This study focuses on the career paths and career projections of teacher professionals who are at a stage in their professional roles where they have not embarked upon senior leadership positions in the schools in which they work. Often research has focused retrospectively on the career paths of those already in leadership posts rather than those who are expected to be aspiring to leadership, have discounted this option or are yet to make a decision. Increasing numbers of re-advertisements for headship posts indicates a lack of willing or suitable candidates applying. Changes to school staffing structures and the role of headteachers in recent years have resulted in greater responsibilities including financial matters and the maintenance of premises. Government policies in favour of schools becoming academies has removed local authority support and placed increased pressure on individual school leaders. These factors coupled with the external inspection system and the media focus on so called failing schools has led to the role of head becoming unattractive to many and this study aims to collect the views of a sample of teachers regarding this role. Six schools of similar type were selected from within one local authority and a survey was utilised in order to collect data. This was initially in the form of a questionnaire completed by seventy nine teachers from which twelve participants took part in two interviews each. Teachers were subsequently organised into one of four career categories; 'careerist', 'serendipity', 'active choice' and 'stuck'. Analysis of the data indicates that many teacher professionals do not plan to become senior leaders or heads. This is in agreement with many serving heads who in existing research claim not to have planned their routes to headship. However, the majority of the sample in this study have already ruled out the role of head, finding the pressures and perceived stress of the role unappealing and not wishing to lose their identity as classroom teachers. The underrepresentation of women in headteacher posts does not look likely to be addressed in the near future as females in the study are more likely to feel unable to pursue leadership roles often due to family commitments. A larger proportion of females have made the choice not to pursue leadership roles than males, even when those females did not necessarily have the pressures of home responsibilities. For many females future decisions regarding starting families and seeking promotions produced dilemmas that men did not appear to have to confront. These factors look likely to lead to continued headteacher shortages in the short term with no real incentives to encourage females to pursue such posts now or in the future.