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Zen & The Art of iTunes Failure 

What a recent iTunes failure taught me about attachment to work and memories.

REBUILDING iTunes library from scratch over two days got app working again. Fine use of lazy weekend.

Had to sacrifice all custom playlists dating back to 2002, including An Event Apart playlists and delivery room mix from Ava’s birth.

Playlists still exist on old iPod but can’t be copied from it back to iTunes. (All software I’ve tried freezes & fails.)

Playlists still exist as code snippets inside .itl file in old iTunes folder, but numerous trials prove iTunes can’t launch from that folder any more. Thus I can’t temporarily launch from old folder, export playlists, switch back to safe new folder, and import them, thereby saving them.

And iTunes can’t import old .itl files. I Googled. I tried anyway.

13 years of custom playlists. From before, during, and after my marriage. Including one my daughter called “princess music” and danced to when she was three. Gone.

But, really, so what? Over time we lose everything. This loss is nothing. Attachment is futile. Always move forward, until you stop moving.

By Jeffrey Zeldman

“King of Web Standards”—Bloomberg Businessweek.

Hi! I’m a principal designer at Automattic, Inc. Also: Publisher and founder, A List Apart “for people who make websites.” Publisher and co-founder, A Book Apart—brief books for people who design, write, and code. Co-founder and co-host, An Event Apart UX & front-end conference. Faculty, MFA Interaction Design, School of Visual Arts, NYC. Host, The Big Web Show. Have written two books, notably ”Designing With Web Standards,“ currently in its 3rd Edition, and, on last count, translated into 15 languages and used as a text in 85 universities.