Grade-assessment-method of monitoring progress against target learning outcomes, in our observed opinion, is essentially a “production-factory” model. Leadership and success are not necessarily a function of academic achievement but are also reliant on key virtues of an individual. Virtues fortify through use and diminish through neglect. Within this context, in our study, we have: (1) identified 23 outliers over 2500 years and analyzed emerging pattern of virtues that can be attributed to having played an impelling role in life outcomes of these individuals; (2) addressed three key questions – Is there a pattern of virtues? If so, is it significant enough to emulate? Is it possible to structure a targeted intervention and measure results? We have concluded that: (a) 8 intellectual virtues can be isolated as having played a definitively influencing part and the pattern of occurrence warrants prioritizing their development in the next generations; (b) a key curriculum objective must be to focus on providing the tools to facilitate pupils in exploring and developing their potential for these 8 skills; (c) original research is required to evolve a set of methodologies for “enabled” development and an “indicator” mechanism must be fashioned to assess pace of individual (not relative) progress.