In order to increase the cost-efficiency, availability and ease of accessing and delivering mindfulness-based interventions (MBIs), clinical and research interest in mindfulness-based self-help (MBSH) interventions has increased in recent years. Several studies have shown promising results of effectiveness of MBSH. However, like all self-help interventions, dropout rates and disengagement from MBSH are high. The current study explored the facilitators and barriers of engaging in a MBSH intervention. Semi-structured interviews with members of healthcare staff who took part in an MBSH intervention (n = 16) were conducted. A thematic analysis approach was used to derive central themes around engagement from the interviews. Analyses resulted in four overarching themes characterising facilitation and hindrance to engagement in MBSH. These are “attitude towards engagement”, “intervention characteristics”, “process of change” and “perceived consequences”. Long practices, emerging negative thoughts and becoming self-critical were identified as the key hindrances, whilst need for stress reduction techniques, shorter practices and increased sense of agency over thoughts were identified as the key facilitators. Clinical and research implications are discussed.