were those jobs fun? Certainly havent been for me

To a certain extent, you always have to manage your boss, whether as an individual contributor or as a subordinate manager. A boss managing multiple people does not have the same mental bandwidth as all the people in their team combined, so the employees cannot bring every matter to the boss's attention. Choosing which matters to bring (and how to present them) is precisely what managing upwards means.

(In fact, if you're being praised

When someone says that they need to manage their boss, what they usually mean is that the boss reacts poorly or unproductively to bad news, or that they like to interfere in parts of the work process that would best be left to the employees, and so this normal part of everyone's job turns into a constant walk on eggshells.