@Malcat those are very interesting thoughts. I'd come across a couple of the themes before, but your synthesis results in a very intriguing framework for understanding the twin dysfunctions of consumerism and careerism.
It must be frustrating to Show People The Path only to be argued with because your path looks a lot different than the path that led them to their current misery. I imagine a lot of the people you talk with expect in their heart of hearts that their current path will lead to sustainable contentment, and all they expect from you is some cheerleading and motivation to keep plowing through.
But why should they be so attached and committed to a particular path? Sunk cost fallacy? Your use of the terms "brainwashing" and "deprogramming" intrigue me here.
I think the deep belief in consumerism/careerism comes from years of repeated exposures to the assumptions that more stuff or more job will lead to more contentment. Every time we look at our phones, walk past a TV, or see a billboard we absorb one more message along these lines. News articles celebrate high achievers and treat the daily struggles for a good life as meaningless. The propaganda effect is real, and thanks to smartphone addiction we are exposing ourselves to more and more of it, devoting multiple hours per day to looking at ads in exchange for the little shots of dopamine between the ads.
People who do addiction treatment have recognized the necessity to dial people down rather than cold turkey, and that's why we have needle exchanges, methadone clinics, etc. Like your weight loss journey, taking on too much change at a time can lead to failure, even if the change is one's own assumptions and orientation toward extrinsic self-esteem.
Yet there's a deeper, scarier truth from the point of view of the counselor or Mustachian casual observer: The cultural norms we receive from the world are often toxic. Culture can destroy hundreds of millions of lives and still self-perpetuate, because perpetuation is not at all connected to the delivery of benefit to the "users".
Culture (values, language, behavioral norms, ways of doing things) was originally invented by our species as a way to transmit behaviors that were advantageous, such as how to produce food, how to defend oneself, how to communicate and cooperate with others, etc. We're a LOOONG way from that original purpose when we're looking at targeted ads or keeping up with the Kardashians. Yet our brains are still primed to internalize and repeat what others are doing as if our lives still depended on it.
Ads that perpetuate a negative body image, work cultures that perpetuate the importance of career advancement over one's personal life, varous trinkets and status symbols and SUVs for sale - all these messages can continue ruining the happiness of their users forever, because people are not examining them or rejecting them. We cannot even avoid them. It's time to be more judgemental about the worth of what we're consuming, including ideas. Especially ideas.
So even as we nudge people toward the better path, we must be aware that we ourselves have probably internalized some toxic shit too. Just as the consumerists and careerists don't know they are self-destructing, we may think we're fine according to metrics we've internalized. Actually we might be on a treadmill of our own, working against our self-interest or communal interest in a way we cannot see, and wasting the opportunities our lives offer. Maybe it's not work or consumption, but some other domain of life such as parenting, health, meaningfulness, or the sources of our own sense of self-worth.
This line of thought always tempts me to ditch my smartphone and TV, use a painfully slow computer for work only, and to live more in the present world of experiences and sensations. The "why not to do that" reasons look a helluva lot like the arguments of the consumerists and careerists, about being a social outcast, failing in various ways, or falling behind in some way. And then we're back to talking about incremental change and framing the status quo as failure, aren't we?