Recent research and professional interest in planning for sustainable and resilient cities emphasizes the assessment of a broad spectrum of urban ecosystem services. While such assessments are useful to establish specific benchmarks, and for measuring progress toward sustainability and resilience goals, they do not motivate, or support the innovations required to provide specific ecosystem services as an intentional part of routine urban and infrastructure development activity by municipalities and professionals. In this context, predictions for unprecedented future urbanization and development of new urban infrastructure represent a unique opportunity to “learn-by-doing”. Significant advances in urban sustainability have recently been made through transdisciplinary collaborations among researchers, professionals, decision-makers and stakeholders. However, these advances, often through pilot projects, have limited transferability to other cities due to the inherent biophysical and cultural uniqueness of the city in which they originated, and of the projects and plans themselves. The promise of practicing “learning-by-doing”, therefore, remains an elusive goal, not yet fully integrated with urban development. In this essay, a framework for “safe to fail” adaptive urban design is proposed to integrate science, professional practice, and stakeholder participation. The framework is a transdisciplinary working method, and includes experimental design guidelines, monitoring and assessment protocols and strategies for realizing specific urban ecosystem services integral with urban development. The “safe-to-fail” adaptive urban design framework encourages and rewards innovation in a low-risk context – while assessing the achievement and performance of the specific intended ecosystem services.