Moosepilot had some interesting data points...I'll share mine...
I left active duty at 14 years. I took the first bonus at year 7 because the airline I wanted (Delta) wasn't hiring big in 96 and I was marginal on total time for Fedex or Delta. I also was offered the job I wanted a long time--an F-15 to Europe. So...I've been a company man and "stayed blue".
I left in 2002 at 14 years...passing up an active duty retirement to fly part time in the ANG. So I've been a "quitter" too...
I also elected not to pursue an AGR full time spot AFTER I had started at FedEx and had enough points to coast less than 5 years to get an active duty retirement. I realize for many, the 20 year retirement check is the "Holy Grail" of financial security...but I passed on it. Here's why:
The biggest gripe I ever had with active duty was never the money, it was the constant hectic pace and inabilty to control any of my life away from work. The wonder thing about the ANG and airline life was I got a "vote" in what I did next. I got to build equity in a home, start a business, become a church committee member, etc etc. I'm not saying you can't do those things active duty, and I've seen some uber-officers pull it off..but for me my life is so much happier and richer NOT having to move every 3 years and being able to have a few more days off here and there. And, as someone else pointed out--I like being able to work MORE or LESS based on our time/money tradeoffs at the time. Working in the AF was based on real world contingencies, ORIs, and needs of the service--they determined when and how much time you'd get off. I passed on the AGR option because after having the ability to have lunch with my wife on a Tuesday or go out of town on a whim to visit family or friends, I became addicted to that freedom. After a couple years of relative freedom and control surrendering that back to the organization just seemed too big a bite to swallow. My wife was happy, my kids were happy, my business was taking off, and I just didn't want to drive to the base EVERY day for 5 more years. I figured that while on paper the AGR retirement was a better deal financially, the price for it was higher than I wanted to pay. So--I allowed myself the abilty to not "maximize" every decision and follow my heart for a while. And...you know what....we were blessed. Our business(s) have done very well since then , we have moved into new areas (a horse farm), and so far life is good. Your mileage will vary...and we all have to go our own path. But for me...its been a wonderful life on the outside. Its been a gut check, but put us down in the W column. Watching guys get out now (about the time I could have retired) and seeing SWA not hiring and 1200 names behind me at FedEx lets me know the first decision to bail was smart. Passing on the AGR has allowed me to do some things I wouldn't have been able to do as well...it just put that check of the month on hold 17 more years. I think we'll squeek by between now and then...
Now--I'm proud of my service--and I woundn't be who I am today without the training and skills I learned as an officer and pilot. And I probably wouldn't have the professional credibility, either. However, what was perfect for me at 25 and 30 wasn't the best fit at 35 and 40....life changes, we change, and our goals change along the way.
What I can say is my experience financially has been outstanding since I left the service. I lost my pilot bonus in the 2000-2001 stock market downturn. However, since then I've gotten a great airline job (FedEx), started a business, and my wife's career (since we aren't moving!) has blossomed and she does some great work too. A real estate deal or two have gone well, and so far, so good. So--if you look beyond your airline paycheck and see what your dreams are, you can do okay on the outside. Airtran or Jetblue won't make you rich...sorry. However...if you have other skills or interests outside of flying those jobs will afford you the time to try your hand in other areas.
Whatever you do---I like the ANG/Reserve until 20 option. You still get to be on the team fighting the bad guys, even when the organization is still sometimes a pain in the @ss. You've got a small safety net with money and insurance down the road if necessary.
Good luck. This is a great thread and I wish everyone the best--whether they stay or they go...