Based on anecdotal evidence from talking to homeless people, I suspect it would not have been fantastic. Consider this episode:
But I was just going along, starting some start-ups that never quite started up when I met Olga, an Andorran beauty, and fell hard. My relationship with stuff quickly came apart.
I followed her to Barcelona when her visa expired and we lived in a tiny flat, totally content and in love before we realized that nothing was holding us in Spain. We packed a few clothes, some toiletries and a couple of laptops and hit the road. We lived in Bangkok, Buenos Aires and Toronto with many stops in between.Travel is an extremely expensive luxury. With a decent career I still have to work to scrape up the money to visit my very geographically dispersed family and friends. I think few people without financial assets would be able to simply pick up and live in a succession of expensive, world-class cities. Again, my homeless person surveys are strictly anecdotal, but beautiful women or dashingly handsome men as companions seem absent from their accounts of living rough.
As for being poor, it made a huge difference for my freedom in the periods of my life that I had the cash to compensate for mistakes or broken things. It's much less of a sacrifice to live in a studio apartment if you can rent a suite at a local hotel whenever it gets claustrophobic.
It is fine to be able to make the decision to have few possessions. It is completely different to not have a choice in the matter.
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