This contribution aims to examine the change of perspective of Roger Caillois which took place between 1927 and 1939. Caillois, indeed, after some events, came to understand that it is necessary to defend the societies created by men. One has to create the order and keep it. The absence of rules leads to nothing: the rules are freedom. Nothing can be without being determined by precise and severe laws. To be successful, man must necessarily discipline himself: passions must necessarily be sacrificed. Hence the mirage of vertigo, that is, the desire to satisfy all his needs in a single instant. He is tempted to rely on the forces of intoxication, ecstasy, delirium, any form of automatism, which appears to him as supreme freedom with respect to his condition but in reality it is only forms of slavery. The conquest of order and its conservation are difficult and precarious. Humanity must contain these forces to build civilization in spite of barbarism. These forces must be disciplined but not subjected and only those who succeed in doing so can aspire to a real life. Man needs to be distracted, to escape from the constraints that everyday life imposes on him. Caillois understands it well but, to do so, man cannot abandon himself completely to the forces of vertigo: through the use of willpower, man needs to know when it's time to get back to real life. Only by keeping these primary instincts at bay is it possible to build civilization in spite of barbarism and this is a job that must be done constantly. The Sisyphus-man must not be tired of rolling up his sleeves every day, of always carrying the boulder up the mountain again, even knowing that when he takes it to the top it will roll down again, apparently frustrating his efforts. The efforts are not thwarted, this fate is not absurd, it is what it must be: man is destined to civilization and civilization remains his final goal even after his decline. This contribution aims to examine the change of perspective of Roger Caillois which took place between 1927 and 1939. Caillois, indeed, after some events, came to understand that it is necessary to defend the societies created by men. One has to create the order and keep it. The absence of rules leads to nothing: the rules are freedom. Nothing can be without being determined by precise and severe laws. To be successful, man must necessarily discipline himself: passions must necessarily be sacrificed. Hence the mirage of vertigo, that is, the desire to satisfy all his needs in a single instant. He is tempted to rely on the forces of intoxication, ecstasy, delirium, any form of automatism, which appears to him as supreme freedom with respect to his condition but in reality it is only forms of slavery. The conquest of order and its conservation are difficult and precarious. Humanity must contain these forces to build civilization in spite of barbarism. These forces must be disciplined but not subjected and only those who succeed in doing so can aspire to a real life. Man needs to be distracted, to escape from the constraints that everyday life imposes on him. Caillois understands it well but, to do so, man cannot abandon himself completely to the forces of vertigo: through the use of willpower, man needs to know when it's time to get back to real life. Only by keeping these primary instincts at bay is it possible to build civilization in spite of barbarism and this is a job that must be done constantly. The Sisyphus-man must not be tired of rolling up his sleeves every day, of always carrying the boulder up the mountain again, even knowing that when he takes it to the top it will roll down again, apparently frustrating his efforts. The efforts are not thwarted, this fate is not absurd, it is what it must be: man is destined to civilization and civilization remains his final goal even after his decline.