Hi Pharoah,
I'm 44 and started flying at 28 after another career and stayed in that career whilst training part-time.
The Green Goblin has it all figured almost exactly and whilst funny, you have to be careful that you don't keep driving yourself towards the jet job
at any cost.
I personally started out doing some multi-engine charter with my own business but it cost me a lot and didn't really take off so then got an instructor rating and ended up doing s/e charter which lead to theory instruction and eventually flying. I ended up getting my multi-engine and instrument training approval as a grade 2 which made a huge difference as every hour over 1000 was multi.
Thereafter did some multi charter. regional airline for 5-6 years and now s/o for a major carrier. In one sense I got to where I wanted to go and real proud of what I've accomplished but you will get asked in an interview about how you feel flying alongside a captain who is 10 years younger than you and whilst I always ( and still do feel ) felt that if they're more qualified than I am they'll always have my respect. Thats true but sometimes you can't help feeling that you'll be doing that training when you're 50 but thats what it is.
What I'm saying is that I worked my way up from a junior in one profession and it just feels a bit challenging as you get older because in some respects it would be nice to be at the
top of your tree in your mid forties rather than looking down the barrel of another several years before you get the chance ( if ever ). With the benefit of hindsight I'd probably stay as a regional captain and enjoy that life but I wouldn't change from what I'm doing as I still get a thrill to be doing long-haul and be living that lifestyle and its enabled me to live a very different lifestyle than I would as a regional captain.
Look very carefully at every stage and if you like it maybe thats where you want to stay.
I didn't hit the majors til 42 so never give up on the dream. Every moment was a blast for me and still is.
Good luck with it all. There is some good advice in these posts especially from Green Goblin and Gear up.
GUARD
