A LOT OF INVESTMENT math focuses on how money grows over time. But as an attorney who’s worked with many clients hoping to retire in comfort, I find myself thinking more about risk—and how the math can work against us. Consider five sets of numbers:
Inflation’s toll: 0.98
Got cash? If you multiply that sum by 0.98, you’ll see your money’s purchasing power a year from now. This assumes 2% inflation, which is the Federal Reserve’s stated target.

IS THE STOCK MARKET too high? It’s a question I’ve heard a lot recently. Each time, I’ve offered this recommendation: It’s impossible to predict where the market will go next, so your best defense is to have an appropriate asset allocation. But how exactly can you determine an ideal allocation?
The textbook method originated in the 1950s, with the work of a PhD student named Harry Markowitz. Up until that point, investors had mostly picked stocks and bonds in a vacuum,

WARREN BUFFETT doesn’t have the best investment record over the past three decades. That accolade apparently belongs to Jim Simons. Buffett also isn’t the world’s richest person. In fact, he hasn’t held that title for the past dozen years and currently ranks No. 6, with barely half the wealth of today’s richest person, Jeff Bezos.
I doubt Buffett feels bad about this. Is your surname neither Simons nor Bezos? I don’t think you should feel bad,

I WAS 24 YEARS OLD when I started working fulltime. My salary at that first job wasn’t great—I was making about $16,000 a year—but the retirement benefits were stellar. As a government employee, I was entitled to enroll in the state’s pension plan. Every month, the government contributed an amount equal to some 17% of my salary. The money was guaranteed to never earn less than 8% interest a year. Most years, the rate of return was much higher.

THE PRODUCERS of retirement commercials would like us to believe that all retirees are the same. They aren’t. To be happy in retirement, we need a good handle on what our needs are—financially and otherwise—and then find ways to satisfy them each and every day.
That might sound difficult, but it isn’t. To help get you started, here are the three general types of retiree I discovered during my research on retirement:
1.

IN NOVEMBER 2019, my 92-year-old widowed mother took an uncontrolled trip down a flight of wooden stairs in her home and got a helicopter ride to the regional trauma center.
Before her fall, we had a tenuous but semi-functional system of care in place. But the chaotic aftermath plunged us into unknown territory and claimed incalculable amounts of time, money and other resources from her caregivers. We spent months struggling with a new, impossibly complex set of rules and referees.

MANY EYEBROWS WERE raised during a recent city budget meeting in Portsmouth, New Hampshire. According to the Portsmouth Herald, the city manager told city councilors that Portsmouth’s mandated contribution to the state retirement system would balloon from $290,000 to a whopping $1.9 million per year. Councilors called the development, which would cause a sizable increase in the city’s 2022 budget, “ugly” and “a kick in the shins.” Had anyone been paying attention,