Leadership in the Waiting and the Winning: Reflections from Two Dreams

Leadership is more than a title—it’s a journey shaped by moments of preparation, transition, reflection, and impact. Sometimes, the most powerful leadership insights don’t come from seminars or strategy sessions, but from deeply personal and symbolic experiences—like dreams. In this blog, I reflect on two dreams that offered timely lessons in leadership development, emotional intelligence, resilience, and service. These reflections are not only insightful for emerging and experienced leaders but align with essential principles in coaching, mentoring, and transformational leadership.

By sharing these dream-based stories, my goal is to help leaders recognize the subtle ways leadership shows up in everyday life and how it calls us to act—even when no one is watching. Let us explore what these dreams revealed about preparation, presence, and purpose.

The Train Station Dream (3/21)

Sometimes leadership lessons don’t come through books or boardrooms—but through dreams. On March 21st, 2025, I dreamt of standing in a train station, waiting, pushing a barbecue grill. It wasn’t just about standing still—it was about *positioning*. I maneuvered to the opened middle lane and prepared for movement the moment the train arrived. I wasn’t alone. Another person held a grill, suggesting others, like me, were preparing something valuable.

The dream shifted. My mother and I were overnight guests at someone’s home. She began tidying up where I had slept on the couch. When the host saw this, she complimented both of us. I remember saying to the host my mom was stubborn—an odd but honest reflection of how the traits we inherit can shape our leadership. The dream concluded with me helping a church member manage their home and children, stepping in not because I had to, but because I could.

Leadership Insight:

This dream reflects a season of strategic waiting—of preparation. The grill represents the value we carry. The station is the staging ground. Leadership often looks like service before recognition, action without applause, and care rooted in character. The train will come. When it does, what will you bring?

In executive leadership, this dream can symbolize a call to remain mission-ready even when progress feels slow. The middle lane represents intentional positioning—avoiding extremes and embracing balance. It’s a reminder that impactful leadership is often formed in the quiet moments when no one is looking.

The Classroom and the PorcupineQuill (3/24)

This dream was equally layered. I was in a classroom visiting two boys who felt like my own—one of whom looked like one of my brothers when he was a toddler. Then I was in military uniform, but my hat had no rank. I knew I needed to go back and get it. From there, I was speaking life into a young kid who led his team to victory, giving him praise while still honoring the team as a whole. Later, I found myself giving my sister guidance in a storage room—a mirror of real-life moments over the past two weekends, helping her organize and lead her storage setup. The dream ended with me pulling a porcupine quill from my finger, unsure how it got there.

Leadership Insight:

This dream spoke to multiple layers of leadership: mentorship, identity, affirmation, family, and healing. The missing rank on the hat reminds us that leadership is often recognized internally before it’s affirmed externally. The encouragement of the young leader reflects the importance of celebrating individuals *and* their teams. The storage room shows that influence extends into the everyday moments—family, organization, and quiet direction. And the quill? A reminder that sometimes we carry hidden pains or burdens unnoticed until we pause to remove them. Leadership includes healing too.

For seasoned leaders, this dream echoes the importance of self-awareness and vulnerability. True leaders are not defined by their insignia—but by their actions. Whether we’re mentoring others, helping family, or facing internal challenges, these experiences mold our capacity to lead with authenticity, clarity, and compassion.

Final Reflection

These two dreams reminded me that leadership is not about titles or timing—it’s about service, preparation, awareness, and authenticity. Whether waiting in a station or organizing a storage room, leadership is in how we show up—with purpose, with value, and with heart.

If you’re a professional navigating leadership transition, managing teams, or balancing multiple roles, I encourage you to pause and reflect: What spaces are calling your leadership today? How are you preparing to bring your value when the opportunity arrives?

Let these reflections inspire a renewed perspective on the way you lead—quietly, consistently, and with intention.

Dr. Calvin McDowall is a leadership strategist, international bestselling author, and executive with over three decades of experience in healthcare leadership, military service, and coaching. He empowers leaders to navigate change, lead with purpose, and transform challenges into opportunities. Through storytelling and relatable analogies, Dr. McDowall is on a mission to make leadership more digestible, impactful, and memorable for today’s world changers.

© Dr. Calvin McDowall. All rights reserved. This post reflects original insights and research on leadership. Do not reproduce without permission.