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 🙂
Comfort is king - don’t be afraid to pad roll or headband mod.
I’ve tried too many times to make good sounding headphones fit well even though they’re just a bad match for my head. Always end up returning or selling them. I also learned that I like velour pads on everything. Timbre be damned I’ll fix what I can with EQ.
If I’m not comfortable I’m not enjoying my music.
If headphones aren’t comfortable, no matter how good they sound, you won’t use them.