While in general I love my Mac, my iPhone, my iPod and most everything mac – iTunes is not part of that love fest. iTunes drives me crazy.

Now I’m sure I’m not the average itunes user: I have over 80,000 songs in my library. No, I’m not kidding. I love music and I like variety. I had over 5,000 cds before the dawn of digital music. I hate wanting to hear a song and not being able to have immediate access to it. iTunes generally makes it easy to manage music, but there’s some serious issues with the application that I hope apple addresses in future releases.

1: Why can’t I export my whole library? I mean all the songs AND all the playlists I’ve made and genius has made and import them to a new library? Every time I get a new computer, or set up a new external hard drive to play music off of – I have to go through the entire tedious process of adding all the music, and importing each playlist painfully one by one. This should be easier. If it is I haven’t found a way.

2: Why can’t I import multiple playlists at once? Manually adding playlists one at a time is a annoying and wastes time I don’t have to spend messing with itunes.

3: Why can’t I open up two libraries at the same time? I finally figured out how to have multiple libraries, but they have made that practically a secret to perform: hold down the option key (shift on a pc) when you open itunes and it will let you pick which library you want to open (or create a new one). This is very helpful if you have more than one external hard drive with music on it like I do.

4: When I change external hard drives, why can’t I just edit the xml file or tell itunes point the entire library to this directory? The entire structure of the directory is the same, all I did was get a new smaller portable hard drive and load all the music on it. Because it was named differently from my other drive itunes refused to recognize it. I had to create a whole new library, then add all the music (takes about 2 days to add as many songs as I have) and then import each playlist one at a time, and I had to make sure I had exported the genius playlists to be able to import those because itunes doesn’t save them in a place I can access the list of songs. Annoying and time consuming.

5: The default “let itunes manage my music” – why is that the default? If I delete a song off my ipod – it doesn’t mean I want to delete it off my hard drive! Yes I can shut this “feature” off, but why is there or turned on to begin with? To me, this will just cause confusion for users who think they have a song – not realizing they deleted it when they took it off the ipod. Yes there’s a warning, but still I just think the option shouldn’t be there to begin with. I’m pretty sure the first time I used itunes I did this and deleted some songs before I realized what I was doing.

6: Sync my ipod with my library is a useless feature to me too – until ipods can hold 500 GB of music there isn’t enough room on the ipod to put even half my collection on it. Manually manage music should be the default. I attempted to use this feature with my iPhone and it became so annoying that it wanted to sync all the songs each time I had the phone hooked up. Which of course deleted the songs off of the phone when I didn’t have the external hard drive plugged in one of the times I plugged the phone in.

7: ‘Keep itunes music folder organized’ this is another feature checked by default that drives me crazy. I appreciate that itunes wants to make my life easier, but this just makes it more difficult. If I rip a compilation cd – let’s just say Dark was the Night (which is a great cd btw). I use this cool app called Max to rip the songs in 192 VBR (I am a big fan of variable bit rate) and then I put them in a folder called Compilations and another folder in that called ‘Dark was the Night Disc 1′ & Disc 2. Now let’s say I have that “feature” checked and I add the songs to my library.. boom.. Dark was the Night folder is suddenly empty and iTunes has created a new folder called Compilations and THEN made a folder for EACH and every artist and THEN put the one song by them on that album in the artist’s folder. Which makes it NEARLY impossible to find all of the damn songs on a compilation if you want to copy the album to another hard drive! Keep an album together – no I don’t want one album divided into 35 different folders under each artist. I can’t imagine anything I want LESS in fact.

8: Why oh why can’t itunes volume adjust songs automatically for me? Why do I have to manually go in and raise or lower the volume adjustment for each song? Surely itunes can figure out a way to auto level the volume on songs. This is seriously a drag at parties when one song is blasting and the next one is barely audible. Now see THIS is a feature that would make my life easier!

9: Why is this app so slow to load and close? Maybe it’s because of the size of my library, but I can’t be the only person with a lot of songs? Can’t apple find a way to speed this process up? Or make that xml library file smaller? Mine is well over 100 MB (I know I have a lot of meta data stored about my files, just seems rather large).

10: Genius playlists. Ok yes – I really like them. I discover new songs I didn’t realize I had sometimes, but often it puts the same 10 songs on every playlist. Pick stuff that isn’t on all my other playlists already. But that isn’t really what my gripe is about. A few months ago – I had genius make me a playlist off of “When you Sleep” by My Bloody Valentine. Which is definitely one of my most favorite songs ever. The 25 songs it pulled together for a playlist were nothing short of awesome – in fact genius I would say. I LOVED this playlist. It was by far the best playlist genius had/has ever created for me. I listened to it every day. I should have exported it to a playlist… Because one day I accidentally clicked the “refresh” button when I went to move the itunes window.  I could have screamed.. where’s my warning that I am about to overwrite/lose the best playlist ever? Where? Nope nothing. No warning. Poof – vanished. Gone just like that – replaced by 25 new songs that simply just didn’t measure up. I think that happened a few months ago and I’m still not over it.

I am sure I am forgetting a bunch of things that annoy me, but this is a good start.

So tell me, what annoys you about itunes? Or if nothing, what do you love about it?

I once heard those exact words in a meeting when I asked why the user interface and experience of an application was so boring and uninspired. I was told this is a ‘real business application‘ – fun was never a requirement. Then I wondered – why did people feel fun and work had to be mutually exclusive? They don’t have to be!  Having some fun at work doesn’t make people less productive; in fact, I would argue it does just the opposite.

Several years ago I designed the UI to a web application – I had used color (not like a circus, but I had a liberal use of color) and icons to give visual cues to the user what was going on. I thought it looked pretty slick (design is always subjective though) and had a rich enough feature set that the power users were happy too. To me, it was kind of like a pair of Cole Haan heels with Nike Air – sure it’s a slick and stylish patent leather heel, but it functions well too.

I showed some folks the mockups I had made in addition to the detailed functional specification I wrote to back up the pretty face. Many thought it was great and ready to move forward, but then there were others that were hesitant. These folks said it “had too much color and too many icons.” That it “looked great for a consumer product, but for a business product… well to be taken seriously, it has to be an all gray color scheme and text only menus. No one would take an application seriously with menus that had icons and text – no business would buy that kind of application”. I said but it has all the functionality one would want, why wouldn’t they buy it?! I can understand that argument if it looked really slick, but then didn’t have any decent functionality – but that wasn’t the case here at all – it was packed with great functionality. Wasn’t it an added bonus that it looked nice too? It didn’t matter. Nor did it matter that it was PEOPLE not businesses that used this software, and at the end of the day all people are consumers. I lost the argument and we ended up with a colorless, boring UI with text only menus. *sigh*

When was it decided business applications had to suck to be taken seriously? Can’t something look fantastic AND function? Anyone who still believes it can’t hasn’t walked into an apple store lately. They are proving users/consumers can really have their cake and eat it too. And with social media tools proliferating into businesses it’s happening to web applications too – people want tools that are easy and fun to use, can be configured to how they work, have slick user interfaces, and function well. And contrary to some folk’s beliefs – you can really have that!

And in the end, that lack of appreciation for good user experiences drove me to move onto opportunities elsewhere. It also led to that product’s demise (the company later pulled the plug on it).

Finally getting a chance to set up my wordpress blog and update the theme to look like my site. Still tweaking it – feedback always welcome =.