You make an important, VERY important and often over-looked point: focus and attention... and entertainment... hear me out:

On a bike: have to pay constant attention, be alert, but also, enjoy the scenery blah blah blah -- your attention is on too many things to "notice" the helmet and it's inconvenience. Not to mention you want the helmet for safety so your brain is LESS likely to be like "yo... take this fucking thing off"

Listening to our Audeze: your focus is, most likely, on your music - maybe split with work or a movie if you're using your cans that way... your brain is MUCH more likely to complain because the cans are PART of what you're focusing on... maybe the MOST focus is on your cans, so of course any discomfort is going to show up "faster"

When I'm playing video games, I can wear my Fidelio X2 for a long time, when I'm on my computer working, I can't for nearly as long.