Given the current global trend of mimicking real life situations into digital counselling games and its related digital counselling platforms, we decided to contextually understand from the Ghanaian senior high school students, their life challenges arising from their life stories. The study also explores the extent to which ICT is currently being used to provide counselling services to students. Questionnaires and interviews were used to collect data from selected students and a school counsellor. The selected students were made to write about their life stories subjectively. The content of the data was analyzed. After that, students' financial status was identified as the main challenge to their academic pursuit, though several other difficulties were revealed in the study. The study also showed that students had little knowledge about the use of ICT in counselling and only used email as the only digital tool for counselling delivery. The purpose of the study is to use the findings as a basis to develop a digital counselling game in our next study. Again, the study is intended to serve as a guide for researchers when designing a digital counselling platforms for senior high schools.