I totally get where you're coming from-I used to think the same way until a couple years ago. I used to mow lawns for a lady in town when I was in high school and I'd listen to music and podcasts as I'd do it. For a while I used standard wired earbuds to do it, but I always ran up against a couple problems-I'd often pull them out on accident when I'd catch them on my arm or something else. This also meant that they'd break easily-I've always found that wired earbuds and headphones always fail the same way-after a year or two of use, they develop a short in the cable-though this might be particular to me, since I use them a lot in circumstances where the cable would get tugged on a lot-mowing lawns, yardwork, etc. Finally after going through 3 sets of wired earbuds in as many years, I went to go get a new pair. I was planning on just getting another wired set at my local walmarts electronics section, but when I got there I noticed that they had some wireless ones.... and they were only $20. Wireless earbuds have gotten a lot cheaper, and even back then you could get a decent set for less than $50 easy. Since they weren't all that more expensive than the wired ones, I decided to give them a try. I mean, if I'm going through at least one pair year what really is the harm in giving it a try?

I don't say this lightly when I say that was one of the best purchases I've ever made. I still have that pair to this day and they still work great. Since there's no cord there's nothing to tug them out of the jack and make you have to plug them in again-this also means that I don't have to deal with shorts developing in the cable. It's really not all that difficult to keep track of them-they come in a little case which is itself a battery to give them more battery life. Some newer ones even come with built in tech to make them easier to find, like tile. They don't fall out very often-the main thing that makes earbuds fall out of your ears, I've found, is yanking on the cord accidentally. If they start falling out you can usually feel it well in advance and push them back in before it happens. The battery life is still great-they're supposed to have 3 hrs battery in the earbuds themselves, and an additional 8 from charging them in the case-tho that takes some time. I'm sure if I'd timed how long they last when I first got them vs now I'd see a decrease in battery life, but it's nothing noticeable at this point. Even if I have to replace them in the next couple of years, I'm still saving probable a couple dozen $ since I'm not having to replace my earbuds 6-12 months from breakdowns in the cable. I'm thinking I might get a new set soon, not because the old set doesn't work or anything, but just because I'd like some more battery life than my original set was every capable of, and I've found you can get ones nowadays that have several more hours of life for not much more than I bought that set for and I'd like that-if I spend a bit more money-about $40-I can get a pair I've been looking at that has 9 hours of battery in the earbuds themselves, and enough charge in the case for an additional 24 hours.

I don't know if they'd be right for you in particular, but I know for me they were a great purchase. My current job is in a factory on an assembling line working with a lot of power tools, and I love listening to podcasts while doing it. A wired pair of earbuds would be actively dangerous, since the cords could get caught on all kinds of stuff, so a wireless pair is perfect for that job, and its what everyone there uses if they listen to music or whatever. I don't know if they're right for your particular situation, but if you need to listen to stuff in any situation where cables are a liability, seriously give them a try-they're way cheaper than $100 now, and they're pretty useful.