Traditionally, the relationship between engineering, social sciences, and the humanities (SSH) has often been, to varying degrees, fraught, imbalanced and/or non-existent. Engineering has oftentimes been guilty of envisaging SSH as either providing a ‘soft’ window dressing or counterbalance to ‘hard’ projects representing ‘real’ progress, or to be used to more effectively ‘communicate’, for example in overcoming public reticence around such projects. The stories, histories, (her)stories, myths, language, text, images, art, provocations and critical insights which emanate from and characterize SSH are in this (dulled and marginalized) context more likely to be conceived as mere frivolous pursuits to help fill and support leisure time or promote cultural pursuits. This, we argue, not just feeds into the disconnect between respective disciplinary approaches, but seriously and dangerously miscomprehends the value (and values) that SSH can and indeed must bring to the table, in particular when facing emerging and emergent contemporary interconnected challenges around (un)sustainability. SSH can also benefit from such authentic and pragmatic engagement with engineering and science, while highlighting the necessary and invaluable contribution it can make to society, and across our universities, in particular in facing contemporary meta-challenges. This chapter draws upon academics and practitioners from both sides of the house in an Irish university context, who have journeyed together upon such pathways. The terrain and nature of some of these journeys are described, including some of the inherent difficulties and challenges. We highlight the need for journeying together with ‘disciplinary humility’, as equal partners, if we hope to make authentic progress. Finally, some historic and contemporary examples of potential points of convergence are proposed.