Background: Self-directed learning or more precisely SDL is an important part of UG curriculum that can be used at all levels. In this form of education, the student or the learner plays an active role in knowledge, skill, and attitude acquisition. It is a lifelong learning process and requires a student to be familiar with the concepts of self-directed learning. Since it is a newly introduced concept, various challenges were faced while designing and implementing the SDL session. The online teaching due to the coronavirus disease 2019 pandemic also added to the teething problems in CBME implementation. Aim & Objectives: To identify the challenges faced and their possible redressal for proper designing of a SDL session and to understand the precise principles of SDL and share it with the faculty members of the department. Methodology: In the personal experience with the MBBS batch while conducting a SDL session it was observed that SDL is confused with self learning as initially the students were given a topic and then asked to prepare it. The personal experience and experience of other medical teachers as well as of the students was taken into consideration. Then several publications on SDL were reviewed to understand the concept, and theories related to SDL were also studied. Results: An exhaustive online search along with discussion with other medical teachers in this regard was very helpful as various doubts got clarified and some facts came into light indicating that concept of SDL is based on experiential and student-centred learning and with stress on higher order cognition. Therefore, the SDL conduct can be designed for two contact sessions and a gap period of few days. The first contact session can focus on introduction and instructions. The intersession period can be designated as the actual learning period for the students. The second contact session can involve debriefing and assessment. Conclusion: The research helped to impart confidence in designing of the SDL session properly and helped to clarify various doubts and we got an in depth understanding of SDL. Hence, we were able to disseminate this knowledge to other faculty members also. Now we can plan the SDL session accordingly.