Navigating the Lonely Helm: Insights from a Four-Time CEO

 As I scroll through my news feed, I am seeing more stories of first-time CEOs stepping into their roles, reminding me of a poignant piece of advice from the late Reverend Marylen Stansbery, an Episcopal priest who once handed the reins of a small nonprofit to me. She warned, "It’s a lonely job, and you need to find an outlet for release." At the time, I didn’t fully grasp the depth of her words.

My journey as a CEO has been marked by constant learning and adaptation. In 2019, when I assumed my current role, I stumbled upon an enlightening article from Harvard Business Review titled "The 3 Challenges Every New CEO Faces." The piece resonated deeply with me, reflecting on the stark reality that nearly half of all chief executives find the role startlingly different from their expectations.

The Core Challenges Faced by CEOs:

1. Unexpected Role Realities: The disconnect between what many CEOs anticipate and what they face can shake their tenure and impact performance. This realization explains why the median tenure of CEOs in major corporations is shortening.

2. Managing Energy and Time: Successful CEOs must master the art of energy management, dedicating time to activities that recharge them while steering clear of those that deplete their resources. This balance is crucial for efficiently navigating the demands of the role.

3. Building Strong Relationships with Board Members: Fostering robust relationships with board members is key. These interactions should be viewed as opportunities for gaining insights and support, transforming potential energy drains into sources of vitality.

4. Engagement with External Stakeholders: Establishing trust and maintaining relationships with stakeholders like investors, the media, and regulators is challenging but essential. Effective communication and frequent engagement are vital for adapting to changes that could influence the business.

5. Managing Information Flow: A CEO must meticulously manage the flow of information to ensure that accurate and necessary details reach the appropriate individuals. This balance between detailed, daily operations and broader strategic decisions is crucial for effective leadership.

Throughout my career, I've held the CEO position in different contexts, from nonprofit organizations to corporate settings, each bringing unique challenges and learning opportunities. For instance, I've navigated unexpected changes to retirement plans, shifts in community investment strategies, and crises like the aftermath of Michael Brown's tragic death in 2014. Even the onset of COVID-19 threw a wrench into my early days at a new bank position, proving that the role of a CEO is anything but predictable.

Despite these challenges, I've consistently tried to implement structured 90 or 100-day plans and annual strategic agendas, as recommended by leadership books and articles. While these plans provide a roadmap, the dynamic nature of business often requires abrupt adjustments and sometimes even a complete overhaul of strategies.

Being a CEO is not just about steering the ship; it’s about being prepared to navigate through storms, adjust your course as needed, and sometimes endure the loneliness of command with resilience and foresight. The journey is challenging, but with the right mindset and strategies, it can also be extraordinarily rewarding.

Hi, I’m Orvin Kimbrough, volunteer, board director, chairman, and CEO. I help professionals move from feeling stuck to being strengthened by reshaping how they think, lead, and live. My work focuses on confidence, leadership, and influence through mindset shifts, expanded networks, and bold, values-aligned action. My perspective is rooted in lived experience, from growing up in foster care to leading complex institutions as a CEO and shaped by faith, resilience, and a deep belief in human potential.

Rectangle 19461

Books for Every Stage

Twice Over a Man

A memoir often described as a leadership guide wrapped in an honest, relatable story of perseverance, healing, and growth. It explores how pain can be reframed into purpose and how ordinary people build meaningful lives through courage and clarity.

More Than a Conqueror

Written for teens and young adults, this book encourages confidence, resilience, and identity formation during the years when self-belief is being shaped.

Ward and the State

A children’s book that gently introduces big ideas like belonging, courage, and hope, helping young readers see themselves as more than their circumstances

INTRODUCING: The Thriver’s Path™

This blog is part of The Thriver’s Path™—a growing ecosystem of writing, courses, reflections, and community designed to help people of all ages reframe their thinking, reclaim their agency, and take their next meaningful move.

→ Ready for your next move?

Explore more writings, resources, and ways to engage at orvinkimbrough.com, or join the conversation inside the Thrivers Club™ community.

Enjoyed this post?

 Stay connected and continue the journey with insights on leadership, growth, resilience, and intentional living delivered straight to your inbox. 

Typing+Blog+Still

Subscribe to the Leadership Insights Newsletter and receive: 

  • Thought-provoking reflections and leadership perspectives
  • Practical strategies for personal and professional growth
  • Monthly insights and inspiration
  • Early announcements and updates from The Thrivers Path™