IN HER BESTSELLING book Thinking in Bets, retired poker champion Annie Duke stresses an important point: As kids in school, it was regarded as a failure if we ever answered a question, “I don’t know.” But in the world outside the classroom, the only honest answer to many questions is, “I don’t know” or “I’m not sure.” This isn’t due to ignorance. Rather, it’s because, in many cases, the precise right answer simply isn’t knowable.

YOU MAY BE SAVING and investing for retirement. But what you’re really doing is buying future income. How much income? That brings us to a little number crunching, which I hope will illuminate five key financial ideas.
Let’s start with the numbers. Imagine stocks notch 6% a year, but inflation steals two percentage points of that gain, so you collect an after-inflation annual return of 4%. If you socked away $1,000, what would it be worth in retirement?

THE TAX LAW RELIEVES most Social Security recipients of income taxes on their monthly checks. But it requires middle- and upper-income households to count up to 85% of their benefits as reportable income. Sound punishing? It can be especially punishing for couples who are cutting the knot—but they may live happily ever after.
Taxes on Social Security benefits are triggered when recipients’ MAGI exceeds specified amounts. MAGI is an acronym for modified adjusted gross income (and not the term for the three wise men who bore gifts to the infant Jesus).

I FEEL FORTUNATE there weren’t any iPhones or iPads when our son was a toddler. I’ve recently seen two-year-olds mesmerized by the magic of a smartphone. The kids can whiz around a screen like they were born with one in their diaper pocket. It scares me to think how we would have managed these “toys” if they existed in the 1990s.
But they didn’t. From our perspective, Saturday morning cartoons were the biggest threat to our child’s financial development.

MY FATHER WAS AGE 19 and my mother was 11 when the Great Depression started. They were married in 1942 and I was born in late 1943. Their view of money matters was surely tempered by their life experience.
They had no investments to speak of and always kept what little money they had in a checking account. They would never borrow and didn’t know what a credit card was.
Many years ago, I convinced my mother to buy 75 shares of the company I worked for—a large utility.

MUCH PERSONAL finance literature, including most of what I write, focuses on how to handle money—how much to save, which investments to buy, and so forth. But what if you have a more fundamental question: How do I earn more in the first place?
To help answer that question, I have five new summer reading recommendations. Each of these books offers strategies to help you increase your productivity—and your happiness—on the job. That, in turn,

YOU WILL RETIRE ONE day—and, if you want to spend your final decades in even moderate comfort, it won’t be cheap. Not too concerned about saving for retirement right now? Here are five uncomfortable realities:
1. You’ll almost certainly live to retirement age. Sure, you could go under a bus before then. But that isn’t something you should bank on: If you’re age 20 today, there’s an 85% chance you will live to 65,

AS I CHILD, I REMEMBER reading a series of “choose your own ending” adventure books. These novels allowed the reader, at different junctures, to choose how they wanted the main character in the book to proceed. I always enjoyed rereading these books, creating a different story each time I progressed through the pages.
At this point in my life, I’m beginning to feel like my eventual retirement is a bit of a “choose your own ending” adventure.

WHO’S YOUR WORST financial enemy? Got a mirror? For millions of American workers, their employee benefits play a significant role in their financial life—and yet this noncash portion of their compensation is often undervalued, overlooked and misused.
I designed and managed employee benefits for nearly 50 years. During those years, I tried every form of communication I could think of to get employees to pay attention to their benefits. I retired with a sense of failure.

WHEN I DECIDED TO retire, I kept asking myself, “Do I have enough money?” If I’m lucky enough to live a long life, my savings might have to last 35 years.
My coworkers, however, had a different question. “Hey Dennis, what are you going to do with all your free time?” I was asked that question so many times it became annoying. I soon realized they had doubts about how they would stay busy during retirement.

IN SUMMER 2011, a rural Illinois man named Wayne Sabaj was in his backyard picking broccoli, when something caught his eye. Half buried in the dirt, he found a sealed nylon bag. Inside was $150,000 in cash. For Sabaj, who was unemployed and had, in his words, “spent my last $10 on cigarettes,” this was a godsend.
Though it remains a mystery who had buried this particular stash of money, these sorts of finds are not uncommon.

SOCRATIC DIALOGUE, anyone? Today, we’re tackling three questions. Almost all HumbleDollar readers will, I suspect, readily answer ”yes” to the first two questions—and balk at the third.
1. Are markets efficient? We can debate just how efficient the market is. But most readers, I suspect, will agree that the financial markets are sufficiently efficient that there’s no easy way to score market-beating gains—especially once we factor in the investment costs involved.
It’s the brutal logic of investing: Before costs,

TWENTY-FIVE YEARS ago, I found myself quite unexpectedly spending a night in Reno, Nevada. Gambling was the obvious form of evening entertainment, but money was tight back then. A friend convinced me to splurge and spend $20 playing a slot machine. My measly 25- and 50-cent wagers kept me entertained for nearly an hour, but when I was down to my last few quarters, I bet them all on one final play.
The machine immediately lit up with a colorful array of flashing lights and I waited patiently for my winnings to start spilling out.

IT’S HARD TO IMAGINE, when your child is five pounds and 19 inches long, that one day he will be a responsible adult with friends, a college education, a job, strong opinions—and a credit score.
Getting to that point is part of the adventure of parenting.
Where to start? After getting our son’s birth certificate finalized and receiving his Social Security number, one of the first things we did was set up a 529 college savings account.

A FEW YEARS BACK, I was conducting a retirement planning seminar. At one point, I talked about survivor benefits under our company’s pension plan. As I outlined the benefits, I noticed a strange look on one woman’s face. She was the spouse of an employee.
A few minutes later, I spoke about health benefits, explaining that a surviving spouse was required to pay 100% of the premium. Upon hearing that, the woman took a rolled-up newspaper and began beating her husband about the head.