I would probably do what most on here already said, keep your day job and get all your ratings on the side and then instruct when you have free time and build up your hours in this horrible hiring environment. Then when hiring picks back up, you have the option of shooting in a resume or staying put at your current high paying IT job.
[QUOTE=pompeync;484875]I try to be realistic and realize I will never be flying 747's on Pacific routes or 777's on trans-Atlantic crossings, but If I could get back to what I am making in my IT job, but flying, then I would be "living the dream".
The person who thinks he can and the person who thinks he can’t are both right, just pick one. Sure you are 40 now, if you work hard at your training and finish all your ratings in 18-24 months and then flight instruct for another 2 years, you would be 43-44 with a decent amount of flight time for the regionals. Add another 5-6 years at the regional level and you’ll be ready for the majors. So now you are 50 entering the majors with 15 years left to at least make into the right seat of that 747, 777, 787, or 767 on a trans-atlantic crossing!

This is all a very, very long shot, but doable providing that the economy holds up and you survive furloughs. Now that’s what I call a gamble if you dare!