Recent observations that personality traits are related to later‐life health and wellbeing have inspired considerable interest in exploring the mechanisms involved. Other factors, such as cognitive ability and education, also show longitudinal influences on health and wellbeing, but it is not yet clear how all these early‐life factors together contribute to later‐life health and wellbeing. In this preliminary study, we assessed hypothesised relations among these variables across the life course, using structural equation modelling in a sample assessed on dependability (a personality trait related to conscientiousness) in childhood, cognitive ability and social class in childhood and older age, education, and health and subjective wellbeing in older age. Our models indicated that both health and subjective wellbeing in older age were influenced by childhood IQ and social class, via education. Some older‐age personality traits mediated the effects of early‐life variables, on subjective wellbeing in particular, but childhood dependability did not show significant associations. Our results therefore did not provide evidence that childhood dependability promotes older‐age health and wellbeing, but did highlight the importance of other early‐life factors, particularly characteristics that contribute to educational attainment. Further, personality in later life may mediate the effects of early‐life factors on health and subjective wellbeing. © 2016 The Authors. European Journal of Personality published by John Wiley & Sons Ltd on behalf of European Association of Personality Psychology