In my junior year at Boston College, I signed a contract that took me into a world I was completely unprepared for, except that I liked people. Over the next 49 years, my career as an insurance broker blessed me beyond anything I’d imagined.

Money planning isn’t about mastering every decade. It’s about seeing clearly where you are as a finite human being and responding wisely when you can’t see the future. This isn’t a performance review. Rather, it’s an attempt to see where you are and gain insight into where your kids or parents might be.

“Old men ought to be explorers.”
T.S. Eliot wrote those words late in life, not as a call to ambition, but as a warning against becoming stuck. The danger, he suggests, is not age or change—it is standing still out of fear. For many business owners approaching a sale, that fear is very real.

“Now run away and play with your toys. I’ve got some thinking to do.” —Taylor Caldwell, Bright Flows the River
In Taylor Caldwell’s novel Bright Flows the River, a character speaks this line with equal parts exasperation and clarity.

From a young age, most of us have heard the phrase, “It’s better to give than to receive.” The holiday season calls this maxim to mind more often than other times of the year. And while it sounds nice and noble, but is it actually true? The research says yes.

In the category of Christmas movies about money, it is impossible to compete with It’s a Wonderful Life. The depiction of the bank run alone nearly stops the conversation. But if we’re going to talk about the best Christmas movie about money and grace not named IAWL, we have to talk about The Holdovers.