For as much time we spend estimating a project, it is just one likely scenario among many others. Agile teams are not shy of this, overthinking story points estimates and velocity. It doesn’t mean estimates should be thrown away, but that it should be completed with risk management at least (or its big brothers, scenario-based planning, real options, etc.).

My most vivid and teaching experience comes from a memorable adventure in my youth, sailing through the Channel islands that taught me real-life risk management metaphors that I ended up applying in my practice. Here’s how we did the pilotage plan and how it turned out.