The Leadership of Not Knowing

In a recent gathering with poet, musician, and spiritual teacher Eden Pearlstein, I found myself captivated by his exploration of the concept of "nothingness" and the transformative power of embracing the unknown. As he shared his insights and read from his mind-bending book of poetry, "Nothing is for Everyone," I couldn't help but reflect on the profound principles his poetic prose holds for leaders navigating an increasingly complex and uncertain world. Pearlstein's work challenges us to question our assumptions, embrace discomfort, and uncover wisdom in the space between knowing and unknowing.

One of the central themes that emerged from our discussion was the idea of the "holy thief" - the notion that creativity and innovation often require breaking rules, stepping outside of our comfort zones, and stealing (or borrowing, if you prefer) from unexpected sources. Inspiration may come from anywhere, but only for those who have their eyes and minds open. In life and leadership, we are often called upon to challenge the status quo, to question long-held assumptions, and to forge new paths in our journeys. Like the mythical figures who stole fire from the gods, we must be willing to take risks and embrace the discomfort that comes with venturing into uncharted territory. With risks there are also consequences, but that too may result in lessons learned, resilience strengthened, and opportunities for redemption. As leaders, we have the opportunity to model this kind of courageous curiosity, inspiring those we love and lead to do the same.

Another powerful insight from Pearlstein's work is the recognition that every obstacle contains within it the seeds of opportunity and growth. Just as the shattering of the vessels gives rise to the possibility of repair and transformation, the challenges we face as leaders can serve as catalysts for profound change and development. By approaching setbacks and roadblocks with curiosity and openness, we can uncover hidden portals to wisdom and self-discovery. Life to death to rebirth – it is the natural order of things. Failure is better than not trying at all. When we “fail forward” we cultivate resilience in ourselves and create a culture that values learning and growth over perfection and certainty.

Perhaps most importantly, Pearlstein's poetry reminds us of the positive power of silence and the willingness to dwell in the space of not knowing. In a world that often demands quick answers and easy solutions, true leadership requires the courage to sit with complex questions, to listen deeply to the wisdom of others, and to allow space for new insights to emerge. Why ruin an awe-inspiring question with a mediocre answer? By cultivating a relationship with the fertile void, we open ourselves up to the possibility of profound creativity and connection. How often do we really feel heard? And how much less do we hear? As leaders, we have the opportunity to create environments that value reflection, contemplation, and the pursuit of deeper understanding.

In life and leadership, embracing the creativity of not knowing can be a powerful tool for transformation and growth. As we navigate the challenges and opportunities, we draw inspiration from the pages of poets like Eden Pearlstein, who remind us of the beauty and potential found in the liminal spaces between knowing and unknowing. By cultivating a sense of wonder, a willingness to take risks, and a deep appreciation for the wisdom that emerges from silence, we can tap into a wellspring of creativity and resilience to serve us well on the path ahead. By embracing this profound wisdom, leaders unlock unprecedented levels of creativity, resilience, and transformative power, reshaping their journeys and inspiring those they lead to embrace the infinite possibilities within the leadership of not knowing.

With love, gratitude, and wonder.

Scott