I've done this thought exercise many times, traveled extensively, and continue trying different types of work. The truth is that most of us (HN users) have pretty comfortable lives and would be making huge quality of life sacrifices to live the dream of the romanticized past.
There is definitely something to sort out around "what does the high paid knowledge worker do when they no longer have hardship defining their life for them" but I don't know if artificially handicapping yourself and LARPing struggle is the answer.
If you do find the answer then please let me know.