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.

Greg and Tim Ferriss dive into the art of prioritizing meaningful relationships and self-transcendence in this reflective conversation. They explore the concept of focusing on essential connections, sharing insights on setting priorities, fostering secure attachments, and tackling life's distractions. Tune in to discover how these thought leaders prioritize the "thousand X" relationships that matter most while navigating modern life's challenges and distractions. Follow Tim on LinkedIn, Instagram, X, Facebook, and YouTube Check out Tim's 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.

In Part 1 of my conversation with Richie Norton, we discussed his countercultural but transformational approach to time management, program stacking and how they can help you generate huge results. In today's episode, Richie and I are picking up where we left off to talk about the importance of changing how you are paid. Listen in for the stories and actionable advice that will help you revolutionize your time and your day-to-day life. Join my weekly newsletter. Learn more about my books and courses. Join The Essentialism Academy. Follow me on LinkedIn, Instagram, X, Facebook, and YouTube.

Warren Berger is a bestselling author, journalist, and an expert in innovation and creativity. He is best known for his book, "A More Beautiful Question," where he explores the power of asking thoughtful, transformative questions to drive innovation and change. Warren has been featured in several publications including The New York Times, Wired magazine, and Fast Company. As a self-described "questionologist," he proves how asking the right questions can propel individuals and organizations towards meaningful progress. Episode Summary: Greg is joined by Warren Berger, author of "A More Beautiful Question," as they explore the power of questions to unlock innovation, deepen relationships, and enhance critical thinking. Warren shares how asking the right questions can propel personal and professional growth, illustrating through compelling case studies and practical examples. Discover how leaders can foster a culture of inquiry and why framing mission statements as questions can engage and empower teams. Key Takeaways: The art of questioning is fundamental to learning, innovation, and problem-solving, as it drives understanding from different perspectives. Emphasizing the value of beautiful questions can lead to unlocking potential in both personal and professional environments. Leaders should strive to ask more questions and foster a culture of inquiry, which can lead to better communication and engagement. Mission questions can serve as dynamic alternative to mission statements, inviting participation and growth from all stakeholders. Overcoming fear and vulnerability associated with asking questions is crucial; authentic curiosity can result in more effective and open dialogues. Notable Quotes: "Questioning is the way we attack the unknown." — Warren Berger "A lot of questioning is about figuring out what's in your own mind." — Warren Berger "Great questions propel you forward." — Warren Berger "Mission questions offer humility and are an invitation to your people." — Warren Berger Resources: Warren's Book: A More Beautiful Question Website: A More Beautiful Question Follow: Warren on X Affiliate links are used where appropriate. We earn from qualifying purchases, thank you for supporting the show! Join my weekly newsletter. Learn more about my books and courses. Join The Essentialism Academy. Follow me on LinkedIn, Instagram, X, Facebook, and YouTube.

Have you ever felt like there were just too many tabs open in your mind? Today, I've invited Alison Jones, the author of Exploratory Writing: Everyday Magic for Life and Work. By the end of this episode, you will have the simplest of tools that can produce extraordinary results. You'll discover an idea so simple, you'll get it immediately, and yet you've probably never done it before in your life. It will help you to be able to turn the chaos in your mind into clarity and even creativity. Learn more from Alison here: https://alisonjones.com/ 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 as he introduces the Essentialism Planner, a tool designed to help individuals focus on what truly matters. Drawing from personal experiences and a decade of development, Greg guides listeners through key components of the planner, including the personal quarterly offsite, weekly design sessions, and the transformative power half-hour. Learn about the planner's bonus features, the 100-year vision, and the empowering no list, all crafted to navigate life's noise and distractions. Embrace essentialism and discover a more intentional, impactful way to live. Key Takeaways: Two Types of People: Recognizing that knowing you're lost allows for recalibration and better decision-making. Power of Reflection: The Essentialism Planner emphasizes reflection through personal quarterly offsites and weekly design sessions to align with essential goals. 1, 2, 3 Method: A structured approach to day-to-day prioritization focusing on projects of major significance and urgent tasks. Intergenerational Impact: Understanding the profound influence of past and future generations encourages sustainable life decisions. Saying No: Developing a "no list" alongside a to-do list enhances decision-making power and helps in maintaining focus on essential tasks. Notable Quotes: "There are two kinds of people in the world: those who are lost, and those who know they are lost." "Airplanes are off track 90% of the time. They only reach their intended destinations because they constantly correct their path." "What matters most is what lasts the longest." "If you don't prioritize your life, someone else will." "It's not rewarding activity; it's rewarding completion." Resources: The Essentialism Planner Affiliate links are used where appropriate. We earn from qualifying purchases, thank you for supporting Greg! Join my weekly newsletter. Learn more about my books and courses. Join The Essentialism Academy. Follow me on LinkedIn, Instagram, X, Facebook, and YouTube.

Dr. Nicole Cain is a respected authority in psychiatry, clinical psychology, and naturopathy, with extensive experience in both mental and holistic health care. She has authored a book addressing the treatment and prevention of panic—a subject deeply personal to her, driven by her battle with anxiety and her professional pursuit to empower individuals through their struggles. Dr. Cain serves as a clinician, teacher, and thought leader in advocating a holistic and personalized approach to mental wellness, emphasizing the body’s inherent ability to heal itself. Episode Summary: Join Greg and Dr. Nicole Cain as they explore the vital connection between understanding symptoms and reclaiming personal health agency. In this discussion, Dr. Cain shares insights from her book, "Panic Proof," which aims to empower individuals with tools to decode anxiety's root causes through a holistic lens. Discover the importance of asking the right questions, understanding nine types of anxiety, and developing a personalized 'Panic Proof Protocol' to foster healing. Key Takeaways: Discover the nine types of anxiety as identified by Dr. Nicole Cain, each with distinct symptoms that require unique understanding and treatment. Learn about the Panic Proof Protocol, a holistic and personalized framework for managing and overcoming panic attacks. Explore the vital role of patient agency and self-advocacy in the diagnostic process, encouraging proactive engagement with one's health journey. Understand the importance of diagnosing the root causes of anxiety rather than focusing solely on symptom suppression. Appreciate the value of creating a supportive space that enables the body and mind to naturally heal and balance themselves. Notable Quotes: "I believe that everybody can heal. I have seen impossible things as possible." "Our bodies are designed to heal themselves, and sometimes it’s a matter of being curious about what they have to say." "The authority's probably not going to figure it out for you; they're going to be able to provide you excellence from their area." "That which remains in the unconscious will continue to affect us and we will call it fate." Resources: Nicole's book: Panic Proof Follow Nicole on Instagram and LinkedIn Affiliate links are used where appropriate. We earn from qualifying purchases, thank you for supporting Greg! Join my weekly newsletter. Learn more about my books and courses. Join The Essentialism Academy. Follow me on LinkedIn, Instagram, X, Facebook, and YouTube.

Israa Nasir is a distinguished author and therapist known for her work on mental health and productivity. She is the author of "Toxic Productivity: How to Reclaim Your Time and Emotional Energy in a World that Always Demands More." Nasir's expertise lies in helping individuals navigate the intricacies of productivity culture and identity, especially within the context of first-generation immigrants and diaspora communities. Her insights draw from her experiences as a Canadian South Asian and her professional practice assisting young adults in exploring and integrating their multifaceted identities. Episode Summary: Greg invites Israa Nasir, the author of "Toxic Productivity," to explore the pitfalls of relentless striving and the quest for identity. Nasir shares insights on developing a rich, multifaceted existence and the dangers of living fragmented lives due to cultural and societal pressures. They discuss how upbringing influences values of achievement and how understanding one's emotions can lead to a more authentic life. Key Takeaways: The Nature of Toxic Productivity: Understand the detrimental effects of productivity that focuses solely on achievement rather than genuine fulfillment. Identity Integration: Learn how to integrate disparate parts of your identity to create a holistic and dynamic sense of self. Role of Family Dynamics: Explore how familial and cultural backgrounds influence our attitudes towards achievement and belonging. Skills for Emotional Regulation: Gain insights into the importance of emotional literacy and how it enhances personal resilience and authenticity. Intergenerational Self-Understanding: Discover the significance of having an intergenerational perspective to build resilience and a sense of continuity in life's narrative. Notable Quotes: "People want to put you in a box so that you are easier for them to understand." "As long as you're achieving, people were loving you. And so you learn very quickly that you can barter achievement for praise." "We can just show up in our lives more authentically by connecting with our emotions." "Therapy is not accessible to everyone, but the process can be therapeutic without a therapist." Resources: Israa's book: Toxic Productivity Follow Israa on LinkedIn Affiliate links are used where appropriate. We earn from qualifying purchases, thank you for supporting Greg! Join my weekly newsletter. Learn more about my books and courses. Join The Essentialism Academy. Follow me on LinkedIn, Instagram, X, Facebook, and YouTube.

Stephen Riggio is a visionary leader and former CEO of Barnes & Noble, where he played a crucial role in its transformation into the largest bookselling chain in the United States. His extensive career in the book industry, spanning over four decades, includes pioneering work in e-commerce and publishing. Beyond corporate endeavors, Riggio is deeply engaged in philanthropy, working with organizations like the National Book Foundation and the National Down Syndrome Society. In recent years, Riggio has turned his focus to translating and promoting classic Sicilian literature, especially the "Sicilian Avengers" series. Episode Summary: Greg hosts Stephen Riggio, former Barnes & Noble CEO, as they explore the transformative power of literature and the significance of connecting with one's heritage. Riggio shares his journey in translating "Sicilian Avengers," a historical epic rooted in his Sicilian ancestry, and how this project intertwined with personal tragedy and discovery. The conversation covers themes of intergenerational legacy, resilience, and finding purpose through challenging times. Key Takeaways: Legacy of Literature: Books are powerful portals that connect us to different cultures and eras, enriching our understanding and empathy. Intergenerational Connection: Exploring family history can provide insights into personal identity and resilience, bridging the past and future. Personal Healing: Transforming personal tragedy into purpose by engaging in meaningful projects like translating significant literary works. Cultural Appreciation: The translation of "Sicilian Avengers" unveils the diverse and multicultural history of Sicily, challenging common stereotypes. Future Endeavors: Taking on translation as an epic adventure, paralleling personal journeys of self-discovery and cultural preservation. Notable Quotes: "Books are more than paper and ink. They are a portal through which we can experience places and times and people we otherwise wouldn't." – Greg McKeown "Raising a child with a disability is a challenge... our deepest wish is that this book didn't exist. However, our daughter's presence in it is undeniable." – Stephen Riggio "It gives me a great deal of satisfaction to know that I've arrived here... It was my destiny." – Stephen Riggio "The best historical fiction... is that people would prefer to be given a compelling narrative that is rooted in history." – Stephen Riggio Resources: Stephen's book: "Sicilian Avengers" Affiliate links are used where appropriate. We earn from qualifying purchases, thank you for supporting Greg! Join my weekly newsletter. Learn more about my books and courses. Join The Essentialism Academy. Follow me on LinkedIn, Instagram, X, Facebook, and YouTube.

About the Guests: Jeremy Utley: A notable faculty member at Stanford University's D School and author of "Idea Flow: The Only Business Metric That Matters." Jeremy is known for his research and insights into creativity, innovation, and the interplay between human cognition and technology. He has been instrumental in exploring the applications of AI in problem-solving and productivity. David McRaney: A researcher focused on the concept of genius and cognitive biases. He hosts a podcast where he explores these themes extensively, having Jeremy Utley as one of his guests in exploring the cognitive bias in people's collaboration with AI. Henrik Werdelin: Known for his exploratory insights into AI, its capabilities, and implications for the future. Henrik is an entrepreneur and author best known for co-founding Bark, as well as starting Prehype, a venture building research and development group headquartered in New York. Episode Summary: Greg continues the engaging dialogue exploring the potential and limitations of AI in enhancing human understanding and communication. Joined by his distinguished guests Jeremy Utley, David McRaney, and Henrik Werdelin, they discuss how AI could be used as a tool to facilitate better communication and understanding among individuals. The episode touches on the daily use of AI technologies like GPT, which have notably started to replace traditional search engines for some tasks. and they all explore the possibility of AI-improving interpersonal relationships by offering insights and mediating communication, questioning the biases  Key Takeaways: AI as a Mediator: AI has the potential to assist in mediating conflicts and misunderstandings in human communication by functioning as a second, unbiased listener. Epiphany Generator: Using AI in daily workflows can transform it into a tool that not only provides information but also stimulates new ideas and insights. Towards Better Conversations: The episode emphasizes the importance of rethinking how we engage AI and challenges the notion that it’s primarily for problem-solving rather than for facilitating understanding. Bias Acknowledgement: It’s crucial to recognize our biases toward AI capabilities and to shift our perspective to appreciate AI as a tool for both interpersonal and intrapersonal dialogues. Designing for Listening: Future AI technology should intentionally be designed to foster deep listening and enhance understanding, moving beyond merely responding with solutions. Notable Quotes: "I used GPT as an epiphany generator, an elaboration encourager." "I believe that the primary limitation right now is the interface between us and the machine." "We need the Mediator app. It's not just the fingers problem." Resources: Jeremy Utley's book: "Idea Flow: The Only Business Metric That Matters" Follow Jeremy on X, Instagram, and LinkedIn Follow David on X, Instagram, and LinkedIn Follow Henrik on Instagram, and LinkedIn Affiliate links are used where appropriate. We earn from qualifying purchases, thank you for supporting Greg! Join my weekly newsletter. Learn more about my books and courses. Join The Essentialism Academy. Follow me on LinkedIn, Instagram, X, Facebook, and YouTube.

About the Guests: Jeremy Utley: A notable faculty member at Stanford University's D School and author of "Idea Flow: The Only Business Metric That Matters." Jeremy is known for his research and insights into creativity, innovation, and the interplay between human cognition and technology. He has been instrumental in exploring the applications of AI in problem-solving and productivity. David McRaney: A researcher focused on the concept of genius and cognitive biases. He hosts a podcast where he explores these themes extensively, having Jeremy Utley as one of his guests in exploring the cognitive bias in people's collaboration with AI. Henrik Werdelin: Known for his exploratory insights into AI, its capabilities, and implications for the future. Henrik is an entrepreneur and author best known for co-founding Bark, as well as starting Prehype, a venture building research and development group headquartered in New York. Episode Summary: Joined by Jeremy Utley, David McRaney, and Henrik Werdelin, the discussion takes a deep dive into how AI could act as a facilitator in human interactions, potentially bridging gaps in communication. The episode addresses the potential of AI as a tool for mutual understanding and its limitations in conveying authentic emotional connections. There is a focus on how AI can strive toward becoming a "faithful translator," aiding in better translating human thoughts and emotions into shared understanding. This interplay of AI, cognitive biases, and communication brings forth a rich conversation on the collective and individual impacts of AI on productivity and personal clarity. Key Takeaways: AI has the potential to bridge gaps in communication, acting as a "faithful translator" to help humans better understand each other. Cognitive biases and the ambiguity of language highlight the challenges AI faces in truly capturing and conveying authentic human emotions. The importance of AI lies not just in providing organized information but in facilitating deeper layers of connection and understanding. Practical applications of AI in summary and synthesis show promise, yet the depth of understanding requires further development. AI can serve as a catalyst for personal insights, yet users must actively guide it to achieve exceptional results. Notable Quotes: "As our ability to understand each other approximates zero, so does our ability to do anything else." "The medium is the message. The technology you use uses you." "AI's best use is in establishing a shared conceptual framework before we start the conversation." "It's not the utility of the communication, it is the emotional connection." "If this could be exceptional, how could it? What would I need to say for it to be truly exceptional?" Resources: Jeremy Utley's book: "Idea Flow: The Only Business Metric That Matters" Follow Jeremy on X, Instagram, and LinkedIn Follow David on X, Instagram, and LinkedIn Follow Henrik on Instagram, and LinkedIn Affiliate links are used where appropriate. We earn from qualifying purchases, thank you for supporting Greg! Join my weekly newsletter. Learn more about my books and courses. Join The Essentialism Academy. Follow me on LinkedIn, Instagram, X, Facebook, and YouTube.