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I am as different from Cadillac Man as I am from Alex Honnold. Is nostalgie de la boue the right term to apply to Cadillac Man's yearnings? Or is that too harsh?

One often hears the claim that it is hard to get the homeless off the streets because they don't like the curfews imposed at shelters, nor do they like their access to street drugs constrained. But it seems that for Cadillac Man, he really just likes a minimalist, nomadic, contingent existence.

How many men and women among us leading conventional lives have a similar aspirational profile?

I live an conventional life now but I keep thinking about the vagrant life. I slept in my car for 6 months to see how it would be like and in a tent in my friend's backyard for a week. I also lived in hostels for two months, and in college I thought I wanted to be Thai Forest monk.

I'm married now and living the apartment life but I still keep consuming content about tents and vans and houseboats.

Monastic life often appeals to this nomadic, freedom seeking sensibility, but I think out of ignorance. Monastic life can be quite strict, and you're crowded in with a small set of people you cant get away from.
There's no frontier left where one can be free. Off grid living and homelessness (if you're are logistically minded). Might be the place to be free left.