If you're anything like me, your music collection from ripped CDs and iTunes Store purchases has far outstripped your iPhone or iPod's storage capacity. While the iPod Classic delivers a massive 160GB, I suspect that that vast majority of people run with 32GB or less. Although that used to be a massive amount, 32GB is really quite a paltry amount. That means that, somehow, we need to find a way to carry the right music. Here's how I do it.

Step 1: Create a Random Playlist in iTunes
One of iTunes niftier features is the ability to create Smart Playlists. A Smart Playlist is a playlist that's assembled based on a set of criteria that can dynamically update.

As you can see from mine, I've simply set the content to include files smaller that 5MB (I'll need to bump that up to a higher number now that I think of it. 10MB might be better), exclude anything spoken (I have several audio books) or played in the last couple of days and randomly filled with 500 songs.

Step 2: Use the Recently Added Smart Playllst
When you install iTunes a Smart Playlist for recently added items is created automatically. You can fiddle with that by to ensure that you sync the content you want. For example, by limiting the file size, you can ensure you don't sync videos.

Step 3: Sync your new Playlists
Now, connect your iPod or iPhone and change the sync settings so that the Smart Playlists.

One of the reasons I love this approach is that it lets me rediscover music I'd even forgotten I had. For example, today I listened to The Alleluia Chorus from Handel's Messiah, Whitesnake, Michael Jackson and Eminem.