Family Matters

This newsletter is unlike any I've written before. It is not one person’s story, but a composite of sentiments drawn from years of conversations I've had with clients, friends, and colleagues across the country. My hope is that, in its own way, it inspires someone to begin a conversation they have been avoiding.

Every family has a monetary policy, even if no one has ever called it that.

With summer upon us, it’s lake house season.

I am writing this from a hotel that is hosting an event called Nerdtacular 2026. The tagline is, “We are the dorks you’re looking for.” Amazing!

Aristotle believed courage was the first of the virtues because, without it, the other virtues remain merely aspirations. Honesty requires courage because the truth can be uncomfortable. Love requires courage because real love eventually asks us to be vulnerable. Forgiveness requires courage because it means loosening our grip on injury. Even wisdom requires courage because knowing what is right and doing what is right are not the same thing.

Most of us spend time thinking about the people who came before us. We tell stories about grandparents, founders, parents, teachers, and mentors. We remember the sacrifices they made, the values they carried, the mistakes they survived, and the paths they cleared. In families of wealth or enterprise, this story can be especially powerful. Someone took a risk. Someone built something. Someone protected what mattered. Someone made decisions that shaped lives they would never fully see.

Your reputation isn’t what you shout, it’s what people whisper. There is something unsettling about that idea, mostly because it is true. We spend so much of our lives trying to manage what is visible: what we say about ourselves, how we present, how we explain our intentions, how we frame our decisions. But reputation is built somewhere quieter. It lives in the conversations we are not in. It takes shape in the stories people tell after the meeting, after the conversation, after the deal. It is formed not by our declarations, but by our patterns.

Trust rarely forms in the moments we plan for; it’s built in the ones we barely notice. The rides to practice, sitting at the kitchen counter, quick check-ins at the end of a long day. It’s not what we declare to our families that shapes relationships most; it’s what we do, over and over again, when no one is keeping score.

Words are not neutral. They don’t simply describe our reality; they shape it. The language we choose, both out loud and in our own minds, has a direct impact on how we experience people, events, and ultimately, our relationships.

Adam Grant wrote something recently that has stuck with me, given our work with families: “A sign of wisdom is choosing not to believe everything you think. A mark of emotional intelligence is choosing not to internalize everything you feel. Thoughts and emotions are possibilities to ponder, not facts to accept. We don’t always invite them in, but we do decide whether they deserve to stay.”

Forgiveness is one of the hardest things we’re asked to do. Not because we don’t believe in it—most of us know forgiveness matters—but because of what it requires. To forgive is to let go of the hurt, the disappointment, and the story we’ve been holding on to about what happened and what should have been different. In families, this is especially difficult. The wounds are layered over years of history, expectations, and love. The pain lingers because the relationship matters. And yet, forgiveness may be one of the most important skills we can develop—for our health, our relationships, and our peace of mind.

We all know the quiet frustration of wanting someone we love to change. It shows up in small moments and big ones. A parent who won’t step back. A sibling who avoids responsibility. An adult child who hesitates to step forward. Conversations circle the same topics. The same patterns repeat. We see the risk. We see the strain. Often, we see the potential. And because we care, we try to help.