Ten years ago, my favorite possesion was my CD collection. I had spent years collecting, sorting and listening to music and whenever my friends would come by, I always delighted in showing them how extensive my collection was.

Whether it was the mainstream hits or the classics, somewhere in my collection there was a song for whatever mood I happened to be in. At that time, most of my collection stemmed from countless hours spent bargain hunting at independent record shops or from massive binge buying from CD clubs like BMG and Columbia House. As my collection grew, I found that storing them became an escalating problem and remember having to spend more money on a CD storage rack then in on any other piece of furniture I owned at the time.

This collection was never cheap and it took many years to build up, but it was a labor of love and one of my favorite things to do would be to continually reorganize the collection either alphabetically, categorically or chronologically. Like an old miser who delights in counting his gold, I would continually flip through one CD after another even if there was never enough time to listen to them all.

Somewhere along the way technology developed though and it rendered my CD collection useless.

It started with Napster where I learned that I didn’t need physical CDs. I could suddenly build up a digital database of songs and by the time I realized how easy it was to convert my legal CD collection into mp3′s, things quickly evolved into a full scale ripping project.

As my ripping project moved forward I quickly learned that I was going to need space. Just like I needed a CD case to store my albums, I needed external hard drives to store my mp3s. My first external drive was a 200 GB drive that I thought would last me for a couple of years at least. When 200 GBs turned out to be inadequate, I added more and more and more drives until I eventually had over a terrabyte of storage dedicated to my storing my mp3s.

It wasn’t until I got a few years into this process that I began to realize that I had made a big mistake by embracing the hot 1.0 technology of the day. The hard drives turned out to be nothing but problems. In the last few years, I’ve had at least five hard drive failures and while three of those were still under their 1 year warranty, getting the data back was about as much fun as being the one stuck with having to clean Alice Cooper’s hotel room after a concert.

After a couple of data failures I learned to start backing up my music, but after constant I/O device errors and continually being prevented from backing up my music by what I suspect were DRM laced music files, I finally gave up on trying to save multiple copies of my mp3 files.

Because of the size of my collection, I could never get any music players to effectively manage the entire thing. Whether it was using Media Player, iTunes or Winamp, every system seemed unable to respond after I would import the collection into their software. To make matters worse, everytime my computer crashed, I could never prevent my external drives from trying to autoplay the entire collection everytime I restarted.

While I’ve loved having an extensive music collection, my problem now though, is that over the last few years technology has innovated so fast that we’ve moved from a web 1.0 world to a web 2.0 world and I’ve been left behind.

Just like my CD collection is largely irrelevant today, my mp3 collection has become less relevant by the shift toward networked solutions. This fact was highlighted to me when I was reading a great review of the Sonos music system, which Joel Spolosky titled “The Infinite Music Collection.”

By combining a wifi Sonos sound system with a Rhapsody music service, Joel has been able to replicate my entire music collection (and more) without the headaches of hard drive failures, loss of data or buffer overrun issues.

In retrospect, had I been able to think forward five years, I would have been better off putting off innovation and using Rhapsody (or more likely Yahoo! music because Real Network sucks), then to try and assemble a collection on my own.

Of course there are downsides to a web 2.0 solution. Because you don’t own the music it’s more difficult to share it or move it onto other consumer electronic products, because the all you can download services are subscription based, you have never ending fees instead of a one time purchase, and of course there will always be DRM restrictions associated with these services, but given the amount of time and money I’ve spent on my music collection, I think I would have been much better off renting 2 million songs, instead of trying to build my own music catalog.