Working in Aviation
I have not flown for a living in more than eight years, but I still want to respond.
Mostly, I always enjoyed the actual flying. My last job was training Middle Eastern students on a fat contract. The company for whom I worked was owned by three United captains. Its primary business was selling type ratings and training United applicants for the United sim ride. These people knew nothing about civilian flight training in light airplanes.
We did a lot of long dual cross countries in that job. The students really didn't need me along, but the managers insisted that we go along because (1) the company supposedly was hemmoraging and they wanted to earn revenue on the contract, even if it was a ripoff to the students' sponser and/or (2) they were ex-AF coneheads who understood nothing about civilian flight training and because of their military mindset felt that an instructor must always accompany a "student." In any event, although I was logging tons of multi time I rarely was touching the controls and was bored to death, mostly.
All I ever did in aviation was flight instructing. While it never really and truly seemed like real work, such as what I do now, I did relish the times I could put my hands on the controls. On the other hand, I was gratified every time I had a "pass" on an FAA checkride or a Riddle stage check.
The company aspects are probably not that different from other industries. I found that aviation is a real personality business. You meet all kinds of people and you have to be able to deal with them effectively. I had a boss or two who treated me as an adult and as a man. I encountered many more who treated me and others as punks (I was 40 years old!), who had horrible people skills, who were protecting empires and promoting agendas, and who were liars. I had students who were dedicated and mature, who were special people and ordinary people, and those for whom I felt that I was a high-priced babysitter. I worked with instructors who were professional and mature, and who were punks, politicians and backstabbers. I thought that I was through with such people after I left broadcasting. Then, I found many of the same types in the legal profession.
I don't think anyone likes to have his/her abilities put into question by checkrides. A lot depends on the type of checkride and how its conducted. I remember that I was scared to death on my first 141 checkride at ERAU. I understood that if I didn't pass it I wouldn't be hired. I did fine, but I found out much later that people were given multiple opportunities to pass their rides, and some needed the extra chances. So, I shouldn't have been so nervous. My other 141 rides there were pretty mellow. My 141 rides at FSI were extremely superficial, and at Mesa there wasn't that much to them.
My point to all this is it probably doesn't matter where you work or what you do. You'll always be watched and scrutinized. People are basically the same, no matter where you go or what you do. You'll encounter all kinds of people and will have to learn how to navigate around them. Just choose something you enjoy doing or at least like doing.