A Night Of Creative Play...

So yeah, I recently got into this thing called DDLG with this guy who's a bit older than me. He's really good at making me feel like... well, let's just say he can make an artist see the world through different eyes! Last night was kinda wild, we had this whole setup in his place where everything felt like stepping into one of my paintings but bringing it to life with all sorts of textures and colors that aren't usually there. And man, when he starts talking about brushes and paints and how I'm the canvas... It gets me every single time. Anyway, enough painting metaphors for now! My question is: How do you guys handle stepping into roles so completely different from your usual self? Do you find it easier to dive in with a clear goal or more organic, letting things evolve naturally...?