The "Thinking School, Learning Nation" national policy agenda set forth in 1997 has been considered a watershed moment in the history of Singapore education as well as the nation. It has brought about a raft of new educations reforms that are both comprehensive and intensive in nature. It has also brought about a succeeding education policy initiative coined as "Teach Less, Learn More". This education policy initiative further strengthens, widens and deepens the spirit of the "Thinking School, Learning Nation" movement, albeit confined to the Singapore education context. In education, both these gargantuan policy initiatives have immense impact on education and educators likewise. This paper seeks to bring to light these two policy initiatives in terms of its influence on teacher professional learning, albeit focusing on the developments of professional learning communities. The critical discussions and propositions laid forth in this paper seek to engage readers to reflect deeper on how the policy intent and spirit of "Thinking Schools, Learning Nation" can be further fulfilled.