Why Your Kids Stop Listening to Your Wisdom | Steve Legler

Have you ever tried to pass your hard-earned wisdom on to your children, only to realize they aren’t listening? I’ve been there. And the harder we push, the more likely they are to pull away.

In this episode of The Long Strange Trip, I sit down with my old friend Steve Legler, who works with wealthy families navigating the complicated relationships between generations. We talk about why parents often struggle to stop parenting their adult children, why the wisdom we want to give is better received when it’s invited rather than pushed, and how successful entrepreneurs sometimes bring the same management style they use at work into their family relationships.

Steve shares why humility, vulnerability, listening, and admitting our mistakes can help rebuild trust—even when years of hurt have created distance. We also explore forgiveness, sibling disagreements, family harmony, and why understanding someone doesn’t mean agreeing with them. I know this isn’t just theory. I’ve struggled with some of these things in my own relationship with my children. And one thing I’m learning is that repairing a relationship isn’t a destination. It’s a journey. Sometimes the best thing we can do is stop trying to be right and start making room for a real conversation.