Urban planning is in a crisis as rigid, deterministic models cannot cope with evolving cities. Rem Koolhaas identified the crisis and argued for a shift from authoritarian planning to a more tolerant, participatory approach. François Ascher and many others argue that modern urbanism, before based on solid city models, has to learn to accept uncertainty adapting to unprogrammed change. Rather than enforcing rigid rules, urban planning should be directed towards strategic, performance-based systems that allow for continuous revision. This requires abandoning deterministic assumptions and guiding changes through adaptive, place-specific methods. Urban plans in Italy must either improve the current settlements or introduce new spatial patterns to enhance urban competitiveness. What is required is a “light urbanism” approach that balances flexibility with coherence, resists disciplinary fragmentation, and focuses on shaping spaces for evolving needs. By replacing conformity with strategic flexibility, urban planning can cope with uncertainty while fostering sustainable, equitable urban development.