Flying Solo, Walking Together: The Sacred Passage of Leadership in the Unknown

 

In every leader's life, there comes a moment not of triumph, but of disorientation. The map dissolves. The familiar lights go out. What remains is the weight of choice, the pull of responsibility, and a vast, unsettling not-knowing. 

Dante wrote, "In the middle of the journey of our life, I came to myself within a dark wood where the straight way was lost." This is not mere poetry. It is a precise description of the human journey-whether in personal life, leadership, or the thresholds that mark both. 

We often mistake leadership for vision, direction, or confidence. But these are byproducts. The deeper task of leadership is to stand consciously in the liminal. To recognize when the old forms have crumbled, when no amount of past knowledge can anchor us-and still, to stay present.

The Call to Unknowing: The Hero's Journey Begins

Joseph Campbell's Hero's Journey starts not with the hero's victory, but with their disturbance. The Call to Adventure is often an upheaval: a loss, a crisis, a profound challenge. It's not sought out. It seeks you.

Every leader-every human being-encounters such calls. And in truth, most refuse them at first. We seek distraction. We crave the comfort of known answers. But eventually, life insists.

Answering the call is less about action than surrender.

The Dark Wood: Dante's Inferno and the Loss of the Straight Way

The dark wood is not a metaphor we outgrow. Dante's journey through hell is not a descent into evil, but into the fragmented self. In leadership, the inferno appears when our strategies fail, when relationships fracture, when outcomes defy control.

Even the inferno has a guide-Virgil, the voice of reason and wisdom. This guide cannot remove the darkness. Only accompany us through it.

The Dark Night of the Soul: Embracing the Sacred Not-Knowing

The mystic John of the Cross spoke of the Dark Night of the Soul not as punishment, but purification. A stripping away of false lights.

In leadership, this dark night is the breakdown of certainty. Not-knowing becomes the only honest position. And this not-knowing is not passive. It's an active, courageous stance.

The Hidden Wisdom of Ma: Holding the Space Between

The Japanese concept of ma-the meaningful space between things-is what your reflection named as "holding space without filling it."

Most modern cultures fear emptiness. But emptiness is not lack. It is the womb of potential.

Flying Solo, Walking Together 

Your inner journey is yours alone. Yet you are never truly alone. 

After the abyss comes the Return with the Elixir. What is learned in solitude becomes wisdom shared in community. Leadership becomes the art of walking solo and together. 

Reflection: 

Can I stay present in the ma of not-knowing? 

Can I discern when to walk alone and when to accept companionship? 

Am I willing to let the unknown transform me before I seek to transform it? 

Leadership, like the soul's journey, is not about avoiding the dark. It is about finding the light that can only be seen there.

 

 

About the Author

Lead True Global Leader Andrea Henning’s vision is that when people discover their authenticity and dare to follow their bliss they are happier and more successful in their lives while serving as an inspiration to their communities.

 

 

Read more from Andrea Henning below.

Andrea Henning

It is Andrea Henning’s vision that when people discover their authenticity and dare to follow their bliss they are happier and more successful in their lives while serving as an inspiration to their communities.

Andrea helps people and organizations clarify what is essential to them, then challenges them to get “all hands on deck” to produce the kind of results that make them want to jump out of bed in the morning. She gets right to the heart of matters, is enthusiastic about what she is doing and builds a long-term partnerships with her clients. She completely invests herself in the transformation process with her clients, guiding them to recognize their own power. She also has quite a bit of fun along the way.

Andrea’s foundational coaching principles include achieving tangible results, growing consciousness and taking personal responsibility. She knows to create an atmosphere of trust where transformation and growth can actually happen.

Andrea is a certified trainer and coach and holds various licenses for team coaching. She is educated in the enneagram, Otto Scharmer’s Theory-U Presencing Process, dialogue and systemic work. She is one of the global leaders for Tiara International LLC and founder of wezenlijk werken training and coaching.

Over the years she has worked with companies as Unilever, Econcern, ABN, NIBC, SNS Reaal, Fortis Mees Pierson, Hasbro, Price Waterhouse Coopers, LogicaCMG, ETC Leusden, Alterra Wageningen, Wageningen International, Royal Haskoning, ANWB, HAN, Sanofi Aventis, ROC Da Vinci college, ROC Landstede, ROC Frieslandlandcollege, Zeeman textiel supers, KPMG and Police Department Amsterdam.

Follow Andrea on social media:

Facebook: https://www.facebook.com/andrea.henning.520

Linked In: https://www.linkedin.com/in/andreahenning

Twitter: https://twitter.com/ahenning_tiara

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Fractals, Leadership, and the Power of Coherence