20 year career, huh? Well, let me give you some of the experiences I've seen from my time in the fighter community as a WSO (and remember right off the bat: there is no TYPICAL pilot career. There are MANY paths folks go down in their careers. I think the saying is "Results are not typical...")
- Pilot training. Between your start at Flight screening until you get
assigned (selected into a specific airframe) = typically 1 year. Assignment to an airframe usually is based on your class ranking.
- Flight Training in your specific airframe (and since my background is fighters, I'll use them as the example) = about a year. Learning the airframe, and how to basically employ it. You'll also throw in some other training either before or after, like land survival and water survival.
- Arrive at your first Ops unit. Typically spend the next 3 years there (unless its an "unaccompanied" overseas assignment (i.e. not married, no dependents), then they can be shorter. Spend the first 3 months or so of that first assignment going through "Mission Qualified" training (learning how to employ to operational standards for each unit). You'll be a "wingman" (lead by someone else), and you'll spend the three years working towards upgrading to 2-ship flight lead (you lead someone else!), then 4 ship flight lead (you lead the basic combat package for fighters!)
- 1st Permanent Change of Station. Lots of folks try to go to Squadron Officer School (SOS) between leaving your first Ops base en-route to your next one. 7 weeks in sunny Maxwell. The AF "Cheer-leading" academy.
- As a fighter pilot, most want to do an "Ops-to-Ops" next assignment (go from one ops tour to another). Your "hard-chargers" and "golden boy" pilots usually get this. The rest go for an "Alpha" tour (something other than flying, as a "career broadening" move). I'll assume you're a "golden child". You spend this second Ops tour working to upgrade to "Instructor Pilot", the guy who teaches the newbies and enforces the squadron standards. If you are THE golden boy, your leadership will be grooming you to go to
Weapons School. I would say think "Top Gun", but Top Gun is not even close (WS is 6 months long, Top Gun is 6 weeks). "Patch" wearers (WS grads) are groomed to go back to an Ops unit and become the Instructor of Instructors, the Weapons Officer in the squadron, sets the standards, drafts new tactics, and overall they are the guy who leads the squadron into battle (next to the Commander, of course).
- OK, you've now done 2 Ops tours (maybe 3 if you went to WS). You'll be getting close to competing for Major, if not there already. I'll assume you have continued to be a "superstar", and you got selected to attend an Intermediate Service School (year long school for Majors) along with your promotion to Major. The really good ones get to go to a Sister Service School. Each service has one.
(Oh, Btw, I haven't mentioned "Gate Months". Every month you're flying counts towards your flight pay. You have to make a certain number to guaranteed flight pay for a certain number of years. I think the number is 120 months (yep, 10 years of flying) to guarantee flight pay (which maxes out at $850/month) to the 20 year point. The AF manpower folk strive to get every pilot who wants to to at least their second gate, and usually their 3rd (so you'll get flight pay for the full 20+ you are in).)
- Graduate ISS. Go to your next assignment. Most likely some staff job somewhere, like the Pentagon or a Major Command's (Like Air Combat Command) HQ. Most folks do that for 3 years.
- But you're lucky -- you made some "connections" in the past. Former bosses (i.e. squadron commanders) who have moved onto to higher things, remember you (they most likely were the one to groom you for WS), and want to "hire" you to lead a squadron somewhere. You get to leave the Staff after 2 years, and become an "Operations Officer" in a flying squadron (second in command). This is your "job interview" for a future squadron command position.
- About this time, you'll also be competing for Lt Col. You've been a superstar so far, so I'll assume you get it. And you've been selected for Senior Service School in residence as well. You Wing Commander, who thinks you are "his guy" wont send you. His reason? Well, he wants you to be his next....
- Squadron Commander! Perhaps the best job in the Operational part of the AF. YOU are leading the men and women under you, at the tactical and operational level. The squadron is yours to lead to new heights, or new lows (I've seen and experienced both). 18 months of the best days of your life, topped off with taking your troops downrange as part of an Air Expeditionary Force (AEF). Of course, this is assuming we are still in combat somewhere...
- OK, hot shot. Decision time. You'll finish your squadron command sometime around your 18 year point (yep, it went that fast). Do I stay and try for O-6? Based on your career, your a shoe-in. But if you accept that rank, you have to stay in at least another 3 years to retire at O-6 pay (i.e. more than 20 years). Also, the AF KNOWS this, and knows you won't turn down that sudden "you're moving to Iceland" notification. Tours at O-6 normally last about 18 months, and unless you're on the track to be a future General, most of the jobs are NOT in flying.
- But I'll assume your in for a penny, in for a pound, being such a superstar and all. You go to SSS, pin on O-6, and do ANOTHER Staff tour after wards. Then, about a year later, you get the call: they want you to be the "Operations Group Commander" at a flying Wing (the person in charge of all flying operations on the base, second only to the Wing King). You're now at that 22 year point or so, eligible to retire as an O-6 if you want. Then comes the real hard choice. Do I stay, or do I go? Have I made enough "clout" to one day get that Star o my shoulder? Or do I answer that call from an old buddy of mine, hooking me up with a great second career. The choice is yours.
OK, long enough answer. And like I said, the results aren't typical. In a "bottom line" answer to your question: most likely you WON'T fly the full 20 years in your career, you WILL attend graduate level schools, you WILL get a Master's Degree, and you WILL move (A LOT! 11 times in my 20 year career).
But you're a future superstar. Come back here in 25 years and let us know if you decide to stay and try for that Star on your shoulder!