I was 35 when I started, I'm 38 now, I just got right seat in a Lear 55. This is the path I took, it was tough, I had to sell everything I owned and now I live on less than I paid in taxes in 2001.
2001 PP-SEL
2002 PP MEL, Inst, comm se, me, inst, cfi, got my first job as a jump pilot
2003-2004CFII worked as a flight instructor
2004-2005 135 scheduled in a Caravan
2005-Now 135 Lear co-pilot
I'll add that it was 2002, when I decided to pursue the career. Is it worth it. I don't know, had I a wife and kids, I probably wouldn't have pursued aviation as a career.
I will say that I learned a lot along the way that I wish I had known ahead of time, it would have saved me a lot of frustration. For example, there are no cushy jobs for low time pilots, unless you get lucky and even then, don't try to skip being a flight instructor, or a jump pilot or one of the other traditional time building jobs. The experience you will get is invaluable.
Stash as much cash as you can, and if you can, double whatever you stash. You are going to spend about 20k on training, books, and other supplies, and then you are going to spend another 10-20k to build up enough time to get a job. Even though you can get your CFI-I and MEI, Multi time is key, and very few places are going to let a newly minted MEI in a twin to teach.
My recommendation is to get your CFI-I and teach a bunch, spend what ever extra money you make that you don't need to survive on to either split ME time with someone who also is trying to build time, or find someone who will let you rent a twin solo with minimum twin time.The more the better.
I think after the time building stage after you have the requirements for 135 IFR if you want to find a job flying, cargo, such as Airnet, Empire or Ameriflight would be a good option for you. You can start out in a Baron, or a Caravan, and work your way up from there. The living can be good, but the schedule may be tough if you have a family. Some guys just stay there and are happy. If you do that for a while, say you are 50 and you have 3500tt and 1500me, you might be able to find a corp gig that will carry you past 60 if you can keep your medical that long. But that will require intensive networking and there are VERY experienced and connected guys who still can't hook up. Timing and a little luck are everything.
So, it can be done, but it all depends on how much you want to sacrifice.
Do I think it was worth it?? I've had a lot of fun, especially flying the Caravan in Hawaii, one of the most fun jobs I think I've ever had, and now flying the Lear, when I'm on my way home after a trip and it's been my leg to fly, I'm on top of the world. But when the thrill wears off, and it will, finacially, I'll tell you in a about 3 years

If I'm still eating Top Raman and Tuna, probably not.
good luck,
sb
PS.. ha!! listen to me.. I sound like a freekin old timer.. Hey, I might even know what I'm talking about... I'm sure that a few of you who read this will remember me asking the same questions a couple years ago. Thanks for all your help
