Any working sustainable system is based on three basic principles: the ability to attract, retain, and increase its resources. The Chilean forestry sector, between the 1970s and the end of the 1990s, was successful in these three aspects. Since it could attract workers from other sectors and retain them, the system allowed these laborers to develop technical skills that gave them better economic and professional prospects, despite the poor initial preparation of this group. This was also possible by improving conditions of life such as forestry camp and strengthening work security issues. However, based on recent research, the Chilean forestry sector is failing to attract and retain workers; neither does it offer its workers professional development. The objectives of this chapter are to discuss, first, based on a literature review, the initial steps of the development and improvement of the working conditions in the Chilean forestry sector that allowed to attract, retain, and increase workers and their resources. After that, based on a recently published research, we discuss the present and future of the workforce in the Chilean forestry sector from a social and ergonomics perspective and conclude if today, in the forestry sector, foundations are being laid for a sustainable workforce.