Time to Cut?

Let's talk about hair.  Primarily the length of hair.  At what age do you think you should cut your hair and go for a shorter style?  Or do you think long hair is always the way to go?  Or are there other factors that come in to play?  Your career?  Your social life?  Maybe how much time you have to spend getting ready every day?  My hair style is like a roller coaster.  I spend months, sometimes years, growing it out only to get a glimpse of a cute cut and then I chop it.  I generally keep it short for a cut or two and then I start growing it out again.  And so the cycle continues.  I think I'm coming close to the top of that roller coaster hill right now.  I've been growing my hair for several years, with the normal trim to keep it looking neat.  Lately I've been itching to cut it.  Here are a few reasons why. 
1.  I recently went back to work full-time in an office.  This requires me to get up very early and actually get ready every morning.  The amount of time I want to spend on my hair is getting shorter and shorter. 
2.  I have really thick hair.  This can be a good thing or a bad thing.  It takes me a long time to dry and style it.  On the flip side, it holds a style pretty good so I generally can stretch out my washes. 
3.  With working and trying to keep a full schedule with the kids, I'm on the go a lot more now.  I find myself fighting to keep my hair out of my face.
4.  The "it" style right now appears to be about shoulder-length hair.  Its everywhere right now!  And I for one am loving it.  I like it worn straight and curly just the same.

Reading this list makes me want to skip out and go get a cut right now!  Then I quickly start thinking about the negative to having short hair.  Here are few that come to mind:

1.  Its not as easy to pull it up when you are in a rush.

2.  The different ways to wear you hair is more limited.

3.  It sometimes can require just as much, if not more, work to make it look good.

4.  I'll see someone with long hair and wish for mine back :(

So there's my dilemma.  Do I make the jump and go for a new style?  Stick to the long hair and fight through the urge?  What is your current hair situation?  Do you also suffer from hair-envy?