Brad Feld

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It Ought To Be Easier

Nov 27, 2005
Category Technology

Lyle Lovett’s “It Ought To Be Easier” was the 195th song on Amy’s iPod Shuffle playlist that I manually recreated for her this morning. 

Someone at Apple on the iPod user experience crew needs to go to the Apple Store in Palo Alto, buy two shuffles, three iPods of different flavors, and a G5.  Then, they need to go to Fry’s and pick up two desktop PCs, a server, two laptops, and a wireless router (I assume all the machines have wireless cards in them.)  Now – set it all up, rip all your music, store it on the PC server (or Mac server, I don’t care), point all your iTunes clients at the right directory on your server, and make a bunch of playlists.  Yeah – that was fun, wasn’t it. 

Now, for shits and giggles, synchronize your server music file on one of your laptops (c’mon, it’s not that hard to figure out how to do it, but you will need new and exciting software.)  Make a playlist on that laptop (using iTunes of course), associate a Shuffle with it, and copy the playlist to your Shuffle.  Now, give your laptop to someone else (e.g. your IT guy because you got a new laptop – just pretend).  Try – just try – to get the Shuffle to automatically associate with another computer without wiping out the playlist.

Now, stare at your orphaned Shuffle for a while.  Your wife – who you love very much – just wants to make a few changes to it.  Try to explain to her why it’s not that easy (since nothing recognizes what’s on the Shuffle).  Watch as she looks at you as though you are a total freak of nature.  Continue to watch as she starts to scream and then cry.  Seriously.

You – like me – will become determined to figure out how to get this damn playlist off the orphaned Shuffle and into a copy of iTunes so your wife can be in music change happy land.  Anapod looked like it would work, but after spending $30 on it, it turns out that it doesn’t handle playlists (and recreating them in iTunes) with Shuffle’s very well (it works very nicely with the other iPod versions.)  Thankfully, Anapod can figure out what’s on the Shuffle and gives you a nice list of it.  Try to figure out how to print this list.  You’ll eventually give up and resort to opening a Word document, hitting Shift-PrtSc, and Ctrl-V into the Word doc, followed by PgDn in Anapod, Shift-PrtSc, … until you’ve got a nice document of your screen shots (5 pages to get the full 250 or so songs in the play list).  Then – print (to your network printer of course).

Hold your breath.  Plug the Shuffle back into your wife’s desktop computer (I’m not going to make that laptop mistake again – this is her computer).  Fire up iTunes.  Song by song, recreate her playlist.  After 30 minutes of this, walk outside and scream at the top of your lungs (or – if you have neighbors – go in your garage and scream). 

Fucking stupid.  There’s got to be a better way.  Apple has mastered the user experience.  These are not the droids you want.  Oh – and don’t bother trying to explain this to your wife – just smile and show her how to update her playlist on her desktop computer.