During their school years, students encounter difficulties of various types from both content-related and emotional aspects. Often, when asked directly about their learning difficulties, students struggle to express these difficulties explicitly and clearly; as a result, teachers find it a challenge to provide them with a suitable and satisfactory response. In order to help students express their scholastic difficulties, particularly cognitive and emotional ones, and foster their ability to chart out courses of action for coping with these difficulties, we have developed a tool we call "Corresponding with the Professor". Specifically, this involves writing a letter to an imaginary Professor which contains a description of a difficulty (or difficulties) followed by writing a detailed letter of response from the Professor (to oneself actually) that offers suggestions and recommendations aimed at possible ways of coping with the difficulty (or difficulties). In developing this tool, we have relied on research literature related to writing a "letter to myself". In this paper, we shall present the tool and its theoretical basis.