Self-sabotage Is Puzzling Why would someone intentionally undermine their success in achieving their goals and living their dreams?  Sounds crazy, doesn’t it?  You would think it would be just the opposite–intentionally taking constructive action to achieve that success, wouldn’t you? The Reason Most People Self-Sabotage The truth of the matter is, unless a person seeks to punish themself (for whatever reason) and chooses to do so by intentionally acting in a subversive way,  the reason why the majority of people self-sabotage is for self-protection.  They are fearful of something they believe achieving their goal (or even trying to achieve it) would bring about.  One female client (75 pounds overweight and.