Illini, some good stuff in there - between your other ramblings! Just don't get so depressing!
Enfuego, good question....I've sat here and thought about the question and I'm not sure, if you're a goal oriented person, you will ever have "made it".
As a professional firefighter a goal I had was to make officer (I did)....and to get to my pension (I will).
As a member of the military I had two goals: make officer (I did)....and get to my pension (I will).
As a runner...my goal was to break 3 hours in a marathon....I did...then I set a goal to break 2:55...I haven't...and probably won't (I'm getting older).
Financially I still have plenty of attainable goals ahead of me.
I think when I officially say, "I'm retired", that will be a day I can say "I made it". And when I get there it will mean I am financially secure and can be at ease knowing I have gotten all of my ducks in a row (income, medical insurance, will, estate planning, etc). It will mean I am comfortable and can sleep at night knowing I have set myself up for success.