The purpose of this article is to explore what kind of (land-use) regulation is more compatible with a radical acceptance of the idea of the complexity of socio-spatial systems and of the intrinsic limits of explanation and prediction. The article applies insights from complexity sciences to planning practice, critically comparing different land-use regulatory instruments (in particular, patterning-instruments and framework-instruments). The main result and conclusion is that it is necessary to embrace the challenge of complexity and self-organisation, and consequently to start profound revision of regulatory instruments.