Discovering Your Why: A Conversation with Perry Gladstone

Episode Overview: In this episode of the Enclave Podcast, host Jake Knight engages in a deep and insightful conversation with Perry Gladstone, a successful entrepreneur and strategic advisor, about navigating the journey of self-discovery, the importance of understanding one’s purpose, and how this influences personal and professional fulfillment. Perry shares his life experiences, from his early days in the action sports industry to his evolution into a coach for high-achieving individuals. The discussion touches on critical themes such as purpose, impact, legacy, and the hero’s journey, providing listeners with valuable insights into how to lead a fulfilling and authentic life.

Key Discussion Points:

• The Hero’s Journey and Self-Discovery: Perry emphasizes the importance of the hero’s journey, particularly for rising generations. He discusses how the journey often starts with disillusionment and the necessity of challenging societal and familial expectations to discover one's true self.

• Purpose, Impact, and Legacy: Perry offers his definitions of these often-overused terms, highlighting how purpose leads to fulfillment, impact concerns making a difference beyond oneself, and legacy involves the responsibility that comes with the influence one has on others.

• Challenges of Rising Generations in Wealthy Families: The conversation explores the unique challenges faced by those growing up in or marrying into wealth, particularly the struggle to establish one's identity and purpose within the expectations and pressures of maintaining and protecting family wealth.

• The Role of Culture in Family Dynamics: Perry argues that focusing solely on wealth preservation without considering the underlying family culture can lead to dysfunction. He stresses the importance of creating space for individual exploration and growth within family systems.

• Personal and Professional Growth Through Challenges: Perry shares personal anecdotes about his marriages and business ventures, illustrating how significant life challenges have shaped his approach to coaching and advising others.

Quotes to Remember:

• "Success to me right now is knowing that I can support my family financially, emotionally, and show up fully present because it's the in-between times that are the ones you miss when they’re gone." - Perry Gladstone

• "Culture eats strategy for breakfast, and starting with structure is a mistake every time." - Perry Gladstone

Actionable Takeaways:

1. Create Space for Exploration: Both individuals and families should prioritize creating time and space for personal discovery and growth, beyond financial concerns.

2. Challenge the Status Quo: It’s essential to question the roles and expectations imposed by society and family to truly understand who you are and what you are meant to do.

3. Define Success on Your Terms: Success is not static; it should evolve as your life circumstances change. Focus on what truly matters to you at each stage of life.

How to Connect with Perry Gladstone:

• Website: perrygladstone.com
• Perry is open to discussions with those who are interested in living their best lives and creating space for those they love.

Join the Enclave Community:

• Visit joinenclave.com to learn more about the Enclave community and join other rising gens on