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Managing Audiobook CDs in iTunes

I used to rarely listen to audiobooks. I'd typically buy them to prevent going insane during the eight hour drive my wife and I sometimes make to visit my family in Ohio. They also help distract me from the tedium of I-95 traffic that turns what's supposed to be a 4 hour trip up to Rhode Island into a 6-and-a-half hour crawl.

Recently though, I bought Barack Obama's "Dreams From My Father" in the iTunes store on a whim during the pre-election swirl. I listened to it on my commute to work, which consists of about 20 minutes of walking and 20 minutes on the train each way. I discovered a few things:

• Books that normally don't hold my interest in printed form do hold my attention in audio form.
• I needed better headphones.
• I dislike DRM protection on audiobooks just as much as I do on music.

"Dreams From My Father" is a fun audiobook in large part because Obama reads it himself. The story itself is compelling, but what's great is that Obama mimics the voices of the people in his life - Kenyan relatives, Chicago ministers, his grandmother - as well as any professional actor.

What surprises me is that I've made it through less engaging audiobooks without a problem. I never dozed off through Bill Clinton's "My Life", and I'm currently working through Al Gore's "The Assault on Reason" without much problem, despite the fact that it's not read by him and is intensely dry and academic at times (shocker).

I'm not sure I would have made it through any of these books in printed form. At home, television and the internet compete for my attention, and when I do read it's typically before bed. Since I'm not a huge fan of reading anything too complicated before trying to go to sleep, I usually end up limiting my reading materials to tomes on par with "Goodnight Moon".

But I walk around and ride the train a lot. It's not smart to read books while walking (I've had near misses with cars on several occassions reading email on my phone), and since my train rides are typically short I find I'm rushing to put a book back in my bag while trying to get off the train not long after I got on.

My commute is also highly repetitive and boring, so pretty much anything with an entertainment factor on par with Gregorian chanting or yodeling will keep my attention. Hence the perfect time to catch up on history, current events, and political biographies!

At first I relied on the cheap Apple headphones that came with my IPhone to listen to my audiobooks. Big mistake. I had to turn the volume up to a near-deafening level on the train, and even then I had to press my hands against my ears at times to hear. This lent me a Rainman-esque quality that occasionally attracted unwanted attention.

After a little research I invested in a pair of Etymotic HF2 Earphones. These gave me the sound-isolation I needed and work as a headset with my iPhone so I don't miss calls. They key feature is the pause/play button on the headset cord that allows me to quickly pause a book when it's my turn to order at the coffee shop, rather than looking like a freak while I grope around in my pockets trying to figure out how to unlock and pause an iPhone while simultaneously ordering coffee and a scone.

The last problem I had to deal with was DRM. I don't like DRM because I use both Apple and Windows Media devices. So I typically buy DRM-free music from Amazon, but they don't offer DRM free audiobooks. The next-best thing is to get them on CD and import them into iTunes.

There are a couple of problems with this. There might be up to 10 audio CDs or more in a single audiobook, with each CD containing 10 or more tracks. So you end up with 100 different files for a single book. And by default, iTunes won't recognize an imported CD as an Audiobook, so you lose out on the "resume where you left off" feature when listening on an iPod or iPhone.

The best way I've learned to deal with this is to follow this simple, but admittedly tedious process:

1. Import the CDs into iTunes. Watch what you are doing because sometimes iTunes pulls different metadata for individual CDs within the same audiobook set.
2. Use the free MediaJoin application (Windows only) to combine all of the individual audiobook tracks into larger files. For example, I usually join all the files from a single CD in one file, so if there were 10 CDs in the audiobook I end up with 10 files. Make sure to name the files appropriately so you don't screw up the sequence.
3. Add the new joined files to your iTunes library, and edit the info on the files to provide the correct author, track number, and track title information.
4. In iTunes select all the files in your newly imported audiobook, right-click and select "Get Info". Go to the "Options" tab and set the "Media Kind" option to "Audiobook", set the "Remember position" option to "Yes" and set the "Skip when shuffling" option to "Yes".
   
5. Now your all of your files should should show up in the "Audiobooks" section of iTunes, and you'll get the desired "resume from where you left off" when you listen in iTunes or on an iPod. You can delete the all the unjoined files from your library if you want.