The subject of this paper is twofold (1) towards review and revision of extra-curricular learning model in the form of a student workshop as an extended environment and a reflective arena, and (2) towards generating workshop content aimed at examining modernity in contemporary conditions of urban transformation. The paper is structured in three parts. The first part introduces the concept of an architectural workshop with a discussion of general methodological perspectives that shape this approach that takes place through three continuous stages during which students develop the process of analytical thinking, architectural programming and architectural design. The second part of the paper contextually and conceptually position the content of the workshop aimed at examining modernity in contemporary conditions of urban transformation between imagined, realized, and lived space. The third section introduces the content of two student workshops as an illustrative example of the implementation of methodology with specified assignments and substance.