The study investigates the relations between secondary school teachers work–role fit, job enrichment, supervisor relationships, co–worker relationships, psychological meaningfulness of work and intention to leave. A cross–sectional survey was used. The participants were 502 secondary school teachers in Namibia. The following measuring instruments were used: Work–role Fit Scale, Job Enrichment Scale, Co–worker and Supervisor Relationships Scales, Psychological Meaningfulness Scale and Turnover Intention Scale. Work–role fit and job enrichment both had direct positive effect on experiences of psychological meaningfulness at work, while poor work–role fit and low psychological meaningfulness both had a direct effect on teachers intentions to leave. An analysis of the indirect effects showed that poor work–role fit and poor job enrichment affected intention to leave due to the concomitant experience of low psychological meaningfulness. These findings have implications for the retention of teachers in secondary schools.