365. The Systems Leader with Robert Siegel

In this conversation, I’m joined by Robert E. Siegel, author of The Systems Leader, to unpack the essential mindset shifts leaders must make in a complex, fast-moving environment. We explore the tensions leaders face—like balancing innovation with execution, and strength with empathy—and how the most effective leaders navigate these paradoxes with clarity and purpose. Drawing from real stories of leaders like Jeff Immelt of GE and Michael Dowling of Northwell Health, Robert shares why systems thinking, strong relationships, and the ability to adapt are no longer optional—they're essential. If you want to lead with greater clarity in the chaos, this episode is for you. Buy Robert's Book ⁠"⁠The Systems Leader"⁠ Visit Robert's ⁠⁠Website⁠⁠ Follow Robert on ⁠LinkedIn⁠ Join my weekly ⁠⁠newsletter⁠⁠. Learn more about my ⁠⁠books and courses⁠⁠. Join ⁠⁠The Essentialism Academy⁠⁠. Follow me on ⁠⁠LinkedIn⁠⁠, ⁠⁠Instagram⁠⁠, ⁠⁠X⁠⁠, ⁠⁠Facebook⁠⁠, and ⁠⁠YouTube⁠⁠.

What if the only thing standing between you and the life you truly want is the courage to begin? In this episode, I speak with Jenny Wood—former Google executive and author of Wild Courage—about what it means to pursue the essential with boldness. Jenny shares how she walked away from a high-powered role to write the book she felt called to create. We explore the power of being shameless, curious, and even a little reckless when the moment demands it. You’ll hear how she faced down fear, navigated imposter syndrome, and embraced the uncomfortable path toward growth. This is a conversation about clarity, action, and living with wild courage—the kind that leads you not just to success, but to meaning. Buy Jenny's Book ⁠"Wild Courage: Go After What You Want and Get It"⁠ Visit Jenny's ⁠Website⁠ Follow Jenny on LinkedIn Join my weekly ⁠newsletter⁠. Learn more about my ⁠books and courses⁠. Join ⁠The Essentialism Academy⁠. Follow me on ⁠LinkedIn⁠, ⁠Instagram⁠, ⁠X⁠, ⁠Facebook⁠, and ⁠YouTube⁠.

Greg and guest Ben Greenfield continue in this Part 2 conversation about endurance training strategies, focusing on preparing for Ironman triathlons. Ben shares insights on pacing, nutrition, and psychological resilience, offering tips from the trenches for race day success. They explore the challenges of juggling athletic goals with personal life, emphasizing the importance of maintaining relationships alongside intense training. The conversation also touches on building community and male friendships, with Ben revealing his ongoing efforts to invest more in these areas. Buy Ben's Book "Boundless" Visit Ben's Website Join my weekly newsletter. Learn more about my books and courses. Join The Essentialism Academy. Follow me on LinkedIn, Instagram, X, Facebook, and YouTube.

Greg chats with Ben Greenfield, a trailblazer in health and human optimization, about unlocking potential and redefining personal limits. We put a magnifying glass onto Ben's journey from novice to Ironman, and discover two key breakthroughs: a time-efficient high-intensity training method and a game-changing nutrition strategy for optimal endurance. Gain insights into sustaining high performance and recovering from setbacks. Whether you're an athlete or pursuing personal growth, this conversation with bestselling author Ben Greenfield offers invaluable guidance on pushing boundaries and achieving excellence. Buy Ben's Book "Boundless" Visit Ben's Website Join my weekly newsletter. Learn more about my books and courses. Join The Essentialism Academy. Follow me on LinkedIn, Instagram, X, Facebook, and YouTube.

Greg speaks with Derek Sivers, an entrepreneur and thinker, exploring the power of perspective in shaping life's outcomes. They explore the concept of "useful, not true," emphasizing the flexibility and mindset required to break away from limiting narratives. Sivers shares personal insights on journaling as a tool for processing thoughts and decision-making, highlighting its role in enhancing clarity and agency. The conversation also touches on using AI for personal growth and the importance of understanding diverse worldviews to stretch and evolve one's thinking. Buy Derek's Book "Useful Not True" Visit Derek's Website Reach out to Derek Join my weekly newsletter. Learn more about my books and courses. Join The Essentialism Academy. Follow me on LinkedIn, Instagram, X, Facebook, and YouTube.

Drew and Linda Scott go into detail on their vastly different upbringings, and how their parents and families have molded them into the people they are today. Greg, Drew and Linda discuss how the world can be changed for the better, and the individual steps it takes each person along the way to create an effective and lasting change.  Join my weekly newsletter. Learn more about my books and courses. Join The Essentialism Academy. Follow me on LinkedIn, Instagram, X, Facebook, and YouTube.

Greg speaks with Courtney Carver, author of the upcoming book "Gentle: Rest More, Stress Less, and Live the Life You Actually Want," exploring practices for simplicity and rest in a complex world. They discuss the crucial concept of resting first, creating personal rituals like Little Saturday, and using the metaphor of a circle to prioritize what is truly sacred. They also explore cultivating radical gratitude, managing emotions with poise, and gently navigating life’s pressures. Discover practical steps to protect your peace and enhance well-being. Buy Courtney's Book Follow Courtney on LinkedIn Check out Courtney's Website Join my weekly newsletter. Learn more about my books and courses. Join The Essentialism Academy. Follow me on LinkedIn, Instagram, X, Facebook, and YouTube.

Greg engages with Jeffrey Sanow, a former CIA senior intelligence officer, to explore the nuances of decision-making under pressure and the art of interpersonal communication. Jeffrey shares insights from his career, highlighting strategies for effective manipulation and persuasion, the importance of understanding others, and the balance between professional skills and personal relationships. Follow Jeffrey on LinkedIn Check out Jeffrey's Website Join my weekly newsletter. Learn more about my books and courses. Join The Essentialism Academy. Follow me on LinkedIn, Instagram, X, Facebook, and YouTube.

Greg and Anna McKeown discuss the art of listening, exploring its transformative power in relationships. They discuss a pivotal moment from their dating history where effective listening shifted their connection and emphasized how empathic communication fosters understanding. Drawing insights from Carl Rogers' listening techniques, they share personal anecdotes about applying these principles in family dynamics and their marriage. Join my weekly newsletter. Learn more about my books and courses. Join The Essentialism Academy. Follow me on LinkedIn, Instagram, X, Facebook, and YouTube.

Join Greg and Moses Kagan as they dive into an insightful discussion on entrepreneurship, intergenerational wealth, and the power of gratitude. Moses shares his journey from a tech startup to founding Adaptive Realty, emphasizing the importance of ownership and relationships. The conversation explores narrative, legacy, and the pivotal role of recognizing one's ancestors' struggles and successes. Learn how adopting an intergenerational perspective can impact personal and professional growth, and how stories define both individual lives and broader cultures. Follow Moses on LinkedIn, and X Check out Moses' Blog Join my weekly newsletter. Learn more about my books and courses. Join The Essentialism Academy. Follow me on LinkedIn, Instagram, X, Facebook, and YouTube.