I love that Socrates quote! As someone who has gone from being insanely busy to giving myself a bit of time, I am learning that self worth does not come in what we busy ourselves in.
In terms of the "should" I'm so with you. I've been meaning to write something on "should". The times when we are like I "should" phone X person, I "should" go to the gym, I "should" sort out my taxes.
Sometimes our shoulds, like you say are simply a sense of obligation. Sometimes we don't have to do it at all. Sometimes we do.
Thank you for highlighting such an important internal dialogue. We hold ourselves prisoner with this I feel.