In this Deep Enquiry Interview, we speak with John Kennedy about his transition from working in established companies to starting his own venture. John shares with us his previous professional experiences, including his roles at a digital agency and big tech corporation, and he expresses the challenges he faces in decision-making, prioritising tasks, and adapting to a less structured environment in his new role as CEO of a start-up.Together we uncover John’s lesser conscious motivations, fears, alongside his relationship to failure and perfectionism. We encourage John to develop a leadership style based on his values and to embrace the uncertainties of his new role, and unpack his concerns about decision-making, impacting his team, and handling his public profile as a CEO.The conversation also touches upon the importance of recognising one's skills, overcoming fears, and the role of a business coach. We offer principles and practices that could support John in collaboration, managing different viewpoints, and dealing with discomfort in decision-making. We also discuss the pressures of leading a start-up and the need for recovery and self-care, and the importance of incorporating recovery time into one's routine for better creativity and productivity.Enjoying Time To Show Up? Try out our community for free: https://www.timetoshowup.org/ Key Themes:1.     Transition Challenges: John's move from structured corporate roles to starting his own venture.2.     Leadership and Decision-Making: Developing a framework for effective leadership and decision-making as a CEO.3.     Psychological Aspects: Exploring motivations, fears, and anxieties in a leadership role.4.     Prioritization: Challenges in prioritising tasks and managing time effectively.5.     Perfectionism and Fear of Failure: How past experiences and personal traits affect current decisions.6.     Cultural Development: Creating a company culture based on openness, honesty, high performance, and motivation.7.     Role of a Business Coach: The impact of coaching on personal growth and decision-making.8.     Collaboration and Discomfort: Balancing collaboration with assertiveness and building tolerance for discomfort in decision-making.9.     Recovery and Self-Care: The importance of incorporating recovery time for maintaining effectiveness and creativity.10.  Entrepreneurial Mindset: Embracing fear, risk, and learning from mistakes as part of the entrepreneurial journey.