The aspect of “sustainability” is subject to different contextual interpretations. In 2009, the small STIR foundation in the Netherlands introduced a contextual approach from an “existential natural human development” point of view. STIR introduced five existential values for our sustainable existence as a living species, considering these values as a shared responsibility, including education. As STIR approached the different silos, including educational departments, to join prioritized activities, it received enthusiastic acclaim from teachers and students. However, at the executive level of the educational institutions, the interaction was initially firmly rejected. The executive level considered education as a service for the political financial ecosystem through the development of job-related creativity, knowledge and skills. STIR looked at education through a contributive lens to our existential awareness development and engagement, empowering young people to develop a critical and innovative view on our integral human existence. This initial local executive rejection gradually changed as STIR started to work with all the other local societal silos through, for instance, the “integral healthy city” approach. STIR was now invited to the accreditation table for new bachelor and master programs. It interacted with PhD researchers and introduced human values-related modules for primary and secondary schools.