Creating Astonishment with Chicago Bears CEO Kevin Warren | A Bit of Optimism Podcast
Here are the top 10 key takeaways from a conversation between Simon Sinek and Chicago Bears CEO Kevin Warren that reveal timeless wisdom about leadership, personal growth, and finding joy in everyday life.
1. Transforming pain into fuel
Kevin Warren shares a pivotal childhood experience when he was hit by a car at age 10. This accident left him in traction and a full body cast for nearly a year. The traumatic event taught him the value of time management and the fragility of life. It forced him to mature quickly, transitioning from a child to an adult at just 11 years old.
Warren credits this painful experience as the catalyst that shaped his future success. He states unequivocally that he wouldn't be sitting in his current position if not for that accident. The experience taught him to maximize every minute of his day and to appreciate life's fragility. Warren views painful experiences not as setbacks but as fuel that propels personal growth and achievement.
2. Building your own pool
The podcast reveals how young Kevin used his injury settlement money to build a swimming pool in his parents' backyard. This decision came after his doctor suggested swimming would aid his recovery. His parents initially refused his request, but Kevin persisted through what he calls his "first real negotiation in life."
This experience taught Warren valuable lessons about passion, self-investment, and ownership. He learned the difference between having others invest in you versus investing in yourself. This childhood experience became so formative that he titled his upcoming book "Build Your Own Pool." The story symbolizes taking initiative and investing in your own healing and future, even when faced with resistance.
Warren connects this early experience to his leadership philosophy today. When you invest your own resources in something, you naturally take better care of it. You become more vigilant about maintenance and protection because you have skin in the game. This principle extends beyond physical possessions to education, relationships, and career pursuits.
3. Valuing time over possessions
Warren shares a touching anecdote about his father, who would park far away from Arizona State football games. When Kevin finally asked his father about this puzzling habit, his father revealed it was to spend more time with his son. Those long walks provided guaranteed time to hold his son's hand both to and from the stadium.
This revelation changed Warren's perspective on parenting. He notes that young parents often work tirelessly to provide financial security and protection for their children. However, with age and wisdom, parents realize what children truly desire is their time and attention. Material possessions mean little compared to quality time spent together.
The story illustrates how seemingly inconvenient moments can become treasured memories. What appeared to be a logistical decision about parking was actually a deliberate choice to create meaningful connection. Warren suggests we should all look for opportunities to create these "mile walks" with important people in our lives.
4. Embracing astonishment in everyday life
Both Warren and Sinek discuss the importance of maintaining a sense of wonder about the world. Warren describes stopping to admire the moon, a cardinal bird, or a sunset. Sinek shares how he sometimes becomes hyper-aware of the sounds when making morning coffee, appreciating each individual sound as if adding sound effects to a movie.
This ability to be astonished by ordinary things contributes significantly to happiness and well-being. Warren suggests that astonishment and curiosity are two attributes that would make the world more special if more people possessed them. The conversation emphasizes how this childlike quality of showing genuine astonishment often diminishes as we mature.
Warren notes that children naturally express their astonishment openly and enthusiastically. Adults tend to restrain these reactions, perhaps for self-protection or social conformity. Both men agree that maintaining and expressing genuine astonishment not only enriches your own life but proves contagious to others. Their conversation suggests actively cultivating this sense of wonder rather than suppressing it.
5. Balancing productivity with rest
Warren acknowledges a significant shift in his approach to work-life balance. Raised to believe productivity meant constant activity, he has only recently recognized the importance of rest and "frivolity." He now understands that quality rest enhances productivity rather than detracting from it.
Simon pushes the conversation further, distinguishing between physical rest (sleep) and mental leisure. He describes the value of unproductive time—doing puzzles, building Lego sets, or simply allowing the mind to wander. Warren admits he's still learning to leave work behind occasionally, such as traveling without his briefcase.
Both men agree that stepping away from productivity can spark creativity and provide fresh perspectives. Warren compares constant work to driving a car at maximum speed without breaks—eventually, it breaks down. He's now proud of getting consistent sleep and recognizes that downtime isn't wasted time but essential for sustainable performance and well-being.
6. The importance of deep human connection
Warren discusses his realization about human connections after delivering eulogies for family members. He was surprised to discover new things about people he thought he knew well. This experience prompted him to commit to knowing people more deeply while they're still alive. He doesn't want to be surprised at any more funerals.
In leadership, Warren believes that genuine care for team members and their families creates willing followers rather than reluctant ones. He extends this consideration beyond employees to their families, noting that what someone does for his children or wife captures his heart forever. This approach builds deeper loyalty and commitment than focusing solely on work objectives.
Warren emphasizes that truly special leaders focus on the journey and the people rather than just the end game. He creates opportunities for families to participate in the hiring process, recognizing that job decisions affect entire households, not just individuals. This holistic approach recognizes that work-life balance is somewhat artificial—we bring home stress to work and work stress home.
7. Finding value in struggling together
The conversation explores how shared hardship strengthens relationships. Warren discusses how his experience leading the Big Ten during COVID made him a better leader. Sinek references military training, where going through boot camp together transforms individuals into a cohesive unit.
Warren extends this concept to childbirth, noting the powerful bond between mother and child that forms through this intense shared experience. Sinek explains this connection has biological roots in oxytocin release during both childbirth and shared struggles. This chemical creates feelings of love, trust, and bonding.
Both men reflect on how our most vivid memories often involve overcoming difficulties. Warren observes the "interesting dichotomy" that humans crave comfort but thrive in discomfort. The things we remember most vividly are typically challenging experiences—the "pain points" in our lives. This suggests intentionally embracing certain struggles may actually enhance our lives rather than diminish them.
8. Creating legacy moments through sports
Warren views sports as multi-layered experiences that transcend the game itself. He describes sports events as opportunities to create lasting memories and meaningful connections. These events bring families together and can become milestone moments in people's lives.
His vision for the new Chicago Bears stadium extends beyond creating a building. He sees it as a place where people will create memories with loved ones, perhaps even the last memories they'll share with certain family members. Warren appreciates all aspects of the sports experience—the food, music, ambiance, gear, and colors—recognizing they all contribute to the overall impact.
Warren shares how former Vikings coach Bud Grant pointed out that sporting events keep the national anthem alive in American culture. This observation highlights how sports serve as cultural touchpoints that preserve traditions and create shared experiences. For Warren, sports venues become spaces where people can become "astonished" and where transformative moments occur that may influence lives for decades to come.
9. Treating relationships like we treat our phones
Warren shares a powerful metaphor about how we prioritize our cell phones over human relationships. He notes that people treat their phones with incredible care—charging them nightly, checking them first thing in the morning, immediately repairing cracked screens, and constantly verifying their presence. He wonders how different our world would be if we treated our relationships with the same attentiveness.
This insight came partly from a conversation with Sinek about phone etiquette. Warren now turns his phone off during meetings rather than just flipping it over. He recognizes that even having a visible phone signals divided attention. By putting phones completely away, he demonstrates that the person in front of him deserves his undivided attention.
Warren used this metaphor in a wedding speech, suggesting that if we treated our significant others the way we treat our phones, "this world would be a magical place." He observes how people will clear their schedules and wait hours for phone repairs while claiming to be too busy for relationship maintenance. This perspective has changed how he prioritizes face-to-face interactions over digital distraction.
10. Investing in creating astonishment for others
Throughout the conversation, Warren emphasizes creating moments of astonishment and wonder for others. He describes letting young visitors sit in his office chair, bringing families to games, and investing time in learning about people's interests outside work. These actions stem from his own transformative experiences seeing a Supreme Court justice's office as a teenager.
Warren believes providing access to inspiring environments can have "cataclysmic" positive impacts decades later. He notes that a child who experiences the roar of a stadium crowd might become an NFL owner, commissioner, coach, or technology innovator. These experiences plant seeds that may grow into future accomplishments.
The conversation concludes with Warren's philosophy that putting people in positions where they can become astonished creates magic that extends far beyond the moment itself. Both men agree that creating these opportunities for others represents a profound gift. Warren's leadership approach centers on facilitating these transformative moments of wonder and connection for everyone he encounters.