Last summer I had a little bit of extra cash to spend, and I thought, "Hey, I listen to a lot of music, but I'm always buying these cheap $10 earbuds. I know there are more expensive headphones out there, so why don't I buy some!" I didn't know much about what I was getting into other than that the Apple Store and Best Buy sold what I considered at the time some expensive headphones, so I began there. Naturally I looked at Beats first - I thought they sounded okay, but I could tell they weren't worth the price tag. I wandered around a bit more and eventually found myself in the Magnolia area where I was drawn to the B&W P5's. The build quality was a thousand times better than the Beats and the sound didn't disappoint. I listened to a few other headphones in the same price range as the P5's before deciding they were the best cans in the store. However, I'm the kind of person who has to Yelp every new restaurant I eat at, so I didn't throw down the cash right then and there. I went home and watched a few YouTube comparison videos and read some reviews, and to my delight the P5's garnered a lot of praise. Shortly thereafter I picked up a pair, and for about 5-6 months they were one of my most prized possessions. I thought they sounded awesome and I received quite a few compliments from various friends, family, and strangers. Needless to say, I was quite happy with my purchase.
Then I met you ********. 
I had never heard nor read a bad word about the P5's until I visited Head-Fi. Of course, it's not like the reviews here were absolutely horrible (I probably would have cried if I had gone with the Beats), but I couldn't help feeling disappointed that there might be better sounding headphones out there that actually cost LESS than the P5's. I had to hear this for myself, so I look through some of the headphone "rankings" and see that the ATH-M50's are frequently cited as a great pair of headphones for the price point. Luckily, the local Guitar Center carried Audio-Technica gear, so I zipped over there for a listen. I was impressed! I bought them on the spot and decided these would be my "home" headphones and the P5's would be my "on-the-go" headphones. Nice.
But I'm not exactly a stranger to forums and message boards, and I could tell there was a wealth of headphone knowledge here like no other. Curious, I continued to lurk. I kept coming across threads referring to Grados and the "Grado sound." I was excited to see that these were considered another great pair of headphones for the price, so I decided to see if there were any Grado dealers near me. I located one about 15 minutes away, a local hi-fi shop. I stopped in and - woah - what the hell is all this stuff? DACs? Headphone amplifiers? This is what they were talking about on Head-Fi! Eventually I make my way to the back where the Grados are and start listening. Thanks to Head-Fi, I've already been primed to believe that you either love or hate the Grado sound. Well, I loved it! I bought a pair of the SR80i's and brought them home to join the M50's and P5's. I was quite content with my little headphone collection and couldn't help but feel I was a budding audiophile.
One other thing about that trip to the hi-fi shop, I had one of the guys working there explain to me what exactly a DAC and headphone amplifier do. He suggested the Audioengine D1 as an entry-level DAC/amp. Upon returning home I jumped online and read some reviews - another great piece of equipment for the price! I was back later that day, and my wallet took another hit. I was very pleased to notice an immediate difference in sound quality, however, and so I was ultimately very happy with my purchase.
Well, after a couple weeks I realized that I was spending more time at home listening to the SR80i's than anything else, despite their position as my least expensive pair of headphones. Since the P5's were solidified as my portable headphones, the M50's weren't getting much use. So then I thought, "Dude, you clearly don't need three headphones - just return the M50's and use the money to upgrade the Grados!" So I return the M50's and upgrade to the SR325i's. Man, they sounded awesome, especially coming out of the D1. The detail was unbelievable, and although I recognized they were a very bright set of headphones, I enjoyed the sound signature. Now, I have to admit that not everything sounded spectacular on the SR325i's, and since I listen to a lot of different music, I thought, "Hmm, it would be nice to have a complimentary set of headphones for some other genres." I also found myself unable to concentrate on much while I was listening to the SR325i's - they are just so bright, detailed, and aggressive. After a bit of research, I found myself particularly influenced by DavidMahler's extensive review of flagship headphones and his praise for the Beyerdynamic DT880's. As the 600 OHM version was considered the best, I knew I would need a better amp than the D1 to properly drive these cans. The Schitt products had already caught my eye, and so I was happy to see a lot of people pairing the DT880's with the Valhalla. Happy, of course, because now I had a pseudo-excuse to buy more "Schitt." 
I order a pair of the DT880's and the Valhalla. The headphones come first, and I am a bit underwhelmed. It must be the D1, however (I figured it couldn't properly drive the 600 OHM version anyway, which is why I bought the Valhalla). Finally the Valhalla arrives and, once again, I am disappointed. To my ears I guess they were a little too flat and boring. I end up returning the headphones, but I keep the Valhalla, since I enjoyed its sound with my SR325i's.
At this point, I am still determined to buy a set of "complimentary" headphones. Quick flashback: Prior to the DT880's, I was fortunate to stumble across another hi-fi shop where I was actually able to demo the fabled Sennheiser HD650's. I didn't expect to like the sound signature, as I was led to believe that there is a bit of a dichotomy between those who enjoy the Grado sound and those who enjoy the Sennheiser sound, but as it were I liked it very much. Dark, smooth, but still detailed, they were an excellent candidate to compliment the SR325i's. Why didn't I just get those, you ask? Well, simply put I thought they were just too much money. After my disappointment with the DT880's, however, my mind turned again to the HD650's. I was surprised to see how cheap you could get them if you bought used, and since I already had the Valhalla I decided (a few days ago, actually) to bite the bullet and pick up a pair.
And so here I am today, waiting for my HD650's to arrive in the mail. Of course, this all explains how it happened, but not exactly why. Fortunately that is a much shorter story: Rediscovering my music collection with each new purchase is just too much fun! I suspect this is how it is for most people, though. My next upgrade will likely be a DAC (I have my eye on the Schiit Bifrost or the Peachtree DAC-IT).
This continues to be a fun ride for me. Somehow I doubt my wallet shares the same sentiment.
