I have to be honest.. I have had this same quesion come up recently.
I was whining to my boyfriend about going to my reunion in a few years and not being able to say that i had my own business and made lots of money each year. He bitched to me asking why I even cared what they thought.. and it got ME to thinking..
If i went to my reunion and couldn't say that I was happily married and a mother of three.. I wouldn't care. If I couldn't say that I worked for a big ,multi-million dollar company and had benefits and worked in a cubical all day.. I wouldn't care... because I don't want any of that for myself.
But if I couldn't say that I owned my own hair salon and clothing shop then I would be ashamed. The reaoson is because, similar I would supposse to the Saturn return, many of us view events such as our reunions as a checklist and time line of what we have accomplished in life. "Have we accomplished any goals we had set for our 20's?", deadline would be th 10 year reunion. Then there are goals you set when you'r ein your 30's and so on.
When we know we are going to run into an old boyfriend or whatever we get nervouse if we don't look a certain way or are living a cartain lifestyle.. not because we are envaloped in what someone we barely know thinks of us, but because it makes us re-think about if we have reached our own personal goals in life. It makes us look at the things that we always wanted and if we haven't gotten them, it makes us think about what we should be doing instead of what we ARE doing, to make those dreams come true.
If you look good and you want to show off at the reunion.. it's a great pat on the back because YOU reached a goal that YOU had for yourself.. most likely not a conscious goal or deadline, but you did reach the deadline. The deadline can be any time mark that means somehting to you.. makes you look at yourself and re-examine your life and makes you look at what you've done with yourself compared to what you would like to be doing.
I have started to hustle thinking about if I would be proud to tell others of my accomplishments.. meaning am I proud of myself for what I have done over the years?
I think I have gotten lazy and lost sight of my goals lol.. but that reunion.. even if I decide not to go, has woken me up to focusing again on them

Congrats!