Well when I started playing it I wanted to just do the most embarrassing shit. Like asking everyone for money or telling them I remember nothing. It was funny but then I didn't realize the game the run ends if I don't keep the morale and health. Fortunately I saved prior and stopped damaging the morale in the next run.

Its the most "Wait can I do this actually?" game. In my money begging phase I asked that boat lady some money and she gave some. Also explore every nook and cranny to find money. Put points to internalize thoughts like precarious world, which helps with rolls.

I also hit dead ends and kept roaming around exploring. Just remember to look at the journal and see if you didn't get to something.