In this paper, we examine the trend in Japan towards nonregular employment and its effects on marriage, childbirth, and childcare from the viewpoint of a decreasing societal birthrate. Although the decision to marry includes personal values and preferences, socioeconomic status factors such as income and employment type are also associated with the determinants of marriage. Nonregular employment workers have a lower rate and motivation for marriage than regular workers. Thus, socioeconomic disparity caused by employment needs to be minimized through governmental measures and policies. Nonregular employment is increasing among younger generations, and for them, maternity and childcare leave are especially vital. Employee insurance coverage should be expanded to function as a form of income security during these leaves of absence, such that nonregular workers are also covered. During the childcare period, which lasts more than 10 years, it is necessary to cover childrearing costs and also the time required to spend with children. If a single working parent is involved in childcare alone, there is the burden of both work and childcare. Additionally, long work hours can also impact workers that are not involved in childcare. This is a dilemma: a stable and regular employment is often necessary to achieve a higher education; however, it is difficult for nonregular employees to take care of and prepare children for higher education owing to limited financial means. Properly designed measures and policies are necessary to break this chain. Importantly, considerations about life and work are important for all workers, including nonregular workers, who are especially affected in terms of marriage, childbirth, and childcare.