Strategic thinking should be encouraged with a challenge-oriented entrepreneur, as is the case with many of the other types of entrepreneurs I have identified. This patience and persistence often comes to the fore when a challenge-oriented entrepreneur traces out the consequences of frequent moves not just in terms of financial costs but also in terms of the personal costs for other people with whom the challenge-oriented entrepreneur is working. It is important for this type of entrepreneur to fully appreciate that her motivations and search for flow might not be aligned with the motives of people with whom she works (who may be more oriented to security-based ground anchors).

This deep appreciation for the motives of other people is often particularly important because the challenge-oriented entrepreneur frequently is highly talented with regard to short-term sales and visionary marketing. She can get other people to believe in her and the product or service she is selling. Then, when she abandons the project and moves on to something else, these other people are left in the wake and feel betrayed. The entrepreneur must confront these costs and consider a different kind of challenge—namely the challenge of remaining with the product or service she has invented. How does this type of entrepreneur find a way in which to stay excited about this project and to find flow in the daily work that is needed to sustain the effort? How does she justify the trust other people have placed in her as a challenge-oriented entrepreneur? These are the kind of challenging questions that this entrepreneur must ask themselves.

Lifestyle Entrepreneur

I turn finally to a very special kind of entrepreneurship—the life-style advocate. These often-flamboyant entrepreneurs are selling something more than a specific product or service. They are selling an entire way of life—they are selling anchors! The lifestyle entrepreneurs are producing and selling something that relates to “the good life.” Some are emphasizing nutrition or exercise. Others are marketing a specific form of spirituality or a fashionable way of decorating their home or hosting a 15 person dinner party. These entrepreneurs have ranged over the past couple of decades from Deepak Chopra to Martha Stuart, from Richard Simmons to Werner Erhard, and from Andrew Weil to Tony Robbins. In many instances, these lifestyle entrepreneurs are doing not much more than saying: “Live like me.”

Just as many professional coaches are inclined themselves to be challenge-oriented entrepreneurs, so we find that many professional coaches who focus primarily on the personal development of their clients are very much oriented toward lifestyle entrepreneurship. These coaches are often portrayed as sitting on their deck in Wyoming with the Grand Tetons in the background. They are on the phone with their client in Cleveland or Houston—extolling the need for their client to find their bliss or their bling.  Or they are portrayed sitting in a beach chair on Malibu Beach or on a Kona beach seeking to assist their downtrodden and overstressed corporate executive in Omaha or Toronto find their way to the beach and their spiritual core. The irony in this mode of personal coaching is that the coaching client often wants to fully emulate their coach’s lifestyle by becoming a coach themselves.