THE ROOF is the timeless tale of a poor Jewish dairy farmer in Russia during the early 20th century. What makes the musical timeless? It tells the story of a worker, husband, father and religious believer who’s trying to succeed in all these facets of his life.
One of the show’s most famous songs is, “If I Were a Rich Man.” As the title implies, the farmer dreams of a life of wealth and how wonderful that would be.

WHAT WILL BE YOUR legacy? It’s a question many of us ponder as we get older. My conclusion: It’s the wrong question to ask.
The fact is, the whole notion of a legacy is a tad delusional, and very likely a trick played on us by our genes, which want us to care deeply about future generations. The reality: Most of us will leave scant mark on the world and we won’t be remembered for very long after we’re gone.

I LED A RETIREMENT seminar some years ago at a large manufacturing company. During the question-and-answer session that followed my presentation, a 60-something welder told the group he’d never retire. I asked why. His response: All his friends who’d retired before him were already dead, and he didn’t want to follow in their footsteps.
What he said resonated with me—because I knew someone who suffered a similar fate. Gino was a client back in my banking days.

“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.

ROGER PENSKE STARTED as a race car driver, but soon found he’d be better off as a team owner. Penske’s holding company also has stakes in Penske Truck Leasing, among other businesses, as well as the Indianapolis Motor Speedway, home of the Indy 500.
One of Penske’s criteria when hiring race car drivers: select folks with a burning desire to win. Penske has said he can guide a driver’s thinking about the best way to pursue wins,

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.