This paper critically examines fail-fast culture and its compatibility with fragile contexts. It argues that to address complex global challenges, a nuanced ‘fail well’ approach is required. Drawing on the Gothenburg innovation ecosystem—among others—the paper highlights the importance of fostering partnerships between industry, government, non-government organisations, and higher education institutions to prepare emerging innovators for uncertain futures. Cross-sector cases emphasise the need for place-based, collaborative innovation, highlighting that successful innovation is non-linear and emerges through dynamic social processes and contextual influence. It calls for a shift in education towards inclusive, bidirectional pedagogies that integrate sustainability principles and systems thinking across disciplines. The paper concludes by advocating for a shift towards regionally focused, inclusive innovation cultures that prioritise context and community well-being over pursuing only economic goals. This approach is crucial for ensuring safe and just futures in the face of mounting global challenges.