Open AccessThe family is a paramount source of happiness, giving individuals a sense of place that is relevant to developing satisfaction and fulfilment. Consequently, this study examined the attitude of retiring HeadMasters and Assistant HeadMasters’ towards family involvement in pre-retirement preparation in Ondo State, Nigeria. Using descriptive survey, 150 participants were purposively drawn from three Local Government Areas accidentally selected for the study. ’’Family Involvement in Pre-retirement Preparation Questionnaire (FIPPQ)’’ was used for data collection. Data collected were analysed using descriptive statistics, t-test, and ANOVA. Descriptive results indicated participants’ general poor knowledge on the need for family involvement in pre-retirement preparation, positive attitude towards family involvement and low actual involvement of their family in pre-retirement planning. Results of the tested hypotheses revealed that sex, educational qualification, and religion had no significant influence on the participants’ attitude towards family involvement in pre-retirement preparation .Recommendations were made based on these findings.