How are you supposed to handle the higher rank jobs?

So how are you supposed to deal with the health/happiness penalties tied to the higher jobs?
I can’t seem to find a way. You don’t make anywhere near enough money to keep boosting items going, and events don’t come anywhere close to what’s needed.

I might be able to get 15 Happiness from an event. But I’m losing 50+ for a day’s work. Which is insane.

Are we just not supposed to take the higher jobs?