I wish I hadn’t have discounted iems, since I now use them much more than my over ears, even when I’m at home. I also wish I had have had a better understanding of the type of sound signature I preferred, would have saved myself a lot of time and money. That being said, I did enjoy the journey itself to finding my end game 🙂
If headphones aren’t comfortable, no matter how good they sound, you won’t use them.