Jerry was a 20 year old young man who was the son of a very successful small business person who had founded and run a well-regarded construction company for over 30 years.  Jerry had a core belief that he was destined to take over the business when his dad retired. This is a common expectation in these family-owned businesses and one that is fraught with problems.  Jerry did not want to own/operate the business, and upon careful assessment, including business based personality profiles and in depth interviewing, it was clear he did not have the aptitude nor interest to do so.  His path lay in another direction, although that direction was not yet specified.  Careful conversations with Jerry and with his mom and dad (separately), enabled us to to allow Jerry to pursue a different path, free of the guilt he felt at not “having” to be the heir apparent.  It also allowed us to explore other alternatives for the father’s eventual exit planning through building a more engaged and aligned management team and the recruitment of a key employee who was seeking a business to buy.