Originally Posted by DashAviator

Disclaimer: I was never a controller.

We had a retired Air Traffic Controller here who spent a few years working at our regional airline. He hit age 56, retired from ATC, and almost immediately came to work for us as a pilot. He'd done quite a bit of flying on the side while he was in ATC, so he already met ATP minimums at the time he was hired. I can't remember if he ever upgraded or not, but he sure seemed to enjoy the heck out of flying the Q400 and helping out with new-hire ground training. Nice guy.

After reading your post, my recommendation is for you to keep your day job until you meet the basic qualifications for some kind of flying job. Right now, you don't. I'd suggest you get VFR and IFR current, finish your commercial certificate, multiengine rating, and CFI/CFII (if you plan to instruct). At this point, you could probably get a job as a flight instructor. It won't pay $150K a year, but would allow you to build flight time toward ATP minimums.

I made a career change from engineering to flying when I was in my mid-30's. My part-time job as a flight instructor allowed me to build flight time and experience, and my "real" job as an engineer paid the bills. The pilot job market was terrible at the time, so I decided that I wouldn't leave my engineering job until I had my ATP certificate. I figured at that point I could maybe get a job doing something. It was a hard few years, and I ended up living in my car for while. In retrospect, I'd say that it was worth it, but I also think that most normal people wouldn't be willing to put up with what it took.

Good luck!