My story is probably buried here in an old thread, as this comes up from time to time...
Its a huge gut check. I bailed at 14 years. Here were some whys:
1. Flew 14 straight years...staff tour and remote both looming hot...
2. Wife had great career and was happy
3. Kids in school and happy
4. Had very nice house...not "dream house" but waterfront, good neighborhood, good schools, etc etc. Couldn't have afforded to buy another like it as prices shot up 2-3 years after we bought. (2012 that has changed...)
5. Had ANG job lined up
6. Had Airline job lined up (x 2)
7. Most important--ALWAYS dreamed of one day being an airline pilot, not a squadron commander
I'd say point 7 was as important as any. If your goal was to be a WIC IP, Sqdn CC, and maybe an OG the best airline job in the world won't make you happy. Conversely, if your dream is putting down roots, building a dream home somewhere or getting that family farm, no job in the military will take its place. I was on my to my 2000 hour patch in the Eagle, a big goal for me. That--and being an IP/Flt CC were pretty much my targets, and I hit them. I overshot my target O-3 rank by a couple pay grades...the first while active and the second while a Guardsman. In short--I had "checked off" all my mental target boxes. One of the most important steps in making this decision is being extremely honest with yourself about what truly motivates you and makes you tick.
Also--family is huge. If the kids hate your current place, and the wife it itching to move every 3 years...the military is fun. I am grateful I got to see so much of the world for my 14 years. Conversely, if you have a professional spouse who wants her own career too, it gets tougher and tougher to keep moving depending on his/her profession. Some kids--like my youngest--crave new places and would move tomorrow. She wants us to go back to Alaska--next week. Others--like my first two--take great comfort in the stability of being raised in one place and being part of a community.
My story has been storybook. My wife is very happy, and these days I am known around here as "Melissa's husband" as her career has blossomed. Kids are happy and doing well in school, including oldest off in college. I have my farm, my boat(s), my plane...all the stupid man toys that keep my spending too much. But ..this is important...
I got hired at one of the few companies not gutted by post 9/11 contracts.
I did a bunch of work in the ANG...busted my butt the first couple years working a lot of man days which may or may not be available in this environment....
I started a successful business....
I also started a couple unsuccessful businesses but didn't let them eat us up....
I had a spouse who LIKED working and also provided extra income and although never required could have provided health insurance and other benefits.
So--take an inventory of your life. What do you WANT? Do you have a plan B, C, and D if plan A stalls or spins in? Are you the kind of person who craves opportunity more or security more? There isn't a right answer, but you can be honest and do an assessment of your comfort level.
If you do bail, I have a few recommendations.
1. Stay in the Guard/Reserves. Its a great insurance policy, a back-door back to active duty if you need it, and a great place to stay connected to who you are NOW as you gradually adjust to becoming a civilian.
2. Put your spouse to work or at least educate them so they can work if required.
3. Don't move for a while. Lots of new stuff going on...hard to adjust to new job(s) and lifestyle if you are also changing schools, churches, and trying to move into new circles of friends. If possible, sit still 12-24 months, figure out how the new job(s) are going to work, and then make an assessment if moving is smart. Lots of pilots rush to buy in a new domicile only to discover they could have commuted happily OR they end up getting displaced. Nothing wrong with moving to be close to work--just make sure you understand the new job and stuff before disrupting the family.
4. Be ready to work hard. A lot of the success we have is because my wife and I were working our own business, our day jobs, and the ANG for a while. It wasn't easy, but it was satisfying because it was our choice. If you are looking to sit back and be taken care of, this lifestyle isn't for you. If you are willing to roll from a drill weekend into a 4 day trip, then do a little freelance research work for that DOD firm while on your layover--you are probably doing the right thing. When I worked harder in the military--I just go more work assigned to me! When I work harder now, I get paid more. Its a different game. Only you can decide if its for you.
By my math, I gave up about 17 years or so of military retirement (43-60) to get my airline career started, get a business rolling, and plant some roots. Provided the "contracts" hold...my airline retirement, guard retirement, social security, etc I will have come out way ahead this way. But even if any or all of those "guaranteed" benefits fail, I've had a heck of a good time the last 11 years doing what I love and getting to mix in some airline, military, business and family adventures. I don't regret it, and it worked for me.
Best of luck whatever you decide....