Following the Iranian Constitutional Revolution’s failure and the emergence of a new atmosphere of political and cultural awakening, the second generation of Iranian intellectuals adopted two divergent paths in their encounter with Western modern civilization. Using historical analysis and content examination of two key Iranian periodicals, Kaveh and Iranshahr, this study undertakes a comparative analysis of the perspectives of Sayyed Hassan Taqizadeh and Hossein KazemzadehـIranshahr. The present study investigates how these two secondـgeneration intellectuals conceptualized and interpreted Western civilization, and examines the implications of their divergent approaches for understanding the project of modernity in Iran. The findings show that Taqizadeh, using the metaphor of a “broken house,” attributed Iran’s underdevelopment to the inadequacy of its cultural, political, and civilizational structures, and consequently advocated for the unconditional adoption of Western civilization. On the other hand, KazemzadehـIranshahr, using an ethically grounded critique, warned of the spiritual crisis in Western societies and called for a critical appropriation and indigenization of Western civilization based on the “national spirit” and the reconstruction of collective ethics. The findings demonstrate that although both thinkers were concerned with Iran’s development, the divergence between Taqizadeh’s positivist, techno-centric outlook and Iranshahr’s humanistic and spiritual perspective highlights the profound discursive divide concerning modernity, cultural identity, and the possibilities of development in twentiethـcentury Iran. These findings contribute to a critical rethinking of modernization projects and their historical challenges in contemporary Iran.