The purposes of this study were: (a) to examine the relationship between parental/occupational role reconstruction and psychological well-being in middle and old age, (b) to investigate the psychological factors to affect parental/occupational roles reconstruction. The role reconstruction was measured as the extent to obsess with parental and occupational role in transition. Mail survey was conducted on 378 Japanese married men and women in ages between 50 and 69. As results, the hypothetical pathway was identified in women as follows. The obsession with parental and occupational roles raised parental and occupational role loss anxiety. And both of role loss anxiety lower psychological well-being. For men, obsessed with the occupational role was significantly influenced by autonomy, gender role attitude, social support network. For women, gender role attitude significantly influenced on occupational and parental role obsession, and social support networks had significant impact on parental role obsession. Results of this study were discussed in terms of the importance of role reconstruction in middle and old age, gender difference in role reconstruction according to gender role socialization.