Rapid digital transformation is taking place due to the COVID-19 pandemic, forcing organizations and higher educational institutions to change their working and learning culture.This study explores the challenges of rapid digital transformation arising during the pandemic in the higher education context. This research used the Q-methodology to understand the nine challenges that higher education encountered, perceived differently as four main patterns: 1) Digital-nomad enterprise; 2) Corporate-collectivism; 3) Well-being-oriented; 4) Pluralistic. This study broadens the current understanding of digital transformation, especially in higher education.The nine challenges and four patterns of transformation actors serve as a starting point for organizations in supporting technological choice and strategic interventions, based on individual, group, and organizational behavioral levels. Moreover, five propositions, based on the competing concerns of these challenges, establish a framework for comprehending the ecosystem that enables rapid digital transformation. Strategies, prerequisites, and key factors during the (digital) technology development process benefit the cyber-society ecosystem. As a practical contribution, Q-methodology was used to investigate perspectives on digitalization challenges during the pandemic.