This was a thought provoking short post without much advice on how to approach this. I'm dealing with this personally quite a bit now - just starting my college, but alongside I already have a (compared to my peers) well-paid SWE job. I would love to go traveling this summer and take some of my closest friends with me, but just offering to pay for majority of the expenses felt... weird? Just as described in the article. Also, with traveling you can't really apply the point about owning/renting - one doesn't simply own a train.
