The great existential questions that have accompanied man throughout his history are really no more than a handful. But they are so resilient and constant that they transcend any given historical time, the culture where those questions are asked, the country that shelters that culture, and the traditions that sustains them. The thinkers of each new generation pick them up and rethink them from another angle, from another perspective, with new elements of judgment giving fresh new answers to the same profound questions. This philosophical essay hopes to explore only one of these huge questions: Why do we keep on repeating the same behaviors over and over (many times expressed as mistakes, or negative behaviors) as if we had not learned anything from those that preceded us? The following essay is but the effort of an amateur in the philosophical arena. I will attempt to answer this profound question for myself with a more satisfactory answer than the ones that I have received through my teachers. I fi rmly believe that what counts is not what some else has said, nor how he has said it, but that each one of us makes the personal effort of refl ecting on the same questions and fi nding similar or different satisfactory answers. This effort is what builds the personal outlook on life, its meaning and the ultimate quest for the never fi nished answers to those never ending questions.