This study explores the experience of self-doubt of four self-employed coaches. The study sought to explore the metaphorical meaning-making of the participants, and semi-structured interviews were augmented by imagery created by the participants to visually depict their experience of self-doubt. The data were gathered and analysed using an Interpretative Phenomenological Analysis approach. The findings suggest that the skills and knowledge required to fulfil the roles of both coach and business owner are dynamic and complex and take time to master. As well, the experience of self-doubt has symbolic, psychological and economic impacts, and has the potential to prevent the self-employed coach from being able to do their work in the world. The findings point to the need for safe places for the self-employed coach to explore the increased complexity of their world. The implications of the use of participant-created imagery in qualitative research are also considered.