I read that newsletter as well. Very honest, and it does a great job of highlighting the power of normative cues.
I spent a decade in one of those "high-consuming" upper middle class professions. When everyone around you takes expensive vacations, has a big house, drives a Mercedes SUV, wears a $4,000 watch, etc., it takes a tremendous amount of discipline to be the guy in the condo with a 12-year old station wagon who only owns three suits.
Switching into government half a year ago was an eye-opener. I am now considered a big spender because I bought by bike new instead of building it from parts and I wear a $400 watch instead of a $40 one. I am still frugal, but it is just so much easier when the normative cues around you match your value system. I am no longer wasting a bunch of valuable willpower resisting high-consumption normative cues every single day.
I would expect that a lot of upper middle class $250,000 a year folks simply never have particularly deep interactions with anyone who is not like them. That makes it hard to gain the perspective that the high-consumption lifestyle is entirely voluntary, unless one consciously focuses on it.