Breakthroughs in science, technology & innovation due to serendipity or accidental breakthroughs are rather rare. Chance is an event but serendipity is a capability. Collecting the dots is easy but connecting the dots that are seemingly unconnectible is a capability that leads to serendipity. How do we create this capability? Can we design for `organizational serendipity’? These and other questions will be answered through the analysis of the history of serendipity and also through lessons learned while chasing anomalies and discontinuities in personal scientific research and innovation pursuits.