Effective teaching, among other things, can be seen as a series of orchestrated moves between different kinds and levels of knowledge, be they between personal, everyday and technical knowledge, between school knowledge and the world beyond, and between knowledge in different disciplines. This article is about bridging the gap between what students learn in school and their out-of-school experiences. It focuses on the dimension of connected learnings, which is one part of a three-dimensional analytic framework developed for a study in Singapore. By examining transcripts of English language and social studies lessons in Singapore secondary schools, this article shows how teachers can make what is taught in the classroom relevant to the outside world as well as incorporate and infuse students' prior knowledge and out-of-school experiences into classroom teaching. It argues that such connected learnings not only increases motivation and engagement levels for the students but also makes learning more meaningful and purposeful. In this sense, students are no longer just learning basic literacy competencies within an academic context but endeavour to develop life skills that take them beyond classrooms and examination halls. Put simply, they are going beyond learning how to read and write, rather reading and writing in order to learn.