The purpose of this study was to examine the life history of a female teacher who has served in a vocational high school in a rural area. Through this, we needed to look into her life as a teacher, the realities of a vocational high school in a rural area, and the dilemmas of vocational teachers. Adopting in-depth interviews, the research period was from March to July in 2008. The following is the result of the study.The middle-aged female teacher's experiences reflect through the rise and fall of vocational high schools, and now she is facing the downward trend in a teacher's life. Marriage became an important factor for her entering upon a new phase of life history. She came to take students precious with childbirth and child-caring experiences and it caused her to change her views on students. In order to take an active part of education in a vocational school in a rural area, she thought that the most important role of high school teachers is to build personal intimacy with students. The participant was in a serious dilemma, such as experiencing exhaustion caused by downfall of rural areas and vocational high schools, and feeling anxiety from the effects of the reduction or elimination of specialized subjects.