Another new batch of iPads, another cycle of tech pundits determining what these new iPads—and their discounted, previous model brethren—mean for Apple and its customers. In short, Apple’s going to make a buttload of money. I’m more interested in what the iPad means for myself as an iPad owner, and my plans to upgrade. I have a 3rd Generation iPad, the first model with the Retina Screen, and the one that many describe as compromised. It’s thicker and heavier than the iPad 2, and it does get pretty warm at times. On top of that, the A5X processor is taxed enough by iOS 8 that my iPad now lags on simple tasks.

When I bought my iPad, the plan was to use it as a test bed for retina web graphics. It served that role well when redesigning Sanspoint. It replaced my Kindle for reading as the Retina display was so much easier on the eyes than my old Kindle Keyboard. Though after realizing the effect the blue light was having on my eyes when I read at night, I switched to a Kindle Paperwhite for most reading. That left it as a portable writing device, but that ended when I stopped going to my weekly writing group. I stopped attending that, because it was a pain in the butt to get from work, to the gym, to 62nd and Broadway. Also a pain in the shoulder: a bag of workout clothes, an iPad 3, and a bluetooth keyboard were heavy.

So, my iPad stays at home for the most part. I could try doing what Ben Brooks does, with keeping my iPad open on my desk to take notes, but I just don’t work that way. If I’m going to keep something on my desk to take notes, I’d prefer a paper notebook. Less friction, and less worry about battery. I don’t like using my iPad for pure content consumption, either. For videos, I have my giant monitor hooked up to my MacBook Pro. For books, there’s the Kindle. I can read comics and RSS feeds on my iPad, but ComiXology is a chore to use since the Amazon acquisition, and I can read RSS anywhere.

What keeps me from using my iPad for all these things? Friction. I’ve spent over half my life with a keyboard and mouse, tethered to a desk. I rolled with a desktop and laptop setup for a while in college: taking my iBook G4 to class, while my Mac mini sat on my desk. Before that, I did the same thing with a custom-built PC, and a school-supplied ThinkPad. Those were the days. I could do that with my iPad. It sure weighs less than my iBook did. Problem is, I have a computer on my desk at work. It’s a crappy Dell laptop, but it’s still a computer. There’s little I can do on my iPad at work that I can’t also do with the computer, and now that I’m using Trello to manage my work tasks, I don’t have to use my iPad as a separate task manager—and I don’t know what else I’d use it for at work.

Which brings me back to those new iPad models. I do use my iPad 3 enough that its iOS 8 related lag has become a problem. My plan was to pick up a new iPad mini after the holidays, and see if the smaller size and lighter weight were enough to get me to use it more. If I found the size of the mini to be more of a detriment, I could just take it back to the store and get an Air. Apple’s decision to give up parity between the mini and the Air this cycle has thrown a wrench in this plan, albeit a small one. The power of the iPad Air 2 excites me, both in terms of processing, and the extra gig of memory it has over previous models. But, will I use it? I just know it’s good for future-proofing. I might still get an iPad mini 3, though is the extra $100 for TouchID worth it? [1]

The most important question is whether I really need an iPad at all. Perhaps, I should change my plan. Instead of buying an iPad mini, and exchanging it for an iPad Air, I should buy an iPad mini and see if the size and weight issues are really what keep me from using an iPad. If that’s the issue, then I can comfortably roll with the mini until its limitations become obvious. If the iPad mini ends up just staying at home, with its Smart Cover closed, except for the occasional game of Threes!, or whenever I remember there’s a new issue of Sex Criminals… well, that’s what Gazelle is for.

I’ve found myself thinking back to the Gruber-Mann Theorem of Obsession Times Voice (see also Gruber’s essay), and my work. For those unfamiliar, the Gruber-Mann Theorem of Obsession Times Voice is a strategy towards creating good, and successful content on the Web, and elsewhere. Find your obsession, find your voice, and combine the two in whatever you make. Don’t worry about the money—worry about making something good. The money situation will sort itself out, assuming the stars align in the right way.

This is valuable and true advice. I don’t disagree with it in the slightest. I’m thinking about the Gruber-Mann Theorem, and how it relates to my work, in a different way. After ten-plus years of making stuff for the Web, I’ve found a voice, but I’ve come no closer to determining exactly what my “obsession” is. Over the decade, this site has gone from a personal blog, to writing about books and literature, to a focus on “technology and culture”—which is to say not a focus at all. I do have obsessions, the band DEVO being one, but I’ll need to get in line behind Michael Pilmer there.

In the SXSW talk that defined the Gruber-Mann Theorem, Merlin suggests not just starting “a blog about Star Wars,” but a blog about “the third Jawa from the left.” It’s obviously tongue-in-cheek advice. The’s only so much you can say about one Jawa in one scene. Though you don’t need to give consideration to reaching the widest audience, you need to give consideration to whether you’ll have enough steam with your theoretical obsession to make a go of it in the long-term. Part of why the lit-blogging period of SansPoint ended when it did was that I just ran out of steam. I didn’t have much else to say about books, writing, or literary analysis. There’s certainly people out there who have that covered, though. More power to ’em.

How many of us have a driving obsession that we can continue to make stuff about, day-in, and day-out? I don’t know if it’s that many. I think about Patrick Rhone, as an example. He’s a man of multiple passions: technology, theater, and handwriting and notebooks, and splits his online presence among a couple of silos for these obsessions. The silo approach works for him, but I’m not sure it works for me. I care a lot about technology, but only in certain sense. I care a lot about culture, but only certain forms of it. I could split my writing and thoughts on both between two silos, but I don’t like the idea of spreading myself out that thin—it’s part of why I cancelled Crush On Radio. For those of us with multiple things we can claim as our “obsessions,” we need some other theorem.

“Obsession Times Voice” is just one strategy towards creating great work and building an audience, but it is not the only one. We can ask ourselves questions about an ideal audience, though all-too-often, audience is bogged down in “monetization,” which leads to clickbait and viewing your audience as mere vehicles to clicks. It’s nice to be like Myke Hurley and not care about the numbers, but when you’re out there trying to put your name, face, and your thing in front of people—and when you’re trying to find the right people to put it in front of, the numbers are going to matter. Even if you’re not trying to necessarily make money. Just the satisfaction of knowing you’re reaching people, and that they’re coming back for you, goes a long way. And, yes, it can help you make money if you want to. (I do, but not by compromising what I want to write about, which is a tricky balance to find.)

There’s other things we can consider instead of just “obsession.” “Purpose,” for example, and to Ben Broeckx. It’s one thing to write about technology, and even if you have a distinct voice, the space is crowded enough that a voice alone is not enough if you’re just writing about the same five topics the big sites and big names are covering. If you’re trying to change how people think about technology, on the other hand, you may have a chance to be spotted. There’s “experience” or “knowledge,” which is a big part of the value add of both a Dr. Drang, and a Ben Thompson. People come to you to learn something. Perhaps there’s more, and these are all multipliers to Obsession on top of Voice. I’m going to keep thinking about this in the back of my mind, and try to find, if not the Obsession, Purpose, or Experience that I can multiply with my voice, I’ll find the other noun that fits the equation.

Another new version of iTunes, another round of whinging and complaining about the changes to the interface. People have been griping about iTunes since the days in which it was a big, chunky Brushed Metal app. Supposedly Bono told Steve Jobs that iTunes looks like a “spreadsheet” back in 2009, but the most dramatic criticism came with iTunes 9 and the “Grid” view for albums becoming the default view, along with the removal of the sidebar (as a default) in iTunes 11.

I don’t get the hate, to be honest. iTunes has problems, and I’ll get to those later, but the interface isn’t one of them—at least for me. iTunes does what a media player should do, which is to play music, organize music, and get out-of-the-way. In an informal, to say the least, survey on Twitter, the organizational side of iTunes is where it seems to fall down. I don’t see it, especially as picky as I am about how my music is organized. [1] Organization is a set it and forget it operation. Clean up the tags, set your sort options, and forget it. There’s ways to improve how iTunes handles editing metadata, but it works well enough. I don’t expect Apple to incorporate something like MusicBrainz into iTunes any time soon.

Maybe I just don’t do stuff in iTunes that runs into the same issues as the complainers. I don’t mess with playlists much, or use iTunes for much in the way of non-audio media. For me, my iTunes workflow is based on patterns I developed in the Physical Media days. Back in high school, way before I got my first iPod, my way of putting on music worked something like this:

“I would like to listen to some Pink Floyd…”

*Opens his CD binder to the Pink Floyd section and flips through*

“Oh, Wish You Were Here! That would be good.”

*Puts CD in player and proceeds to listen*

In iTunes, I decide on music in much the same way.

“I would like to listen to some David Bowie.”

*Cmd-Tab into iTunes and type “Bow”*

“Hm… Scary Monsters (and Super Creeps) would be good right now.”

*Double-clicks on album, and enjoys the music*

iTunes current UI works perfectly for that. I infinitely prefer the “Grid” view to the old column browser. Maybe I’m just visually oriented when it comes to selecting albums. I’m often as anal about album artwork (perfectly square, at least 500×500 pixels, larger if possible), as I am about my tags. I enjoy scrolling through the little squares of album art, finding the artist I feel like playing, and choosing the album. It’s visceral in a way that the boring old Column Browser isn’t. When it comes to organizing music, iTunes 12, with the “Recently Added” section at the top of the “My Music” view makes sorting and tagging new additions to the library easier, too.

iTunes still has problems. It’s still a Carbon app, with all the modal dialogue boxes and performance issues that implies. It is a bit heavy, though I’m not sure I agree with those who want to take a jigsaw and split it into component apps of Store, Music, and Movies like on iOS. Device management, especially trying to organize apps within iTunes is a pain in the butt, and Wi-Fi sync is still flaky. These are all issues, but they’re not ones that get in the way of using it as a media player.

If there’s an Apple media app that deserves UI criticism, it’s Music on iOS. Since iOS 7, the Music app has been frustrating and borderline unusable for me. I tend to listen to one album at a time, though if I go to select an album in Music from under an artist listing, it’ll play through that artist’s entire discography by album—in alphabetical order, no less. Sure, I could rotate my phone into Landscape mode and pick from the sort-of Grid View there, but that just lists every album on your device alphabetically, which doesn’t jibe with how I organize my music at all. Reverting the layout of the app to iOS 6 would go a long, long way to making my life easier. Instead, I’ll just use Ecoute.

In the meantime, if someone can explain in a little more detail where iTunes falls down for you as a way to play and organize music, I’d love to hear it. I just know it works for me.

I, like many others, was bitten by the bizarre HealthKit bug that causes the Health app to lose data. Coming on the heels of iOS 8 renewing my interest in self-tracking this frustrated me to no end. I have a reasonable theory as to what caused the app to die and lose data—too many apps were trying to feed data into HealthKit. Like I suspect many other enthusiastic self-tracking iOS 8 users, I dumped a metric ton of HealthKit enabled apps onto my Phone as soon as 8.0.2 came out. In my case, this included: MyFitnessPal, Jawbone UP, Centered, MotionX 24/7, and FitStar. This was too many at once, and I wouldn’t be surprised if some of those apps had bugs in how they communicated with HealthKit at launch.

To start, I uninstalled every single app that used HealthKit, and along with them, removed all the data they stored in the database. I then went back in and deleted every last piece of data that had been added in Health—either by hand, or by apps I ditched. This was a bit more tedious than I expected… until I noticed the “Clear All” button in the top left corner. In the end, I had a clean slate to experiment with, so I could identify when and where things failed. I reintroduced apps one at a time: MyFitnessPal was the first, and I built my Health App ecosystem up around it, trying to avoid redundant apps that would conflict when writing and reading data. Among these, was replacing MotionX 24/7 with the updated version of Sleep Cycle, to avoid another app that collected and wrote steps data. I knew it was working when my sleep data finally started to appear in Jawbone UP again.

After running with this streamlined setup for three days, it seemed to work well, except for a connection issue between Jawbone and MyFitnessPal for food tracking. Unfortunately, when I went to write this piece, I found Health had choked and died again. That’s when I found Apple’s Knowledge Base article on Health data not updating. After following those steps, including the awful forcible rebooting of my iPhone, my app came back, minus a few steps and the 100 calorie bag of cheese popcorn I ate at my desk. The iOS 8.1 update arrived as I wrote the above, with a potential fix included. In the afternoon and evening since updating, it’s been… intermittent. I did try the force reboot solution a few times before and after the upgrade. A day later, it looks like most data is synchronizing correctly, except the step counting, which is the most frustrating.

I’m disappointed, to say the least, that such a flagship feature of iOS has been so flawed. For an app with such potential to change people’s lives, and serve as a centralized back end for the growing ecosystem of health data collection, Health feels like a step backward. The broken step counter on my phone is mind-blowing, since the Pedometer++ app, which pulls data straight from the M7 without using HealthKit, is still keeping an accurate count. None of this makes any sense to me.

I have a folder in Dropbox with 380 files of notes, running lists, and piece of writing, ranging from finished posts, to running lists, to one-line note snippets. I have nearly 2600 bookmarks in Pinboard, and they’re all badly tagged. My life exists in various chunks of disparate data, largely living in the cloud, and it’s become a mess. Finding things, even with the great search tools in Pinboard and nvALT, is still a challenge. The point of a filing system is to be able to find things when you need them—fast. My system, or lack thereof, has failed me. And every piece of data I add is only making the problem worse. This is my fault, of course. Only a poor craftsman blames his tools. Part of how I got into this mess was first not defining just what belongs, or doesn’t belong, in these buckets of stuff. 

I had this problem once before, and my solution has been to live life in Plain Text (well, Markdown). I built a system around Merlin Mann’s txt system. Combined that with occasional use of Evernote for anything that required images or PDF files, and I was off to the races. My cardinal sin, however, was using nvALT as home for more than just “notes”. I used it to house my writing. When I first realized my nvALT was getting crowded, I set up a rule in Hazel to move anything tagged with #archive in the file name to its own folder. This worked, but I ran into a bug with nvALT when I changed a file name and Hazel moved it out, if I was editing another file name, it would switch the file I was renaming it with the one below it in the list, which only made my tenuous file organization even worse.

As for Pinboard, back when I started with Delicious for bookmarking, I was somewhat religious about tagging everything that ended up in my database. However, it’s so easy to pipe stuff into Pinboard—every Tweet I fave has its attached link saved, as well as everything I save in Instapaper—and so hard to go back in and tag things. I love Pinboard. It’s the best service in its class, as I discovered after trying to use Evernote to store bookmarks for research. However, it does not reward sloppy bookmarking, and a lot of the tools I used to load things into Pinboard were extremely sloppy.

It’s looking like the only solution is to start over again. Drop a bomb on my Notational Data folder and my Pinboard, clear out the years of cruft, and vow to be more disciplined as to what goes where. I don’t want to give up Pinboard, but I suspect my writing and notes workflows might need a revision. I’ve been experimenting with using Trello to track tasks and lists, and I can see it as a great way to offload a lot of the running lists of media and the like to check out into a more structured system. I also could shunt off my Writing to a dedicated space in iCloud and have that all live in Byword. Evernote can take over for quick capture, notes, and reference files.

The “Everything Bucket” app I’ve dreamed of for years isn’t going to work. I’ve tried nearly all the options over the past decade: Yojimbo, DEVONthink, MacJournal, and even Evernote. The way my mind works, and the lackadaisical way I tend to organize things make dumping all my data into one silo a bad idea. I need to make sure that I’m vigilant in policing what goes in, where, and how. I also need to make sure I clear out what’s no longer valuable. I doubt there will ever be an application that can organize my information for me without some intervention. The right tools, however, with the right mindset, will put me in a good place to keep up with what comes in.