I love wearing IEMs, but I know people struggle with them. Some people’s ears are interestingly shaped which makes iems difficult to use unless you find more specialized eartips. Some people also react almost allergically (or actually allergically, with swelling and all) to silicone eartips, though some also react poorly to hard plastic buds. There are different grades and types of silicone that might cause less of a reaction in your ears, it depends on the kind of aftermarket eartips you get. For me the first few weeks with IEMs caused some amount of pain as my ears adjusted to having something inside, and I don’t think there’s a way to tell when pain is no good and when pain means you can still adjust, but I adjusted and now they’re perfectly comfy. I also got wireless earbuds with silicone eartips late last year, and those still cause some amount of pressure regardless of how they’re inserted into my ears. The plastic housing just doesn’t fit my ears very well, and the nozzle is very shallow compared to wired IEMs. I had a similar thing going on with the airpods pro 2 and another set of chinese wireless buds, so I think that’s a curse that applies to me with a wide variety of wireless earbuds. Just my 2 cents.