This study explores the design and preliminary evaluation of the "Well-being Journey" (WB Journey), a digital tool aimed at enhancing student well-being within educational environments through tailored recommendations for students. The study examines the WB Journey prototype's user experience and its effectiveness in meeting learning analytics goals related to student preferences. To achieve both goals, we employ a mixed-methods approach, combining quantitative data from the User Experience Questionnaire (UEQ) and the Student Expectations of Learning Analytics Questionnaire (SELAQ) with qualitative feedback from a student discussion. Conducted among 25 students from an engineering school in a Spanish University, the study's data collection involved a 120-minute workshop. The findings suggest opportunities for enhancing the prototype, highlighting the importance of aligning similar digital tools with student needs and preferences for a supportive learning environment, which can be achieved by leveraging tools such as UEQ and SELAQ.