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.

With the release of iOS 8—well, 8.0.2—I’m dipping a toe back into self-tracking. Now that there’s a way to view information about myself, and do stuff with it that doesn’t require pulling it from twelve different apps, I feel like I can get a better picture of my activity and sleep than I was able to get before. That is, when the app works right without losing data. I was bitten by this bug on Saturday, and lost the data on a 15,000+ step walk. My body remembers, at least.

I’m tracking all of this data with my iPhone, rather than a separate fitness tracker. The apps in my toolkit are Pedometer++ for step tracking, MyFitnessPal for food, MotionX 24/7 for sleep tracking, Centered for meditation, FitStar for workouts, UP Coffee to track caffeine consumption, and the Jawbone UP app as a dashboard and to get insights. I don’t actually need Pedometer++, but I use it because it has a good, if a bit oversized, Notification Center widget. Also, UP Coffee doesn’t use HealthKit (yet), but works with the main UP app.

Right now, I’m still in “collection” mode. I want a sense of my daily routines, and standard habits before I try to shake things up. Anything I was already doing to reach my health goals, such as trying to walk 10,000 steps, or keep under 1800 calories is still ongoing as I collect this data, of course. What will be important is determining what I do with all of this information. If, after a week or two, I don’t feel like something needs to be changed, I can drop tracking that particular metric. What I would love out of all this collection is something Matt Birchler hit on a while back. I want to know when I’m trending the wrong way.

There’s nothing in HealthKit that will have it keep me informed out of the box. A standardized platform for health tracking is good to have, if only to build out services that can provide the Skinner Box style reinforcement that actually changes habits—at least for some people. As I’ve said in other essays on self-tracking/Quantified Self, having a goal in mind is more important than just collecting data. You don’t need a fitness tracker, in hardware or software, to lose weight, get in shape, or whatever your goal is. You just need to do the work. Knowing can keep you going, but you still have to do the work.

When I was twelve or thirteen, I was convinced I would go to school, learn to code, and make it big in the Valley. This was in the mid–90s, at the start of the dot-com boom, though like any good teenager, my interest was in making video games. I had a small group of friends in middle school who were also interested in programming, video games, and technology. Though in the intervening years, we all drifted away from it in one way or another. One studied Chinese, and now makes a living as a translator. One is a mechanical engineer. One dabbles in iOS programming, but only as a hobby. I’m the only one who makes a living, in some form or another, in technology, although in an area I didn’t plan on.

In my circles online, I see a lot of exasperation about the technology world. Some of it rubs off on me, and some of the exasperation is my own, thank you very much. Even just sitting on the edge of the swimming pool as a technology observer is getting a bit much. If you’re not getting paid to write one of the thousands of 300-word fluff pieces about the recent Apple announcement, it’s hard to muster up a whole lot of enthusiasm from our vantage point. Jamie Ryan, in his final post on his site, puts it this way:

…I’ve just gotten tired of the whole thing… Too many imaginary rules, too many opinions and too many people constantly judging you by some arbitrary measure of success. None of it matters.

Somewhere along the line, technology has become less fun. On a personal level, part of that lack of fun comes from the rough experience of working for a real, live, technology startup. That’s my own hang up. But, there’s no sense of fun in the larger tech space. The best minds of our generation, if they’re not dreaming up new ways for finance guys in suits to bilk more money out of the system, they’re out in the Valley, dreaming up new ways to repackage old ways to bilk more money out of finance guys in suits. The rare, exciting new thing in the technology space is either vaporware, or going to be snapped up by Google, Apple, or Facebook in a year. New, powerful, democratized mass communication tools are turned against women and minorities who upset the status quo. Why get excited, when we’re just going to get burned again?

We’re growing up. I’m 30 years old, part of the generation that remembers life not only before the Internet, but life before Omnipresent Internet in our Pockets. Technology, as an industry, is growing up too. I’m part of the generation that remembers the big promises about technology—how the Internet was going to create a new Enlightenment, reform social discourse, and usher in a new leisure age. These aren’t new promises that my generation was the first to get, either. They said the same thing about electric lights. Twitter didn’t start the Arab Spring, but it’s a darn good line to work into “investor storytime”. Twitter’s too old for high-minded idealism. They need to make money now.

I’ve said before about how we’re still figuring out what all these new technologies, all these changes, actually mean for our lives. What if they don’t mean much of anything, in the end? They probably don’t. So, what is it that keeps me interested in technology, even from the periphery of the tech world? I still see the potential and promise for technology to actually make our lives better, somehow. Not just ours, as the savvy, first-world, enlightened types, but everyone. It’s a bigger picture view of technology. Google wants to float Internet-connected balloons over Africa to get more ad impressions. Bill Gates wants to wipe out Malaria. Both use technology, but only one can be said to really improve people’s lives.

Improving lives and making money are not mutually exclusive, but I don’t think the system we live and work in is set up to make it work. This is a result of what Ethan Zuckerman calls “The Internet’s Original Sin” of the advertising-supported model, at least in part. There’s also the conspicuous consumerism of shoving yet another gadget down our throats, from tablets, to wearables, to the annual upgrade cycle. Yes, I want an iPhone 6, but I don’t need one. It’s not going to measurably improve my life in any way by having a bigger, faster phone—or a smart watch. (Your mileage may vary. Some settling of product may occur. Offer void in Utah.)

If I have a goal for myself, and my writing, it’s to communicate ways in which we can use technology better. Not to use it more. Not to use more of it. Just… better. To know to apply technology, where it works best, in our lives and the lives of others, but also know when to pull back. Too much of the rhetoric around technology is about solving problems with technology, with little thought given to consequences. Not every problem can be solved with an app, or a new piece of consumer electronics. Not every problem technology tries to solve is actually a problem. You don’t need to sling code to work towards these answers, either. We can all push towards finding, if not the answer, at least a sense of where it all fits for ourselves.

This past Saturday, as I headed into town for a concert, I stopped to check my email and found two messages from PayPal UK, saying someone had set up an account, and added a mailing address, with my gMail address. Well, almost my gMail address. Instead of the gmail.com domain, they’d used googlemail.com as the domain. I assumed it to be some kind of phishing scam, logged into my PayPal, changed the password and removed my gMail address from the account for safety. Then, to be sure, I forwarded the emails to PayPal’s spoof checking address. Content I’d done the right thing, I hopped the subway and was soon having my eardrums split open by the Buzzcocks.

Still a bit concerned, the next day I initiated a password reset of the account with the googlemail.com email. I got the password reset email with a verification code. Upon providing the code, I was asked to send a message to a strange phone number. Weird. When I logged into my PayPal, everything looked kosher. No new addresses, no new emails, no new phone numbers. My account was untouched, as far as I could tell. Later in the day, I got an email saying the new account was “ready to shop” and that’s when I called PayPal.

It took some explaining. This wasn’t just “my account has been compromised.” This was someone creating a brand new account with an alias of my email address. Known to me, but unbeknownst to PayPal, is that gmail.com and googlemail.com are aliases of each other. If you have gMail, and send a message to yourusername@googlemail.com, it will show up in your gmail.com inbox. Since my gmail.com address was on my account as a secondary email, if PayPal knew the two domains were equivalent, the stranger should have gotten an error. What really confused me was that they were able to log in, add an address, phone number, and credit card to their account. Which lead me, and the first manager I spoke with at PayPal, to conclude my gMail had been hacked.

This seemed impossible. I have a huge, complicated 1Password-generated Google account password. I use two-factor authentication. Google showed no unusual login activity, or anything of that nature. Even if someone had access to my Google account, I can think of a million more interesting, useful, and subtle ways to use it than to set up a new PayPal account. In any case, I changed my Google password, re-set up two-factor authentication, and revoked all third-party access to my account. That was Sunday night, and I went to bed paranoid and angry.

Monday, while at work, I figured I’d try again. Knowing they had a phone number on the account, I hoped I could reach someone who could try to contact the ersatz account holder. I called PayPal and began trying to get help via angry messages on Twitter. Multi-tasking, as best I could, I spoke with a manager on PayPal’s fraud team and someone on the AskPayPal Twitter account, trying to explain the situation and see what could be done. Both agreed to contact the person in the UK, and it looked like the AskPayPal person got to them first. I got one final email, saying the account was deleted, and that was it.

Turns out, it was a fat-fingered email address after all, and the account wasn’t actually activated and verified. I gave myself a full security audit for nothing, it seems.

Part of my anger and paranoia was that this came hot on the heels of the iCloud security nightmare. The other was the incredulity of the people I spoke to at PayPal, and the lunacy that they were unaware that gmail.com and googlemail.com were aliases, and had been for the better part of a decade. At least, now that it’s sorted out, I’ve added my gMail account back to my PayPal account with both domains, just to make sure this can’t happen again. I covered my bases, and did everything right. Someone else dropped the ball on account and data verification, leaving me to wonder if I’d left a hole somewhere in my defenses.

When a user’s sense of security can be violated by someone else mistyping their email address, it’s the fault of the company whose security the user has put their trust into. Sure, it’s also a limitation of email, as a technology, but a known limitation that should be worked around. Why was this person able to even interact with PayPal, adding their personal data, without verifying their email first? Because of that lapse, I had access to the personal data of a stranger: their name, their mailing address, the last four digits and brand of their credit card. Information I neither need or want. In this paranoid age, companies—ones that handle our finances, especially—must be on top of the dangers. What happened to me, and to my mysterious UK stranger, is unacceptable.