follow the lead thread
for instance, from the leather side, go straight through and try and pierce the sharpie line and then on the return trip, squish it down to get close and probe until you find the hole.....(super want to make a joke right now)
Does that make sense? I'm seeing it in my head really well and may not be putting it in words well enough at all. The toughest hole would be the first one on each start.