These life-style entrepreneurs look at the whole pattern of living among those men and women whom they are seeking to influence. They are not so much concerned with balancing life and work. They are much more interested in the complete integration of life and work—they believe that work should itself be life-giving. Like the challenge-oriented entrepreneurs, the life-style entrepreneurs are captivated by the moments of “flow” and by the moments when they can not only heal themselves but also help to heal the world. They may even take long periods of time off work themselves to indulge a passion such as sailing or world travel. Or they are active entrepreneurs for a limited period of time and then follow their own advice and retreat from the demands of entrepreneurship.

If the life-style entrepreneur is truly interested in reflecting on their own work, then this reflection needs to be something more than a narcissistic excursion into their own dreams. D. W. Winnicott (a noted psychoanalyst) describes the splitting that can occur between the “true self” and a “false self” (that is based on unrealistic expectations regarding the role one plays in the world). While the false self is typically created in childhood (often as the result of one or more doting parents), it can also be created and reinforced in later life by those who become life-style gurus. There is a profound challenge in reflecting on one’s own authentic sense of self. This is done not to put down the values held by the entrepreneur or to discredit the entrepreneur’s perspectives on life. This challenge is not about discounting the entrepreneur’s personal and professional accomplishments. Rather, the challenge is to enable the lifestyle entrepreneur to find a safe place in which he can reflect on his own decisions and on his own future life plans.

While these entrepreneurs are busy selling anchors, they might have lost their own anchor. The life-style entrepreneur is not perfect and faces his own difficult life choices. Typically, there is not much benefit in sharing these imperfections and difficulties with the devoted followers of the entrepreneur. This not only will hurt the entrepreneur’s business, it will yield reactions from the followers that are not necessarily reliable or helpful. The life-style entrepreneur needs his own sanctuary in which to discern his true self and in which to distinguish between the self he is presenting to his “public” and the self he is presenting to the significant others in his life – and to himself.