Covering the almost 40 years of my career story would fill pages, so I'll abbreviate.
I've lived in the NY metro area my whole life. I was an almost prodigy musically, starting on piano and moving on to organ and voice. My parents were gracious enough to get me good teachers. I started playing professionally at age 12. I was an under-achiever in high school except for music, where I was the accompanist for the school choir, sang with the barber shop quartet, played keyboards in the jazz band, and played harpsichord with the baroque orchestra and with two baroque ensembles; I also worked on the school plays. I was regularly employed musically at 16 as a church organist and played piano and was audio tech for a dance school. Almost all my money went into buying equipment. I had a Wurlitzer electronic piano, a fire engine red Acetone organ and a Moog synth with a nice mixer, amp, etc. at 16. And, of course, there were the obligatory rock bands.
After high school I followed the "I want to be a rock star" path. Lots of crappy gigs, lots of partying, lots of groupies and lots of fun. However, I still worked day jobs (pumping gas, waiting tables, etc.) in addition to the bands, the church organist and dance school gigs. I still managed to practice a couple of hours a day. I was fortunate enough to be heard by and have a long discussion with John Hammond (
http://en.wikipedia.org/wiki/John_H._Hammond). That discussion changed my life. He told me, bluntly but kindly, that I would never, ever be a "rock star", whatever that is. However, I had all the makings of a "side man", musical director and arranger. And that is the path that I followed. I also got to know Tina Weymouth of Talking Heads, who advised me that I could spend my time and money partying or spend it on my career, advice I took to heart. I did cover bands and hotel bands (spending my time practicing while my band mates were drinking, drugging and wenching), and worked my way up the ladder to become musical director for the Del Vikings (
http://en.wikipedia.org/wiki/Del_Vikings).
It was not until I was well established with the Del Vikings in my early 30s that I had anything resembling a personal life. I finally married my long-time girl friend, we bought a house and had our first child.
I was completely career driven until I had reached my goal. But it's only something that you can do when you're young and don't have "responsibilities" (although I did manage to reinvent myself in my 40's when arthritis curtailed my performing career). I was also fortunate enough to get some honest, objective advice from "heavy hitters" in the biz.
The point of all this drivel is to say that now is the time to pursue your dream while you're young. The problem is defining you goal, and knowing when to change your career path. If you want to direct you have to find the place that will present the most opportunities, and then you have to relentlessly, ruthlessly pursue that goal. Everyone believes that they are the next big ______________ (fill in the blank). But at some point you have to honest with yourself, and have something to fall back on.
So sit down and have a long think about your life and your goals; you'll figure it out.