Excellent thread with a lot of good info. This site is the best!
My two cents.
I think most people concern themselves with the financial aspect first-and that is important-in particular if you still have a mortgage or a lot of other debt hanging over your head. Debt is non discretionary-you have no choice. So while you can always avoid buying a new toy or taking a trip, a mortgage payment is another thing. So for you "young" guys who are looking down the road, think of that-will you be done with that mortgage by the time you want to pack it in?? If not better adjust that retirement date.
The next thing in my mind, is having "another life". Most responses have covered this-if you don't have other interests and the ability to AFFORD those interests that is a problem. My guess is, by their nature most of the people who frequent this site have plenty of interests-regardless of its color-green, orange, blue etc.
One thing that I don't think has been mentioned or not stressed enough is your personal surroundings. In other words, some guys worked forever because they couldn't stand being "around the house"-if you get my point. Not a good thing. When I retired, I asked a co worker who was older than I.."so when are YOU going to pack it in". His answer-"are you kidding? my wife takes care of 7 grandkids". End of discussion. If your wife is going to drive you nuts in plain English, you can't have enough hiding spaces.
In retrospect, I've been "out" 3 years in May after 44 years and a few months shy of 67. I felt great and enjoyed my work but was in a position in which when my phone rang at 10PM, it was not good news. I can tell you, when the phone rings now, I don't clinch my teeth!
So to those of you sitting on the fence, hopefully all of these posts taken with a grain of salt will serve you well. And the fact that you are reading them puts you one leg up on the situation.
Good Luck:thumbsup: