Your post is reflective of the situation in which a high percentage of pilots find themselves at some point during their careers. When I started flying big airplanes for other people I was a bit older than most in the field, had accumulated a stash that eliminated any money worries for our lifetimes and had a long background in financial planning and related issues (taxes, strategies, techniques, yada yada.)
As a result of these circumstances, the word got around and I found myself somewhat besieged for advice by the guys who had reached (or were approaching) the same age level and uncomfortably contemplating what they needed to do about their as-yet-unfunded retirement. Frankly, many of them are in a world of hurt. On a side note, has anybody noticed how many former GA pilots take jobs with the FAA late in their careers? Anybody ever wondered why? Does anybody really think it's because they want to work there?
And as recently as last Friday I was involved in a round of discussions with pilots and MX personnel whose professional and highly-respected flight department is being eliminated due to a buyout. Ten pilot jobs and almost as many other flight department jobs are out the window, only a few of which are held by young guys who can easily cut back or start over. Why? Flight departments don't survive hostile takeovers.
Then over the weekend and yesterday I was involved in several conversations with career pilots in their 40's during which all of the frustrations, uncertainties and financial issues were aired. These issues haven't changed for the 25 years I've been involved in the staffing side of the industry and never will. The reason is simple. In spite of all the bluster and bullshlt "when I'm flying this jet, I'm the boss" pilots simply have no leverage.
A good friend is a former 121 pilot who bailed out after reading the tea leaves and now runs a financial planning organization with a number of pilot, FA and other aviation-related clients. Many of the stories are heart-wrenching, especially the lost retirements.
For kids like David who are flying and thinking they have good jobs, my question is whether they will be able to buy their 17 y/o kid a $100k Mooney. I've been playing and watching this game for 52 years since my first opportunity (that I declined) to fly for TWA, and have yet to meet a pilot who has become wealthy from sitting on sheepskin seats. If it's such a great career, where are those guys?
I did well. I was able to put my wife through school, pay for my family's needs and garner a comfortable retirement. Admittedly my wife will make 10X what I earned over her career compared to mine, but I got immense satisfaction out of my flying career and got to do and see things most can't imagine. I met and flew with some of the most gifted and inspiring folks on the planet and helped a good number of folks along the way. I do not think flying for the majors would have fit me well, but I lucked into my niche, with some hard work I admit, and wouldn't change a thing. I don't think a lot of folks in cubicles can say that.
I paid $22K for all my ratings. As a CFI I made $30K in a SwissAir contract. Good money for the effort and the effort was minimal. M-F with top notch students. They were all already hired and all they could do was lose their job. Talk about motivated students!
After that I did my regional airline thing. Upgraded within a year in a CRJ. Times were good. Topped out at around $65K and things began to slip backward. Displaced to FO. Furloughed.
New job at the worst airline ever flight freight...Amerijet. Told some stories here that ended up getting the thread locked. The stories were true though.
Now I fly corporate. 15 years into this 'aviation' thing and I'm making more money than ever. I'm clearing around $108K per year for a week on / week off sched. So I get $108K for 6 months work minus vacation.
Maybe I've made it. This is the goal...
But, my company scares me every payday. I don't know if I'm getting paid or not. I text my bank every payday morning at around 2am to see if Im going to get up and fly or not.
For the past few years my family has refused to pull the trigger on big purchases like cars due to the uncertainty. So both our cars are fully paid but mine has 125K on it and my wife has 150K. We are going to have to do something soon...but I know not what.
We are going to England this summer. My wife was born there and all her family is there. She hasn't been to England since 2003. I don't like spending the money to go now but find it hard to deny my wife from going home at least once a decade.
So, there's a glimpse into how a pilot who has maybe 'made it' is doing. I do not look at myself as have making it. I know there are tons of guys that have and I don't count myself among them.