Leading with Outlier Vision
Join Kassi Kincaid for an inspiring conversation with Scott MacGregor, founder of The Outlier Project, a global community designed to help people stop sleepwalking through life and start showing up differently. Scott shares how his journey—from a curious, unconventional kid to a transformational leader—led him to embrace outlier thinking and build a platform that empowers individuals to take the road less traveled.
In this episode, Scott reveals how adversity became a gift, why your past doesn’t define your future, and how creative leadership begins with meaningful connection and lifelong learning. With tactical insights from top advisors in leadership, wellness, entrepreneurship, and innovation, this conversation is a powerful reminder that success often lies in choosing the path most people overlook.
Leading with Outlier Vision
Scott MacGregor brings a bold and refreshing take on creativity through the lens of outlier thinking. As the founder of The Outlier Project, Scott works with individuals who are tired of playing it safe and are ready to lead extraordinary lives across career, relationships, finance, and wellness. His journey—from a curious kid who never quite fit the mold to a purpose-driven leader—reveals how embracing what makes you different can become your greatest strength.
Through stories of overcoming insecurity and taking the road less traveled, Scott shows how creativity isn’t just about ideas—it’s about intentional living, meaningful connection, and continually choosing growth over comfort. His insights challenge leaders to stop sleepwalking through life and start showing up with curiosity, courage, and conviction.
Episode Highlights:
(0:45) Where Scott’s Outlier journey began and how it shaped his purpose
(4:16) What The Outlier Project is and why it matters
(8:34) Building a leadership platform for lifelong learners
(12:00) Developing across the four key life buckets: career, relationships, finance, and health
(14:40) How to break free from past limitations and view adversity as a gift
(18:18) Where to find The Outlier Project and how to get involved
This episode is packed with insights for HR leaders, executives, and high-performers who want to lead differently, live intentionally, and unlock creativity as a path to transformation.
Connect with the Scott MacGregor:
Website: https://www.theoutlierproject.live/
LinkedIN: https://www.linkedin.com/in/macgregorscott/
Instagram: @theoutlierproject_official
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