I’ve been thinking a lot about this middle phase of life and leadership, one that I, like many of you, find myself in. It’s marked by a particular kind of weightiness and a tension between what feels safe and what feels possible.
I’m feeling like responsibilities seem to expand in every direction. Some of us have children who are growing up, becoming young adults, and needing us in more complex ways. Our parents, if we’re fortunate to still have them in our lives, are aging, sometimes slowly, sometimes all at once, asking of us a different kind of presence and care. And somewhere in the middle of all of this, we begin to feel the undeniable shifts in ourselves. We notice that our energy needs to be managed more intentionally, our bodies ask for more attention, we have a growing awareness that time and life is no longer infinite, and we sit in the tension of who we once were and who we are becoming.
For some, our minds may feel sharper than ever. We have more perspective, we have experience, we have a deeper understanding, or at least curiosity, about people, systems, and what truly matters. And for many of us, we have a sense that there is still more to do, more to contribute, and more to be and become.
I’m sentimental so I’m reminded of the song, Both Sides Now by Joni Mitchell*. When Mitchell first recorded it in the late 1960s, her voice carried a kind of lightness and innocence in how she understood life’s complexities. Decades later, when she performed it in 2007, her voice was so different – deeper, slower, weathered from life’s experiences. The words are the same but the meaning feels much deeper. This song reflects this very phase of life where we no longer see things from just one side or another, but from multiple perspectives at once, holding both the idealism of what could be and the reality of what is.
In my work with leaders at this middle phase of life and career, often moving into more senior leadership roles, a familiar question surfaces: ‘What’s next for me?’ Or ‘What is required of me at this higher level of leadership?’ On the surface, these can sound like practical, career-oriented questions. But more often, they are pointing to something deeper: moving beyond the ‘what’ to the ‘who’. My role is rarely to help them find a quick answer. Instead, it’s to slow the question down, look beneath it, and cultivate curiosity about what is really being asked. This is not simply a transactional career decision, it is usually a meaningful transition in one’s adult life, and an inflection point that invites deeper consideration of the person and leader one is becoming. Perhaps this is also what leadership asks of us now: to slow down, to embrace moments of silence, and to trust that depth and clarity often emerge not in the noise, but in the pause.
The conversation often shifts away from the urgency of what’s next’ and toward questions that invite reflection, depth, and honesty. The questions themselves begin to change.
From ‘What should I do?’ to ‘Who am I becoming?’
From ‘What role do I want?’ to ‘Who is the leader this team, this organization, this moment is asking for? And am I willing to be or grow into that?’
From ‘How do I manage it all?’ to ‘Where will I choose to direct my energy, and how do I want to show up in service of something larger than myself?’
Alongside this, a more personal inquiry occurs:
What patterns or assumptions am I holding onto that may have served me before but no longer do?
Where can I stretch into new ways of being?
What am I not allowing myself to step into?
These are the questions that begin to shape the way we lead, live, and move through this season of transition.
In my own life, and in my work with leaders, the question then becomes less about certainty, and more about how we move within that in-between space of tension. Do we reach back for what is familiar as we seek reassurance in what we already know? Or do we allow ourselves, even briefly, to reach forward toward something not yet fully formed?
I believe that this in-between space, the one that can feel the most uncertain and uncomfortable, is also the one where the most meaningful shifts begin to take place. In my occasional wiser moments, I know that this phase of life is not something to resolve, but something to learn to move within. It is a time to trust that the space between what was and what will be is not empty, but alive with possibility.
Perhaps this is the gift of this phase of life. Not that things become clearer or easier, but that we begin to see more fully and feel more deeply. Like Both Sides Now, the story of our life may be familiar, but its meaning deepens with time. If we allow it, there is a kind of wisdom available to us here, one that comes not from having the answers, but from being willing to stay present to the questions, and to move forward with possibility and the wisdom we now hold.
*Here are the links to both versions of Both Sides Now by Joni Mitchell – the same song, sung decades apart and such a beautiful reflection of how meaning deepens with time. 1969 and 2000