The average person is just so much better off today with the things that they can enjoy in life than Rockefeller had access to with his fortune back in his day. All luxuries become necessities in due time. The way things are right now is indistinguishable from magic, relative to how things used to be. Low expectations don't make you depressed. They do the opposite. They make a little gain feel amazing.
The knee-jerk way to set expectations is to anchor to what everyone else has right now. But imagine the tragedy of there being unbelievable progress throughout your life and you enjoy none of it because you expected all of it.
This episode is all about expectations, and how the key to happiness in so many things in life is to aim low.