This article is an extended exploration of this Greek myth as sensemaker, first introduced in a previous article.
Sisyphus rolls his boulder to the top of a hill in the underworld, and just before it reaches the summit it rolls back down, every time, and he has to start again, every time. That much is familiar, and it’s why his name has become classical shorthand for Groundhog Day, minus Bill Murray’s eventual way out. What’s less often understood is why Zeus condemned him to that fate in the first place.
Sisyphus was a king clever enough to cheat death itself, twice. First, he chained Thanatos, Death personified, when Death came to collect him, so that nobody anywhere could die until the gods forced him to let him go. Then, when sent to the underworld for good, he talked Persephone into letting him return briefly to the world of the living, to scold his wife for failing to bury him properly, and once back among the living, he simply refused to go back down. His punishment fits his crime with an almost vicious precision – he tried to escape the natural order of things through sheer cunning, and he is condemned to an eternal cycle that no amount of cunning can escape.
But not everyone takes this myth at face value – that is, that Sysiphus’ plight is surely the epitome of eternal suffering. In stark contrast, Albert Camus’s reading of the myth refuses to treat the boulder as pure punishment. The struggle itself is enough to fill a life, he argues, and “one must imagine Sisyphus happy,” not despite the repetition but because of it.
What feels counterintuitive about this story is that Sisyphus’s didn’t lose to the gods through weakness. Here he lost through cleverness aimed at the wrong problem. He treated mortality itself as an obstacle to be overcome rather than a limit to be lived (is that sounding in any way familiar?), and the gods’ reply was to hand him a smaller, permanent version of exactly the thing he’d tried to escape. Oh, the irony.
Most organisational cycles get treated the way Sisyphus treated death: an obstacle, not a condition, something to be solved, escaped, or at minimum endured until it finally stops. The same budget arguments every year. The same governance reviews. The same business cases remade from scratch regardless of what was learned last time. The same system errors. The same conversations with customers. Yes, Groundhog Day.
Of course, none of these organisational experiences are solvable in the way a project is ‘solvable,’ and treating them as though they might be is where the exhaustion actually comes from, not the repetition itself. What actually exhausts us is the quietly held fantasy that this particular cycle/conversation/process/error is the one that’s finally going to stay solved, quickly met by the fresh disappointment that arrives when it doesn’t, as if feeling that disappointment for the very first time.
The ‘cleverer’ version of this mistake is worse than the naive one, and it’s the reason Sisyphus earned his sentence rather than any reprieve. A team that tries to outsmart a structurally unavoidable cycle, gaming a review process instead of engaging with it honestly, treating a recurring requirement as a box to tick rather than a constraint to work within, doesn’t escape the cycle any more than Sisyphus escaped his. It tends to entrench itself more deeply inside it, buying nothing but a more permanent version of the very thing it was trying to avoid. The workaround becomes the trap, for the same reason it became Sisyphus’s trap. It treats a genuine limit as a puzzle to solve, but as we learn over time, organisational life is not a series of puzzles to solve, but an array of interactions to navigate – all different, yet similar in subtle ways – interactions that can generate deep discomfort, and yet demand steady resolve.
Maxwell’s research on leadership teams found that teams able to tolerate the discomfort of a genuinely difficult, ongoing state, rather than settle that discomfort prematurely through a clever shortcut, made better decisions over time than teams that kept trying to engineer their way out. Accepting the cycle is not resignation. It is an approach that can provide a clearer view of what can actually be changed.
One practice worth trying.
For any piece of recurring, structurally unavoidable work, name it out loud as a cycle rather than a project: not “the Q3 forecast” but “the forecast we do every quarter, permanently, for as long as this team exists in its current form.” Then ask honestly whether the team’s current approach to it is trying to make the work sustainable, or trying to make the cycle stop, since only one of those is actually achievable. Separately, watch for the clever workaround that seeks escape from a genuine constraint. It rarely delivers escape. It usually delivers a longer sentence.
The boulder was never going to stay at the top. The only real choice on offer is whether the climb back down feels like defeat each time, or like a rhythm a team has learned to sustain, one turn of the cycle at a time, for as long as the work requires it.
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Sources
Apollodorus. (1997). The Library of Greek Mythology (R. Hard, Trans.). Oxford University Press.
Camus, A. (1955). The myth of Sisyphus and other essays (J. O’Brien, Trans.). Alfred A. Knopf.
Drummond, K. (2025, July 21). Bryan Johnson is going to die. WIRED. https://www.wired.com/story/big-interview-bryan-johnson/
Fry, S. (2018). Mythos: The Greek myths retold. Penguin/Michael Joseph.
Maxwell, C. (2022). It’s just not that simple: A complex adaptive systems approach to understanding changing dynamics in leadership teams [Unpublished doctoral thesis]. University of Technology Sydney.
Stacey, R. D., & Mowles, C. (2016). Strategic management and organisational dynamics: The challenge of complexity to ways of thinking about organisations (7th ed.). Pearson Education.
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