Twenty-Five Years in the Air, and What's Been in My Ears

The first pair of headphones I actually cared about on a plane were wired — cheap earbuds jammed in, cable tangled in whatever jacket I was wearing that year. This was over twenty-five years ago now, back when a long-haul flight meant a tangle you had to manage, an ear that would start aching by hour four, and no isolation to speak of beyond jamming them in tighter.

Bluetooth, once it arrived, didn't fix things so much as reshuffle them. There was a chunky over-ear pair early on that clamped like a vice and made every long-haul flight feel like a small act of endurance. There was a sport-style neckband pair that kept slipping out mid-flight and that I eventually stopped trusting. There was a big, glossy over-ear pair that sounded genuinely good sitting at a desk and turned into a sweaty, headache-inducing ordeal by hour six in an economy seat. Every one of them solved the cable problem and introduced a new problem in its place, and I just adjusted, the way you do.

AirPods felt like the first real fix. No cable to catch on a tray table, painless pairing, good enough sound that I stopped thinking about the alternative. For a long stretch of years, that was enough. Then came the Bose noise-cancelling earbuds, which felt like the real endpoint — isolation that actually worked against an engine, bass that could go head to head with cabin drone and mostly win. Somewhere across that whole parade of earphones and headphones, I never once thought of it as a system I was building. It was just what you did: whatever wireless option was best that year went in your ears, and you didn't ask more of it.

There was always a small, half-rational worry sitting underneath all of it, too — the nagging thought of a radio transmitter sitting an inch from my brain for ten or fourteen hours at a stretch, flight after flight, year after year. I never had anything to point to that made it a real concern, and I don't think it is one. But it was there, quietly, every time I put a Bluetooth earbud in for a long-haul sector, and it never quite went away no matter how many times I told myself it was nothing.

What changed wasn't a single trip. It was noticing, slowly, that the Bose started to feel like a compromise somewhere past the three-hour mark of a long sector — not uncomfortable exactly, just present in a way I hadn't clocked before. And around the same time, almost by accident, I started actually using a little DAC I'd owned for years and mostly ignored — the iFi hip-dac, bought on a whim, left in a drawer more than it was ever in my ears. Once I paired it with a proper IEM instead of wireless earbuds, the difference wasn't subtle. It wasn't even really about sound quality in the abstract — it was that I could finally shape what I was hearing to the specific flight I was on. A quiet narrow-body wants something different from a droning 777 at cruise, and for the first time in twenty-five years of doing this, I had a way to actually respond to that instead of accepting whatever a fixed Bluetooth profile decided to give me.

It took a flight where the Bose just weren't quite doing it anymore, and a DAC I'd been carrying around and ignoring, to finally notice.

So this isn't a story about AirPods or Bluetooth being bad. Every step along the way was the right call for its moment — AirPods because wireless finally worked without a fuss, the Bose because they were, and still are, genuinely excellent. It's more that twenty-five-plus years of doing something the same way makes it very easy to stop noticing there might be a better way sitting in a drawer.

The AirPods are long retired to a drawer somewhere. The Bose still fly with me — they're the easy choice for a short hop or a call. But for anything past about four hours, it's IEMs and a DAC now, and it took a quarter century to admit that was worth the extra cable.

What I didn't expect is how much I'd genuinely enjoy this part of it. Twenty-five years of just accepting whatever pair was newest, and now for the first time I actually look forward to the tinkering — a different IEM for a different mood, a different pairing with the DAC depending on the flight, the small ritual of choosing a source chain the way I used to choose what to read. There's a whole shelf of combinations I haven't tried yet, and for once that feels less like a chore and more like the fun part of flying.