Neo-Aristotelian forms of character education often draw on literary sources as materials, although rarely poetry. This article offers retrospective reflections on a poetry-based character-education intervention, conducted in an Icelandic secondary-school setting. Having run into practical difficulties during the implementation phase, the challenges of implementation were reflected upon through consultation with ten subject experts who shared their views about the enablers and barriers encountered when running such an intervention. The interviews yielded a rich data set, which often took interviewees beyond the boundaries of a poetry-based curricular context to focus on more general conditions for effective, character-inspiring school-work. Through thematic analysis, four themes were identified: freedom, time, creativity, and wonderment. Of these four, creativity had been identified in advance as an interview theme, meaning that the researchers expected to find it. The remaining three provide an insight into how, according to the interviewees, the ideal Icelandic school system should be designed. The theme of freedom addresses both negative and positive aspects of the current state of affairs, while the theme of time mostly reflects negative aspects of the Icelandic curriculum. The theme of wonderment has solely positive connotations in the minds of interviewees, and is the core of this analysis because it seems to hold the key to the question: what factors would enable an effective intervention of the sort under scrutiny here? This theme is analysed in detail, and some specific and general educational implications are elicited.