Why is it so Hard to Lead?

At its core, the fundamental challenge in being a successful executive lies in the tension between existentialism and pragmatism—the philosophical struggle between individual agency and leadership’s practical demands.

Existentialism calls attention to the inherent freedom and responsibility of individuals to define their own existence and purpose. In the context of leadership, this translates to the need for authenticity and self-awareness...a deep understanding of one’s values, motivations, and aspirations. However, pragmatism introduces logical realities: constraints, uncertainties, and the necessity of action in the face of ambiguity.

People at every stage of their lives are consciously and subconsciously asking themselves: “What is the best path forward (for me) in this moment?” Leaders must navigate this tension. The key is to balance their authentic, best selves with the pragmatic nature their role’s demand. Perhaps it is best to think of the challenge as an individual’s desire for self-control clashing with the need to “make a living” in the vast sea of opportunities, which means decisions must be made about how to live within the economic realities of the modern world.

“What is the best path forward (for me) in this moment?”

Clearly, it is this emphasis on the human condition that adds another layer of complexity to leadership. Humans are inherently multifaceted beings, influenced by emotions, biases, and unconscious motivations. They can be filled with joy and enthusiasm in one moment and change the next. People are capable of amazing gifts, but the mind is shuffling through countless impulses every second, perhaps most importantly those that the individual does not even know are happening in the subconscious.

These complexities manifest in organizational settings where leaders must navigate interpersonal dynamics, conflicting interests, and varying perspectives. Authentic leadership requires not only technical expertise and strategic acumen, but also emotional intelligence and the ability to connect with others on a deeper level.

The dynamic nature of the business environment adds another dimension to the challenge. Technological advancement, globalization, and socio-political changes constantly reshape the organizational landscape, presenting leaders with new opportunities and threats. In this context, leaders must demonstrate adaptability, resilience, and foresight to steer their organizations through uncertainty and change. They must abide these principles, but then also find methods to spread them across a business, getting buy-in from some percentage of the workforce so that they can collectively achieve the organization’s objectives.

Whether it is a crisis in one’s office or the consequences of a global trauma, people look to their leaders for answers and direction. In real-time, this is all taking place quickly and answers are often blurry. Ambiguity, or simply situations out of the leader’s control, also define a company’s culture, which can rock even the best-intentioned executive. Yet, when a leader rises to meet a challenge, that can be inspirational and calm frayed nerves. For a leader, many situations and events feel like a building on fire. Do you run headlong into the emergency, be the first to call the fire department, or wait for someone else to help? Throughout the workday, many circumstances feel like that crisis decision-making crossroads.

Despite the myriad challenges, effective leadership is essential for organizational success and growth. It requires a commitment to continuous learning, self-reflection, and personal development. Deep thinking, deep learning, and contemplative practice are invaluable tools for leaders seeking to navigate the complexities of leadership. By engaging in introspection, critical reflection, and dialogue, leaders can gain deeper insights into themselves, their teams, and their organizations. This heightened awareness enables them to make more informed decisions and inspire others.

Deep thinking, deep learning, and contemplative practice are invaluable tools for leaders seeking to navigate the complexities of leadership. By engaging in introspection, critical reflection, and dialogue, leaders can gain deeper insights into themselves, their teams, and their organizations. This heightened awareness enables them to make more informed decisions and inspire others.

Let’s be realistic, though. If cultivating a culture of trust, innovation, and resilience across any collection of individuals were easy, then every organization would run well. Most families do not get along well for extended periods of time, let alone virtual strangers tasked with solving complex problems together for the sake of the whole. And, it is this constant state-of-mind juggle between individual and group that is both the strength of organizations and the cause of much strife.

Bob Batchelor , an acclaimed author and biographer, has a unique talent for weaving historical insights into contemporary contexts. He is known for writing captivating biographies and cultural histories, including Stan Lee , Roadhouse Blues , and The Bourbon King . With The Authentic Leader, Batchelor combines his passion for storytelling and his deep understanding of human nature to offer leaders a blueprint for success in the modern world. Also a strategic communications thought leader, he is Vice President, Global Marketing and Communications at Workplace Options .