A transformative meditation retreat experience revealed a profound truth about Ecclesiastes (Kohelet): its concept of *simḥa* (joy) stems not from material success or philosophical certainty, but from gratitude itself. Through autobiographical narrative methodology spanning decades of spiritual evolution - from Orthodox observance through rabbinical education to mindfulness practice - this deeply personal theological meditation traces how different life stages reshaped interpretations of Kohelet's seemingly pessimistic worldview. The pivotal spiritual awakening during meditation practice illuminated that authentic joy, in Kohelet's framework, emerges through conscious appreciation of life as divine gift, particularly in quotidian experiences of eating, drinking, and labor. When viewed through the lens of grateful recognition, Kohelet's apparent nihilism transforms into meaningful affirmation of life's fundamental blessings. This interpretation provides fresh insight into the text's liturgical placement during Sukkot, the harvest festival of thanksgiving, suggesting that gratitude serves as the hermeneutical key to understanding Kohelet's theological message about finding purpose amid life's apparent futility.