John Yeigh

STOCK MARKET INDEXES are at all-time highs, share prices are expensive relative to earnings and global economic growth is slowing. Is it time to consider rebalancing our portfolios and perhaps adopting a more defensive approach?
If you believe in rebalancing—maintaining a relatively consistent allocation to stocks and bonds—then, at some point in this bull market, you must sell stocks. I am hugely hesitant to do so, for three reasons. First, I am fundamentally a buy-and-hold forever investor,

THE CLASH, THE U.K. punk-rock group, famously asked, “Should I stay or should I go?” Retirees and job changers need to tackle the same question when they leave their employer.
At that juncture, you have four options for your 401(k) or 403(b) account: You can leave the balance in your old employer’s plan, roll over the balance to a new employer’s plan, roll over the balance to an IRA or close out the account.

EMPLOYEES WHO accumulate significant company stock can end up with a problem, though not necessarily a bad one: concentrated stock holdings. When these employees retire, their challenge is to sell those shares in a way that maximizes their value—taking into account the share price, dividends and taxes. One strategy: Utilize covered calls.
Selling a concentrated stock position can take many years because of tax considerations or restrictions on selling. For example, if appreciated shares are held in a regular taxable account,

MY WIFE AND I TAKE some over-the-top precautions to protect our financial accounts. Why? After 40 years of working, our life’s savings boil down to digits stored on computers. No one anymore holds stock and bond certificates, stuffs money in mattresses or buries gold in the backyard. The integrity of those digits is all important.
Here are our 11 strategies—which go way beyond the normal account and password protection recommendations:

We only deal with major institutions.

WHILE FINANCES ARE critically important to retirement, it wasn’t the biggest challenge that my wife and I faced. Instead, when I quit the workforce two years ago, a stranger moved into our house.
It was me.
For the prior two years, I had worked in Texas, while my family remained in Maryland, so my son could complete high school there. Even before my temporary Texas move, I worked longish hours, traveled overseas regularly and had lengthy daily commutes.

“YOU’RE FIRED” WAS made famous by Donald Trump as host of The Apprentice. Imagine my surprise when my broker delivered the same message to me two years ago.
In 2015, my job was transferred to Texas. I opted to become a long-distance commuter, while my family stayed in Maryland. Around that time, we moved homes, so our son could attend a better high school. In addition, I was helping to launch two huge long-term work projects.

STICKER SHOCK IS common when families begin the college search—with good reason. According to the U.S. Department of Education’s National Center for Education Statistics (NCES), inflation-adjusted college costs have more than doubled over the past 30 years.
Annual tuition, fees, room and board for fulltime undergraduate students at four-year colleges averaged $26,100 in 2015-16, the last year for which NCES data is available. That average drops to $22,400—if you include junior colleges. On the other hand,

THE NCAA BASKETBALL season concludes every year with the March Madness playoffs. Many Americans engage in bracketology—trying to figure out which teams will get knocked out in each round and which will advance. Warren Buffett even offers an annual bracket-picking challenge, where Berkshire employees can win $1 million a year for life.
This year, however, Americans with substantial retirement accounts might also want to try another form of bracketology: studying the 2017 tax law—and asking whether it offers a unique opportunity to convert hefty amounts of traditional IRA money to a Roth IRA.

WHO DOESN’T LIKE free money? I know I do. If you’ve worked for a major U.S. corporation, you have probably also been offered free money. But there’s a potential downside—in the form of a large, undiversified investment bet.
What am I talking about? Let’s start with the matching employer contribution that’s offered in about half of 401(k) plans. You put in a portion of every paycheck and your company then matches all or half of your contribution.

WE ARE A NATION obsessed with youth sports. Time magazine says it’s a $15 billion-a-year industry. As many as 60 million kids participate.
Sports are good for kids for all kinds of reasons: promoting exercise and a healthy lifestyle, enhancing team work and relationships, providing structure, instilling confidence to overcome challenges and delivering the joy of playing.
During our children’s sports journeys, we parents are often led to believe that our little sports stars are on the path to the holy grail—a full athletic college scholarship.

WE’VE ALL GOT STUFF. Too much stuff. George Carlin was among the first to highlight our obsession with stuff in his 1980s standup comedy routines. I hadn’t thought much about Carlin or stuff for decades—until 2015, when I inherited my parents’ stuff.
Not only did I inherit their stuff, I inherited some of their parents’ stuff and their grandparents’ stuff. Boxes, drawers and shelves full of unlabeled stuff. I wouldn’t call my parents hoarders.

AFTER THE MARKET turbulence of recent months, the idea of a 100% stock portfolio would strike many folks as crazy. Yet, when I was in the workforce, that’s pretty much what I owned.
I never felt my all-stock portfolio was particularly risky. My wife and I had solid paychecks to rely on. We always maxed out our retirement plans, while also adding to other accounts, and then lived on whatever remained.
While the stock market’s volatility and the occasional downturns may have been disconcerting,

WHEN OUR DAUGHTER landed a great job after her 2018 college graduation, we expected her to soon move off the family payroll. She immediately budgeted to take on all routine living expenses, including housing, food, car and utilities. We did volunteer to cover some smaller expenses, largely in situations where family plans are available, such as cellphones, Netflix, Amazon Prime and AAA. We also kept her on our employer-provided health insurance, which involved no added cost.

I WAS SINGLE-TRACK mountain biking with two friends. We had stopped for a rest—which was when I discovered how completely wrong I’d been with most of my financial decisions.
We had all recently retired from the same company and were debating when to claim Social Security. One buddy stated that he planned to start at age 70, so he would receive the maximum monthly payment possible. He defended his position by arguing that he was in good health,