The Futures We Haven’t Given Ourselves Permission to Imagine
Carla Madeleine is an attorney, executive leader, and advisor who guides executives in integrating unexamined inner aspects so their leadership becomes examined rather than reactive. Her work bridges authority, authenticity, and inner transformation, particularly during moments of personal and organizational transition.
There are moments when the lives we have built no longer fit us in quite the same way. Sometimes the change is unmistakable. A career ends, a relationship shifts, a loss rearranges our understanding of ourselves, or circumstances force us to reconsider what we thought was certain. Other times, the change is quieter. We continue fulfilling our responsibilities, occupying familiar roles, and moving through routines that once made sense, while becoming increasingly aware that something has shifted.
We may know that we cannot continue exactly as we have been. What we do not necessarily know is what comes next.
That space between what is ending and what has not yet emerged can be profoundly uncomfortable.
Our discomfort with the unknown
Much of our sense of self is organized around identities we have spent years, sometimes decades, developing. We become the capable leader, the dependable partner, the caregiver, the problem-solver, the person who always knows what to do.
These identities are not necessarily false. They may reflect meaningful parts of who we are, the experiences that have shaped us, and the contributions we have made. But they can also become so familiar that we struggle to distinguish who we are from the roles we have learned to perform.
When those roles begin to loosen or become draining, especially as we age, we may find ourselves confronting an unsettling question: Who am I if I am no longer who I have been?
There can be a kind of darkness in that question. Not necessarily a darkness of despair, but one of unfamiliarity. We cannot yet see the contours of what is emerging, and the absence of a recognizable future can feel like an absence of direction, purpose, or even identity.
Our reflex is often to escape that discomfort as quickly as possible.
We search for the next job, the next relationship, the next project, the next version of ourselves. We begin planning, solving, and moving, sometimes before we have fully understood what is changing within us.
Movement offers relief. It gives us something to do, something to pursue, something recognizable to become.
But movement and possibility are not necessarily the same thing.
When the familiar disguises itself as the future
One of the more subtle ways we limit our futures is by imagining them almost entirely through the lens of our past.
When contemplating a career change, we may immediately search for another position that uses the same skills, carries a similar title, or affirms an identity we have worked hard to establish. When a relationship no longer works, we may imagine a different partner without examining the patterns we bring into relationships. When an organization confronts the limits of its existing practices, its first instinct may be to improve those practices rather than question the assumptions underlying them.
We may be reaching toward something new while remaining firmly within the boundaries of what we already know.
Sometimes, even when we recognize that a familiar way of living is no longer sustainable, its familiarity makes it feel safer than the uncertainty of alternatives.
This raises a question worth sitting with, "Are we choosing what comes next because it reflects who we are becoming, or because we recognize who we have been?"
The distinction is not always obvious. Nor does it mean that familiar paths are inherently wrong. It means that familiarity alone may not be a sufficient basis for choosing our futures.
What becomes possible when we pause?
What if, rather than immediately filling the space left by an ending, we allowed ourselves to inhabit it for a while?
Not indefinitely. Not as an exercise in withdrawing from life or ignoring the practical demands that continue around us. But long enough to notice what is happening beneath our urgency to move forward.
What are we afraid might happen if we do not immediately know what comes next? What identities or expectations are we reluctant to release? What have we come to believe we must continue being, even as something within us is asking for a different relationship with ourselves?
The pause creates an opportunity to examine the assumptions that shape our sense of possibility. This examination is rarely linear.
I think of it as running water through a sieve. We return again and again, allowing the water to move through what we have accumulated over time: expectations, fears, responsibilities, inherited narratives, desires, and beliefs about who we are supposed to be.
Some things begin to loosen. Others remain. We recognize aspects of ourselves that are still deeply true, even as we discover how much has shifted. Sometimes we uncover something we had forgotten. Other times, something entirely unexpected catches the light.
We notice, discern, reconsider, and notice again.
The purpose is not to emerge with a completely new identity. It is to become more aware of what is genuinely ours, what has changed, and what might now be possible.
Giving ourselves permission to imagine
There is another difficulty we encounter when considering unfamiliar futures: we often subject them to the demands of practicality before we have even allowed ourselves to imagine them.
An unexpected desire surfaces, and almost immediately we begin explaining why it cannot happen.
It would require too much change. We are too old, too established, too responsible. We have invested too much in the life we already know. Other people depend on us. We do not have the resources, qualifications, connections, or certainty. People will think that we have lost our minds.
Some of these concerns reflect real circumstances and constraints. Others may be assumptions we have carried for so long that we no longer recognize them as assumptions. But what if we did not require every imagined possibility to arrive with a plan?
What if we allowed ourselves to wonder about lives we have never seriously considered, places we have never imagined belonging, ways of contributing that do not resemble our current roles, or relationships with ourselves and others that operate differently from those we have known?
Imagining a possibility does not obligate us to pursue it.
It does not require us to abandon our responsibilities, deny structural realities, or pretend that every future is equally accessible.
It simply allows us to encounter a wider range of possibilities before deciding which ones deserve our attention, which resonate with who we are now, and what it might take to bring them into being.
Discernment and practical considerations have an important place in that process. But when we demand feasibility before imagination, we risk allowing the limits of our past programming and present circumstances to determine the boundaries of our future.
Beyond the futures we already know
This inquiry is not limited to individual lives.
Communities, organizations, and societies also inherit ideas about what is normal, necessary, realistic, or possible. When familiar systems cease to serve us, we often attempt to repair or reproduce them without first examining the assumptions that shaped them.
Our collective imagination can become constrained by the same attachment to familiarity that shapes our personal choices.
What might become visible if we allowed ourselves to question not only how our existing arrangements could work better, but what other arrangements we have not yet given ourselves permission to envision?
There are no guarantees that pausing will produce clarity, or that every possibility we discover will become a life we choose to live. Sometimes we will return to familiar paths with a different understanding of why they matter. Sometimes we will recognize that something once central to our identity no longer belongs in the same place. Sometimes we may begin moving toward a future we could not previously have imagined.
Perhaps the invitation is not to know what comes next. Perhaps it is to become curious about how much of what we believe is possible has been shaped by what we already know.
To ask ourselves, "What futures might become imaginable if we gave ourselves permission not to know who we are becoming just yet?"
Read more from Carla Madeleine Kupe
Carla Madeleine Kupe, Executive Leadership Advisor
Carla Madeleine is an attorney, executive leader, and trusted advisor who works with leaders navigating power, responsibility, and transition. With a background in law, executive leadership, and organizational change, she helps individuals identify and integrate unexamined inner patterns that quietly shape decision-making, authority, and trust, particularly during periods of uncertainty, contraction, and reimagination. Carla writes at the intersection of leadership, inner work, and change, offering grounded insight for those shaping the future.
