Mindfulness has attracted increased interest in the field of health professionals’ education due to its proposed double benefit of providing self-help strategies to counter stress and burnout symptoms and cultivating attitudes central to the role of professional helpers. The current study explored the experiential aspects of learning mindfulness. Specifically, we explored how first-year medical and psychology students experienced and conceptualized mindfulness upon completion of a 7-week mindfulness-based stress reduction program. Twenty-two students participated in either two focus group interviews or ten in-depth interviews, and we performed an interpretive phenomenological analysis of the interview transcripts. All students reported increased attention and awareness of psychological and bodily phenomena. The majority also reported a shift in their attitudes towards their experiences in terms of decreased reactivity, increased curiosity, affect tolerance, patience and self-acceptance, and improved relational qualities. The experience of mindfulness was mediated by subjective intention and the interpretation of mindfulness training. The attentional elements of mindfulness were easier to grasp than the attitudinal ones, in particular with respect to the complex and inherently paradoxical elements of non-striving and radical acceptance. Some participants considered mindfulness as a means to more efficient instrumental task-oriented coping, whilst others reported increased sensitivity and tolerance towards their own state of mind. A broader range of program benefits appeared dependent upon embracing the paradoxes and integrating attitudinal elements in practising mindfulness. Ways in which culture and context may influence the experiences in learning mindfulness are discussed along with practical, conceptual, and research implications.