Second language learning strategy has received great attention for its role in helping learners to actualise language skills and improve performance, including writing. Congruent with Pressley and Harris (2006, pp. 270), growing evidence has demonstrated that “one approach that works better than any other for ensuring learners actually learn strategies” is strategy instruction. Though studies into strategy instruction have reached the ripe age of 40, one proposal has been recently initiated for innovating the design of strategy instructional packages which shall equally consider developing students’ willingness to learn, in addition to improving their language skills. The present paper hereby takes on the “skill plus will” nature of second language learning and teaching and suggests bringing “hope” from Snyder’s Hope Theory – a Positive Psychology construct that helps people push through the rough times, and acts as an indicator of one’s willpower and mental health – into strategy instruction research. The theoretical underpinnings of hope indicate potentials for being intertwined with second learning strategies for a holistic view of “skill and will” development among learners. Moreover, traditional strategy instruction designs can also draw insights from hope intervention to be more useful in empowering learners.