Roughly how much did you save up? I just turned 27 and am also in NYC. Have 85k cash. Just wondering.

But yeah, I would ease into it like the others said. If you have a well-paying job that you kind of like, that's not a bad thing. Me myself, I've taken long travel breaks before so I know what I'd be getting into (with tweaks from maturing).

Take a 2 week vacation and disconnect. If you like it, then ask for a 2 month sabbatical. If they say no, then just quit and go for a 3 month slow travel trip around Europe or SA. Hit some meditation retreat and a music festival.