Enterprise Architecture (EA) aims to align IT with business goals, but the concept of “future viability” remains academically abstract and practically elusive, creating a significant theory-practice gap. This study addresses this gap through a qualitative content analysis of semi-structured interviews with seasoned EA practitioners. Our findings reveal that practitioners define future viability not as a technical property, but as a direct outcome of business strategy, making its assessment highly context-dependent. While confirming that business capabilities serve as a “central anchor point” for translating strategy into design, the analysis also shows that the primary obstacles are not technical but organizational: the significant impact of technical debt and pervasive institutional inertia. By empirically validating and nuancing theoretical concepts, this paper contributes a practitioner-grounded understanding of future viability, offering actionable insights into the real-world challenges and strategic imperatives for building resilient and adaptable enterprise architectures.