Stuart Chittenden

I help people explore life’s big questions—Who am I? What matters now? How do I live well?—through one-to-one coaching, small-group workshops, and thoughtful public conversations, including those on Lives, my radio show and podcast about how we live and why. As a Certified Humanist Professional, existential coach, and humanist thinker, my work blends deep listening, philosophical reflection, and grounded guidance. Whether you're feeling uncertain, are facing a transition in life, or simply seeking a more meaningful path, I offer space to pause, reflect, and move forward with clarity and purpose.

A collaboration partnership with Dan Gilbert, and as an extension of my work with Squishtalks, Gilbert + Chittenden helps organizations and individuals envision their very best futures. Using design thinking and creativity principles, we turn challenges into possibilities and put possibilities into action.

Lives Radio Show & Podcast is where meaningful conversation meets the art of being human. Each week, I sit down with creators, entrepreneurs, activists, philosophers, and changemakers to explore life’s big questions: How do we live well? What matters most? How do we create meaning—in work, in community, in our own lives? Now in its third season on Omaha’s NPR affiliate, @KIOS-Omaha-Public-Radio, Lives is more than a broadcast—it’s a space for reflection, connection, and discovery. The conversations are intimate and unscripted, uncovering the human stories behind professional identities and the personal philosophies that drive people forward. This work is deeply connected to my vocation as an existential coach and humanist thinker. In my coaching and workshops, I help individuals and teams navigate uncertainty, transitions, and purpose. In Lives, I bring that same curiosity and presence to my guests—listening for the moments that reveal who we are, what we value, and how we might live more intentionally. Lives offers more than inspiration. It’s a reminder that our work is always embedded in a larger human story—and that empathy, creativity, and self-awareness aren’t “soft skills,” but essential ones. The show offers perspectives that challenge assumptions, spark new thinking, and expand our understanding of leadership, resilience, and meaning in an AI-shaped world. Whether you tune in for insight, fresh ideas, or simply the pleasure of hearing another person’s story, Lives is an invitation: to pause, to listen, and to reflect on your own life and work with renewed depth.

Squishtalks designs and delivers training programs, community experiences and dialogue-based interventions grounded in the principles and practices of conversation. Stuart Chittenden founded Squishtalks in 2010 driven by the belief that conversation helps us to live better and work well. Squishtalks has worked with Fortune 500 and small business entrepreneurs, non-profit organizations, and for public and community purposes. Business outcomes include self-aware leaders, high-performing teams and engaged workplace cultures. Community outcomes include increased understanding and stronger social capital. Squishtalks’ latest community project was a couple of 830 mile long conversations. In an RV, Stuart Chittenden adventured nearly 2,000 miles for four weeks along the side roads and among the small towns of Nebraska to talk with Nebraskans. Traveling through conversations, discovering the lives, cultures and stories of the people and places encountered, the project was a long hello to community.

David Day Associates is an Omaha-based company that awakens the value of brand in business. We get to the heart of your brand to energize it and help it connect with the people who matter. For more than 25 years, our team has delivered strategic positioning, creative transformation, internal and external activation, and ongoing brand management solutions to organizations that are seeking to maximize their potential. We love our clients, we love what we do and we have a really good time doing it.

Commercial real estate legal transactions with deals aggregating around $2 billion in value.

Writing Op-Ed columns and magazine features.

Commercial real estate legal practice.

Legal services.