Should humanity have been created at all? An ancient rabbinic debate between the Schools of Shammai and Hillel wrestles with this profound existential question in an enigmatic baraita from B. Eruvin 13b. Through personal theological reflection and comparative analysis of interpretations by Ephraim Urbach and Rabbi Yitzhak Hutner, this research challenges traditional commentaries that frame the text as merely addressing specific transgressions or presenting a philosophical paradox for religious development. The study proposes a novel hermeneutical approach to the baraita's pivotal phrase "examine one's deeds," arguing that the possessive pronoun references God's works rather than human actions. By integrating textual analysis with theological reflection, and drawing connections to Ecclesiastes and the tension between pessimism and optimism in Jewish thought, the research demonstrates how contemplating divine works and blessings can serve as an antidote to existential despair. This reinterpretation not only advances talmudic hermeneutics but also offers practical spiritual guidance for transforming melancholy into gratitude through mindful attention to divine creation.