Apple’s EarPods had been my go to for video calls at work because they sound pretty decent, fit my ears well, and I never have to worry about battery life or weird Bluetooth pairing issues.

But I recently started tinkering with a fifth-generation iPod again, which naturally doesn’t support Bluetooth. I ended going down a bit of a rabbit hole because of this and thought I’d share my random thoughts about headphones.

• I like not having to deal with Bluetooth pairing and yet another battery to charge.
• One of the few things I miss about AirPods is connecting them to the Apple TV while I’m cleaning. I often have to move toys into other rooms, go to the kitchen to throw something in the garbage, or move folded clothes into bedrooms. Being able to turn something on and listen to it across the whole house with a simple pair of headphones was nice. But that’s not enough to bring me back because I can easily just play the same media on my phone and listen through wired headphones instead.
• I don’t like the idea of in-ear monitors because I don’t want to stick anything into my ears.
• I still want headphones that are compact enough to stick in my pocket and have with me for spontaneous listening.
• It seems like flat-head style earbuds are the best option for me because they are compact, but just sit outside of your ear, not in it.
• I’ve purchased a couple of flatheads — Fiio ff1 and Faaeal Iris 2.0 — but the earbud shell is larger than EarPods and they fall out too easily. I can put foams on them, which actually improves sound quality, but it doesn’t help them stay put. The ff1 also came with silicon rings and silicon rings with a hook. The hook ones help keep them in my ears, but it’s not the most comfortable thing in the world. And the silicon ring somehow makes them sound worse.
• I’m using Apple EarPods at the moment, which do stay put for me — the earbud shell is smaller — but the sound quality isn’t to my liking and the cable is awful. The cable gets tangled like crazy and never wants to go straight. It retains the shape from when it’s rolled up, which is annoying as heck.
• I’ve looked for headphones with a similar shape to Apple EarPods, but they’re all from junk brands with bad reviews.
• Are there any flat-head or similar headphones that are sized/shaped more like EarPods, but have a nicer cable and sound better? I’ve seen recommendations for the NiceHCK YDX, which appear to be smaller than the ff1 and Iris 2.0, but still have a larger shell than the EarPods.
• On the other end of the spectrum, I have the Sony WH-1000XM5 that I occasionally use with a wire, but they’re heavier than I want for longer listening sessions and, when I use them wired, there’s a lot of noise in the ear cups when I bump or rub up against the cable. There are also a lot of times when I don’t want to be so isolated and want to hear more room noise than these allow for.
• I just received the Moondrop Old Fashioned. I don’t know if on ear headphones are going to be a good fit for me, but the Old Fashioned looks super cool and I like the idea of that retro vibe. I’m still putting them through their paces, but they aren’t compact enough to carry around with me like the EarPods are. Listening at my desk is really the only place where I can see the Old Fashioned fitting into my life.
• I’m finding myself wishing that the iPhone still had a headphone jack. I didn’t get it when people complained during that transition period, but I get it now.
• I have Apple’s USB-C headphone adapter (DAC) ordered because, based on my research, it seems to be the absolute best inexpensive option on the market.
• I’m using a cheap DAC that came as a freebie with the Fiio ff1 now. It sounds fine, but it runs loud and the volume steps don’t afford a lot of options. In Prism, I’ve actually enabled the equalizer just so I can use the preamp option to reduce the volume output. But that doesn’t help when listening in other apps.
• The world of DACs seems nearly as deep as the headphone market. There are fancy ones with high powered outputs for headphones that require it, there are gimmicky DACs with retro aesthetics, there are more simple dongle DACs, and everything in between.
• I might end up ordering the Fiio Snowsky Tiny DAC. I like that it’s compact, allows you to charge while listening, and doesn’t extend the length of the headphone cable at all, which can make them a bit unwieldy when using dongle DACs.

At the moment, I’m looking at upgrading the cables and ear pads on the Moondrop Old Fashioned and am still on the look out for EarPod-style earbuds that have a better cable and good audio quality, but aren’t an in-ear monitor.

Audio gear seems like an infinite well at the moment and I’m excited to have an entire category of gadgets and accessories to explore.