This study identified the employment-adaptation skills required for homeless people and elucidated the improvement of perception of skills that facilitated self-esteem recovery. A total of 152 homeless people participated in the questionnaire survey. The survey comprised items regarding employment-adaptation skills collected through an open-ended questionnaire and three scales: personality, communication skills, and self-esteem. First, resourceful and sociable behaviors were identified as factors of behaviors required for job performance. In addition, tolerance for unfair situations and tolerance for fraudulent situations were identified as factors of emotional regulation for unpleasant situations. Next, conceptually significant associations between these factors and personal traits were confirmed. Finally, the main effects of the factors of job performance and the interaction effects between these and the factors of emotional regulation were clarified. Ultimately, we suggested that improvement of the self-evaluation of resourceful and sociable behaviors in people who were homeless effectively helped their self-esteem recover.