I have more than 40 years of flying under my belt and loved every moment of it. Looking back, would I do it again? Probably not.
I was the classic aviation addict. Model building and flying, reading all available literature on aircraft and aviation.
My father, who had dropped out of a law degree at Cambridge to volunteer for the RAF when WW2 broke out, was an ex-Cranwell instructor and Mosquito pathfinder and had ended up as an airline pilot. He saw all the signs of addiction, and knew the implications. He warned me to get qualified in something else, then look at flying, but I knew best.
I was obsessed, and very lucky. I soloed at 16 , had my PPL at 17, got my first command at 19 in a Beech D-18S. A year later, I was in the right seat of a corporate Gulstream 1. This was heady stuff, and my luck and passion held. By 25, I was chief pilot for a small commuter airline, by 30, Ops manager. a couple of years later I was flying jets. I was in heaven.
Then the creeping erosion of the job started, first of all pressure on T&Cs, then a blizzard of paperwork, leaving a paper trail from before on-duty, until after off-duty, recording minute details of everything.
Then 9/11 hit and security paranoia made everything that much more of a hassle.
It was a good life up until 9/11 but by then the economic writing was already on the wall, and I was just hanging on to make retirement and qualify for retiree travel.
No sooner have I retired, than my employer decides to go out of business, and my retiree travel is evaporating. Due to several re-structurings, my pension is lousy, and I probably won't be able to travel during retirement as I had been planning. I may even have to take a "Sears job" to help make ends meet. (411A please note; no boat, no alimony, same wife for 30 years.)
Then I look at my cousin's son, who went into oil 8 years ago. He is now a directional driller, and makes nearly 3 times what an airline Capt at a major carrier makes. He can afford an airplane to play with. I think if you love flying that is the way to go.