13/11/2025
Ever feel like you’re pushing the same boulder up the hill every day, no matter how far you get?
You’re not alone. Even the strongest leaders face the quiet repetition of effort, doubt, and endurance.
This reflection explores what Greek mythology and existential philosophy can teach us about leadership in the climb.
Sisyphus and the Art of Leadership
In Greek mythology, Sisyphus was condemned to roll a boulder up a mountain forever, only to watch it fall again. Most leaders I work with know that feeling all too well.
The endless pressure. The repetition. The invisible weight that never seems to lift. Leadership often feels 'Sisyphean' - an unending climb that demands strength, awareness, and meaning without ever promising arrival.
The Modern Boulder
Albert Camus reimagined Sisyphus not as a victim, but as a symbol of conscious defiance. His conclusion was unforgettable: “One must imagine Sisyphus happy.”
Happiness, for Camus, was not in escape but in awareness - in the choice to continue with eyes open. Leadership demands the same awareness. You cannot always change the weight you carry, but you can choose how you carry it.
Grace in Repetition
In a world obsessed with speed and success, we forget that growth often hides in repetition. The daily effort, the unseen labour, the quiet perseverance, this is where authenticity is forged.
Leaders who find grace in the climb do more than succeed. They inspire. They remind others that meaning is not something waiting at the summit, but something created along the way.
The Conscious Climb
Existential leadership is not about eliminating struggle, but transforming it. It is the art of choosing your attitude when you cannot determine the outcome. Each day, the boulder rolls back. Each morning, we begin again. And in that repetition lies the proof of who we are.
Maybe Sisyphus was never cursed. Maybe he was awake.
If this reflection resonates, join the waitlist for my upcoming book
Unmachine Your Mind: Why You Must Think Differently Before AI Does It for You
(See first comment for the link).
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