Youth is a gift of God, and live it! Pope Francis stresses that in the Christus Vivit, his apostolic exhortation in 2019. It sounds nice and exciting; however, questions arise about what the gift is specifically. How do people recognize it? How can he or she enjoy this stage of life in the right way? Answering these questions is indeed a challenge to the youth - the object of the letter and, at the same time, the main protagonist of their life. Therefore, this article shows a clearer explanation by examining the quote in the Book of Sirach 14:11.14 which says: “My child, treat yourself well, according to your means, and present your offerings to the Lord; do not deprive yourself of a day’s enjoyment, do not let your share of desired goods pass by”. First, by using historical and literary readings, the author tries to analyze the real meaning of the enjoyment and pleasure in the Book of Sirach. Second, the author realizes a connection of this passage with the suggestion of P. Francis in the exhortation letter, because more than two times he quoted it to encourage the young to treasure their youth. Finally, based on what has been clarified, the article ends with an idea to apply to the mission of accompanying the youth in the Society of Jesus, as one of four universal apostolic preferences of the Society.