A FEW WEEKS AGO, life changed for 24-year-old Manuel Franco of West Allis, Wisconsin. The winner of a recent Powerball lottery, Franco took home $326 million—and that’s after taxes. With a sum that large, it shouldn’t be hard for Franco to make his winnings last a lifetime.
And yet, more often than not, such windfalls deliver heartache rather than happiness. Consider Lara and Roger Griffiths, an English couple who, in 2005, won the equivalent of $3.2 million from their local lottery.

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.

I FIRST BEGAN tracking my net worth in 2013. Back then, I was newly divorced, in my mid-40s and struggling to figure out what my financial future would look like. I painstakingly logged into my various bank, retirement and investment accounts, and entered their values into an Excel spreadsheet.
As a result of my divorce, I’d lost 50% of my state pension. I did, however, receive half the equity from the sale of our home.

WHEN I LAUNCHED this site at year-end 2016, my main goal was to take my money guide—which I’d previously published as an annually updated book—and make it freely available. I also planned to keep blogging once a week and run occasional articles by other folks. Beyond that, my plans were vague: I viewed HumbleDollar as a part-time venture—one of many I was then involved with.
Since then, the site has exploded. Traffic has tripled over the past two years,

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.

ON APRIL 3, MY HUSBAND Jim and I were among 262 pilgrims who made our way into Santiago de Compostela to receive an official pilgrim’s certificate for completing the required distance along one of the famous El Camino’s several routes—the most popular of which is some 500 miles. We were now certified peregrinos, or pilgrims.
Because it was early in the season, ours was one of the slow days for Camino completion.

MOST AMERICAN families are living paycheck to paycheck. This was highlighted by the recent government shutdown. Many federal workers quickly found themselves in financial trouble, when they didn’t receive their regular pay. In fact, a Federal Reserve survey found that four out of 10 Americans either couldn’t cover a $400 emergency or, to do so, would need to borrow or sell something.
That brings us to a question I’m often asked: Why do financial advisors insist clients establish an emergency fund?

ON DEC. 7, 2005, a curious thing happened in a Harvard classroom. Prof. Michael D. Smith stood in front of a group of computer science students to introduce a guest speaker: entrepreneur and former Harvard student Mark Zuckerberg. What was curious was that the room was nearly empty. The class met in a huge lecture hall, but there were barely a dozen people in the room.
How could that be? Why was there so little interest in Zuckerberg’s presentation?

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.

SIMON SINEK BROKE onto the scene in 2009, asking us to “start with why.” His TED Talk has been viewed millions of times and inspired countless articles. He commands attention and captivates audiences with his message. All good things. For both individuals and organizations, there’s immense value in asking, “What’s my why?”
But what about “who”? In all the enthusiasm over “why,” I don’t think “who” has gotten its due.
When I talk about “who,” I’m talking about your community and your sense of connection to others in that community.

ONLY ABOUT 40% of Americans have a will, including just 58% of those ages 53 to 71. The good news is, among those of us 72 and above, the percentage is much higher—81%.
Putting in place a will, trust documents, powers of attorney and so on is no easy task. I’ve been through the process twice and it’s not fun, mostly because a good attorney will ask a lot of uncomfortable questions you’d probably rather not think about—like,

I WORKED FOR MORE than 30 years in manufacturing, poring over data and paying attention to every detail that would impact production. As a project manager, I was responsible for making sure hardware was delivered on time, with no cost overruns or quality issues.
If we weren’t meeting deadlines or spending too much money, I was required to report these problems to upper management. They would ask me three questions: “What are you going to do about it?

“IS CBS PIPING FAKE birds into its Masters coverage?” That was the headline on a recent Slate article, which speculated that the television network might be adding “enhanced audio” of fake bird chirping to its coverage of the golf tournament.
This is not a scandal for the ages. But it serves as a timely reminder that we have fantasized notions of life that marketers and the media don’t hesitate to exploit.
Make no mistake: The PGA,

SINCE ENTERING THE workforce in late 2010, I’ve been giving advice to others on how to put their money to good use. There are few things I enjoy more than having a conversation with a couple about such a complex subject. Along the way, I’ve pushed myself to learn more about specific financial planning strategies, as well as about human behavior and psychology.
These readings have not only taught me how I can better help my clients,

I RECENTLY CAME across an academic paper with an attention-grabbing title: “It has been very easy to beat the S&P 500.” Not just easy, but very easy. 
That got my attention because, in recent years, beating the S&P 500 has been anything but easy. In fact, it’s been maddeningly difficult. In eight of the past 10 years, domestic markets have outperformed international markets—by a wide margin. A dollar invested 10 years ago in the S&P 500 would be worth $4.37 today.