The ‘love for wisdom’ among philosophers gave birth to several schools of philosophy, which later influenced and widened the scope of education to a greater extent. The dominant among those schools which influenced the renowned thinkers and nation builders of the gone era are Idealism, Naturalism and Pragmatism. While the most of the Oxidants embraced pragmatism after experiencing the pros and cons of Naturalism and Idealism, most of the Orients adhered to the convictions of the latter two. The present study therefore showcases and compares the ideologies and postulations of Jean Jacques Rousseau, a great western thinker and Swami Vivekananda, an effective Indian thinker, to show the magnitude of influence of the different schools and exchange of thoughts that occurred in the area of ‘education’ irrespective of their zone.