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.”
-Tom
Tom McCallum is a Sounding Board to brave leaders ready to lead massive change in their business or organisation. He is passionate about “Open Leadership” and “Leading from Purpose”, frameworks that came as distillations of his thousands of blogs. He chose not to put any of that into a book, but instead you can “talk” to him through his GenAI, AskTom.chat