This qualitative self-study brings philosophies of weak education to bear on the author's leadership practice situated within the belly of a business environment. The study investigates the author's practical application of weak educational theory into a weak educational leadership practice. This research reflects the author's struggle with reconciling the reciprocal influence of becoming a weak educational leader and working within a fast-paced neoliberal culture. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]