In order to think the so called out of the box, first define the box. We live in an age of Alt Facts and Post Truth, where the secular data point is twisted beyond recognition. Knowledge of the boundary conditions of the ‘Box’, helps us to detect bias. Too many of us shallow jargons and theories in a lazy manner, be it in engineering or in the social sciences. Thinking of the cognitive limitations, is the most hardest as it means jostling with our assumptions and thus the mighty educated ego. We all wish to feel good,however this is not the best mental state to learn. Vulnerability and Humility are starting points to authentic conversations with the Self and hence the community and the wide discourse. There is too little talk on authentic learning in the choppy waters of the corporate sector, where learning is ‘competitive advantage’ to score brownie points in meetings. But learning is emancipation in the truest sense. The Foucaudian perspective ‘Knowledge is Power’ is relevant but learning only takes place where existing assumptions are cracked open. Too much real insights are locked in exclusive networks of power.