I hired out as a loco fireman in 1959 and retired from a railroad related job in 2000. Lots has changed in the railroad industry over the years, but if you like trains working in the industry has the potential to be a lot more "fun" than just working any old job. I joke I was paid to chase trains. But you do need to separate business from pleasure. But how you approach it depends a great deal on what you really want to do, where do you want to end up. I started out in engine service but ended up doing international railroad finance. But I have good friends who started out in engine service and were perfectly happy to retire in engine service. One is not better than the other, but it depends on what you want to do. Class I railroads are big organizations with all the "politics" of that kind of organization, no different than any other big organization. Some thrive on that. Or you may want to work for a shortline with a simpler organization (but "politics" is everywhere because it is the art of getting along with other people). No simple answers, but if you like trains why not try to make a career doing something that you have a passion for.

JBWX