Despite the fact that I was one of the first people I know to have an iPod, my iPod and I have always had a troubled relationship. It's simply a matter of time. I don't really have time to put into making the relationship work.
As a matter of fact the happiest times in our relationship was when my youngest son was still at home. I bought him his own iPod on the condition that he give me a bit of space for me and my music.
It was a great solution. He had time to act as my surrogate, filling my iPod for me; I got to listen to my music and even some of his. If you have kids at home it's a strategy I'd strongly recommend.
iPod After the Kids Are Gone
When he went off to college even King Solomon couldn't figure out how to split our megabytes, so, like any good gadget-loving parent, I gave him the older iPod and bought a new one for myself.
Left on my own, I found out how many mistakes I could make on a device that by now the entire world thought was the most elegant user interface ever invented.
The biggest lesson learned: Don't rip your CDs if you're not connected to iTunes
Ripping a CD involves playing the CD in your computer's CD player and transferring its contents to your computer and then over to your iPod.
I have a pile of old CDs that I love and on weekends we have a 2 hour car ride up to our house in upstate NY. Since I'm always looking for life's efficiencies, I figured ripping my CDs to the computer as we drove North was a great move.
Wrong. The ipod gets its information about what the songs you're ripping from a little code that the iTunes database understands. If you're not connected to iTunes while you're ripping your CD you'll get a song called Track 01 rather than Times They Are a Changin' . Things like the name of the album, artist and song transferred. I burned disk after disk and all that my iPod could tell me about the song was "Track 01 " Track O2.
The Solution:
If you've made this mistake you can fix it. You can connect to the Internet and can replace the Track # information with the real CD information-song name, artist and so on. Go to the Advanced menu and after selecting the offending songs simply choose Get CD Track Names. iTunes will retrieve the names of your selected songs and apply them automatically, even if the CD is no longer in your computer.
http://tech.yahoo.com/blog/raskin/72;_ylt=AoJ6vpKFVIhoWJjyd1Hsp1ASLpA5