Nairobi has a recurring traffic congestion problem in the region and non-motorised transport is a prefered means of transport for the majority population. From studies carried out it stands at a more than 50 percent . Perception of Cycling from a mental models acceptability is at conflict with usage as a means of transport translating to a below 4 percentage preference. In a deliberate strategy to learn and promote the uptake of cycling in the city, this study monitors brain activity during cycling in various parts of nairobi and employ a data science approach to map what might be going on in the minds of avid rider in the city as a baseline to mindset teaching for new cyclist in the city. The finding of this study seeks to identify, determine and eliminate stress points in the journey of cyclist.