Jonathan Clements

WE WON’T KNOW UNTIL we get there.
How much do we need for retirement and what will it take to amass that coveted sum? It sometimes seems like the entire financial advice business—brokerage firms, fund companies, financial planners, online calculators and more—is solely focused on this conundrum.
That’s mostly a good thing. It is indeed crucial to amass enough for a comfortable retirement. Still, let’s acknowledge an inconvenient truth: The resulting retirement projections imply a degree of precision that’ll likely look hopelessly naïve once the real world intervenes.

WE HEAR ABOUT highflying stocks and hotshot money managers, and it’s easy to imagine the streets of lower Manhattan are paved with gold. But the truth is a tad more mundane.
Want some reasonable assurance of investment success? We should shun the excitement of trying to pick winners and instead focus on more prosaic portfolio tweaks. The overriding goal: ensure the compounding of our investment dollars encounters as little friction as possible.
Minimizing this friction will,

WHAT’S THE BIGGEST financial risk we face? Today, many folks would point to the possibility of a recession, a stock market plunge and perhaps both. Indeed, those are perennial perils—but perhaps they shouldn’t be our biggest worries. Looking to lose sleep? Here are 50 other dangers we face:

Really, really long-term care.
Your financial advisor turns out to be a crook.
Your spouse leaves.
Double-digit inflation.
Your new neighbor specializes in personal-injury lawsuits.
Your son just got his driver’s license.

HERE’S A SOBERING thought: Much—and perhaps most—of the money you’ll accumulate for retirement will reflect the raw dollars you sock away and not the investment returns you earn.
Consider a simple example. Let’s say retirement is 40 years away and your goal is to quit with $1 million. Let’s also assume you can earn an after-inflation “real” annual return of 4%, which is my best guess for the long-run return on a globally diversified,

PAST PERFORMANCE is no guarantee of future results. But we keep hoping.
Over the 10 years through August 2009, the large-cap stocks in the S&P 500 shed an average 0.8% a year, even with dividends included. Meanwhile, U.S. value stocks beat U.S growth stocks, smaller-cap U.S. shares notched 5.5% a year, developed foreign stock markets 2.7% and emerging markets 10.4%.
Fast forward one decade, and the leaders have become laggards and vice versa. Over the 10 years through August 2019,

I OFTEN FEEL LIKE the Grinch, who “puzzled and puzzled ‘till his puzzler was sore.” One question I’ve puzzled over endlessly: If what I do barely matters in the greater scheme of things, why in the world do I keep doing it?
Here are four related thoughts that often crop up in my writing:

One of life’s great pleasures is working hard at something we care deeply about.
While striving toward our goals can bring great satisfaction,

I’VE TAKEN TO TELLING folks that HumbleDollar is the site for folks who are striving to be rational about money—but who are acutely aware that they’re human.
Figuring out what’s rational is relatively easy. We should save diligently, diversify broadly, invest in stocks if we have a long time horizon, favor index funds, take on debt cautiously, only insure against major financial risks, avoid buying a house that’s larger than we really need and,

IT’S THE LABOR DAY weekend, which is hardly the time for a nerdy article on the finer points of personal finance. Instead, I’ll leave you to spend the weekend pondering 11 great unanswered financial questions:

Who does more financial damage, stockbrokers or life insurance agents?
Is taking Social Security early and then assuming you’ll make double-digit gains by investing the money a brilliant strategy—or utterly delusional?
Is a home the best investment you’ll ever make or a money-sucking pile of bricks?

ONE OF MY GOALS is not to think about money. This might sound odd coming from someone who has written about money for 34 years, runs a financial website and, indeed, wrote a book entitled How to Think About Money. So let me clarify: I’m happy to think about money in general. I’m even happy to think about your money. I just don’t want to think about my own.
I used to think about my finances all the time.

DECIDING WHETHER to buy bonds or pay down the mortgage used to be a tricky decision. Not anymore: Paying extra on your home loan will almost always be the right choice.
This takes some explaining—because it involves wrapping your head around the standard vs. itemized deduction, investment taxes, and a mortgage’s shifting mix of principal and interest.
First, let’s dispense with the obvious objection: Yes, if you’re inclined to buy stocks rather than pay down the mortgage,

THINK OF IT AS THE ultimate financial Rorschach inkblot test. When you hear about the pitifully inadequate retirement savings of so many Americans, what’s your immediate reaction?
a) This is the inevitable result of stagnant wages coupled with soaring medical, education and other costs; or
b) This is what happens in a financially illiterate society with scant self-discipline and constant temptations to spend.
For me, these differing views were brought into sharp relief by two recent articles on HumbleDollar.

IT WOULD BE difficult to overemphasize how important Vanguard Group is to everyday investors. Many of us have money at the Malvern, Pa., behemoth, which easily ranks as the largest mutual-fund company. But even if investors don’t, they’ve likely still benefited, as other companies have moved to slash their fees and expand their lineup of index funds to compete with Vanguard.
Well aware of this, I follow Vanguard closely—and even more so since Vanguard’s founder,

IDEAS ARE TOOLS THAT can help us see the world with greater clarity. Indeed, I find myself returning to certain financial notions again and again, because they’re so fundamental to understanding the world of finance and how we can make our lives better.
What are the most important ideas? I decided to create a new chapter for HumbleDollar’s online money guide, which covers the 15 notions I consider most crucial:

Humility
Simplicity
Control
Instincts
Future Self
Hedonic Treadmill
Signaling
Human Capital
Be an Owner
Risk and Reward
Opportunity Cost
Compounding
Skewness
Risk Pooling
Enough

Arguably,

STOCKS MARCH EVER higher, portfolios get ever fatter and yet the conundrum facing investors remains the same. We have no idea what will happen next to share prices—and no reliable way of figuring it out. Consider:

Valuations are rich, but they have been for much of the past three decades. Indeed, if above-average valuations were your signal to sell, you likely would have dumped stocks long ago and missed out on substantial gains. The reality: Valuations don’t predict short-term returns,

CALL IT THE NEW conventional wisdom: Forget trying to spend less—and instead focus on earning more.
This change in thinking is no great surprise. We have endless opportunities to make an extra buck, thanks to all the “side hustles” available in our “gig economy.” Meanwhile, many folks bristle at the admonitions to spend less on lattes, happy hours and avocado toast. Let’s face it, will eliminating such expenses really put us on the fast track to financial freedom?