The Leadership Paradox: Embracing the Free Fall to Find Your Purpose
In the lives of business leaders, we often focus on the pinnacle of success, the promotion, the company sale, the new venture. But what happens when the carefully constructed ladder is removed? What happens when you are no longer defined by the business you built, the title you held, or the processes you so meticulously perfected?
This is not a moment of failure, but an invitation into a profound and often terrifying state of free fall. It is the transition from a life of meticulous control to one of courageous commitment, where you must let go of a part of your identity to reconnect with your core.
For a leader, this free fall can manifest in many ways. It is the emotional and intellectual descent that follows selling a business you poured your life into. It is the quiet disorientation of a new, different role within the same company. It is the stillness on a tropical beach after years of relentless travel, where the absence of busyness feels like a terrifying void. In these moments, you are no longer the “business owner,” the “senior executive,” or the “high-performing global traveler.” You are simply you, and the task is to reacquaint yourself with that person.
This personal free fall is often mirrored by a professional one, a reality facing every business leader today. The rapid and relentless incorporation of AI into business processes is an existential free fall for many. Suddenly, the expertise you built a career on, the efficiency of a system you designed, or the very nature of your product is being fundamentally disrupted by technology. The comfortable, known world of business is dissolving beneath your feet, and resisting the change is simply not an option. Your identity might be tied to being “the expert,” but what happens when a machine can process data faster, write copy more efficiently, or analyze markets more deeply? This is a leadership transition that requires you to let go of an old way of working and thinking to embrace a new one.
The wisdom of this journey is not about recklessness, but about an informed and intentional leap. It is about embracing the fear of the unknown with a deep-seated trust in your own capacity to navigate the descent. The poet Jane Hirshfield said, “We cannot let our ideas blind us to our unknowing.” We have so many ideas about who we are supposed to be, but it is in the unknowing of transition that we discover who we truly are.
Finding Your “Sweet Spot” in a Changing World
This idea of purposeful descent is beautifully mirrored in the wisdom of my colleague Rick Tamlyn. In his article, Are you in?, he distinguishes between being “kind of in” and being “all in.” He argues that true commitment goes beyond financial investment; it is an alignment of your words, dreams, and behaviors. When we are “kind of in,” we say we want change, but our actions don’t follow. We are “phoning it in,” going through the motions of our lives or careers without genuine engagement.
For the leader in transition, whether from a career change or a technological disruption, this is a critical distinction. Are you “kind of in” to your new life, holding on to the security of your old identity and the safety of the known? Or are you “all in,” fully committing to the free fall, ready to explore the new terrain that emerges from letting go? The former is a lonely, stagnant state; the latter is a dynamic and fulfilling journey of professional growth.
The Entrepreneur Letting Go
One leader who comes to mind is a dynamic entrepreneur who recently sold his business. Although he was excited about the sale, he also felt a wave of trepidation. For fifteen years he had nurtured this business, shaping the culture, building the systems, and guiding people into becoming seasoned professionals. Walking away meant leaving behind not only a company but also a core piece of his identity.
As he stepped into an uncertain future, the questions grew louder. He knew he was too young to retire, but what would he be if not a business owner? Who was he without the title of entrepreneur? And who would he become next? That unease ran deep because it was not only about his career, but also about his role in his family and his community. At the core, the question was: without this business, who am I?
The Consultant Who Burned Out
Another story comes from a colleague who was a successful management consultant at one of the big five firms. His life was consumed with global travel, complex negotiations, and organizational challenges. Eventually, he burned out.
He decided to step away and spent several months on a tropical island with his family. He recalls that it took at least six weeks of sitting on the beach, staring into the distance, and listening to the waves before he could quiet the relentless urge to keep moving, keep working, keep producing. Slowly he let go of the compulsion to stay busy, and in that space he rediscovered something different. He began to feel like a human being again, not just a human doing. And in that pause, he reconnected with a deeper part of himself.
This commitment is your parachute. It is not a set of skills or a financial safety net, but an unwavering belief in your purpose and your innate strengths. The poet and activist Audre Lorde said, “When I dare to be powerful, to use my strengths in service of my vision, then it becomes less and less important that which I am afraid.” When you are “all in” to your purpose, the fear of the unknown becomes simply a message, a sign that life is about to change in a profound and meaningful way.
How to Navigate Your Next Career Change and Find Your Purpose
To find your way through this transition, consider these questions, not as a checklist, but as a compass to guide your free fall:
- Am I still learning in the life I am living or is it time to leap into a new challenge? Be honest about whether your current situation is a path of growth or a place of stagnation.
- What strengths do I have that will help me fly when I take on a new challenge? Identify your core powers, not just the skills you’ve acquired. Are you empathetic? Resilient? Creative? These are the wings that will help you soar in your next act, even in a world where AI handles the routine.
- When do I feel most fulfilled? Can I use these moments to identify the purpose I want to realize in this life? Fulfillment is your guiding light. The moments that truly light you up are pointing to a purpose that has been waiting to be realized, a purpose rooted in uniquely human values like compassion, connection, and vision that AI cannot replicate.
- What will I do next if my leap doesn’t work out as I had hoped? Acknowledging that the landing might be bumpy is not a sign of fear, but of courage. It is an “all in” commitment to the journey, not just the destination, and a deep understanding that every experience, even the difficult ones, is an opportunity for learning.
The free fall of leadership is an opportunity to move beyond a title and into a true state of being. It is a terrifying, exhilarating, and ultimately transformative experience. It is the journey of releasing who you were, so that you can become “all in” with who you are meant to be. This is the new future of work, one where personal growth and leadership are deeply intertwined.
