On the subject of Machiavelli, a thing said in a book regarding him/his writings has stuck with me. That being, if one is feeling the need to read him? It's time to take a good hard look at one's political leaders.
I started trying to read Machiavelli because he was a character in a historical fantasy series I used to read. I thought it was going to be so interesting, because the character was...
Really? I remember doing fine with my copy of The Prince (barring parents talking at me while I was trying to read.) It needed focus, yeah, but at least it didn't put me to sleep like More's Utopia did.
I actually did okay with book one of Utopia. It was book two where I ran into problems. I eventually figured out that it was because he went into a tedious amount of detail on his created society.
I got through The Prince by imagining him as The Guy You Picture In Your Mind When You Say "motivational podcast". It made it make enough sense to finish.