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TARGET-DATE FUNDS are riding a wave of popularity. Morningstar reports that investors placed $170 billion into these funds in 2021, more than double their 2020 inflow. Morningstar also reports that, as of 2019, 58% of all 401(k) participants were invested in a target-date fund. That percentage is likely higher today. It’s clear why the funds have become so popular. They can be an excellent solution for retirement savers who prefer a hands-off approach. To this end, many employer retirement plans use target-date funds as their default investment choice. But there is, I fear, a...

Perspective Needed

Perspective Needed

THE HIGHEST expression of complexity is thoughtful simplicity. It’s like standing on a mountaintop after navigating the ascent. The work of the mountain’s trailblazer is arduous. He or she must focus intently on the task at hand, glancing left and right, guessing what will come around each new bend. But from the pinnacle looking down, the perspective puts the most efficient path in clear view. It becomes possible to make a map to aid those who will come next. If we ever want to get out of our own way, to enjoy more money success with less unnecessary effort, we must embrace the...

Time to Settle Up

Time to Settle Up

TAX DAY IS ALMOST here, and I have a feeling that some of you may be less than excited. The cash that changes hands every year around this time gets a lot of attention, but it tells an incomplete story. The size of the check you write—or the refund you’re receiving—doesn’t, by itself, say much of anything about your tax situation. Back in the days before technology made transferring money so convenient, did you ever let a tab run both ways with a friend? Perhaps you were traveling and decided to take turns paying for meals, and then settled up any difference at the end of the trip. Just...

Set Up to Succeed

Set Up to Succeed

LOOKING TO IMPROVE your physical and financial health? You might have heard similar sounding advice: All you have to do is burn more calories than you consume—and to spend less than you make. While there’s an element of truth to both platitudes, I don’t find either helpful. There’s a psychological canyon between such abstract ideas and putting them into practice. One thing experience has taught me: If I’m authentically stirred to want to do something, I’ll go miles further than if obligation is my only motivation. I also need to come to terms with my own...

22 Tax Season Tips

22 Tax Season Tips

WILL YOU BE WORKING with a CPA to file your tax return? For eight years, I was one of the folks on the other side of this annual ordeal. Want to make life easier both for yourself and for us green-shade types? Here are 22 insights: 1. Time is money. CPAs sell expertise by the hour. They track everything they do, all day long, in six-minute increments—or perhaps 15. For the business to survive, it must convert time into revenue. It helps to look at the next 21 insights through that lens. 2. Buying insurance. CPAs envy investment advisors, who get paid by drawing a fee right out...

Collecting Taxes

Collecting Taxes

WHEN A FRIEND TOLD me about his newfound interest in buying and selling sports trading cards, it reminded me of the joy that collecting brought me in my childhood. And when he asked me to explain the relevant taxation, it got me thinking: The core of the tax code is more logical than we give it credit for. It’s the ever-changing details that make it squirrelly. If you buy and sell collectibles—whether it be sports cards, coins or antiques—the tax code assigns your activity to one of three tracks: HobbyInvestmentBusiness What factors determine the tax track you should follow? It’s a...

Christmas All Year

Christmas All Year

I GAVE THE BEST PEP talk I could muster, but it didn’t help. Our family of four entered Walmart in solidarity, planning to buy gifts to fill an Operation Christmas Child shoebox. Two of us left early in disarray. I had to wrestle my screaming two-year-old all the way to the car because she knew only one way to approach the toy department—with herself in mind. Eliza melted down over her refusal to part with a cheap plastic toy. As much as we romanticize the idea of giving, it seems we have a hard time actually doing it. A growing body of research shows that giving does more for...

When Fantasy Fails

When Fantasy Fails

I’M A LIFELONG football fan who’s played fantasy football for 20 years. What do I have to show for it? Zero league titles, a staunch ambivalence about fantasy football—and three investing maxims. Every fantasy football season starts with the draft. Three intoxicating forces combine to make the draft a great time: predictions, customization and pride. I’ve come to realize that the draft accounts for about 90% of the appeal of the whole fantasy football concept. One year my friend scheduled our league draft for the same night I had already planned a birthday dinner for my wife. Backed...