The end of the headphone jack has spurred an interest in high-quality audio components, but where does the madness stop?

Everything I do revolves around music. It's always been this way — as a kid I would sit on the floor in my carpeted living room creating hours of mix tapes from my father's classic rock cassettes, returning to my bed to close my eyes and exist between two worlds.

As a teenager, I spent nearly all of my money on headphones, poring through the Head-Fi forums to discover the best possible combination of music source, headphone brand, and emotional state. I amassed a collection of over-the-ear closed headphones and in-ear monitors, of custom amplifiers, DACs and cables. I paid attention to everything, and nothing was good enough. As I approached college and moved into a tiny dorm room, my headphone collection got sold to pay for textbooks and expensive coffee, for first dates and, inevitably, other technology. Though the iPod certainly catalyzed my regression to lower-quality portable audio, it was a confluence of factors that caused me to leave that addictive, expensive world behind.

I spent a long time building a collection of expensive audio equipment only to sell it and start all over again 15 years later.

That itch stayed dormant until a couple of years ago. I re-purchased a pair of headphones, the Beyerdynamic DT770, that I had worn so much as a teenager, the damn things had fallen apart; to push them, I dusted off a solid-state headphone amplifier that had been sitting in storage for over a decade.

But like the multitudinous reasons I left behind audiophilia in the early 2000s, the itch that caused me to re-up on a devastatingly expensive hobby has its roots in my current job, in reviewing phones. For so long — and I largely blame Apple for this — it was the "headphones in the box" appeal that made it useful to plug those recognizable white earbuds into the standard 3.5mm jack. The thin sound wasn't necessarily good, but unless someone was curating a collection of high-quality MP3s, either ripped from an increasingly-ignored CD collection, or downloaded legitimately (or otherwise) from a trusted site, the returns on spending much more than a few dollars on a pair of nice headphones were largely wasted.

I'm not going to pretend that no one used good headphones between the years of 2001 and 2016 — that would be absurd. Of course high-quality equipment was popular and, in many cases, ubiquitous in the right circles. Lossless music files offset the potential inconveniences in leaving behind physical media for the digital. And wireless headphones, an expensive pipe dream when I was growing up, began sounding pretty good, even at prices 15-year-old me wouldn't have balked at.

The iPod made it easy to carry thousands of songs in your pocket, and just as easy to forget what music was supposed to sound like.

But, ironically, the slow death of the headphone jack has, if not facilitated a resurgence in high-end equipment itself, brought the importance of quality components back into the conversation. Phones like the LG V30, Sony Xperia XZ1 and HTC U11 emphasize high-quality DACs and powerful amps as they would impressive cameras and multi-day battery life. The market is also being divided into those companies retaining the classic 3.5mm (Samsung, LG, Sony) and those that aren't (Apple, Google, HTC).

For the most part, I use wired headphones at home and wireless on the go. Given how often I change devices, I can't take for granted that a favorite pair of earbuds will work with the phone in my pocket, nor that I can remember to stuff one of the dozen dongles I've accumulated since the Moto Z shipped with one in the summer of 2016.

I also don't stress too much about sound quality when I'm mobile; as I've grown older, I've come to accept that, unless I am actively reviewing a composition, music is for listening, not scrutinizing. As long as the Bluetooth connection is solid, the seal in my ears good, and the quality good enough to keep me engaged, I don't much care if they're $24 Ankers or $350 Sonys. Of course, the more expensive they are, the more I'm able to appreciate the subtleties in my favorite recordings, and the better the sound displacement, the less I am distracted by the outside world.

One of those great expensive headphones is from a new-ish company trying to compete with Sony and Bose in North America. The $350 FIIL IICONs (pronounced "Fill Icons") are big, plastic, and unabashedly simple, but they have some of the best sound I've ever heard from a pair of wireless headphones. An accompanying app lets you tweak equalizer settings and adjust the intensity of the excellent active noise cancellation, too, which is nice, and a gesture area on the right earcup can adjust volume and switch tracks.

These days, I care more about how easy it is to listen to music for a long time than how good that music sounds.

I've also discovered — and stay with me here — neckbuds. I had largely dismissed the design after receiving and immediately hating a pair of LG Tone headphones from the G4 launch event in 2015, but I heard such good things about the 2017 refresh that I picked up a pair of the sub-$100 Tone Infinims and immediately fell in love. Neckbuds take the pressure off your head and ears by resting most of the equipment around the neck. They sound great, have easy-to-use controls and, most importantly, are incredibly comfortable to wear for long periods.

I've also thoroughly enjoyed testing and comparing the $129 Fitbit Flyer and Jaybird X3 headphones, which I've employed during my workouts to great effect. Unfortunately, I seem to have a weirdly-shaped left ear and can't get a solid seal with either of them despite multiple sizes of tip, wing, and flange.

There's also the V-Moda Crossfade 2 Wireless, which are currently my favorite wired and wireless headphone alike. At home, they stay in my solid-state amp hooked into my MacBook Pro, and are superb on trips and in places active noise cancellation isn't necessary.

And, finally, I just indulged and bought myself a pair of dream headphones: the Sennheisher HD600s. Sort of. These are a custom-built version of those venerable open-back headphones from Massdrop, a company that works with brands to deliver improved or modified versions of existing audiophile products. Back when I was 15, all I wanted was a pair of HD600s, but they were way too expensive, and I didn't have the equipment necessary to drive them properly. Now, a bit older with a fuller bank account — well, here goes nothing.

Here are a couple other things to keep in mind this week.

👋

-Daniel