These 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.

How might a coach assist this lifestyle entrepreneur? First, the professional coach must be careful about not colluding with their client in uncritically supporting the client’s dreams and visions about the world in which they now live or hope to live. If the lifestyle entrepreneur is truly interested in the benefits to be gained from a coaching experience, then it needs to be something more than a narcissistic excursion into the coach’s reinforcement of everything their client has said or done. 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.

A coach can be of value to the life-style entrepreneur by offering challenges to her client’s 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 coaching 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.  As in the case of the coaching strategies engaged when addressing the needs of the other entrepreneurial types, the coach to a lifestyle entrepreneur is in the business of providing challenge and matching support. She is asking the questions that no one else is asking her client at this point in his complex and often shifting life.