How do I build up the confidence to actually make plays?

I've played the game for like 10-15h around half a year ago and stopped. Picked the game up again after the new update and am struggling with re-acquainting myself with the controls, but I'll get back there I think. More importantly, I don't know when to take opportunities to come out and make plays.

For context, I played a round yesterday where I found the boss lair after a single clue which was in the neighbouring compound. I went there by accident and started the fight. Looking for a boss weapon, which I didn't know didn't spawn next to the boss lair anymore, I attempted the Assassin without a weapon and almost got killed. After wasting a sticky, I ran in the attic and hid there for like 35 minutes, listening to my surroundings in the hopes of finding a hunter. Fast forward a little, I managed to find a hunter that's been trying to kill the Assassin themselves for like 15 minutes straight and killed them, then I had like 5 minutes left to kill the boss and extract but didn't get it, so I just extracted.

Ultimately, I just spent 35 minutes in an attic doing nothing which wasn't as engaging. Any tips on how to make myself go out of my way to make proactive plays?