This is good advice, just reminded me, the audiologist that made my custom attenuators (ear plugs) said the exact same thing years ago, and I totally forgot, wee flashback, ha. If I remember correctly, he also suggested you'd be less likely to push wax up into your ear doing it this way...And as silly as it seems, try this: open your mouth, lift up your ear by the top with one hand (these both open up the ear canal), then insert the IEM with the other hand, and while still pushing them in snugly, close your mouth and let go of your ear (to 'close' back your ear canal around the tip).
On another note, I managed to fit these into my custom ear plugs...they sounded like shit...they sealed OK, but didn't go far enough down into them...
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