Interesting set of observations......Allow me to add mine
Let's start with Money isn't everything, then I'll come back to it later.
1984, I just graduated High School, all I wanted to do was fly. I had a bunch of crap jobs (grocery, body shop, automotive machinist apprentice, Elevator finish resurfacing, underground sprinkler installer, pool installer) that paid crap to decent money but all sucked in their own way. I did them to pour everything I could into flying, splitting my time between KDPA and KARR. Inevitably I would always run out of money, then spend a bunch of time making and saving some, only to start three steps back from where I was. Along came marriage, a kid and then divorce. Facing child support payments, I took a job with an Armored car service. Tons of overtime, money was pretty good for then (late 80's) at about $30k a year for a guy with a high school education. But I worked so many hours flying was out of the question, and I stopped with about 30 hours logged.
I needed a way to make pay my obligations, earn enough to live on and have a chance to go to school (hopefully to fly), but having a lot of cash in my pocket (Don't laugh, in 1989 that was decent money) kept me from moving on when I really needed to, call it the bronze handcuffs if you will. Into my third year with Illinois Armored Car we finally had a robbery that involved a guard being killed, a guy I was hired with and went through training with. I got to arrive on scene to transfer the truck contents while he was still lying on the ground. That was the ticket, no job was worth my life in such a way, but what could I do? I made good money, I had bills so I couldn't just up and leave for school, besides I applied and made too much for Pell grants then, more loans? ughhh......
Happened to notice a set of recruiting offices on the way home the next day.
After a week of talking, some tests and a medical exam I had a report date for boot camp in the Navy. I knew in four years I would have the GI Bill, the Illinois Veterans Grant for four years of free school and a chance to get back into flying with no distractions, plus I would learn a lot, travel and serve my country. See my love of aviation started with stories from my father of his missions in B-25's and B-26's in WWII. I put in my two weeks notice as I didn't want to face the same fate as my friend who got robbed before I had a chance to leave. I drove a limo for three months while I waited for boot camp.
Navy money wasn't great, nor was the 12 on, 7 days a week schedule while at sea, but there was an end goal and it wasn't that far away. Besides, I got to work on some cool aircraft, see some great places, and make a lot of good friends. To add to that, NAS Whidbey Island had a flying club. PA-28-140 was $28hr wet, and an ugly C310 was $90. I started flying between deployments again, made it through my long XC and was doing final clean up and prep work for the ride, but time was short before deployment and money was tight, so I put it off, entrusting my log book of 70+ hours to my then wife for safe keeping while I deployed on a 6 month cruise. My wife moved on with someone else while I was gone, but in some bitter moment, burned my logbook. 70 hours and 8 years of training gone with a match in a minute. No big deal, I was applying to Illinois Universities with flying programs, I could make up that time and hell, arriving at school with all that background and training should make the first few courses much easier.
I was accepted to SIU Carbondale. Now out of the Navy I only had to wait a few months and I would be flying again. No big deal.
I was dual major, Aviation Flight and Aviation Management and having a great time. Got an easy A in Flight 101 lab as they had no idea I had previous flight training and just thought I learned quick. In reviewing my Navy training records with guidance folks they suggested I also enroll in Aviation Maintenance as I would get a bunch more credit hours for experience. I did that and before the second semester I took my papers to FSDO, got signed off for Airframes and General mechanic and took the written and practical. Got an instant 28 extra credit hours, cutting the AS in Aviation MX degree to 1 year.
It was in one of my Powerplant classes that an instructor introduced me to a Product Support Executive that was visiting from McDonnell-Douglas. We talked and he suggested I apply for a Co-Op they had. I had no clue what Product support was, but there was money involved, plus free housing and easy credits that would apply to my BS in Av Mgmt degree. I applied and was notified I was accepted, so off I go to St. Louis the next semester and end up writing Maintenance tasks for the Super Hornet for a semester, but I missed a semester of flying by doing it. Its OK, I'll make it up. ....well not really the next semester as I had a crushing class load (I was the idiot that would take 18 credit hour summers and 21 credit hour semesters. I was older, in school with 18 year olds who acted a bit different than my Navy friends and I just wanted to get out and fly).
After the second semester of Co-Op I was given a job offer, it was guaranteed for a year as long as I graduated. I was looking at $40k a year to start (1996), where the guys I was in flight with were barely making $20k, if they could find something. I still had child support to pay too. My choice was dump flight and MX as I needed every credit hour I could take to wrap up the BS in Aviation Management in the time I had left, or continue on and hope I could make it on a hopeful offer of $20k at graduation. I took the quick easy money thinking, well hell with this cash I'll just finish the ratings on my own (I only had a PPL and 90 hours at that point).
I settled in at McDonnell-Douglas and a short time later we merged with Boeing. I found out I was good at what I did and quickly started rising in the company. But each promotion required a move around the country, or overseas. The money was coming in at a good pace, but I was too busy or always travelling and could never find the time to get back to flying. Every other year was another promotion, more hours, more time in Europe or Middle East...and more money. In less than 8 years I doubled my starting pay. By the time I reached my last position at Boeing, C17 GSP Ops and Execution Sr Manager in Long Beach, I had lived in 5 states and two countries and my base pay was 2.5 times my starting salary, but with the COLA for moving to SoCal, it was four times my starting pay (yeah, with one of those "worthless" Aviation Management degrees

)
I found a bit of time and a very flexible instructor at KLGB willing to fly at night or whenever. I also found JetCareers around this time. I was going back for my Instrument at least, but it had been nine years since I last flew. Crap would I even remember how? Would I look like a fool? It actually came back quickly, I finished my review, got signed off and was on to Instrument training. I realized how much I missed flying, and in turn how much my cube job sucked. I had no more desire to move up at work, it just wasn't fulfilling. But my youngest daughter was born, I had to take a break again before I finished up my Inst. ughh, not again....
I got an offer at GE Aviation. More money than my base salary in California, with a West Michigan cost of living in a similar role, but with a bit less stress and no direct reports to me. I took it, moved and within a year was back to flying. Spent the next two years finishing up Instrument, Seaplane, Commercial and finally CMEL. Did it all with cash, so no debt. But my job sitting in a cube still sucks.......
So here I am, late forties, having made six figures for the past decade, but regretting that I took the easy money path 20 some years ago, because "I could get back to flying later". I have my tickets (actually doing CFI stuff now again), but not the hours. By the time I get the hours I will be 50, maybe 51. I'd leave my job in a heartbeat if I had a way to make enough to take care of my family (and they don't expect a mansion and new cars) and go fly. I just don't see it in the near future, though I haven't given up.
Don't pick a career based just on money. It seems really awesome at the time, but its not. Pick something you enjoy, something you wake up each morning and want to do. I'd give it all up if I could just go back 20 years........I see now that I made a mistake. Don't make the same one......
You can make a lot of money, but you can't buy time with it....
So anyone have a flying job for a CMEL with 25 years Defense industry Product Support and Program Management experience?

Oh yeah, I have an Airframes license if that helps.....but the last planes I worked on were Hornets and Intruders
