Freedom Through Redemption

Donald Winnicott’s concept of being stuck in our going on being provides a profound lens through which to understand the paralysis that can afflict leaders and organizations. It’s been a useful way of understanding, for example, the ways in which my clients find themselves repeating patterns, even those they’d consider negative. It’s helpful to understand how we can each be complicit in maintaining the conditions that we steadfastly claim we want to change.

To be trapped in one’s going on being is to exist without agency—to maintain a state of passive endurance rather than active engagement. This stagnation, both personally and, more relevantly, professionally, can feel systemic, enervating, and, ultimately, an obstacle to what I see as the grandest expression of leadership: one rooted in redemption.

Redemption, as I’ve come to understand it, isn’t merely about erasing the past or making up for mistakes—it’s about transforming our relationship to the past so that what once brought shame or sorrow can become a source of wisdom, compassion, and renewal.

For a leader, for those who hold power, this means not only doing the work to redeem themselves, but also taking up the quiet, often unseen task of helping redeem others—creating the conditions where healing, truth, and dignity can take root again.

Redemptive leadership, then, isn’t about perfection—it’s about wholeness. It arises from a willingness to face what’s been broken, within and without, and to lead not in spite of our wounds but through them. The redemptive leader does not seek to erase the past but to reckon with it, to remember rightly, and in doing so, to make space for something new to emerge. This kind of leadership is forged in the crucible of regret, the regret that leads not to self-lacerating guilt but remorse and responsibility. It’s as much about inner work as outer action—a quiet refusal to be hardened by power, a commitment to serve rather than dominate, to liberate rather than obscure. In a world desperate for certainty and performance, redemptive leadership chooses presence, humility, and legacy.

It is, at its core, an act of love.

True Self, False Self, and the Leadership of Self

Winnicott proposed that healthy psychological development requires an environment in which a child’s true self—the spontaneous, authentic core—can emerge. In leadership, this manifests in those who merely perform authority rather than embody it. They sustain operations, meet metrics, and play their role, but their leadership lacks vitality, courage, and moral imagination. Indeed, a leader stuck in their going on being is not necessarily incompetent. They may even be effective within a limited scope. But importantly, they are not transformational. They repeat inherited patterns, unable to make decisions that disrupt the status quo. They maintain, rather than create.

To lead others with integrity, we must first lead ourselves—and that begins with the quiet, often uncomfortable work of self-discernment. Winnicott taught that the true self arises in response to an environment that allows for authenticity, spontaneity, and relational safety.

The false self, by contrast, emerges as a shield—a performance crafted to secure belonging in an unpredictable world. In leadership, these dynamics play out daily: are we speaking from the core of who we are, or from a version of ourselves we believe others expect? Redemptive leadership, or a form of leadership of the self, begins here—with the courage to notice the masks we wear, and the willingness to lead from the self that is real, not rehearsed.

Redemptive leadership demands something more than what most of us are willing to give. It requires a willingness to confront the passive endurance that Winnicott describes and break through the inertia of just going on. Redemption, in this context, is not just about atoning for past mistakes; it is about reclaiming presence—stepping fully into the responsibilities of leadership with awareness, accountability, and a capacity for renewal.

Consider moments of leadership failure—not just in individuals but in entire organizations, and, indeed, in our society at large. What often precedes collapse, what presages a falling apart, is not a dramatic betrayal but a slow erosion of purpose. The organization, like a person stuck in going on being, continues to function, but with decreasing authenticity and conviction. A redemptive leader disrupts this stagnation. They reawaken a dormant sense of meaning, break free from the inertia of inherited habits, and take decisive action to restore vitality.

Redemptive leadership, then, is an act of waking up. It is a call to move beyond passive maintenance toward a fully inhabited presence. The task of the leader is not merely to sustain but to redeem—to retrieve what has been lost, whether that is vision, integrity, or the belief that renewal is possible.

I’d love to hear how this lands for you. Where have you seen redemption show up in leadership—in your life, your work, your own journey?