Despite the promising outcome of modular distance learning, its implementation is challenging. Thus, this study aimed to examine the usefulness and challenges of the implemented clustered self-directed learning modules in entrepreneurship for senior high school distance learning amidst the emerging pandemic using the descriptive-survey research method. This study was conducted at Espiritu Santo Parochial School of Manila, Inc., during the school year 2021-2022, among Grade 12 students using a stratified proportional random sampling technique. The study used both quantitative and qualitative methods of analyzing the data, including descriptive statistics and thematic analysis. As a result, all the modules were inferred to be very effective and very useful in terms of their usefulness for distance learning. On the other hand, there were six emergent themes from twenty-five challenges, as follows: (a) difficulties and limitations in theoretical and practical processes; (b) concerns about time constraints and academic workloads; (c) technical issues in learning modules; (d) problems with communication, lessons, and instructions; (e) issues with online learning, connectivity, and learning management systems; and (f) external and personal challenges as a student. These challenges were the basis in framing the recommendations of the students in addressing the aforementioned emergent themes.