There is yet another personal challenge being faced by many service-oriented entrepreneurs. They often don’t know when to give up. It is not just a case of setting an appropriate balance between personal needs and the needs of their community, it is also a case of being realistic about what can and what cannot be achieved. In this regard, the service-oriented entrepreneur resembles (and often emulates) the creative entrepreneur. Both types are likely to be risk-takers, who don’t know when they have reached their limit. They don’t give up. As Jim Collins has noted, this sense of persistence is a great quality in a leader—but it can also be carried too far and lead to disillusionment and burnout. Like the managerial entrepreneur, service-oriented entrepreneurs are is inclined to take on full responsibility for the project in which they are engaged. They are not only likely to take on the challenge of fighting a large, fire-breathing dragon—they are also likely to take on this battle single-handedly and are likely to persist in this battle, even when bloody and exhausted. A coach is needed to provide substantial support to match the challenge being faced by brave (but often unrealistic) service-oriented entrepreneurs. If nothing else, the entrepreneur’s coach can be there to provide thoughtful and empathetic support in witnessing the battle first hand or listening to the tales of struggle and, hopefully, occasional triumph.

Challenge-Oriented Entrepreneur

Some entrepreneurs don’t have much of a game plan. They just leap from challenge to challenge. Of all the entrepreneurs, the challenge-oriented entrepreneurs are least likely to have much of an anchor at all—other than the loosely tethered anchor of ongoing challenges. These entrepreneurs tend to move from project to project. While they may make quite a bit of money along the way (and may lose quite a bit of money as well) they are most likely to be motivated by a major challenge: “They said it couldn’t be done and I have done it!” Howard Head offers a prime example of this unique type of entrepreneur. Head founded the Head Ski company in 1950. His aluminum and plastic laminate skies revolutionized the ski business (moving from the much heavier and inflexible wood skies). This wasn’t enough for him. He was easily bored and was apparently quite difficult to work with. Having retired and taken up tennis, Head soon reinvented the tennis racket and got involved in diving equipment, as well as tennis balls, sports clothing and athletic footwear. He was always involved in the invention, production and marketing of merchandise associated with sports—but he was all over the place within this broad field and never seemed to settle into one niche.

In recent years, considerable attention has been devoted to the attraction of many people to challenging conditions. Czikszentmihaly studies and writes about something he calls the “flow” experience—which is the highly motivating threshold between boredom on the one hand (too much support and not enough challenge) and anxiety on the other hand (too much challenge and not enough support). Challenge itself becomes rewarding under conditions of flow– especially when the challenge is balanced off with support. Rock climbers and chess masters live for moments of flow. They are always looking for those occasions when they can be intensely focused and when time seems to stand still. The challenge-oriented entrepreneur is similarly looking for this flow experience and will move from project to project in order to find flow—and avoid boredom. These men and women are constantly seeking stimulation and are looking for difficult problems they can tackle. Such people will often change jobs and their career can be quite varied.

While these entrepreneurs can be quite successful, they often don’t move beyond start-ups. As short-term entrepreneurs they often sell their business (as did Howard Head) and move on to something else or look for product-lines or services that will be short-lived (fads).  Like the legendary miners of the Gold Rush era in California they move on to a new potential vein of gold. Ironically, many people who do coaching exhibit this form of entrepreneurship and remain in the field of coaching for only a short period of time which it is still “hot”. The field of coaching itself might not be able to endure as something more than a fad if it is primarily occupied by challenge-oriented entrepreneurs.