AS I PLAN MY retirement, I have the advantage of a strong background in finance. I worked for 35 years in the investment field, primarily managing mutual funds. Early on, I obtained the Chartered Financial Analyst designation, which helped immensely.
Six years ago, when I was age 55, I embarked on a journey to comprehend the myriad rules and strategies surrounding retirement. I studied to become an RICP—a Retirement Income Certified Professional. While the CFA was useful for investment management,

LAST SUNDAY, I discussed six strategies that could help you avoid decisions you’ll regret. But what if it’s too late—and you’ve already made a financial choice that’s left you unhappy? Now what?
Below are six notions to help you manage, and hopefully minimize, your regret over past decisions:
1. Your imagined happy ending likely wouldn’t have happened. Back in 2004, I recall seeing an iPod for the first time. A co-worker had received one for Christmas.

WHEN A FAMILY OPTS to purchase a Mercedes rather than a Subaru, the rest of us might think they’re being extravagant. But you likely won’t find many people saying, “How stupid is that? They could’ve got around town for half the price.” We accept that a car isn’t a strictly utilitarian purchase.
But we aren’t nearly so forgiving when it comes to “suboptimal” investment and personal finance decisions. Today’s contention: We shouldn’t be too quick to deride the money choices made by others—and,

MOST OF US DON’T attempt to make a living trading stocks. Instead, investing is a long-term effort. We’re accumulating wealth to sustain us in retirement. Well, at least some of us try.
To that end, we need to save regularly over many decades, reinvest interest and dividends, and keep our eye on the pot of gold at the end of our rainbow.
How come we find this so hard? We get distracted. We start thinking short term.

WHAT ARE PEOPLE paying for when they seek out a financial planner? Where’s the real value? The answers may surprise you.
Financial planners typically tout their advice on asset allocation, retirement planning, cash flow analysis, insurance, wealth protection, estate planning and so on. But is that really the benefit they bring to consumers?
Consider an entirely different business. When you take your car to get serviced, what are you paying for? Brake repair, transmission diagnosis,

WORRIED ABOUT inflation? You might be drawn to inflation-indexed Treasury bonds—officially known as Treasury Inflation-Protected Securities, or TIPS. These bonds protect you from unexpected inflation, plus there’s no risk of default.
Those features make TIPS attractive to investors who are concerned about rising consumer prices, and especially the impact of inflation on the bond portion of their portfolio. Intrigued? Before you invest, here are six factors to consider:
1. Hedging vs. speculating. TIPS can be used to hedge against inflation or to speculate on it.

WE GO THROUGH phases in our financial life, just as we do in our biological life. There seem to be a least five financial phases that adults pass through, each with their own priorities, risks, opportunities and tradeoffs.
Here’s how I would think about those five phases:
1. Party Time (ages 25 to 30)
Yes, you’re starting a career, and you want to get ahead and make money. But in all likelihood,

MY WIFE AND I BOUGHT our first home in the mid-1980s. We were thrilled to get an 8% mortgage, though we had to pay three points—an upfront fee equal to 3% of the loan amount—to get that rate. Many of our friends had bought a few years earlier and were paying 14%, a common occurrence back then, according to Freddie Mac data.
We kept our eyes open for opportunities to refinance our high rate.

LAST WEEK, I LEARNED the disappointing news that our next-door neighbors—possibly the nicest people in the world—have put their house on the market.
While I’m sorry to see them go, I understand their decision. With a growing family, they’re looking for more room. During the pandemic, in fact, many people are making changes of one sort or another. Will they be happy with their choices?
That brings me to a new project, developed by author Daniel Pink,

THREE WEEKS AGO, I wrote about my plan for generating retirement income, including my intention to make a series of immediate fixed annuity purchases. Immediate annuities are a profoundly unpopular product, so I was surprised when the article generated a slew of questions from readers.
Perhaps that interest reflects today’s miserably low bond yields, which have left immediate annuities as one of the few ways to generate a safe and sizable income stream. Intrigued?

WHEN I WAS IN MY 20s, I joined a large aerospace company. It was my first job out of college. I was an employee who thought all my colleagues were team players working toward the best interest of the company.
Back then, I’d never heard of the term “office politics.” But Ron, my boss, took it to a whole new level. He was an expert at manipulating people.
Ron joined the company a year after I did.

THE MID-2000s WERE my introduction to the investment world—and even today my thinking is heavily influenced by what was happening then.
Take a moment to recall the 2004-07 period. Stock prices were marching higher, foreign shares were crushing U.S. stocks, small caps were doing all right and you could get a decent interest rate on your savings account. Good times. Another feature of the mid-2000s market: a big bull run in commodities.
Back then,

IT’S SCARY TO RETIRE with a pool of money, knowing how you handle it determines your financial security for the next 25 years or so. It must seem even scarier to everyday Americans who don’t think they can count on Social Security.
A recent Tweet caught my eye. It linked to an article about the problems with the so-called 4% rule. As you might recall, the 4% rule states that, if you withdraw 4% of your portfolio’s value in the first year of retirement and thereafter step up the dollar amount withdrawn with inflation,

THIS YEAR’S TAX DAY was the strangest I can remember. Amid the pandemic, the filing deadline had been pushed back to July 15, three months later than usual. And for me, it was our most complicated tax year ever. I had both retirement income and income from various in-state and out-of-state consulting gigs.
But the biggest complication stemmed from last year’s sale of our second home. This was a vacation home that we rented part-time and also used ourselves.

THE TRICKY THING about investing is that there’s no single “right” approach. In an earlier article, I described the approach I favor—what I call the five minds of the investor, which involves being part optimist, pessimist, analyst, economist and psychologist.
But there are many other ways to be successful: You might invest in real estate, or follow a quantitative investment strategy, or invest in private companies. There are plenty of people who do very well with these approaches.