One of the most common questions we hear from small business owners is: “How do I pass my business to my kids?”

Most people assume the answer starts with estate planning, trusts, or taxes. It doesn’t. The first question is more practical: Where is the money going to come from? Quickly followed by: How much are they going to pay me, and what is my business actually worth?

There is a photograph that used to hang in many brokerage offices, the kind of place with wood paneling and a ticker tape machine in the corner, where men in suits watched numbers scroll by on a screen the size of a shoebox. The message was implicit: patience pays.

Avoiding the life insurance conversation can leave families unprepared when it matters most. Here’s why talking about it now can make all the difference.

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.