As I got rid of my ipod years ago, the only actual apple product I use is iTunes and associated store, so it should have been easy to just do it, but the problem was what you might call multidimensional.
1.) Fields and Info - I have like, labeling, and I want to keep my dates modified, added, and last played, and I like number of Plays and my notes on each song's info about if it was acquired due to Vividcon (sometimes), a vid (a lot), or cover (muchly) or random youtube surfing (weird yet strangely effective for tech-pop hybrids).
2.) iTunes Store being, well, right there, and familiar and the Recommended for You almost was useful sometimes and relatively easy to search. Not to mention iTunes Essentials was my favorite place to hunt down songs I couldn't remember anything about but know I heard it in the late eighties. No, this actually worked once.
The real problem here is that two was a dealbreaker, because I'm just that lazy. In a choice between ten seconds to get a song from iTunes and having to make the effort to go to the browser and find teh song at amazon or somewhere else was just too much to deal with on a daily basis. Also, lazy backed by the full power of four years of unrelenting habit, which breaking at this point felt roughly equivalent to deciding to stop breathing. Inertia also plays a role here, as well, rut.
Even with amazon's kind of amazing sales, I was not able to ever remember to go there when I wanted a song (though if I was there already when I thought of the song, that worked. Well, mostly. Again, habit). My Kindle Fire with the music tab was--not really helpful in the quest to shift my music buying. Amazon suddenly adding a year of free unlimited music to my storage account was the first positive step in that with a single program, all my music was now reliably backed up.
Then I got Castiel the tablet, and combined with the Kindle Fire, two of my three primary entertainment, work, and possibly reason for living were amazon-only (as itunes has no android). And yet. Not there.
Then Amazon did the following within the last three months:
1.) For a while there, it felt like everything I bought came with a free mp3.
2.) AmazonLocal did it a couple of times for albums.
3.) Totally betrayed all my trust forever.
Last week, Amazon brutally separated their cloud service into Files and Music, and now there was not only no more unlimited music at all, to keep all my music there and playable instead of only 210 of them, I had to pay for it. While they also offered to upgrade all my music for free that they had available, I was not amused. I sent a firmly worded email about how there was no warning.
(You know what it takes me to like, actually email a complaint? I didn't even know where on amazon i was supposed to complain. I was motivated, though; I searched. Me and a rep had a email chain on the subject. It wasn't sane, is what I'm saying here. I know this. I knew it when I was doing it. And yet, several emails.)
So I tried (hard) to resign myself to me and my tablet at work with only 210 songs on the cloud and no longer having full access to all of my music there, which was a horrible thought, because what if I really really needed Snow Patrol? What if I was in a desperate country mood? How could I choose only 210 songs? It was like that question about you and three books and a deserted island? I'd give myself a stroke just trying to conceptualize the idea of only having three books. I'm not honestly sure I wasn't getting there just staring at amazon's cloud player in my browser--what kind of person is asked to decide the relative value of Joydrop to Metric?
Also, I realized, I buy music off amazon when on my tablet and what would I do...oh. This is when I realized, once again, the sheer power of habit. At which time, my decision was made.
Note: I actually am not sure this was worth $24.99, though amazon did upgrade around 800 of my non-amazon, non-itunes songs to a higher quality for free and both Castiel and Sheldon the kindle are now safe for cloud use and I don't have to acknowledge there is something unsettling about my relationship with my music collection.
However, while I was contemplating the horror of my life musicless and alone on a deserted island with three books (dude, if I'm going to get worked up like this, I go all the way), it occurred to me there is a force far greater than habit or laziness that I could use to finally begin my iTunes migration: paying that much for one year to have the privilege of accessing my own music more conveniently has to be justified by using the player--and its very conveniently attached MP3 store--as much as possible.
I'm not sure, but I think I just literally blackmailed myself into not using iTunes store. More importantly, it seems to be working. And I have learned a valuable lesson about how to manipulate myself into doing something I really wanted to do anyway except it required effort, which in general means it's not happening.
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