Jonathan Clements

I’M PONDERING WHETHER to make my biggest transaction in four years—and it might be the trickiest financial decision I’ve ever made. My quandary: Should I take advantage of today’s low tax rates to convert a big chunk of my traditional IRA to a Roth?
This financial navel-gazing was sparked by an article by John Yeigh, one of HumbleDollar’s contributors. As John pointed out, you can now have a much higher annual income and still avoid the top federal tax brackets,

WE CONSTANTLY STRIVE for more: A bigger paycheck. A loftier job title. A larger home. A more luxurious car. New electronic toys. Higher investment returns.
Make no mistake: There can be great pleasure in this striving—but we may not be so happy with the results. Indeed, on this holiday that celebrates America’s independence, let me put in a plug for a most un-American concept: How about settling for enough—and perhaps even opting for less?

IF I’M EVER FEELING lonely, all I need to do is write about certain financial topics—and soon enough my inbox is brimming with emails, some vehemently disagreeing, others offering vigorous nods of assent.
A dozen of those topics are covered in HumbleDollar’s new chapter devoted to great debates—issues like whether money buys happiness, when to claim Social Security and whether individual bonds are superior to bond mutual funds. But those subjects aren’t the only ones that stir up readers.

AS I GROW OLDER, I find I become ever more deliberate in how I spend my time and money. How can I get maximum happiness from the dollars I have? How can I get the most from the years that remain? As I wrestle with these questions, six notions have come into much sharper focus:
1. Fewer hassles mean greater happiness. When I was in my 20s, I owned a series of clunkers that turned every trip into a nail-biter.

I’M A FAN OF EMERGING stock markets—for two key reasons. But I also have qualms—for two key reasons.
Readers frequently write to me about emerging markets, and those messages usually coincide with periods of stomach-churning volatility, which is what we’ve witnessed recently: MSCI’s emerging markets index tumbled 15% in 2018 and was up just 4% in 2019’s first five months—after being up as much as 14% earlier this year. But as I tell my nervous correspondents,

WHEN FINANCIAL writers tackle the topic of spending, the result is all too predictable: lectures on the dangers of lattes, the glories of budgeting and the financial apocalypse engendered by avocado toast, as well as suggestions that earlier generations were far more prudent.
I’ll admit it, I haven’t entirely avoided these pitfalls.
So how should we think about spending? I would focus on how your income gets divvied up among four key categories:
1.

IN THE FINANCIAL world, making money is the most popular pastime—but having a good argument is a close second.
What do folks argue about? HumbleDollar’s online money guide has always included a handful of sections labeled “great debates.” I decided to expand that collection to 12—and gather them together in their own chapter. Below you’ll find one of the new sections, plus links to the other 11.
Debate No. 8: Is Indexing Dangerous?

THE GREAT RECESSION highlighted the frightening amount of debt—especially mortgage debt—that had been taken on by many American families.
A decade later, the picture is far brighter, with one exception: student loans. Since 2008’s third quarter, education debt has ballooned 144%, according to data just released by the Federal Reserve Bank of New York. But the total of all other debt—mortgages, car loans and credit card balances—is up less than 1% over the same period.

WELCOME TO HumbleDollar’s new financial life planner, which is designed to complement the portfolio builder we unveiled earlier this year.
The life planner’s goal: Guide you through 13 financial steps that’ll help you navigate the journey from your 20s to your 60s and beyond. Below, you’ll find the first of the life planner’s 13 steps—plus links to the other 12.
Step No. 1: Prep for Success. All too many Americans lead shaky financial lives.

HOW WE CHOOSE TO spend our time and money is a declaration of what we deem important. A modest example: We might enjoy watching a wide array of cable channels, while caring little about the clothes we wear, and that’s reflected in our costly cable bill and minimal spending on clothing. And there’s nothing wrong with a choice like that—if it is indeed what we want.
But is it? Often, the things we consider important—and hence how we lead our lives and how we spend our money—aren’t the product of our own careful contemplation.

IF YOU ASK AN insurance agent how much coverage you should have, the answer invariably is “more.” What if you show too much interest? Next thing you know, you could find yourself the unhappy owner of a high-cost variable annuity.
Consumers, meanwhile, take what might be politely described as a barbell approach. Sometimes, they’re acutely aware of a particular risk and buy more coverage than they need—a frequent occurrence with auto and health insurance.

“FINANCIAL WRITERS always seem to assume everybody’s married.” That’s a complaint I’ve heard more than once—and it came to mind as I reviewed our 2018 tax return.
That tax return reflected the impact of 2017’s tax law, which—among other things—roughly doubled the size of the standard deduction, while capping the itemized deduction for state, local and property taxes at $10,000. One result: Many couples now get little or no tax benefit from either the mortgage interest they pay or the charitable contributions they make.

YOU COULD ARGUE that U.S. stocks are reasonably priced, with the S&P 500 companies trading at 22 times their reported earnings for the past 12 months. That’s not much above the 50-year average of 19.3—and hardly outrageous, given today’s modest bond yields.
But you could also argue that U.S. shares are horribly overpriced. The S&P 500 stocks today offer a dividend yield of just 1.9%, versus a 50-year average of 2.9%. Shares also seem pricey compared to both the value of corporate assets and average company profits for the past 10 years.

WE GET MORE PAIN from losses than pleasure from gains—which might explain why I often think back on the five major market crashes that have occurred during my investing lifetime. There’s something about the massive hemorrhaging of money that has a way of focusing the mind and sticking in the memory.
Here are those five crashes, and what I learned from each:
Black Monday. I was age 24—with no money invested in stocks—when the S&P 500 plunged 20.5% on Oct.

WE MAKE COUNTLESS decisions—financial and otherwise—with little or no thought to the dollars at stake:

We purchase items that we know are overpriced and almost guaranteed to lose value, but we do so happily, because they have a meaning for us that’s far greater than their price tag. Think of artwork and vacation souvenirs that are purchased because they remind us of moments we treasure.
We prize family possessions for their sentimental value, even though they typically have scant financial worth.