Dr. Jose de Mesa, a well-esteemed lay theologian, who mentored people locally and internationally in doing theology with the culture in mind, is recognized for his efforts to accompany young theologians in re-articulating the Christian Faith using culture as a rich resource in theological reflection. A synthesis of some notable insights, methodologies or processes and principles which the author learned from her mentor, Dr. de Mesa, are presented in the article. There are six lessons highlighted, namely: 1) the process of doing theology where the mutual dialogue between the two poles of present human experience and the Judeo-Christian Tradition (JCT) is discussed; 2) the cultural analysis using exegesis as a means to unearth the richness of the local culture and its potential to re-articulate the Christian faith; 3) the following of the Way of the disciples in doing Christology in order to make Jesus real in our time; 4) the promotion of the sacramental perspective as the best option to lessen if not totally solve the prevailing dichotomy between faith and life among Filipino Catholics; 5) the use of the local language to authentically present a Filipino theology thereby destigmatizing the culture from the impact of Western colonization; and 6) the use of the pen to proclaim the Gospel and re-educate Christians about our common vocation to seek first God’s kingdom and its righteousness (cf. Mt. 6:33) because this is our primary task as disciples of Jesus.