How is it possible for us to appropriately analyze our experiences and take useful action? My experiences over the past few years suggest that it’s crucial to study and act at the same time – a challenging, but truly fascinating union. From designing novel software interfaces that accelerate personal learning to prototyping a medical screening service in the gritty industrial complexes of Assam, India, I have decided that it is more damaging to delay action in favor of objective validation than it is to quickly note the reasoning and make a decision. Only after my teams had accomplished ambitious goals could we look back and identify the false assumptions, critical actions, and unseen hurdles on the convoluted paths to success. In failure, unless our goal was common enough to have been accomplished by several others, it was difficult to extract useful lessons. Although we could say how to avoid a specific type of failure, the ideas on how to achieve success were little more than speculation