The quantified self (and other web-based nightmares)

My working life and my personal life revolve around data organization and analysis. It's a simple truth for most of us, and those of us who need data most tend also to be the least at ease with the concept. For me, it all comes down to a strange breaking point wherein it's hard to tell how much of it is integral to constructing a better life and how much of it is dragging you completely off-course.

This is at the heart of the Flynn vs. Machine experiment: to what extent can I use this single machine to turn my life into a more focused and cohesive whole? I've made my need for a cloud computing solution obvious, and as app developers work furiously for an ideal solution (currently, I'm experimenting with iWork and its new beta website, Dropbox.com, and Evernote to see what combination might work best for me), I know this need is central to the iPad user's life in general.

At the same time, there is a growing desire for us to be able to track information. We write down what we eat, how often we exercise, what we need to accomplish at work, who to call back, which movies we want to rent. I personally have at least a half-dozen ways of organizing my own information, and I dream of a way to better streamline them all. I use Google Tasks to keep track of my to-do list at the office, my to-do list at home, and my list of random goals for the future (this involves things like "hot air balloon ride.") I use Goodreads to keep track of the books I want to read and Netflix to keep tabs on my movie list. My current favorite songs can be accessed on Hype Machine, and my grocery list lives in the Notes app on my Blackberry. I even make vague attempts to keep track of my progress as a runner on DailyMile.

I know that I'm not alone in this endless organization battle - websites like Quantified Self are devoted to logging the most basic of human functions, from sleep quality to calorie counts. This is all in the hope that future analysis of this data helps us see what we're doing wrong, how we're improving, and how we can better use our time. I live in fear that all of this data entry is actually wasting mine.

This said, without a list of things to do, I will never gain any traction on actually doing them. This is why I'm spending an evening and approximately $25 downloading the first of many list-organization apps on the iPad, and why I think it's worth it if I can the one that changes the way my words work. We all have a sense of where we need to go, and sometimes lists are the easiest way to find a map.

You think it's like this...

I woke up Tuesday morning with two very important pieces of information in my head. First, that I forgot to send an email at work that I definitely should have done, and second, that my throat felt like it was on fire and my whole body ached.

In these moments, you do what's best for yourself: you call in sick, you do what work you can from the confines of home, and you spend the rest of the day asleep. My problem was a bit more complicated: the email that I'd forgotten to send yesterday necessitated an Excel file attachment. Even if I were able to retrieve an old version of the file from my webmail, I couldn't save it on the iPad and re-send. I was stuck, and I dragged myself into work at 7:30AM to send one email before going home to sleep off sickness.

Cloud computing, in theory, is truly a dream. In practice, it's a bit of a nightmare for the layman. I've "grown up" with the idea of cloud music services: I was an early adopter of Rhapsody, and I've always loved the idea of my music library being able to sync to multiple devices. When Apple acquired the online streaming site / "music library on the web" service Lala, I got immediately excited at what this could mean for the consumer who can only understand digital music through the framework of iTunes. (This "consumer" makes up about 90% of people who buy music at all these days.) It seems likely to me that people are only going to latch onto the concept if it's made palatable through what they already know.

Now, I'm faced with the problem of being the consumer who can only understand digital files through the concept of saving on a drive. What counts as the "iTunes of cloud computing storage"? I couldn't even tell you the answer to this. My goals involve creating word processing documents, spreadsheet, and the occasional slide presentation; I want to save them and I want to send them to others.

To Google "cloud computing solutions" is to cry little tiny tears of technological hopelessness. It falls under "it's not fun, don't do it." Instead, I know this solution won't be immediate and I'm going to have to do some trial and error research. MobileMe. Evernote. Various Google Docs hacks. And the continued repetition of a question that seems likely to haunt the rest of my days...

"Is there an app for that?"

Makes No Sense At All

"The point is not to be married to your presuppositions," writes critic Bob Lefsetz in his latest email newsletter.  The context of the article is a familiar argument: Lefsetz is criticising the music industry's reluctance to change the way that it needs to in order to adapt with ever-changing technology and the needs and wants of consumers.

To the best of my knowledge, the first time I heard reference to "the cloud" was at a press conference for a Sansa MP3 player launch, powered by streaming music service Rhapsody.  A co-worker had invited me to tag along with her and write a brief article on the device for PSFK, a blog focusing on innovative ideas that improve lives.  The MP3 player itself turned out to be unique, and I wanted one immediately: it was a device that let you grab streaming music from Rhapsody's service and take it with you on the go - for $14.99 a month, you could have as many albums as you wanted at your fingertips, and it offered new playlists based on your likes and genre-based "channels" that updated each time you synced the player to your computer.

The question everyone asked about the Sansa was simple: did it stand a chance against the iPod?  In reality, the actual problem was larger in scale - the question, really, was "how do you get the average person to understand the value in both this product and the Rhapsody service?"  

People like to own things.  When it comes to digital music, it doesn't matter if you're buying MP3s through the iTunes store or downloading them illegally.  They're still on your computer at the end of the process.  They exist on your hard drive; you own them.  With Rhapsody, you never owned any of this music.  It was unlimited, and you could listen to it as much as you wanted as long as you paid the $14.99 a month, but if you quit your subscription, you had nothing to show for it.  You owned nothing.

The really crazy thing about it all was this: Rhapsody's biggest hurdle was also its greatest achievement.  With the launch of the Rhapsody-supported Sansa device, the company brought itself one step closer to its ultimate goal: a library of music not tied to any one computer or mp3 player or stereo system, but one that would live on its own and feed into all of those devices whenever you wanted to hear it and however you wanted to hear it.  Because you didn't "own" it, your usage became uninhibited and unlimited.  The music would live in a "cloud."



This concept has evolved a great deal over the years, and I will definitely be talking more about it.  Right now, though, I'm floored by how relevant it has become with respect to my iPad.  Because I'm "slow" when it comes to understanding how things work, I didn't really realise what it would mean to be using as a "computer" a device that essentially has no "desktop" or hard drive to speak of.  In practice, this means there's nowhere to save your documents to.  You can download applications (Pages, Numbers, and Keynote) that simulate the experience of desktop word processing, but these documents will be inside your iPad (un-email-able, essentially trapped) until you connect it to your computer and pull them out - presumably to live on that computer's desktop.

That seems kind of crappy.

Yesterday, while trying to write my first blog entry, I found myself faced with this reality as I looked for a place to simply save my file and put it in Blogger.  (Writing in Blogger itself proved a challenge; the rich text editor doesn't work at all, and it took me a good half hour to figure out all I needed to do was switch to the "Compose HTML" screen and pretend I was writing code.)  Google Docs was supposed to be my solution to this - it's the easiest way for "normal people" like me to understand what living in "the cloud" might mean from a document perspective.  But Google Docs doesn't work on the iPad, and no app seems to have been invented to properly fix it.

Eventually, after about an hour of reading tech blogs attempting to come up with quick fixes and downloads that serve as functional "workarounds" for the problem of keeping documents in an editable manner that you can access from your iPad, your computer, or email to anywhere, I have to admit I gave up for the moment and wrote my entry in Gmail and sent it to myself.

Still, the process made me really excited.  After all, what was the worst thing about every laptop I've ever lost?  The files that I lost in the process.  (Sometimes I learned my lesson and I backed things up, but I've seen CDs break and external hard drives crash and does anything really work?)  What if, by not having a place to save anything to, the iPad is giving me a chance to rethink the way I access my files?  All this time, I've been married to a presupposition of how these things are supposed to work. Having ownership of a concrete storage space for this stuff has gotten me nowhere; I want all of my files to live in the cloud!

It's kind of exciting when you think about it - the same way digital music in the cloud sounds exciting when you explain it to ordinary, everyday people like us.  Finding the right way to actually put this idea into practice, though, is overwhelming.  How do I do this?!

I'm testing out applications and websites that try to move closer bit by bit, but for now...I'm writing these in Gmail and emailing them to myself.

Technological Romance

My name is Flynn, and I'm technologically challenged.

Professionally speaking, my world has always positioned me somewhere near the forefront of new technology.  Every job I've had as an adult has hinged on my ability to either adopt or quickly understand what's coming next.  In college, I worked the front desk at the university computing lab, helping design students navigate everything from broken zip disks (remember zip discs?!) to their basic Photoshop woes.  At the same time, I found myself entering the music industry just before it began to undergo radical change through the advance of digital media.  I worked for the first record label to have its entire catalog available in MP3 form; I used that early knowledge to start a path in a career in digital sales and marketing.

The truth, though, is that at the end of every workday, I always went home.  For years, "home" meant an aging Dell laptop computer with two keys missing from the keypad, propped on my old Greek textbook in order to properly aerate the inner fan that no longer felt inclined to spin on its own.  Prone to overheating, it would turn itself off without any warning - usually as I struggled to write my undergraduate thesis.  Eventually refurbished Mac Powerbooks came into my life; as my work life began to revolve around digital music stores, I managed to get an iPod two years after all of my friends, and right before the brand new "in color" versions were introduced into the world, ensuring it would look outdated just months after its purchase.

The newest devices have always failed me, in some way.  The cheapest and most basic of telephones served its purpose for years before work forced me to trade it in for a Blackberry.  I never did buy another iPod.  I still buy records (sometimes on vinyl), and I read actual books with actual pages.  Still, I am curious: I want to know what stands for progress and what makes new technologies useful.  I may have had the world's slowest desktop computer in 1999, but I used it to start what was then called an online journal (later, a blog.)  Through it, I made friends, and I landed my first job.  Social networking has always afforded me the same simple luxuries; I can't say I've shied away from Myspace, from Facebook, or from Twitter, even as I have the most basic understanding of new devices and apps. Even as people around me complain about losing the value of face to face communication, I can't help but think that all these advancements are affording us new and potentially meaningful ways to connect with each other.

And so, after suffering the loss of my fourth laptop in the last six or seven years, part of me wants to go back to give up and only write in notebooks.  What's the point of all this technology if it's always failing so consistently?  Another part of me, though, wants to see this as an opportunity.  What if the problem isn't technology itself, but my failure to embrace it?

I've never used a touchscreen before.  I've never downloaded an app.  When I went to the Apple store last week, I asked a question about Mac / PC compatibility.  "Ma'am," said the Apple Genius, "our iPods have worked with PCs since 2002."

My name is Flynn, and I'm technologically challenged, but I bought an iPad and I'm going to use it as a computer. Along the way, I hope to figure out how to make technology work with me instead of against me, and I'd love it if you came along for the ride.