Twenty years ago, a global trend toward automobility, in which the car is the main transport mode in cities, seemed virtually inevitable. In North America and many European countries, a generation of school children accustomed to walking or cycling to school gave way to new generations expecting to bus or travel by car. Developing countries too began to transition toward more extensive car use, as politicians, themselves drivers, began to push highways and flyways through cities, displacing whole communities and, in many cases, segregating the poor and the most vulnerable even further. Modest but significant social movements nonetheless began to push back: rickshaw drivers in India, for example, launched a major campaign to defend their way of sustenance, winning the hearts and minds of academics, key politicians, and ordinary citizens. Cycling advocacy groups have sprung up virtually everywhere. Indeed, cycling has moved to the fore as a transport mode of interest, particularly for short trips of 0-10km, and many cities are responding with significant measures. A substantial body of practitioner experience and academic literature has documented progress by transitioning cities, mainly in the developed countries. Based on doctoral research, extensive field observation, a literature review, and hands-on experience with the application of Dutch knowledge in the author's home city of Santiago, Chile, this article reviews what we know about planning for cycling. It explores key dynamics that can be used to harness complexity in favour of more cycle-inclusive strategies. It also reflects on some crucial lessons from the past 40 years from the field of cycle planning that could contribute significantly to defining and planning sustainable transport systems, underlining some problematic biases and some lessons to be learned from urban traditions in developing cities.