In a world where the definitions of work and career have been changed radically and where the span and nature of a person's working life has been disrupted by technology, by the options of delivering one's work and by the actual content of work, in a way unprecedented and unimaginable before, the urgency of shifting our perspective on this essential part of life, it imperative. And just as for many people it is not evident that the essence of artificial intelligence is about imbuing the "machine" with human motivation, set of values and purpose, to make it a helper and not a potential hindrance to our civilisation, in the same way, there is now a need to scrutinise and direct our working lives differently. This time, fundamentally from inside out, from our core values and aspirations to the way we enable communication and behaviours that manifest the essence of us, as a critical reference point, for our choices and happiness in work. Unlike the career counselling and career advice, which have a great pragmatic and implementation contributions to make, leading one's working life to happiness is enabled by coaching. This deeper perspective encourages reflection, awareness of the self, the others, the world and what is possible, to a level of wisdom and inner congruence that act as a light, shining ahead of us potential paths, most likely to lead to best possible outcomes.