I haven't had trouble swallowing pills, so I don't how helpful this is, but it's something that still made it easier for me: I used to try to swallow the pill by just pushing it with water on an initially empty throat. Once I started swallowing the water first, then letting the pill ride between gulps in the stream's momentum, it became more comfortable and automatic.
I wish there was a way to explain this without making it sound gross, but get some saltines, chew em up, and sneak the pill into the mash in your mouth before you swallow
Difference is that you can chew the food, it’s much more natural. You can’t, or aren’t supposed to, chew the pill (especially if it’s a capsule). There is a psychological component, for sure.