Adam M. Grossman

IN TODAY’S POLITICAL environment, discourse has become ever more fractious. The investment world, in my view, isn’t much better. Those who disagree generally talk past—rather than listen to—one another.
That is why, in my work as an investment advisor, I maintain a “team of rivals” approach, reading and listening to diverse opinions. Behavioral scientists often talk about confirmation bias—the tendency to seek out only information that confirms our preconceived notions. To counteract this bias,

IN MY HOMETOWN of Boston, there’s an old joke about our dismal winter weather. “February,” they say, “is the longest month of the year.” I don’t disagree and so, each year at Presidents’ Day, my family tries to get away for a warm weather vacation.
On these trips, we often stay at the same hotel and, because of that, we have noticed certain patterns. Among them: Most years, there is the same large corporate gathering.

LIKE MOST PEOPLE, I’ve made my fair share of financial blunders. I’ve also had some successes. But I definitely spend more time beating myself up over my errors than celebrating my successes.
Undoubtedly, my biggest mistake fits into the relatively obscure category of asset location. If you aren’t familiar with the term, I can explain it by way of an example. Suppose you have two investment accounts: a retirement account and a standard, taxable account.

WE’RE USED TO SEEING money as one of life’s limiting factors. But if you receive a financial windfall, money may no longer be the limitation it once was. While that might sound liberating, it can also create anxiety. The reality is, constraints serve a useful purpose: They provide structure. Without that structure, you may find yourself feeling rudderless.
I experienced this when I received a windfall several years back. I remember walking into an Apple Store,

ONE DAY BACK IN 2012, I received a life-changing windfall. Contrary to what you might imagine, however, that day was not very different from the day before it, or the day after. It went something like this: Woke up. Went to work. Came home. Thought about ways to splurge. Ultimately gave up and went to bed.
In other words, there was no visit to the Ferrari dealership, no trip to Las Vegas,