Deckchair Leader: Rediscovering Identity in the Silence of Transition 

by Maria Gray

1. The Deckchair Leader

Several years ago, I found myself in a conversation with a very senior leader, brimming with excitement about his impending retirement. With a typical efficiency, he had drafted a meticulously crafted list of activities he planned to dive into once he traded his office for leisure. “Look at all these interests!” he beamed, detailing plans to travel, play golf, read voraciously, draw, fish, garden, and entertain guests. It sounded like the perfect retirement dream.

Fast forward just under a year, and reality took an unexpected turn. Instead of leisurely afternoons in a sun-drenched deck chair, he found himself passionately involved in local governance. Initially a member of the local council, he soon “almost by accident” ascended to the county council and joined or even chaired various local committees. Just like that, his calendar filled with meetings, initiatives, and interviews on the radio. Every few months, he seemed to add yet another commitment to his plate.

When we later reflected on his initial retirement plans versus the whirlwind of activity he experienced, he chuckled and said, “The reality is, you’re not going to be happy sitting in a deck chair.”

In my coaching practice, I often work with leaders who are approaching a pivot or retirement. While many may not explicitly express their concerns, I can sense a subtle fear of the silence that a transition might bring. It’s as if they wonder, “Am I a thoroughbred racehorse whose best races are behind me? Am I ready to be put out to pasture?”

They grapple with questions like, “If I'm not leading and influencing others, if I’m not constantly busy, how do I ensure I remain relevant? Am I leaving something on the table?” These reflections reveal a deep connection between identity and purpose.

These individuals, successful, driven, and accomplished, stand at the edge of uncertainty, facing what can feel like a daunting void. The silence that accompanies stepping away from leadership roles can be as disorienting as an empty stage before the curtain rises. Yet, navigating this transition offers a unique opportunity to rediscover one’s identity beyond titles, embracing a life that can be rich and fulfilling outside the adrenaline-fueled world of leadership. It invites a re-examination of purpose and a chance to redefine what making a significant contribution looks like in this new chapter.

2. When the Story No Longer Fits

I’m writing this at a stage in life where I’ve begun to notice that some of the identities I’ve long held, or clung to, are starting to feel less like anchors and more like sources of quiet distress. Whether it’s youth, appearance, cultural belonging, career or professional and parenting roles I’ve played over time, I find myself unsettled when reality no longer matches the version of myself I’ve grown attached to.

This reflection has led me to a broader question, one I suspect many of us - whether leaders or not - face at different points in life: What happens when the aspects of our identity we’ve relied on begin to shift or fall away? Why do we become so attached to these parts of ourselves, and how do we navigate the discomfort, or even grief, that arises when they no longer feel true or accessible?

One of the reasons transitions feel so unsettling, especially for leaders, is that identity is never just a role. It is a story.

The stories we tell ourselves about who we are give shape, coherence, and meaning to our lives. These narratives - built from our experiences, roles, values, and the messages we’ve absorbed from our families and cultures - help us navigate the world and relate to others. They can be empowering, grounding, even necessary. But problems arise when we become too attached to these stories - when we over-identify with certain roles (“I am the successful one”), qualities (“I am youthful and attractive”), or identities (“I belong here”) and begin to see them not as aspects of our experience, but as fixed truths about who we are.

For much of my adult life, I’ve carried a clear set of internal narratives about who I am. I take pride in being someone who “gets it together” - organised, self-responsible, well-presented. I’ve always resonated with the belief that while we may not be to blame for everything that happens to us, we are responsible for how we move forward. I also saw myself as a city person - someone who thrived in the fast pace, complexity, and cultural richness of urban life. And my professional identity mattered deeply: I valued being seen as perceptive, insightful, inspiring, thoughtful.

These stories helped me succeed, feel capable, and make sense of my place in the world.

But recently, life has shifted. Although I run my client practice in London and virtually, I now live in the countryside, raising children, and spending large parts of my days doing the kind of slow, practical, emotionally demanding work that rarely gets mentioned in polished bios or job titles. I’m surrounded by people with different values, rhythms, and ways of being - people I’ve come to respect, but who live by a very different script from the one I’ve told myself for years.

This dissonance between my internal narrative and my current reality can feel quietly disorienting. Not because either version is better or worse, but because I realise how tightly I’ve held on to one version of myself, and how hard it is to loosen that grip. Even positive or meaningful changes can feel like losses when they threaten the coherence of our self-story.

What I’ve discovered in my own life mirrors what I see in leaders at moments of transition: the stories we carry can both support us and limit us. Sometimes, the challenge isn’t to reject the old story, but to expand it - to allow ourselves to grow beyond the familiar roles we once relied on. It’s not easy, but there’s a kind of freedom in noticing when we’re clinging on to the past identity, and gently making space for something new to emerge.

At their core, attachments to particular aspects of our identity often stem from deeply human needs - emotional, existential, and relational. These attachments aren’t flaws; they’re usually formed as strategies to meet underlying desires for safety, belonging, and meaning. But when we hold too tightly to them, they can become sources of friction or suffering.

For leaders, the anchors are reinforced daily. From the moment you park in your reserved spot, sit in your office, and share greetings with your team, the steady rhythm of emails, calls, meetings, and decisions acts like a drumbeat: a reminder that you matter, that you are needed, that your story holds. But when the rhythm stops - when the title is no longer printed beneath your name, when people stop asking for your approval or your signature - suddenly the story falters.

Literature often captures these dynamics more starkly than theory. Jay Gatsby, F. Scott Fitzgerald’s shimmering creation, is usually remembered as the self-made millionaire whose life ended in tragedy. But Gatsby’s story is not only about wealth or status. At its heart, it is about love - and the lengths to which we will go to construct an identity strong enough to win it.

Born James Gatz, Gatsby remakes himself into the dazzling figure who throws parties glittering with champagne and jazz, all in the hope of reclaiming Daisy. Every performance, every reinvention, every borrowed phrase is in service of that dream. Yet the tragedy is that the identity he builds cannot bridge the gap between who he is now and the man he longs to return to. He is trapped in the very story he created.

Leaders often recognise themselves here, though in subtler form. Like Gatsby, they have built identities through performance and persistence - roles that dazzle, roles that win admiration. Not for frivolous reasons, but from a deep longing: to make a difference, to belong, to matter. Yet when the role begins to shift, it can feel like the Gatsby dream dissolving in the pool: the carefully constructed self no longer holds.

This is why stepping away from leadership feels so much more than a career change. It touches something existential. The loss of a role can feel like the loss of self.

Philosophers like Michel Foucault remind us that identity is never truly our possession. It is shaped by discourse, expectation, repetition. We do not simply have an identity; we enact it, perform it, live it in relation to others.Which is precisely why, when the stage changes, the performance wavers.

Spiritual teachers offer a parallel insight. Pema Chödrön writes that “to be fully alive… is to be continually thrown out of the nest.” To cling to a fixed self is to suffer, because life will keep shifting the ground beneath us. Brené Brown echoes this in a more grounded way: “Imperfections are not inadequacies; they are reminders we’re all in this together.” Our humanity is not in perfect performances, but in our shared fragility.

So here lies the paradox: the very identities that allow leaders to thrive can also be the ones that make transition hardest.

The executive who has always been admired for decisiveness may struggle with the open-endedness of retirement.

The founder who lived inside the story of building something from nothing may feel hollow after the sale, like a man on a platform watching the train depart.

The athlete whose body was once their currency may grieve its change more than any medal.

These are not failures of character. They are reflections of how deeply we are shaped by our stories. And perhaps the first step in navigating transition is simply to recognise that it hurts because it matters.

3. The Quiet Grief for Selves We Once Were

When we find it hard to let go of an identity - whether as “the very soul of the business”, “the decisive executive,” “the high-achiever,” “the one who always holds it together” or “the one others rely on” - what we are often facing is not mere change but grief. Not always the seismic grief of bereavement, but a subtler, quieter form: the mourning of selves we once were, or still hoped to be. As psychoanalyst Stephen Grosz reminds us, every change, even welcome change, carries its own loss. To grow, we must be willing to grieve not only what has ended, but the self we imagined we would go on being.

I once worked with a senior leader who had recently stepped down after decades at the helm of his organisation. The transition looked flawless from the outside: a farewell celebration, warm words of thanks, a successor lined up. Yet in quieter moments he confessed, “I still feel I have so much to offer - but no clear place to bring it.”

This was not about clinging to power or status. It was grief for the part of himself that had always been in motion, always contributing, always woven into the fabric of decision-making and responsibility. Without the constant rhythm of being asked, needed, relied upon, he felt as though his energy had nowhere to land. The loss was not only of the past role, but of the future he had imagined for himself - one in which his wisdom still had an obvious outlet.

This is the paradox of transition: what aches is not only the absence of what was, but the abundance of what remains.

Grief also shows up in the most unexpected places, and not only in boardrooms. A friend once shared a story that still echoes in me. One afternoon she wore one of her favourite dresses to pick up her young son from school - a dress she loved for its ease and understated style. As they walked home, her son looked up and said, with innocent bluntness, “Mum, you look like an old lady in that dress.”

She laughed as she told me this story, but then admitted quietly, “Oh, it’s such a sore spot. I still can’t help worrying about my appearance. As if it were my only virtue.”

Her son’s comment was neither cruel nor calculated, but it cut straight to a fragile seam in her identity. It exposed the recessional grief beneath appearance - the longing not to fade into invisibility, the fear that worth might vanish if external validation slipped away.

Whether in the corridors of leadership or on the walk home from school, the pattern is the same: grief arises when an identity we leaned on for safety, value, or belonging no longer holds. And because these identities once sustained us, their loss can feel like losing part of ourselves.

Virginia Woolf captured this with piercing clarity in Mrs Dalloway. On the surface, Clarissa Dalloway is the perfect hostess, elegant and admired. But in her inner monologue, she wrestles with aging, regret, and the gnawing sense that her public image is a fragile shell. “She had the oddest sense of being herself invisible; unseen; unknown.” The polished exterior belies an inner grief for lost opportunities and for the fading of a self that once felt secure.

In contrast, Septimus Warren Smith, the war veteran scarred by trauma, embodies what happens when identity collapses entirely. His suffering is unbearable because there is no scaffolding left to hold it. And yet, part of his torment comes from seeing too much, from recognising the emptiness of the polite identities society sustains around him, and finding no role that can hold the truth of what he has lived. Between Clarissa and Septimus, Woolf paints the spectrum of what so many of us experience: the tension between keeping a fragile self-intact and facing the abyss when it falters.

To name this as micro-grief is not to dramatise, but to humanise. These are not failures of character, nor vanity, nor weakness. They are the natural mourning of selves that once anchored us. The work of transition begins not by rushing past the grief, but by giving it air. To acknowledge the sadness, the longing, the mismatch between inner abundance and outer silence, is already to make space for what comes next.

4. Discoveries in Silence

When the scaffolding of a role falls away, silence follows. At first it may feel like a relief - the sudden space in the calendar, the uncluttered mornings, the absence of constant demands. But soon another feeling often creeps in: unease. Without the rhythm of responsibilities or the reassurance of being useful, silence can feel like an empty room echoing back our questions: Who am I now? What am I for?

A client once wrote to me after reflecting on his own journey:

“I think my realisation of the last five years is that I’m not a leader in the conventional sense and much more enjoy the art of being catalytic without hierarchy on journeys that are long, uncertain, uphill and build others’ capabilities. My biggest question is: can I just learn to enjoy a normal field without trying to set a new lap record for grazing?”

His words capture something many of us wrestle with. When achievement and momentum have been our compass, what does it mean to simply be in the field - ordinary, unmeasured, present? Can we allow ourselves that kind of quiet belonging, without turning even rest into another contest?

And then there is the texture of the everyday. When a spouse still dresses for the office and departs, the house falls silent. The rhythm of emails, deadlines, and meetings continues elsewhere, but here, it is just us and the quiet kitchen. Another coffee? The moment is simple, yet it can feel oddly dissonant. Not because anything is wrong, but because the contrast between the world’s momentum and our stillness is so sharp.

Buddhist teacher Pema Chödrön reminds us that suffering is not caused by life’s impermanence itself, but by our insistence that it should be otherwise. We suffer because we expect stability in a world that is always shifting, because we cling to stories of ourselves as if they should last forever.

This is as true for professional roles as it is for youth, beauty, or belonging. The hurt comes from the gap between expectation and reality. When we expect to always be needed, admired, productive, consulted, sought out, indispensable - the moment that story falters, we feel diminished. But when we soften the expectation, the silence begins to change shape. It is no longer a verdict. It becomes a teacher.

What might shift if we released the demand to keep proving our value, and instead trusted that contribution can take gentler, less visible forms?

When silence feels unfamiliar, we often move instinctively toward activity. We take on new projects, fill days with tasks, or seek out responsibilities. At first glance this might look like displacement activities or avoidance of attending to the void, but something deeper is often at play.

We do these things because we still have energy, insight, and care to offer. We long for places where our contribution can land. The ache is not just for the absence of what has been lost, but for the abundance that remains - skills, wisdom, imagination, compassion.

Seen this way, activity in times of transition is not a weakness. It is a sign that life is still moving through us. The invitation is not to suppress it, but to notice: which forms of contribution truly nourish, and which simply keep us busy?

Nature offers a gentler rhythm. A garden cannot be in bloom all the time. There are seasons when nothing appears to be happening - the soil lies bare, branches look dead. Yet beneath the surface, roots are deepening, nutrients are gathering, life is quietly preparing for renewal.

Our own seasons of silence may feel barren on the surface, but they are often the ground of transformation. If we rush to cover the ground with constant surface busyness, we may miss the slow work that is happening underneath. Silence, held with patience, is not emptiness but fertility.

Can we trust that, even when our contribution is less visible, something essential is still taking root within us?

Still, staying with silence is not easy. To sit without old anchors, without certainty, can feel raw. This is why companionship matters. For some, it comes through friendship, art, or spiritual practice. For others, as my personal experience attests, it can come through coaching - not as a place to fix or solve, for there is no silver bullet when you are grappling with something as complex as identity in transition. Instead, coaching can offer a container in which the inner world can be explored without judgement.

In such spaces, we can experiment with loosening the grip of old stories. We can listen to the parts of ourselves that rarely had space to speak in the past. We can begin to trust the possibility that identity is not ending but evolving.

What becomes possible when we share the silence with another - someone who does not act as a head-hunter, does not rush us to perform or to get on the next train, but simply holds the space as we discover where we might journey next?

Perhaps what transition asks of us is not to abandon contribution but to redefine it. Contribution may no longer look like driving growth, setting records, or being the centre of attention. It may instead look like catalysing others’ journeys, offering presence rather than answers, tending a garden so that something new can bloom.

To embrace this is to release the expectation that life must always be impressive. It is to learn, slowly and imperfectly, how to rest in the ordinary field without needing to set a new lap record. And in that quiet field, we may discover not emptiness, but a gentler, more fulfilling, kind of abundance.

5. Presence as Legacy

I think back to the leader who told me, “You’re not going to be happy sitting in a deckchair.” Beneath the laughter was an unspoken truth that his energy, curiosity, and desire to contribute were still alive. It was never about idleness versus busyness. It was about finding new ground for what remained abundant within him.

For many of us, the ache of transition is not only about what has ended. It is about what is still here, waiting for expression. The wisdom gathered across decades, the compassion honed by experience, the creative spark that hasn’t dimmed - all of this longs for an outlet. The challenge is that the old structures which once held our contribution no longer exist. And so, we grieve, not because we are empty, but because we are still full, with no obvious place to bring our offering.

This is where silence matters. Not as a permanent retreat into passivity, but as the ground in which new forms of contribution can take root. What first feels unsettling can, in time, reveal itself as deeply generative.

At the heart of this process lies self-trust. Not the brittle certainty that we will always succeed, but the deeper confidence that we can stand in the unknown and not collapse. That we can survive without applause. That we can enter the quiet field without knowing exactly what will bloom there and still believe that something meaningful will come forth.

And here, perhaps, is where the larger perspective steadies us. Carl Sagan once invited us to see the Earth as a “pale blue dot” - a speck of light in the vastness of space, fragile and luminous all at once, a dot where all human greatness has played out. Percy Bysshe Shelley, in Ozymandias, reminded us that even the mightiest titles and monuments crumble, even the “King of Kings”. Both point to the same truth: our roles are temporary. What endures is not the nameplate on the office door, but the presence we carry into each season of life.

To live from that place is to stop chasing lap records in every field we enter. It is to release the illusion of permanence, and to discover that self-trust - this confident relationship with uncertainty - is what allows us to keep offering ourselves, again and again, in new ways.
Identity is a narrative, and stories can expand. Grief is deeply human, because it hurts to lose what once sustained us. And presence, more than performance, is the legacy we leave behind.

 Written by Maria Gray, 2025

References

Brown, B. (2010) The gifts of imperfection: Let go of who you think you’re supposed to be and embrace who you are. Center City, MN: Hazelden Publishing.

Chödrön, P. (1997) When things fall apart: Heart advice for difficult times. Boston: Shambhala Publications.

Fitzgerald, F.S. (1925) The Great Gatsby. New York: Charles Scribner’s Sons.

Foucault, M. (1980) Power/knowledge: Selected interviews and other writings 1972–1977. Brighton: Harvester Press.

Grosz, S. (2013) The examined life: How we lose and find ourselves. London: Chatto & Windus.

Sagan, C. (1994) Pale blue dot: A vision of the human future in space. New York: Random House.

Shelley, P.B. (1818) Ozymandias. The Examiner, London.

Woolf, V. (1925) Mrs Dalloway. London: Hogarth Press.