"'Should' Considered Harmful" talks about the feeling that you should do something, but can't do it, so you feel guilty. But Soares says that using "should" language can be harmful because it creates an obligation to yourself that says you're a bad person if you fail. Instead, he suggests people to break down the thing we want to do into smaller parts, list out the costs and benefits, weigh the options, and then decide. He says that laying out your options helps makes the thing more finite.
Soares also talks about how if you strip away the guilt and it's something you actually want to do, you will actually be motivated to do them. In "Where Coulds Go," he talks about feeling guilty because you felt like you could have stopped watching a tv show after midnight but didn't. He suggests not to beat yourself up for failing to stop watching tv when you're not capable of doing that yet, because it takes time and effort to change your behavior and do hard things.
I also like the parts about feeling compassion for our imperfect monkey selves who are doing difficult things, and that there is no such thing as a bad person.
In "Desperation," Soares asks if there is anything you would go all out on because you really care about it. Otherwise, "what are you holding out for?" What we're doing is making the future different. This chapter stood out to me because I want to embody resolve and desperation to do things that are important to me.