Along Abdullah Mahmoud Al-khenj’s experience as an Entrepreneur and as an owner of a Mini Delights trademark, which is specialized in desserts, there were many interjections and contradiction that other Entrepreneurs are rare to come across; however, they undoubtedly constitute a correct base to acquire important lessons to any Entrepreneur that wishes enter the world of SME or even for freelancers. Al-Khanji descends from a family in which their father used to work in the field of trade and real-estate; nevertheless, his beginning came through personal efforts; i.e., he did not rely on his family’s financial heritage to start his career, according to him. The other factor was that even though Al-Khanji chose to enter the field of aviation by himself, aiming to achieve clear career goals and then work for the Kuwaiti Airlines his unlimited ambitions, his tendency to be in a constantly motivating environment, his ever-burning passion to develop, and all of his other characteristics resulted in ending his career in office jobs; thus he moved on to the world of Entrepreneur s.The third and last contradiction was that despite Al-Khanji trademark’s-Mini Delights rapid successes, which resulted in transferring it to an international that reached the UAE, Al-Bahrain, and recently, Saudi Arabia, his career took an important turn because of his insistences to help other Entrepreneur s; hence, he begun to draw a new path for himself, aiming to become a lecturer and a trainer.