I’m not alone, I’m sure, in having a huge music collection. With iTunes and my iPod, this translates into a collection of thousands of tracks. Working with such a large collection is a horrible process without some organization. Early on, my wife pointed out the smart playlist option in iTunes, which made life much easier. My first iPod died after being purchased used, having a hard drive replacement, and a year of heavy use. Now I own an 80 Gig iPod Classic. When I upgraded to a new PC, I decided it was time to start over on my music organization in iTunes. This left me with thousands of tracks to work with, and a need to completely reorganize my music collection for more ease of use.

Those who heard me describe my organization style on my iPod always thought I was fairly hardcore in my way of working. Ratings, smart playlists, and genres were effectively used to give me access to what I want, when I wanted it. Still, with so many tracks, I found myself overwhelmed, and my iPod stuffed to the gills with tracks that I didn’t necessarily need with me every day. It was time to go further.

I hit Google, looking for clues from others. I wanted to see how others used the features in iTunes to manage their music, and how I could use those tricks myself. This post is an attempt to gather what I learned, and pass it along.

The first major change I needed was to properly categorize my music into genres that made sense. I like Rock music, but I could care less if it’s Alternative Rock, Classic Rock, Progressive Rock, or Indy Rock. I must have had two dozen genres that, to me, just meant different ways to subdivide Rock and Roll. The same went for Pop, Latin, Christian, Country, and so on. I simplified my collection down to genres that made sense to my own way of thinking. iTunes 8 made this easier
than ever before with the grid view. I could multi-select artists or genres, depending on the view, and right-click them to select “info.” By changing the genre for multiple selections at once, I could simplify hundreds of tracks at once.

Now, using a trick I learned from the web, I created a smart playlist that I called “Music Only.” This playlist gives me everything in my collection that doesn’t fall into certain genres like Spoken Word, Podcast, Audiobook, and so on. In theory, this should give me only music. Is it perfect? No, but I’m tweaking it as I find failures in the system. As you’ll see, I use this playlist as the basis for my other smart playlists, so as I tweak this list, I tweak all my smart playlists.

Next up in my organization scheme is ratings. I use a ratings scheme that makes sense to me. One star is a song that I don’t want on my iPod. Maybe it’s an interview track in an “iTunes Exclusive” collection, a segueway track that I don’t care for, or something so horrible that I only keep it at all to complete an album on my PC. Two stars is for tracks that I keep on my iPod because I may want to keep the whole album for some reason. Pink Floyd’s “The Wall” and The Beatles’ “Seargent Pepper” are examples of albums that I keep the whole album on my iPod, but that contain tracks I don’t care to listen to otherwise. Three stars and above are actually ratings that matter for music I like to varying degrees. My biggest favorites get five stars. Most music I really like is four stars, and anything I generally enjoy gets three stars.

Rating thousands of songs is a pretty huge task. I need a way to make it easier. First, though, I need playlists to represent the music I like. Because playlists are shown in alphabetical order, I call these playlists Aardvark (five stars), Absolute (four and five stars), and Actual (three to five stars). These names ensure that the playlists will appear near, if not at, the top of my list in iTunes and on my iPod. To create these playlists, I made a smart playlist for each. The first option for each is “playlist.” My Aardvark list requires that a track have a five star rating and be in the playlist “Music Only.” See how that “Music Only” playlist up there has become more useful?

Now that I have my playlists for rated favorites, I need a playlist for songs I haven’t rated yet. I call this “Unrated” which puts it down the list of playlists on my iPod. The requirements for this list are that each track be part of the “Music Only” playlist, and have a rating of zero stars. Now, I can take my iPod with me, and listen to the unrated playlist, and rate music as I listen. Two clicks on the center button, and I can select the number of stars to rate the music.

Now, at this point, I’m left with a lot of one-star music on my iPod. To get rid of this, I can go into iTunes after I’ve synced my iPod, and uncheck those tracks. An even better idea, though, is to change the music sync options for my iPod. Instead of syncing all checked music, I now sync only certain playlists. I sync the unrated list, as well as Aardvark, Absolute, and Actual. Now, anything with three stars and up will automatically sync. Since this leaves out the two-star tracks I want just in case I want to listen to “The Wall,” I made a playlist called “Everything” that includes the “Music Only” tracks with two stars or more, and set this to sync to my iPod as well. The only things that shouldn’t sync now are one-star tracks, so each time I sync my iPod, any one-star tracks will automatically be removed. In the image below, you’ll notice that the “Everything” playlist is not synced. This was to make space for episodes of “Top Gear” and “24.”

Even this left me with so large a list of unrated songs that I broke down my unrated list into four lists. One with “Rock” in the genre (not exact, but containing the word “Rock”), one with “Christian,” one for “Latin,” and one called “Misc.” The “Unrated Misc” inludes all zero star tracks that do not contain one of the other three genre keywords in the genre. Now, I can listen to a smaller list of tracks such as “Unrated Rock” and rate them without feeling as if I’m being yanked from side to side by style changes of the music. I also set these individual playlists to sync to my iPod. Note in the two images below, the different ways I looked for zero-star music.

Now, all this is fine and dandy. Each day, I take my iPod to work and play music while I work. As I listen, I rate music as i can. Obviously, I can’t sit all day and rate music, but I am able to get a lot of music rated this way. Each day, my rated lists grow, and my collection is more usable. Still, something is lacking.

When I drive, I often like to listen to more upbeat music. My favorites ratings are great, but they don’t allow for whether a song is good, hard, driving music. I used to have a standard playlist called “Slammin” that I would drag tracks to, but manually creating playlists is the old way, and I need something better. I need a classification system beyond ratings and genres that allows me to divide my collection into more specific playlists. For this, I use the little-recognized “Grouping” tag. If you go to the “info” page for a track, you’ll notice the box for “Grouping” now that I’ve pointed it out. All in all, it’s a pretty useless tag, but we can use it here.

Thinking about how I’d like my music classified, I have three basic classifications. “Slammin’” is for the good hard music I like to drive to. “Radio” is for music that I would play on my perfect radio station, consisting of Folk, Americana, easier-going rock and oldies, and some eclectic things thrown in. I know, perfect is in the ear of the listener, but I like a nice, enjoyable, slow mix sometimes, and “Radio” is the classification I use for that. In addition, I use “Explicit” to classify songs that may have curse words or content that I’d rather not play when my son is in the car. For good measure, I added a fourth category called “Other” that will make sense in a moment.

To classify my music, I simply edit the “Grouping” field to include the tag for that group. If a song falls into multiple classifications, I separate the keywords with a dot. slammin.radio would indicate a song that is both properly upbeat for driving, but also fits the eclectic mix of my ideal radio station. Slammin.explicit might be a really good song for me to listen to, but not my son.

To make use of these new grouping tags, I build a smart playlist identical to my “Actual” playlist of three stars and above, but I add a new option to include songs with “slammin” in the grouping tag for driving music, or “radio” for my eclectic mix. I can make a copy of my “Slammin’” playlist that also excludes the “explicit” tag to make a “clean” playlist for when my son is along for the ride.

Why did I also include an “Other” tag? That’s easy. I’m making inclusive playlists, but I also need an exclusive playlist, so I know what hasn’t been categorized yet. I make another copy of “Actual” but this time, I want it to include tracks that DO NOT have “slammin,” “explicit,” “radio,” or “Other” in the grouping field. These are all songs that need to be classified. Everything will eventually have a tag, but if none of the first three are appropriate, I use the “Other” tag to allow the track to fall out of the unclassified list. Unlike the unsorted list, I don’t tell the unclassified list to sync to my iPod, because the tagging must be done in iTunes anyway.

Isn’t this a lot of work? Yes. The great thing is, it doesn’t have to be done all at once. By allowing the smart playlist system to work to my advantage, I can go as fast, or as slow, as I like. I always have unrated music I can rate, at least for a while longer. I’m down to under 1000 tracks left to rate. On a good day, I can rate 100 tracks with little effort. Classifying can be done in batches. If I know some songs in the unclassified list I want in my slammin list, I just add the tags. I quickly classified a couple hundred songs into my slammin list to make it usable, so any additional work will enhance my experience. If I add a new CD to my collection, I can easily rate and classify it on the spot, and save the rest for later.

Obviously, I could go even further. If I had the years for all my music in the tags, I could easily make a 1980s favorites playlist. The techniques used above can be applied in many more ways, to allow you to make your iPod work the way YOU want it to.

So, in summary:
* Fix your genres so they make sense to you.
* Make a “Music Only” smart playlist that will serve as the basis for all smart playlists you create
* Create smart playlists based on ratings, including an unrated playlist
* Synchronize playlists, rather than simply “checked music”
* Rate your music
* Categorize your music to match the way you listen. (hard, funky, easy, dance, crap, etc)
* Create smart playlists to use your categories
* Take some time to rate, and classify, as you can. Don’t sweat it if you don’t do it every day.

Oh, and one more thing. If you have an iPod and an iPhone, or multiple iPods, you can sync them all to the same music library by selecting which playlists you want to sync to each device. My iPod has most of my music on it, but when I have an iPhone, I may only want my Aardvark and Absolute playlists. More likely, I’ll only have my Radio playlist, but that’s just me.

The funny thing is, when I am driving to work and back, I’m usually listening to an audiobook.