finitude noun | formal | /ˈfɪn.ɪ.tjuːd | the state of having a limit or end
Authentic purpose-led leadership is only fully available to a leader brave enough to confront their own finitude.
This statement is the “executive Summary” of this “long read”, in which I share a new level of awareness in me, and that brought forward this learning that I feel is valuable for leaders brave enough to embrace. So, now to share how I arrived here.
Learning now something that shifted in me four years ago
On March 3rd, 2022, I had a colonoscopy, a routine follow-up to the test done after receiving an invitation for the NHS bowel cancer screening programme after my 56th birthday. They’d picked something up in my sample and asked me to come in.
It was all routine, until the moment it wasn’t, when the Doctor said, “Mr McCallum, there’s one more thing”. They’d found an early-stage cancer tumour; they would be removing half of my colon, and soon. The operation then happened on March 31st.
Whilst the prognosis was and remains excellent, everything changed for me, though it has only been in the last week that I’ve recognised that shift, thanks to studying Heidegger.
Memento Mori (Remember you will die)
I had been studying the Stoics for years, even writing a post entitled Memento Mori, a sentiment I consider to be both very positive and as a tool for leaders. I also talked in that post once again about the Steve Jobs Stanford Commencement speech from 2005, one I have often shared as it is so well constructed and delivered. I now realise, though, that what truly elevated his delivery was his private knowledge that he was dying of cancer. Consider this passage through that mortality lens:
“Remembering that you are going to die is the best way I know to avoid the trap of thinking you have something to lose. You are already naked. There is no reason not to follow your heart.”
I had always sincerely meant my thoughts around the Stoics, around Steve Jobs’ speech, but I now know that I was simply teaching concepts, not fully living them. It was as if I were Marcus Aurelius reading about mortality; I had not yet become Marcus Aurelius confronting his own.
That difference matters enormously, not just for me personally, but for the leaders I work with.
What the Diagnosis Actually Did
From that March 3rd diagnosis, through major surgery on March 31st and three months of chemotherapy through July 2022, I had time to notice what actually happened to me, not as a philosophical exercise but in what I experienced moment by moment.
The first and most immediate feeling was gratitude. From the very day of diagnosis, I anchored myself consciously to gratitude: for the NHS screening programme that caught it early, for the medical team, for family and friends, for the privilege of a life that meant I had nothing financially to worry about while I healed. I wrote about this when I returned to writing in May 2022, after almost six weeks of silence, by far the longest my daily blog had ever been quiet.
However, beneath the gratitude, something else was happening that I am only now finding the right language to describe. The abstract had become concrete. “One dies”, the anonymous, impersonal fact that everyone acknowledges and nobody truly inhabits, had become “I will die, and it could be soon.” That shift, from the philosophical to the personal, from the concept to the body, changed something fundamental.
The questions I had always asked, such as: “What is it you plan to do with your one wild and precious life?” (by Mary Oliver, the first line I ever wrote on this site), suddenly had a different weight. Not an urgency, simply clarity.
In those early days back writing, I found myself on a train ride home from London, just a few weeks after surgery, reading a quote from the film Contact: “how rare and precious we all are”, and writing instinctively in reply: “Something else that has made me feel my insignificance is also tiny. Cancer. About to undergo chemo as they found a single cell cluster 0.4mm in size. Humility and the power of certain tiny things.”
Rare and precious. That was it. That was what the confrontation with mortality had given me as a direct experience rather than as a concept.
Sein zum Tode (Being Towards Death)
I noted earlier that I am only now finding the right language to describe the shift I have experienced. We are four years on from that moment when I learned that I had cancer, and something recently brought me new self-awareness and the insights I now share.
I have recently been exploring the work of Martin Heidegger, specifically his book “Sein und Zeit” (Being and Time), and particularly the concept he named Sein-zum-Tode (Being towards Death). “Being towards Death” The more I sit with this, alongside the work of the Stoics, the more I see that these two traditions are pointing at the same thing, just from slightly different angles.
Seneca puts it with characteristic directness: “Let us postpone nothing. Let us balance life’s books each day.” Marcus Aurelius, ruling an empire, returns again and again in his private Meditations to the brevity of all things: emperors, reputations, and empires all turn to dust. Their message? The contemplation of death is not morbid; it is clarifying. It strips away the noise, the vanity, the borrowed urgency, and returns you to what genuinely matters.
Heidegger agrees on the clarifying function but pushes further in a way I find particularly honest (and challenging, even confronting). Death, he argues, is our own possibility, one that is unique to ourselves, the one thing that cannot be transferred, shared, or delegated. Nobody can die my death for me. Nobody can feel my death for me.
Crucially, Heidegger encourages us to sit with our anxiety, our angst, not to seek Stoic equanimity too quickly. Confronting our own death is meant to remain uncomfortable, unsettling, even unreal, as it is those feelings that keep us truly awake to the choices that are ours to make.
Why This Matters for Leaders
I am writing and sharing my thoughts here for one reason, that I recognise now that the awareness Heidegger has brought to me around my own death, my own finitude, has a direct application for leaders that I encapsulate in the following challenge statement:
Authentic purpose-led leadership is only fully available to a leader who is brave enough to confront their own finitude.
This is not about my having had cancer. It is not about a near-death experience, or illness, or grief, even though all of those can be catalysts. It is about whether a leader has moved from knowing intellectually that life is finite to inhabiting that truth in a way that actually changes what they do.
In my years supporting CEOs and C-suite leaders, I have observed that those who lead most powerfully from purpose are those who carry an acute, almost physical awareness of the fact that their time is limited. Not anxiously, but clearly. They know what they are here to do, and they know they do not have forever to do it. That combination produces a quality of decisiveness, of courage, of willingness to say the difficult thing and take the harder path, that is simply not available to the leader who still, somewhere beneath it all, believes they have unlimited time.
Heidegger called the alternative Das Man “The They”. It is the anonymous force of convention that makes our choices for us when we are not paying attention. We do what one does. We lead how one leads. We pursue the goals that one pursues in our position. Das Man is comfortable, often highly successful, yet someone who stops at “The They” is failing to fully embody their own unique potential as a leader.
The confrontation with death, with finitude, is what dissolves Das Man. It individualises. It makes clear, with a force that no management framework or coaching intervention can replicate, that this life, this career, this role, is yours to lead. Not your industry’s. Not your board’s. Not what the consensus of your peer group considers appropriate ambition. Yours.
Be Brave — Reframed
I have long held Be Brave as one of the four pillars of Open Leadership, alongside Be Open, Be Humble, and Be Hungry. I have written about bravery in dozens of forms: the bravery of the first-time swimmer on the starting block, the bravery of Churchill leading through depression, and the bravery of saying “I was wrong.”
What I understand now, that I did not fully understand before, is that the deepest bravery a leader can practice is this: to look honestly at their own finitude, to let it land rather than manage it away with philosophy or busyness or the comfort of planning for the future, and then, once they have landed, to then lead from that place.
Seneca was right that this is a practice, not a destination. Marcus Aurelius kept returning to it, page after page of his private journal, because it required constant renewal. Heidegger was right that the anxiety it produces is not something to dissolve but something to stay with, because that productive discomfort is what keeps you honest.
From where I now sit, having had that confrontation not as a concept but as an embodied experience, I would add: there is also something on the other side of it that is not anxiety but its opposite. A kind of radical freedom. Steve Jobs put it as well as anyone has: “You are already naked. There is no reason not to follow your heart.”
Be Open. Be Humble. Be Brave. Be Hungry.
All four, I now believe, are easier and deeper and more genuine on the other side of having honestly faced your own mortality. Not because you become reckless, but because you become, finally, free.
Tell me: what is it you plan to do with your one wild and precious life?
Coda: The Less I Am Present, The More I Can Be Present
One unexpected gift of having genuinely inhabited my own mortality is that it reframed entirely why I write.
I began my daily posting in October 2017 to create accountability and discipline — to share what I was learning, to help others, and, honestly, because writing makes me think more clearly. Over 2,000 articles later, something else has become true. These articles, the 100+ video podcasts on WhatComesNext.live, and AskTom.chat (the AI system built on this corpus) are not just learning resources. They are a form of presence that can persist beyond my physical presence.
My sons can read how I think. They can watch how I engage. And one day, they or others can have a conversation with my thinking, even when I am no longer here to have it.
I did not set out to build a legacy platform. I set out to share what I was learning. The legacy dimension revealed itself when my own mortality became concrete rather than abstract. That is precisely what the Stoics and Heidegger are pointing at: you do not find out what truly matters until you are honestly facing the fact that your time is limited.
The koan I arrived at some years ago, “the less I am present, the more I can be present”, was a philosophical observation about ego dissolution. It has since become, quite literally, a description of what I am building: a system by which my presence persists and expands precisely because I have poured it into something that can keep giving without requiring me to be there.
I leave you with this beautiful piece, one I most likely will ask to be played (in decades time, I hope!) at my funeral. For now, you can picture me in a few weeks, when I next visit Barcelona, sitting alone in Sagrada Familia with Rosalia’s voice in my ears. This is “Magnolias”: