The aging society of farmers and lack of motivation to pursue a farming career among farmers’ young heirs could induce a severe labor shortage crisis in the farming sector in Thailand in the near future, especially in the upper northern region, which has been officially declared as the base of the organic agricultural production of the country. The main problem is the decision of farmers’ heirs to inherit or not inherit the farming career of their families. The relevant factors and their effects on the decision must be investigated and analyzed. A set of descriptive statistical tools were used to analyze the significance of each factor. A prediction model based on logistic regression was applied to analyze how sensitive of each factor is to the decision to inherit the family farming career. The discovered results could help the federal organization to plan and establish an appropriate strategy in order to cope with the crisis. Here, there are 519 surveyed samples referring to farmers’ heirs from five provinces in the upper northern region, which are Chiang Mai, Chiang Rai, Nan, Lamphun, and Mae Hong Son. The data were collected using a questionnaire. The following 10 relevant factors were found to have direct impacts on the decision to inherit the farming career: gender, increased age, marital status, increased yearly income, the chance to obtain advice from the Federal Department of Agricultural Extension, attitudes towards the farming career, an increase in the land size for farming per family, increase in the land size for farming in the rural area, the variety of agricultural products produced by the family, and an increased set of farming equipment and tools possessed by the family. However, an increase in the number of new family members could lead to unwillingness to inherit the farming career. All these factors in both the willing and unwilling groups had a statistical significance at the level of 0.05. Since the sample size of the willing group was considerably larger than the sample size of the unwilling group, a technique of minority oversampling was adopted to alleviate the problem of the imbalanced datasets. The classification accuracy obtained was 77.56. In addition to the federal planning and strategies applied to ease the crisis, the factors discovered in this study can be used as a stimulus for persuading and stimulating the young generation to inherit the farming career or become a skillful as well as knowledgeable professional farmer capable of producing high-quality agricultural products for the upper northern region of Thailand.