This is more of a series of puzzles set outside of the text chamber environment (think Chapters 5 and 6), so we'll once again break it down into the sections of the game where we reckon you're may struggle (no point insulting your intelligence by hand-holding you through the easy bits is there)?
Missable Achievement/Trophy Alert!
Show that pit who's boss
Start to run away and wait until you're asked to come back again. Do so and stand over the edge of the pit. Now, whilst you can jump in now for the 'Pit Boss' Achievement/Trophy', we strongly recommend that you simply sit still until he's finished trying to entice you to jump (it had us laughing away unashamedly).