A wise man once told me that he deliberately avoided cultivating expensive tastes, because they are ultimately unsatisfying unless you are uncommonly wealthy. I think this is probably good advice in general, and particularly good advice for cars, wine, cameras, and home A/V equipment. But for headphones, not so much. Sure, you get the urge to upgrade, but you won't end up mortgaging your house to do so. Although you can of course go overboard if you want to, the point of diminishing returns can be reached relatively cheaply.
Dan likes to make the analogy with motorcycles. They perform better than cars, but at a fraction of the price. This is true also of headphones versus a full-blown home Hi-Fi system. However, unlike motorcycles, headphones are more practical than their full-priced competitors. You can even carry them around!
After mildly disagreeing with Dan, I'm going to spend the rest of the article quoting and linking to him. It's a net positive, really!
The only thing you really lose with the headphone experience is that whole-body listening sensation. You don't get to feel that thump in your chest on really deep bass hits. Instead it's all in your head. Which is by no means unpleasant, just slightly different to a live performance or even a good Hi-Fi system.
In case it's not painfully obvious, this post is about headphones. It contains some recommendations and advice about specific types and models, but mainly the message I want to get across is that headphones are an inexpensive and invaluable conduit to musical satisfaction. For a few hundred measly bucks you can experience something close to
musical perfection. Without even bothering the neighbours. (Although you can do that too, just by singing along...)
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