Awakening is to be psychologically present, to be aware, to be attentive of the stream of inner and outer experiences continuously occurring. Awakening is a both a moment by moment pressure or activation of our consciousness, as well as the process of comprehending our mind in regards to the fascinations we have (attachments and aversions) which cause us to psychologically sleep.
To be psychologically asleep is to act in ways which are not conscious.
There are two types of awakenings: positive and negative. We teach the positive awakening of consciousness by comprehending our ego. However, it is possible to awaken within the ego, to become aware of our desires and instinctual drives, but to not care to eliminate them.
Financial success is determined by many factors, most importantly our karma. We can be awakening, but because we have karma, we may have difficulties in business, with money. Someone else may not however. It depends on the karma. There is no conflict between someone on the path of awakening and also being a successful businessman/woman, or to be wealthy. It all depends upon the karma.