THERE’S A MADNESS to crowds—but also great wisdom.
Each of us knows very little about the world. But between us, we know an extraordinary amount. Every time we buy or sell a stock, we each draw on the knowledge and insights we have, and we effectively vote on whether we think the stock’s price should be higher or lower. Because today’s market prices reflect our collective wisdom, it’s hard to find shares that are badly mispriced.

WHEN WE WATCH advertisements, we tend to think of ourselves as stationary, with the marketers coming to us and then, if we don’t respond, heading elsewhere. Like an Einstein relativity paradox, however, we observers are also in motion, being coaxed toward the marketer, often without knowing it.
A good business knows its customer niche—and good marketers know how to speak to that niche. Customer niches are defined by demographic attributes. When I discuss these attributes with students,

WHEN SHOULD YOU claim Social Security? The optimum date for starting retirement benefits is the subject of much debate and analysis. For most people, however, it’s a simple matter of when they need the cash—and, indeed, many folks claim as soon as they’re age 62 and eligible. The experts can run models all they want. But when it comes to Social Security, it seems necessity and emotion rule.
One thing is clear, though: There’s no validity to taking your benefits as soon as possible,

I CONSIDER MYSELF a retirement newbie. I only quit fulltime work in May 2018. Still, it doesn’t take long to pick up a few things about life in retirement. Here are four insights I’ve gained over the past year and a half:
1. It’s important to have a plan. I have witnessed how some retirees, without a plan or direction, struggle to fill the empty time. Here in Spain, for some retirees it can become an endless Groundhog Day cycle of daily drinking and tapas hopping.

WHEN I WAS IN THE workforce, it was easy to give to charity. Now that I’m semi-retired, it seems like more of a struggle—for four reasons:

Because I’m no longer employed fulltime, I can’t donate through payroll deduction, which used to make giving simple and automatic.
Leaving fulltime employment often results in reduced or uncertain income, and sometimes both. Today, I find it harder to know how much I can afford to give.
Retirement heightens thoughts of leaving a legacy to children and other heirs.

IT’S THE GREAT investor fantasy: Quit the stock market at the top and buy back in at the bottom. While the lure of market timing sells millions of books and is standard fodder for financial television, the reality rarely lives up to the promise.
History is littered with the failed dreams of market timers. Less than five years after the nadir of the financial crisis, some pundits were saying U.S. stocks were overvalued. Another five years on and the market had gained more than 60%.

CLAY COCKRELL HAS an unusual job. He describes himself as a psychotherapist treating the “1% of the 1%” in New York City. From this vantage point, Cockrell has gained unique insights into the lives of the extremely wealthy. What conclusions does he draw about money and happiness? “If you have an enemy,” Cockrell says, “go buy them a lottery ticket because, on the off-chance that they win, their life is going to be really messed up.”
This observation fits well with the aphorism that “money doesn’t buy happiness.” There’s a growing body of research supporting this view.

WE WON’T KNOW UNTIL we get there.
How much do we need for retirement and what will it take to amass that coveted sum? It sometimes seems like the entire financial advice business—brokerage firms, fund companies, financial planners, online calculators and more—is solely focused on this conundrum.
That’s mostly a good thing. It is indeed crucial to amass enough for a comfortable retirement. Still, let’s acknowledge an inconvenient truth: The resulting retirement projections imply a degree of precision that’ll likely look hopelessly naïve once the real world intervenes.

NOTHING COMPARES to the human body when it comes to the combination of strength, flexibility and control. Build a strong core, and the possibilities are limitless. Through the discipline of Pilates, you can strengthen your core, while developing flexibility and control. It’s a wonderful tool, but one that’s underutilized.
The same can be said for health savings accounts, or HSAs, which can be funded if you have a high-deductible health plan. With an HSA,

HOW DO DEFERRED income annuities work and how do they fit into a retirement portfolio? I’m a fan of DIAs—sometimes also called longevity insurance—because of their simplicity and range of benefits. Indeed, I sell them through the insurance website I run. But I also realize they aren’t for everyone.
With a DIA, you hand over a lump sum to an insurer in exchange for regular income payments. Like a standard lifetime income annuity, the payments are guaranteed,

AS I GROW OLDER, I realize how important money and good health are. If we have sufficient income to pay our retirement expenses and if our health remains good, we have the makings of something very special.
What is that special thing? It’s the ability to be independent—to live the life we’ve always lived with few limitations. We can continue to live in our home, drive our car, visit our friends and cook our meals.

IT’S IRONIC THAT WE often shortchange retirement savings during the first half of our working lives, because that’s when we can buy future retirement dollars at a huge discount—thanks to investment compounding.
How can we hammer home this point? My proposal: We should adopt a simple mental math rule that allows us to weigh today’s spending against future retirement dollars. That brings me to my ”6 to 2 times 200” rule. The rule covers five age groups: early 20s,

SHORTLY AFTER I retired in March 2017, I was asked to consult on some projects. I knew it was going to be a more complex tax year than I’d faced before. I had earned income from my previous employer, pension income and self-employment income from my consulting.
On top of all that, my wife started a new fulltime job the Monday after I retired. We switched to her benefits, but her company didn’t have a high-deductible health plan with an HSA,

I FEEL LIKE A BROKEN record when I talk about the benefits of index funds. Indeed, index fund advocates—myself included—sometimes get a little preachy, so I won’t bore you with the same facts I’ve cited before.
Instead, I want to focus on a more subtle reason to index, which has been highlighted by the stock market’s behavior over the past year. You’ve probably heard the expression “a rising tide lifts all boats.” When it comes to the stock market,

WE HEAR ABOUT highflying stocks and hotshot money managers, and it’s easy to imagine the streets of lower Manhattan are paved with gold. But the truth is a tad more mundane.
Want some reasonable assurance of investment success? We should shun the excitement of trying to pick winners and instead focus on more prosaic portfolio tweaks. The overriding goal: ensure the compounding of our investment dollars encounters as little friction as possible.
Minimizing this friction will,