I struggle with this question when I write.  On the one hand, I sometimes feel like I am "repeating myself but with rephrasing".  On the other hand, I find that those instances of rephrasing adds content.  I often get accused of being excessively long-winded, yet when I shorten things too much, I get wildly misunderstood.<p>I find that many people don't have the context.  I suspect part of it is that I don't see the world the same way most people see it.  Shorter remarks rely on shared context to be properly understood.  Example:  In my teens, I remarked to my father that I was considering "running" (something).  I was a role playing gamer considering taking up gamemastering.  He assumed I meant jogging for exercise.  I didn't bother to try to correct.  It seemed futile.