09/04/2026
There's a quiet scene in the 1995 rom-com "While You Were Sleeping" that has nothing to do with the romance.
Jack finally tells his father he doesn't want to take over the family business. He wants to build furniture. His own thing. His dad is hurt, then proud, then supportive, all in the span of a few minutes.
Most real conversations like that don't go that smoothly. In fact, a lot of families never have them at all.
Business owners often assume the next generation wants the business. The next generation often assumes their parents already know they don't. Both sides wait, and the succession plan quietly becomes "we'll figure it out later."
If you own a business, the most valuable planning conversation this year might not be with your CPA or attorney. It might be at the kitchen table, asking a simple question: ""Do you actually want this?""
Whatever the answer is, it's better to know now.
It can change how you value the business, how you think about a sale, and how you plan for your own retirement.