It Ought To Be Easier

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.

  • Brad,
    that sounds like a nightmare indeed. If you use the free winamp player by any chance, you should grab the iPod plugin here:
    I’ve successfully used it to retrieve files off my iPod when my playlist had become corrupted and it looks like it now supports the Shuffle.

    good luck

  • this experience is even worse if its your 14 year old daughter who has lost her music.

    trust me.

  • My two cents: the “shuffle” is more to meet a form factor need than any sort of logical extension to the iPod family, and I won’t be surprised if we see it vanish from the marketplace in the next six months or so. Even a watch-size screen would be better than an invisible box and now that Apple has shown off its brilliant engineering again with the Nano, why can’t we have a Nano that’s half the width and twice the thickness? Hmmm…

    Me, I still have two first generation iPods, actually, and they still work fine. One’s just for audio books (exercise, ya know) while the other is our portable music library. 10GB of music: how much more could I possibly need?

    But give the Video iPod another generation or two of evolution and I’ll be very interested in having my DVD library on a hand-held device where I can watch the movies on a plane or hook the device up to a video output device (read “TV”) and watch any of a few hundred movies. Toss in a nice firewire/usb2 connection to a DVR and that would be one revolutionary product!


    All this cr*p is not just because Apple make mistakes in their software that make it hard for people to do what they actually want to do. It’s also there by design so that they can make their version of DRM work, keep the record companies happy and run iTMS.

    Just Say No To DRM, m’kay?

    This is why Apple are now part of the problem. The moment they became a music distributor they had to sell their soul to the devil. And it’s us who suffer because of it.

  • Brad —

    Jeremy Zawodny can commiserate with you on this one


  • C’mon Brad, you are a VC – invest in someone designing synchronization haven.

    In all seriousness though – good synchronization in general is a very hard thing indeed, primarily because it is a moving target. Different people have different images of good sync, or even same person may prefer different sync modes depending on situation.

    Apple tried to simplify things, enforcing “keep your device in sync with one and only one computer” discipline. I, for one, ditched retarded iTunes altogether once I realized that, and now I use Yamipod to synchronize my music between iPod and four computers exactly in the way I want. I am even considering getting my hands on some software that is able to work with Apple internal database, and write a bunch of scripts on top of that.

  • If you were using a Mac, you could use my app, PodWorks. It has a feature that recreates a playlist from a given iPod in iTunes. Not sure about the options for that on Windows though.

  • Amen.

  • I made the mistake of plugging my iPod into a PC, then a Mac. It did me the favor of reformatting the drive for the Mac, so I had to reload all my music from the Mac.

    Then, I brought it home, plugged it into my PC and realized I would have to reformat it again to make it work with the PC.

    I *never* thought something like that would take off like it has.

    It did, though, because people don’t usually do things like that. Their usage model is like my wife’s: she uses one computer, a XP machine where she has her own account. She runs iTunes. There is a narrow path, and it works.

  • Dave


    … take a breath. Its just music.

  • Its still a problem today.. and I love ipods

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