Answer: With his track record, Greg had enough confidence in his ability to innovate and develop a new business model. If at this point, he had been thinking only along traditional career lines, Greg would have been extremely limited in finding a job that he knew fit his entrepreneurial talents. He had already realized a senior agency role was not a fit and he was not qualified for a top corporate position (which had drawbacks in any case.) Here is where I see the values that shaped Greg and his ability to work at the ground level with clients, coming into alignment.
He launched his own company offering consulting services and created a product for a niche market reflective of his rural experience. It is about location-based marketing. It is founded on the belief that an investment in presence (seeing/being at a location) led by storytelling, results in informed visitor/customer decision-making. From that premise, he created messaging and software to support chambers of commerce efforts (with limited budgets) that encourage visitors to explore local regions. Greg could personally present the idea to clients by attending local chamber meetings/conferences and arranging demonstrations.
Greg pursued this concept, while continuing to accept consulting projects that brought him income. He also launched his company. It took several years to become successful. Meanwhile, he was able to experiment with lifestyles that fit his family. At one point he lived on an island with a small town but ultimately found that was too difficult to travel for business. He then selected a small city that was several hours away from his client base and purchased a home. He could then commute to clients or find temporary quarters for short stays. That adjustment seemed to fit their needs, but it did take some experimenting.