Adventures with an iTunes playlist

When it comes to vacation, holiday, or adventure planning I am one of the most on-the-ball people you know. When it came time to plan a three-week adventure in Australia last summer, I had the majority of the trip booked within a few weeks' time. That included my international flights, domestic flights between four cities in Australia, hostels, major attractions, the whole nine yards. The year previous I booked, planned and executed a two-week trip to London, England with my mother, and she is still raving about it to this day. I may have missed a calling as a travel agent. Nevertheless, despite the fact that I can go to Australia with only a forty litre Mountain Equipment Co-Op bag, or a four diamond trip to London, there is always one part of my vacation planning that stresses me out like no other aspect: building an iTunes playlist.

I typically only travel with my 8gig iPhone, so space is a bit limited when I have to pare down a music collection that's now pushing 14,000 songs onto a device that will only hold 1,000 (less if I allow for apps, games, etc on the phone). Anticipating what I might want to listen to on a three-week vacation is like trying to win the lottery; chances of a favourable outcome are not good. I have this really bad habit of having one song remind me of some other seemingly unrelated artist or song, and then I have the desire to listen to that new song. That's normally not a problem when I have my iPod Classic with my fully loaded library on it, but when you're thousands of miles away...well, that's a different beast altogether.

Back in early May, I had a trip planned to New York City. I was meeting up with a couple friends from Australia who were up in North America visiting. This was actually a trip I didn't really have to plan, as they booked the accommodations and stuff to see and do was largely figured out before I arrived. I literally just had to book a flight, pack a bag...and create an iTunes playlist.

I started off thinking I could just dump my entire library into a playlist and weed it down song by song. This proved somewhat impossible because I made this decision two days before I was supposed to fly out. I gave up after only going through about 1,000  songs. I then thought I could set up a Smart Playlist that would capture tracks, except I don't rate my tracks, so I was limited to a selection of either random songs, most recently played/unplayed or most played, and it wasn't really hand-picked. I tried making a Genius Playlist, but after fiddling around with the Genius results for nearly an hour, I gave up, because I felt like it just wasn't capturing the music I thought I would want to hear on the trip.

Then, in complete desperation, I grabbed my copy of The Pocket DJ by Sarah Lewitinn. Published in 2005, Lewitinn carefully compiled some of the best playlists for your mp3 player. She grouped the book into sections: Essential Genres, Essential Artists, Celebrity Playlists, and Other Playlists (thematically). Unfortunately, the book is now seven years old, and Lewitinn has not compiled a follow-up, so the book is unfortunately rather outdated (references in the book about Las Vegas band The Killers indicate that the band are fresh on the scene-- which they were at the time). Despite the outdated nature of the book, it's still one that I highly recommend. It's got some great playlist ideas, even if the songs don't capture material that's been released since the book was published. So my last ditch, final resort for putting together a half decent playlist was a dead-end, and I had less than two days until flight time.

In the end, I ended up grabbing a few of my favorite artists, and putting on their most recent album or my favorite songs by them, and putting into a playlist. It was a rush job (literally hours before leaving for New York City), but it would have to do. As it turns out, I only listened to music on my flights, and for about half an hour each morning while getting ready for the day. All of that stress, for the equivalent of perhaps eight hours of music listening, or approximately a third of the playlist I had set up in the first place. I've learned my lesson, though, and perhaps I should have learned it a few years ago; next time I'll set up a smarter Smart Playlist to capture the songs I'll hopefully want.

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