The extent to which personality type may influence the career experience of midlifemen remains to be more fully explored. Based on Jungian (Myers-Briggs Type Indicator®) personality preferences, ten Intuitive-Feeling males were compared with ten Sensing-Thinking males (40-55 years). Intuitive-Feeling, compared to Sensing-Thinking, were more likely to report fulfilling career dreams held as young men, aspire to work roles which had greater self-determination/autonomy and provided greater opportunities to coach/mentor others, were less likely to seek a change of occupation but reacted with greater disillusionment/cynicism to job loss. However, despite differences, the majority in both groups were positive about work in midlife which was attributed to greater family/community engagement, career mastery and having achieved an alignment of personal and organisational values. With the looming departure from the labour market of increasing numbers of ageing baby boomers, proactive career development strategies that encompass an awareness of personality type can assist in retaining and developing midlife employees.