Real coolness applies to one of my mates.
Not a penny to his name, and no chance of a job in Thatchers Scotland. No safety net to fall back on.
I joined him for a few months in Europe, then went back to 'real' life.
He has managed to travel every continent, with a few marriages and prison terms along the way. I joined him in Greece for a 'job'. It involved hiring a tall car for the day. You drove into farmland with tall crops like corn. Every so often you would stop and stand on the roof of the car. You were looking for a patch of green-ness amongst the yellow.
Stealing the local Greeks hash plantation was a dangerous hobby!
The last i heard, he was living in Brazil.