That's not a problem with a custom IEM. It's nothing like putting on universals, customs are a breeze to put in and don't have any kind of seal issues with the tips. In fact, customs IEMs are even simpler to put on than full size headphones. Example, I can take off my IEM and answer the phone with 1 hand, and when I'm done, I can put it back in with 1 hand. With a headphone, if I pull from one side I risk snapping the headband, when they are around my neck they are bulky as hell, when I want to put them back on, I definitely need 2 hands. The cable, oh the cable. Headphones have massive cables that tug. Almost all universals have pretty awful cables that can carry microphonics. Have you ever seen a cable on a custom?
It's as thin, flexible and lightweight as it gets. I don't even feel it when it's against my body while commuting or in the gym. Comfort wise, there is no contest.
And what about sound quality? I've still yet to hear anything that sounds anywhere near my customs (of course I'm lucky to own JH16s, I can't really vouch for anything in lower tiers). I find it funny that no full size headphone over 1K can top it. I was always convinced that with a custom IEM I'd be paying for comfort and portability while trading off audio quality. I never thought BA drivers could produce better sound than a top of the line dynamic driver, but holy hell was I wrong. The JH16 come with a little booklet that says "Welcome to the best headphone in the world". Maybe that's a bit exaggerated, but it's not far off.
That's too bad. I used to be like that and now I wouldn't buy anything besides a custom IEM. If only I had known before, I could've saved a lot of time and money.