While meditation is commonly associated with positive emotions, many practitioners also report a variety of difficult experiences. A qualitative study of 60 meditation practitioners resulted in a 40-category taxonomy of meditation experiences, with fear being the most commonly reported. Fear arises in response to a variety of contexts and experiences. Sought after experiences practitioners assumed would be positive often turned out to be distressing and destabilizing. This raises important questions concerning trust in the expectations surrounding meditation promoted by teachers, communities, literature, and increasingly scientists and clinical psychologists. Is there a relationship between trusting in particular outcomes and a fear that arises when those expectations are not met? Should practitioners override their fear and doubt to re-establish trust in meditation, in transformative experiences, in teachers and in teachings? Or can fear and doubt be a form of wisdom worth trusting? These questions also concern scientists and clinicians who investigate and often promote the effects of meditation. What beliefs, values, and rhetoric are we trusting? Does our trust in the efficacy of meditation or in prescribed models of health or wellbeing bias our research or our clinical practice? Are we afraid of having our own expectations about meditation challenged?