The retirement age of Indonesian employees ranges from 58 to 65 years and this gives an opportunity for retired employees to develop the second career of being entrepreneurs. The purpose of this study was to identify dominant entrepreneurial characters among male field officers of one of the forces in The Indonesian National Armed Forces in Jakarta. This study relied on a survey involving 200 samples, which were taken by proportional simple random sampling from 1,120 accessible population. Furthermore, the data were analyzed using descriptive analysis with SPSS 25. The results revealed that 1) 69.50% of the respondents were predicted to only enjoy retirement and not willing to work again. This would increase the number of under employment; 2) dominant entrepreneurial characters of Indonesian National Army field officers, i.e., being innovative, risk-taking, and self-determined, had not met the standard score for being entrepreneurs, and only considered having a ‘moderate’ category. The average scores of innovative = 3.16, risk-taking = 3.15, and self-determined = 3.14. Meanwhile, being entrepreneurs needed to reach scores in the high/very high category of 4.0 - 5.0; 3) a program of dominant entrepreneurial character strengthening was required in all professions as retirement preparation.