Michelle Hollingshead is an entrepreneur, author of “Meaning Indicator: Finding Significance through Challenge, Work, and Love.” Michelle delves into the power of vulnerability, inspired by her personal experiences and the loss of her brother post-9/11. Her book echoes Viktor Frankl’s Man’s Search for Meaning, focusing on resilience and intentionality. She stresses the importance of choice and compassion through life's trials.  Michelle explores the delicate balance between challenge and care in coaching, highlighting that love can coexist with direct feedback. She emphasizes that true love involves nurturing potential and moving on when necessary.  Michelle introduces the concept of "and" from her book, which helps manage life's complexities, and reflects on her mother's influence and the need to balance professional ambitions with family life.  Michelle discusses leadership and personal growth, emphasizing the balance between results and relationships and the evolution from command-and-control to inspiring participation. Michelle shares insights into how life stages influence leadership perspectives and her journey as an empty nester exploring new directions.     Key Takeaways [01:44] Michelle discusses embracing vulnerability, influenced by personal experiences and the loss of her brother after 9/11. Her book, "Meaning Indicator: Finding Significance through Challenge, Work, and Love," inspired by Viktor Frankl's "Man's Search for Meaning," explores resilience and intentionality. Michelle emphasizes the power of choice and compassion in life's challenges. [07:06] Michelle discusses the balance between challenge and care in her coaching experience, emphasizing love as caring for oneself, others, and the world. She explains that love in the workplace can coexist with honest, direct feedback and that sometimes the most loving action is for both parties to move on. Michelle highlights that love is about helping others realize their potential. Jim references a past guest who noted the Greek language's multiple words for love, aligning with Michelle's view of love as deep, honorable caring. Michelle's research on meaning in life revealed people often discuss challenges more than love, though they rank love higher in surveys. [17:40] Michelle explains the concept of "and" from her book, highlighting how it helps navigate life's complexities. She acknowledges those motivated by work and solving problems but also notes the tension when work overshadows other aspects of life. Michelle shares how her mother's passion for programming influenced her, wishing she had shared this passion when they were younger.  [19:16] Michelle discusses her research on the "greater good" archetype from Carolyn Taylor's work, highlighting how leaders navigate competing stakeholder needs and make thoughtful trade-offs. Jim raised an interesting point about the tension between significance and happiness, referencing his observations from different cultures. This sparked a discussion on how meaningfulness often involves stress and contemplation, while happiness focuses on satisfying basic desires. Jan shared an inspiring story about Jim's leadership during a challenging expedition in Patagonia, emphasizing how he thrives under pressure and excels at delegating.  [22:53] Michelle dives into the intricacies of leadership and personal growth, emphasizes the balance between results and relationships in leadership, noting the evolution from command-and-control to inspiring willing participation. Michelle reflects on the importance of understanding what drives individuals, highlighting the dynamic nature of personal motivations. They discuss the transformative impact of life stages, such as becoming parents or empty nesters, on leadership perspectives. Michelle shares her journey of balancing professional ambitions with family life, and now, as an empty nester, she explores new personal and professional directions. [28:29] Michelle shares how her father-in-law, Mickey, impacted her life. Despite his cancer diagnosis, Mickey was at peace, reflecting on his great life and embodying leadership through results and relationships. Michelle felt grateful to capture and share his life through this process. [31:33] Michelle reflects on the significance of her book, emphasizing that the things that matter most now are the same as those that will matter in the end. Michelle notes that her book is a short read, perfect for recalibrating during a plane flight. Jim and Jan express their gratitude for Michelle's insights and the opportunity to have her on the show. [32:34] And remember, Don’t aim at success. The more you aim at it and make it a target, the more you are going to miss it. For success, like happiness, cannot be pursued; it must ensue, and it only does so as the unintended side effect of one’s personal dedication to a cause greater than oneself  - Viktor E. Frankl   Quotable Quotes "Leaders go first. I need to be doing my best to walk my walk and role model." "People don’t need my perfectionism. They need my compassion." "Sometimes the most loving thing is for everyone to move forward." "The word I chose for love was caring for self, others, and our world." "Seeing that aliveness in people who are passionate about what they do is very compelling." "Widen the lens, and just having that awareness." "Challenge, work, and love are ways people find significance in life." "Even as an empty nester, I'm reorienting myself to my own relationship with work and discovering new focuses." "The things that matter most in the end are what matter most today. This is an opportunity to reconnect with what is significant for you."   Resources Mentioned The Leadership Podcast | Sponsored by | Rafti Advisors. LLC | Self-Reliant Leadership. LLC | Michelle Hollingshead Website | Michelle Hollingshead LinkedIn | Michelle Hollingshead Instagram | This is the book mentioned in this episode