Stories like your intern skiing for 9 years or the GP ‘5 years snowboarding’ usually omit describing rich parents in the background picking all sort of tabs.
I won't fault you for the not unreasonable assumption but not the case for me. I have fond memories of sleeping behind a friends couch while securing a job at the ski resort. Initially working at the resort from 4 to midnight so I could ride every day. Sleeping in dorm style housing slightly worse than freshman year of college. Working my way up to running the ticket office. Somehow not blowing all my money on new gear, saving just enough to buy a $59k condo at the base of the resort which I still have. No financial safety net, no savings, but also no dependents and nothing to lose living in one of the greatest areas of the country.