The Journey of Transition: Highlights from the All-Hands

Our conversation brought together a dynamic group, including Carol Bergeron, Dan O’Brien, Ryan Thomas, and Scott Lewis to explore what CEOs face during life-changing transitions. Here’s what we covered:

• The Emotional Side of Retirement: Scott shared his personal story of selling his first business at 32, offering an honest look at the emotional and social challenges that followed without preparing for his transition.
  
• Retirement By Design: Carol expanded on this by introducing the Retirement Life Design Journey, a framework to proactively plan for the next phase of life, addressing identity shifts, purpose, and lifestyle changes. 
  
• From Business Leader to Community Advocate: Dan shared his experience transitioning to consulting during the pandemic. He emphasized the importance of staying connected to one’s values and highlighted the meaningful work he’s doing locally, from supporting a food pantry to improving broadband access.
  
• Reimagining Success and Fulfillment: Ryan reflected on how his definition of success has evolved. For many, it’s about creating a sustainable impact, nurturing personal happiness, and embracing new opportunities for growth and connection.
  
• Practical Tips for Planning: Ryan discussed the importance of envisioning a fulfilling future beyond the CEO role. reflected on how his definition of success has evolved. From creating artificial deadlines to setting up stock option pools, the group shared actionable advice for paving a smoother transition.

The session reminded us that transitions are not just about what we leave behind but about the opportunities ahead. Whether planning an exit or navigating a shift, having a clear plan and a supportive network can make all the difference.

You can watch the entire All-Hands event on our YouTube channel.

Book Recommendations

• Love + Work by Marcus Buckingham – World-renowned researcher and New York Times bestselling author Marcus Buckingham helps us discover where we’re at our best—both at work and in life.
  
• From Strength to Strength by Arthur Brooks – The roadmap for finding purpose, meaning, and success as we age, from bestselling author, Harvard professor, and the Atlantic’s happiness columnist Arthur Brooks.

Speaker Spotlight: Carol Bergeron

Carol Bergeron is an executive coach specializing in guiding leaders through major career and life transitions. With a deep understanding of the emotional and strategic complexities of change, she helps CEOs and executives design fulfilling next chapters beyond their leadership roles. 

Carol offers invaluable support to help individuals proactively navigate identity shifts, redefine success, and create purpose-driven post-career plans. Her approach ensures that leaders not only prepare financially but also emotionally and socially for what comes next.

See you at the next All-Hands in April.