To Be or Not To Be

There's something so inwardly depressing about working at a place where co-workers who retire from that place have worked there for the last 30 years or so, or they've already been working there for 30 years or so ... they may have been excessively happy and may have found it meaningful and challenging work, but I always see myself as that person and I think I would be disappointed in myself that I didn't make an effort to find a way to make a living doing something I love or that I had aspired to do. Maybe it helps explain why some people seem pretty ecstatic about retiring. They can finally do something they choose to do that they love. I remember at one job, a guy who liked to tell everyone he'd worked there for 27 years (it would be 35 years now, unless he's retired), and he'd pull the young newcomers aside, every one of them, and tell them they/we don't want to be stuck there for 27 years like him, and that they/we should go apply up the road for a federal job and be a janitor and it would be way better than staying there for 27 years like he did. As far as I know, I don't think anyone ever took his advice.
Since about March, I've come across disappointment after disappointment at my job, and it's really been getting to me. I'm just wondering if I can turn it into a more positive environment, and if I should work harder and smarter. I think of all the other jobs out there, and not a lot appeals to me. Maybe I've always been too selective. I'm so selective that eventually I give up and figure that every choice has its positives and negatives and end up randomly selecting whatever sounds good at the time. I guess you'd call that wafting in and out of existentialism.