The Diary of a CEO

Simon Sinek: The Number One Reason Why You’re Not Succeeding | E145

This episode is part of our USA series, over the coming weeks you will get to see some incredible conversations with guests the likes of which we’ve never seen before. Bringing more value, more incredible stories, and more world-beating expertise. Simon Sinek is an author and public speaker, and one of the most interesting thinkers on business in the world today. His books ‘Start With Why’, ‘Leaders Eat Last’ and ‘The Infinite Game’ have sold millions and millions of copies. 00:00 Intro 01:09 Drifting from your ‘why’ 11:23 How do we create continuous goals? 22:40 How do you find purpose in life? 25:33 The importance of assessment from others & nursing personal relationships 31:29 Practical advice to create a culture of seeking feedback from others 44:32 Long term negative impact of lying in your business 54:39 How to make the young generation thrive and stay motivated 59:59 Workplace flexibility 01:12:06 Steven, what are the reasons you're doing DOAC 01:19:24 What are you working on next? 01:22:47 What is your dark side? 01:30:45 Our last guest’s question Listen on: Apple podcast - https://podcasts.apple.com/gb/podcast/the-diary-of-a-ceo-by-steven-bartlett/id1291423644 Spotify - https://open.spotify.com/show/7iQXmUT7XGuZSzAMjoNWlX Simon: https://twitter.com/simonsinek https://www.instagram.com/simonsinek FOLLOW ► Instagram: https://www.instagram.com/steven/ Twitter: https://twitter.com/SteveBartlettSC Linkedin: https://www.linkedin.com/in/steven-bartlett-56986834/ Sponsors: Huel - https://my.huel.com/Steven Myenergi - https://bit.ly/3oeWGnl Vodafone Business - https://bit.ly/3NIM35n https://bit.ly/3AuPKsA Location courtesy of The Nightfall Group: www.nightfallgroup.com

SSSimon SinekguestSBSteven Bartletthost

May 23, 2022·1h 35m·Watch on YouTube ↗

📖 CHAPTERS

1. 1
   2:00 – 10:30

   Losing Purpose and Discovering the 'Why'

   Sinek explains how drifting away from his own sense of purpose led to burnout despite having what looked like a successful life. A candid conversation with a close friend exposed the gap between his external success and internal reality, catalyzing his discovery of the 'Why' framework.

2. 2
   10:30 – 22:30

   Trauma, Champions, and the Emptiness of Finite Goals

   The conversation turns to how trauma and insecurity often fuel extreme achievement, yet leave people purposeless after the goal is hit. Sinek contrasts selfish, finite goals with service-based purposes using elite athletes and an NFL Hall of Famer as case studies.

3. 3
   22:30 – 35:00

   Goals, Continuums, and Health as Service to Others

   Bartlett shares his failed attempts at getting a six-pack as a summer goal, prompting Sinek to unpack why arbitrary, aesthetic goals are weak motivators over time. They reframe health, habits, and self-improvement as acts of service to others and discuss how small, relational purposes can sustain discipline.

4. 4
   35:00 – 50:00

   Presence, Meditation, and Real Vulnerability vs Broadcast

   Sinek challenges the modern misunderstanding of presence and vulnerability. He shows how practices like meditation are ultimately valuable because they help us be fully present for others, and critiques social-media 'vulnerability' that avoids true relational risk.

5. 5
   50:00 – 1:02:00

   Compliments, Help, and the Social Nature of Self-Awareness

   The discussion dives into how self-awareness is socially constructed and why refusing compliments or help is actually selfish. Sinek frames asking for help as a profound act of service that allows others the joy of sacrifice and builds deeper trust.

6. 6
   1:02:00 – 1:13:00

   Creating Feedback Cultures and Peer Accountability

   Sinek offers concrete methods to build cultures where honest feedback and peer review are normal. Drawing on the U.S. Army Rangers' peer review system, he describes how his own team uses rigorous, emotionally challenging 360-style sessions to build trust and awareness.

7. 7
   1:13:00 – 1:25:00

   Judgment vs Curiosity and the Cost of Little Lies

   They examine how leaders can replace snap judgments with curiosity and how everyday lies erode integrity. Sinek introduces 'ethical fading' to explain how organizations slide into serious misconduct while still seeing themselves as ethical.

8. 8
   1:25:00 – 1:37:00

   Relationships, Ghosting, and the Skill of Uncomfortable Conversations

   Sinek and Bartlett connect lying, avoidance, and ethical fading to romantic and workplace dynamics. They criticize conflict avoidance behaviors like ghosting and quitting instead of talking, and argue that teaching difficult-conversation skills is a societal imperative.

9. 9
   1:37:00 – 1:49:00

   Gen Z, COVID, and the Future of Work

   The conversation zooms out to generational trends and the impact of COVID and remote work. Sinek critiques the language of 'strengths and weaknesses', urges an empathic view of Gen Z, and reframes the Great Resignation as a verdict on decades of mediocre culture and leadership.

10. 10
    1:49:00 – 2:01:00

    Perks vs Purpose: Rethinking Company Culture After COVID

    Bartlett recounts how his company’s famed culture—perks, happiness teams, slides—stopped retaining people once remote work leveled the playing field. Sinek explains that without a compelling cause, perks can't compete with higher pay, and that culture must be anchored in shared purpose rather than office toys.

11. 11
    2:01:00 – 2:11:00

    Defining a Purposeful Podcast Beyond the Charts

    They apply the 'why' concept directly to this podcast. Bartlett shares his mixed motives, and Sinek helps crystallize a higher purpose for the show that sits above chart positions and downloads.

12. 12
    2:11:00 – 2:21:00

    Sinek’s Own Why, Just Cause, and Ongoing Projects

    Sinek articulates his personal Why and his long-term 'just cause', then outlines concrete initiatives he’s pursuing. His work spans publishing, police reform, and helping build 'infinite-minded' companies that prioritize longevity and human impact over short-term wins.

13. 13
    2:21:00 – 2:32:00

    Insecurities, Learning Styles, and the Myth of the 'Genius'

    Bartlett probes Sinek’s 'dark side' and the costs of his perceived brilliance. Sinek demystifies himself, revealing ADHD, difficulty reading books, and deep curiosity as core traits, and explains how those limits actually shaped his communicative style and accessible work.

14. 14
    2:32:00

    Legacy, Infinite Games, and Living a Life Worth Living

    In a closing reflection, Sinek reframes a question about his happiest moment into one about living a life worth living. He defines success as building ideas and tools that continue without him, embodying his philosophy of infinite games and service-driven legacy.