Seven Miles in Central Park with Mikaela Smith

Dialogue Miles™ took us to Central Park in New York City, where Mikaela Smith and I walked 7 miles together. We had a deeply insightful conversation about the possibilities ahead of her. Her thoughtful approach to life, shaped by a strong family foundation is inspiring and I look forward to seeing the impact she will make.

I first met Mikaela through my niece Grace Nanney when she and a few friends joined my wife and me for dinner in Nashville. After the meal, Mikaela asked me for some mentoring, and we’ve stayed in touch ever since.


Reflections from the Walk

  • Multi-Generational Learning
    Perspective flows both ways. Different stages of life create opportunities to learn from each other.

  • Common Ground
    It is easy to focus on differences. The real value is in finding shared threads—background, interests, experiences, and curiosity.

  • Advice vs. Insight
    Asking thoughtful questions creates better outcomes than giving direct advice. It helps uncover what might otherwise be missed.

  • Attitude and Focus
    Clarity creates momentum. When you know what matters, the right opportunities tend to follow.

  • Choices
    Every step carries implications. Taking time to understand those decisions reduces unnecessary noise.

  • Intention
    The most important decisions often live in the grey. Trusted relationships help navigate them.

  • Human Connection
    Connection fuels perspective. When you trust the person you are with, lean into the moment.


Walking and talking with Mikaela reminded me why I love Dialogue Miles™. These conversations go beyond the surface, leaving space for genuine reflection and growth.

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A Cross-Border Connection with Claudia Harvey That Started Before We Met

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A Chance Connection with Tim Dowd That Started in Worcester