Ali, I don't think solving this problem would require spilling the 'secret sauce' of successful people i.e. if there was any.

Analytical data points of people from specific professions is enough to determine the common educational path way, of-course educational degrees are not the sole determinants of a career & there will be outliers; but on average numbers will always correct itself for the outliers.

I agree that so called 'experts' make a killing by selling 'How I became this or that' type of training; but most successful entrepreneurs agree that experts are good for telling you 'What not to do' rather than 'what you should do'. I am myself an Entrepreneur/Startup Coach and I spend much of my time telling 'what not to do', to my clients.

I believe, the key to solve this problem is to collect data points from individuals of different careers right from when they were at grade 6 and target it towards children from grade 6; because targeting those who have just finished high school/college doesn't give enough data points to differentiate between a generic career advice tool.