intertwingly

When I was in my twenties, I did not respect authority.  I colored outside the lines. When a teacher or a boss told me what they thought I should do, I asked "why?".  Most didn't like this much.  When I told others what to do, they didn't ask me why, nor did they particularly enjoy the experience.  I found the satisfaction of being able to tell them "I told you so" later to be quite hollow.

When I was in my thirties, I did not respect authority.  Telling people what to do and asking "why" continued to yield similar results with people who "ranked" higher than me.  But I found that more and more people were coming to me and asking me for my opinion.  Some of them even asked why.  Those that did seemed to like the fact that I would try to answer the question.  Once, one of the people who had sought my opinion remarked about my tendency to color outside of the lines.  My response was instantaneous: "What lines?".

Now, I am forty.  I still do not much respect authority.  I still occasionally ask why.  But mostly I plant seeds.  I do things that cause other people to ask why. Generally, the response is along the lines of "why not?".  When asked for clarifications, I rarely respond with generalities any more, I try to cite specifics. It doesn't always work right away, but I've learned to be patient.  Trying to rush things that can't be rushed doesn't work.  

I rarely have the opportunity to tell people "I told you so" any more.  Instead, I now have people who come back to me and say, "it would have been more helpful had you been more direct in the first place".  To which, I smile, nod politely, and resume my planting of seeds.