iCloud Drive, Finder, and missing folders.

09-23-2015, 1:55 PM
For about the past two months, I’ve been exploring iCloud Drive as a single destination for my working data. I’ve realized that support for it within apps is coming along quite nicely, and I’m already paying for the storage (photos) so why not give it a shot? Since paring back what I keep online in favor of storing at home on my Synology, the total set of data I’d want access to is minimal. Add in iOS 9’s iCloud Drive app and I’d probably be able to get by just fine.

Let’s get something out of the way right now. Many of you are pulling your hair out now, screaming “JUST USE DROPBOX” at your screens. I have been a paying Dropbox customer for seven years now. It’s an amazing tool and has changed the way I use computers. But for the purposes of this experiment, it was an extra point of friction. The goal was to have things be as “normal” and seamless as possible between devices, as a typical user of Apple products and services might experience. And the truth of the matter is that for weeks, it’s been a seamless, enjoyable process, to my great delight and surprise.

I was using iCloud Drive between my 2014 MacBook Pro, my iPhone 6 Plus, and my iPad Air 2. All updated to latest software releases, and all talking to one another consistently. I had built a few new workflows to account for the quirky ways iCloud Drive handles and sequesters certain files in app-based folders, and was pleased with the results.

Yesterday, I restored my former 2013 MacBook Air to a clean Yosemite install and signed in to iCloud. And some of my folders were missing in iCloud Drive. Folders that had been specifically created by apps (Drafts, Scanbot). Every other folder that I created myself and to which I uploaded files was there, and their contents accounted for. Only app-created folders were missing from this machine. So I began testing.

  • I tried restarting, to kick the iCloud Drive sync services again, multiple times. No joy.
  • I tried relaunching Finder via the Force Quit menu, multiple times. No joy.
  • I tried signing out and back into iCloud. No joy.
  • I tried adding files to those folders via my other Mac to perhaps nudge them into existence. No joy.
  • I tried adding files via the connected iOS apps, same rationale. No joy.
  • I thought that it might be that there were no OS X counterparts to those apps (Pixelmator, for example, showed up fine), but this didn’t seem reasonable, as they’re working on another Mac anyway.
  • I tried deleting the folder and the iOS app, reinstalling and recreating the folder, to see if this was tied to the actual creation event. Worked on the MBP, not on the MBA. No joy.
  • I tried creating a folder on the affected system with the same name, wondering if it might “find” the missing folder. No joy. Now I had two “Scanbot” folders.
  • I added a completely new, previously unconnected iCloud-based app (iA Writer Pro) to see if a new folder would be generated. Worked instantly on the MBP, nothing on the MBA. No joy.
  • I tried physically connecting my iPhone, thinking this might have something to do with the “Trust this computer?” dialogue. No joy.
  • I tried syncing my iPhone through iTunes. No joy.

At this point, having read plenty of discussion threads and FAQs on Apple’s site, I’m giving up. The files appear correctly on iOS (iCloud Drive app), on the web at iCloud.com, and on my MacBook Pro, as it’s the computer I’ve been using. These app-based folders remain missing on the MacBook Air. The problem isn’t iCloud Drive – it’s doing exactly what I expect it to (surprisingly well and quickly, I might add). The problem is with the Finder integration… on certain Macs.

I noticed the same issue on my Mac mini, which made me wonder if this could be related to older hardware. This seemed unlikely to me, but it’s the only thing I can think of that would set these machines apart. The only difference I can see across these three computers is their age.

So what about them is causing them to not be able to see these folders? I’m at a loss, and in the process of moving some files back to Dropbox because I need access on OS X and can’t seem to get it. I would genuinely appreciate any assistance, tips, or otherwise constructive ideas. iCloud, for all its improvements, remains a black box. My experience with it has been better than most, and I’ve truly enjoyed its ubiquity the past few weeks. But I need it to work everywhere for it to work at all, so I’m stuck.

09-23-2015, 2:43 PM
I shit you not, the Drafts folder just appeared. Scanbot is MIA.

09-23-2015, 3:00 PM
Scanbot is back.

I don’t know how to feel about this. iCloud is like a variation on ‘the Aristocrats’.

09-26-2015, 8:21 AM
So I’m pretty sure that the missing folders issue is a byproduct of massive network activity during background processes related to iCloud Photo Library. This was suggested to me by my friend Sam as he mentioned noticing some similar weirdness. I was monitoring iCloud Photo Library activity as it was ongoing, but there are perhaps some processes that (like everything else with iCloud) are fairly obfuscated to the user, sucking up network connections and saturating them even after things seem complete.

It makes sense, but it’s still kind of weird to me that file operations wouldn’t be prioritized over photo operations. Some of them seemed to be, since 95% of my iCloud Drive content showed up quickly, but something held up those iOS-related folders for some reason. I guess the takeaway from this exercise is to ensure all your iCloud Drive content shows up first, and then enable iCloud Photo Library if you’re using it. Next time I set up a Mac, I’ll be sure to do it in this order, and hopefully the arcane incantations I performed this past week will be a distant memory.

The whole purpose of going all-in on Apple apps and services is because I’m trying to use these devices as a normal user would, deriving the integration benefits and ease of use Apple offers. But being the kind of person I am, it’s tough to shake the need to debug a problem like this. Had I just waited, evidently everything would have sorted itself out. Perhaps there’s a lesson in here for me somewhere beyond the setup order I’ll use in the future.

Collateral damage.

Generally, by the time iOS beta 3 or 4 rolls out, I can’t help myself and throw it on my carry phone. But I haven’t had time to play this summer. It’s been a particularly busy few months and I needed to make sure my primary phone was as stable as it could be. As such, I’ve been pining away to play with the new Notes app that Apple debuted at WWDC this June. It looks like a tremendous update to one of the built-in apps that could actually change the way I currently use my devices. I’m not alone in these sentiments; I know many other folks in the tech space who are begrudgingly admitting that it’s pretty cool.

Since I’ve been keeping my devices as standard as possible too, I’ve been using Notes between OS X and iOS, even in its current form. I’ve found it to be a useful scratch pad and short-term landing area for little bits of text that don’t even merit creating a new .txt and saving somewhere. And they do sync between devices pretty well (for the most part).

On Wednesday, I’m excited to finally update my devices to iOS 9 and get all the cool stuff I’ve been hearing about, like any other normal user. But something occurred to me yesterday.

When I update my mobile devices, El Capitan is still two weeks away from shipping. Which means that my workflow breaks. If I didn’t have the foresight to think about the disparity in ship dates and extrapolate that one extra step, I’d have been caught scratching my head on Wednesday afternoon as I update and keep working through my day. Like any other normal user.

This isn’t good. For me, or for anyone. But sadly it’s become the norm. Marketing pressure and ship dates trump user experience more and more. Working in software, I understand a great deal more than the average person about how this process takes place and how you don’t always get to make the decisions you want to about the fate of your users when external pressures start exerting force on the business. I know that releasing both mobile and desktop OS updates in the same day is insanity, and I wouldn’t expect that. I know that two dedicated groups of people, working hard to ensure they hit their dates have made every effort they possibly can to make my experience a good one. I know that with the advancements in both operating systems, no decision–no matter how small–is a simple one.

But I’m the end user. It shouldn’t have to matter to me, and it’s not my problem. However, it’s become my problem. What if I don’t want to upgrade to 10.11? What if I can’t? What if my laptop is company-issued and there are no immediate plans to upgrade the OS? My stuff is broken, and I get a big shrug from the company to which I trusted my data. (Which of course, is a much more nuanced and complicated discussion for another time.)

This isn’t the first time this has happened. Apple did this last year with the transition to iCloud Drive. It caused more than a little confusion for both users and developers. But this isn’t just an Apple thing either. Many companies are breaking implicit promises with their users to further push their products into the future, and leaving confusion and doubt in place of a feeling of consistency as people use these products. Apple, of course, has the momentum to carry it forward, and we’ll all forget about this, the way we mostly did when Yosemite shipped and the iCloud Drive transition wasn’t such a big deal anymore. And I fully realize that writing this much because my notes stop syncing (temporarily) seems like absolute overkill. But I spend a lot of my time trying to come up with creative solutions for users so people enjoy the software we produce. I try to solve problems so they don’t have to. It’s the right thing to do. Tim Cook from WWDC 2014:

Apple engineers platforms, devices, and services together. We do this so that we can create a seamless experience for our users that is unparalleled in the industry. This is something only Apple can do.

Software updates have always been risky. I’ve been using computers since I was about five years old, and I know this. I understand it at a level most people don’t. But at this point, with the way software has reshaped our lives, I shouldn’t have to. It’s disappointing that even a company like Apple, so proud of its experiences across hardware and software and delivering the best to its users still falters on these kinds of things. This’ll all blow over. I know that. But it’s a troubling trend, and I don’t have to like it.


PS: It was pointed out to me that iCloud.com will sync/display Notes after the iOS 9 transition. Given the state of the site as an afterthought in almost everything Apple does, I’m not surprised it didn’t occur to me. This will certainly suffice in the time between upgrades, but I wouldn’t have immediately thought about it if someone didn’t point it out. And considering any regular user of iOS probably doesn’t even know that iCloud.com exists as a destination, neither will they.

Using Drafts as an Alfred replacement on iOS.

Lately I’ve enjoyed working from my iOS devices more than ever, due in large part to the great changes in iOS 8. But every day, I still do a great deal of work from the Mac as well for reasons of control and speed. I use Alfred for a ton of functionality, for everything from launching apps and quick searches to basic calculations and defining words. It is a single point of entry for so much of the data I interact with on a daily basis, and I love both the quickness it employs and the flexibility it affords me. I can extend it in completely new and crazy ways with workflows and create chained events to perform actions in the background. If you’ve never tried it, you simply must, and shortly thereafter upgrade to the Powerpack because it completely changes the way you can use your Mac.

Due to the essential nature of how iOS works, something like Alfred simply can’t exist in the same way. The company has released a companion app called Alfred Remote, which is interesting, and allows you to create a palette of quick buttons to launch actions on your Mac. But it’s far from an analogue to the functionality you’d find on the desktop. iOS silos its data for a variety of reasons, and even with the great strides iOS 8 brought to developers, the idea of an always-running, ubiquitous utility ready to assist you from anywhere you find yourself simply doesn’t exist. Even Apple’s own Spotlight implementation, while providing some of that functionality, doesn’t run everywhere–it needs to be invoked from the Springboard.

With these constraints in mind, I began to think of how I could replicate the tools I enjoy with Alfred in an iOS environment. Since getting the iPad Air 2, I’ve attempted to set it up as closely to my MacBook Pro’s app/service configuration as possible, so that I can truly work from either device. I’m also going through a process of discovering how I can slim down the number of individual apps I have installed by replicating functionality in other apps like Workflow and Launch Center Pro. It’s a fun way to pass some time, and I always like consolidating things. Sometimes it’s a little puzzle I want to solve, and sometimes the answer is to just use a dedicated app because the experience is better. But the process leads me to examine how and why I do things, and you know how I like gratuitous self-reflection. Ahem.

I had to examine what I do with Alfred on the Mac, and distill it down for iOS. There would obviously be sacrifices and redundancy in some cases, so I’d need to account for that. For instance, there’s no way I can toggle Wi-Fi or Bluetooth with a key command or a keyword on iOS as I can on the Mac, and between Spotlight and Launch Center Pro, my app-launching needs are more than taken care of. (Although, now that I think about it, you’d probably be able to build a simple app launcher into an action group if you really wanted to. Maybe I’ll give it a shot to see how it feels.) That left the core of what I do with Alfred.

Drafts is an incredible app that I’ve been using since it arrived on the App Store, and one that I’ve spoken about before. At a glance, it’s a notepad, ready to accept input as soon as you launch it. But anyone who’s used it can tell you it goes way further than that. You can send that note to a variety of places, perform actions on that text, even script additional functionality to interact with it. There is a vibrant community around the app and the Action Directory is evidence of that. I don’t have the capacity to explain how truly interesting and powerful this app is in the course of this piece, so go see it for yourself.

Thanks to its robust handling of text-based information, Drafts became my surrogate for this experiment on iOS. Through its Notification Center widget, it’s actually accessible from anywhere on my device (can’t say that for Spotlight), so I can always pull down and jump directly to it. It would be the single entry point for text, and I would apply as many different actions as I could to it to emulate my flow with Alfred. I took screenshots of Alfred’s preferences on the Mac as well as the individual workflows I had installed on top of that, and built a list of what I needed to do.

(Note: I’m not going to cover every single action in this post, but apart from the obvious things like controlling Wi-Fi, I’ve pretty much covered this list or I’m working on something that will. Or I’ve decided to ignore something and use a separate app. Whatever.)

First, the basics. The stuff I use that’s built into Alfred.

  • App launching
  • Search (internet/file system)
  • Basic calculations ️
  • Tools/functions
  • Definitions ️
  • Direct file system access
  • Contacts
  • Clipboard history/management
  • System commands

Then, my custom workflow additions.

  • Send to Todoist
  • Send to Due
  • Post to Twitter
  • Append/prepend text files
  • Wi-Fi/Bluetooth toggle
  • Basic conversions
  • Down for everyone or just me
  • Whois lookup
  • Force empty Mac trash
  • Forecast.io lookup
  • Giphy search
  • IMDb search
  • iTunes Store search
  • Determine current IP
  • New calendar event
  • New text file
  • Open current Safari tab in Chrome
  • Random password generator
  • Custom search (Box files)
  • Custom search (Dropbox files)
  • Pinboard search
  • Quick access to Transmit favorites
  • VPN toggle on/off

Many of these can be handled deftly in Drafts without much, if any tinkering. Some of this can’t be handled at all. Some of it just takes a little finesse. Here’s how it looks.

I created action groups: “Actions”, “Search”, “Notes”, and “Tools” based on the type of functionality I was looking for. With Alfred, it all kind of ends up in one big pool as you are able to winnow down what you’re doing contextually as you type–it’s one of the things that makes the app so cool. In Drafts, you need to browse a little. Different, but not terrible at all. Hey, it’s still iOS.

So, the actions. Anything dealing with plain text/notes–nailed. You can create, append, prepend, modify, and pretty much anything else you want to do as long as it’s text and your destination is somewhere Drafts supports. So all my Dropbox actions are buttoned up. Drafts can write to iCloud Drive as well, so that’s an option too for quick zaps between iOS and the Mac.

Same for quickly adding to apps like Todoist, Due, and Calendar to create new items. As long as a URL scheme exists or someone’s built an action and posted it, you can probably do it. Drafts has advanced clipboard handling, so that’s in there too, as is posting to Twitter.

In as many cases as I could, I applied URLs to these actions to open in a browser. Obviously, this makes sense for things like searches, especially since a lot of local apps don’t support any kind of URL scheme beyond opening. In some cases, I preferred native app integrations to web actions, though. It’s much better to open the Twitter app to do a search with its new deep integration than have to boot over to the mobile web, which frankly, sucks. I created a Pinboard web action for searching my own archives, since the app I like to use (Pinner) doesn’t support a search from outside currently. It’s a great app, but it just doesn’t do this one thing I want it to. I also repurposed some of my focused Duck Duck Go searches here, creating a master list of all the places I might want to hit, as well as a few app favorites (like 1Password).

Where things get pretty interesting is within Drafts’ advanced tagging system. It allows you to logically interpret certain things like dates, times, and even latitude and longitude–which came in really handy with the Forecast.io action. If I want the lookup for where I am right now, I don’t even need to enter text, since the URL adds the location tags independently. If I want to search a different location, I can type in “Austin, Texas” and run the Google weather search, which will take me straight to a page with a small weather module right at the top. I asked Greg about doing simple calculations right in the app, and he told me that’s supported as long as it doesn’t get too complicated. In addition to the action, there’s a script key add-on that does the math without needing to pull the drawer out. Hot.

Other cool things:

  • Giphy search goes right to the excellent custom UI in Launch Center Pro
  • iTunes Store search uses fnd.io which is fast and covers the entire store in a nice UI
  • Down for everyone and whois lookup use clipboard contents, and current IP is just a text-less action that runs, similar to the Forecast action

The things I can’t do at all? Well, as I said, toggling system states (Wi-Fi, Bluetooth, VPN) is out, as is direct file access and search on iOS. What I discovered in my experimentation, however, was that while the Dropbox iOS app seemingly has no deep URL hooks, the mobile site supports a direct search as part of a URL string! So I’m able to pass a search term from Drafts to the mobile site, and after a few seconds (in my testing, under 15-20), I get a list of results, which I can then link to, or open in the native app. It’s not the real-time file access/search that Alfred provides, but it’s pretty damned cool for an iOS device, since my entire file system is based in Dropbox. Is it quicker to just open the native app and pull down the UI to search right there? Probably. But for the purposes of this experiment, this was a fun discovery.

As an extra bonus, I discovered that my WordPress site supports search in a similar way, so now I have a super fast path into my posts if I want to find something I wrote in the past to share with someone, which is something I do frequently.

Overall, it’s a big change in how I use my devices. I’m not sure if this will stick, but I wanted to try it, and see if I could map my Mac mental model of entry field-data-action to iOS. There are limits, but there are also cool things iOS can do that the Mac doesn’t. It’s interesting to me that on the Mac, my information flow out of my head to an action is so different than on iOS, based on how the environment differs.

It did get me thinking about what could be possible, though. I think that someone could definitely build something like Alfred for iOS and have it be as close to the Mac experience as possible, by which I mean that it would require some serious pre-configuration on the part of the user, and you’d still be limited by the iOS filesystem constraints, but between URL schemes and extensions, something really compelling could exist. I think you could build a UI on iOS that intelligently provided target actions based on what you type. I’m sure it would be a ridiculous power user tool, but I think it could work. I have no idea about what potential market this kind of app would find, but I’d love to see someone try. If it was done well, I see no reason why it couldn’t be sold at a premium to people like me who want to get every bit of power and functionality out of their devices.

In the meantime, this has been a really fun experiment for me and I figured out some cool things both about Drafts and how I can modify basic existing URLs to become more action-oriented. As our iOS devices gain more abilities, I look forward to seeing this process evolve. If you have any questions, you know where to find me.

How I’m using Dropbox.

Since I talk about Dropbox quite a bit anywhere and everywhere I can, I’m often asked for app recommendations and about the services that I use with it. The beauty of it is that these things can and do change from time to time because so many apps and services plug into Dropbox that there’s always something new to try. So here are some of my uses and apps as of right now.

For starters, I don’t use my OS X home folder for anything, if I can help it. Everything important lives in Dropbox. I can’t move my Library in there, but if I could, I would. If I lost my MBP tomorrow, I could be back up and running 90% of the way just by logging into Dropbox on a new machine. That makes me feel good. Now, onto some more specific things.

1Password: The alpha and omega of all my Dropboxing. 1Password is the single most useful app on any of my systems, and my world lives inside it. Security’s no joke, and 1P makes it easy. Constant updates, communicative and friendly developers and a willingness to always improve make it my number one app, anywhere.

Notes, Reminders: Notes are stored as plain text files and kept in a folder called Notes. I point the awesome Notational Velocity fork nvALT at this folder on the Mac, and whatever app I’m currently using on iOS at it as well. Right now, that happens to be Elements by Second Gear. It’s clean and fast. Reminders are a different beast. Currently I’m back using Appigo’s Todo, which I’d purchased a million years ago, but which has seen some pretty decent updates. My tasks sync in a Dropbox folder and appear on all my devices. This could change by the time you read this, but that’s what’s great about Dropbox. Another one of my favorites is TaskAgent, although it’s more for lists and doesn’t have reminder functions built in. If you just have one list, you might check out Due, which is also great.

Camera Uploads: This is a service that’s now provided directly through the Dropbox app. Before it was offered, I used many different iOS apps to get my camera roll into Dropbox, and I still use one called CameraSync because it uses geofencing to determine when to activate and upload your pics, taking the manual process away entirely. I set it up for the office and my house, and when I go between them, I get a notification that my pics are uploading. It’s like magic. (I also have Photo Stream turned on as a fallback, but I like that they’re also in Dropbox automatically as well, for obvious reasons – Photo Stream has a 1,000 pic/30 day limit).

Byword: My favorite writing app for Mac and iOS. Hook Byword up to your Dropbox, and your works in progress are everywhere. I store them as plain text (.txt) files for portability into other writing apps as well.

Day One: My journal of choice. Byword is for things I intend to put somewhere on the web, Day One is just for me. A gorgeous Mac and iOS app, with tons of features and improvements. If you’re not using this app, you’re seriously missing out on a flagship writing experience. Again, I choose to store the data file in Dropbox, because I want to be able to pull it apart if I feel like it (or need to) and iCloud’s data container doesn’t sit well with me.

Scanner Pro: A great quick utility by Readdle. If I need a PDF of something I’m looking at in the real world, I grab my phone or iPad, take a picture, and Scanner Pro converts it to a great looking PDF and drops it into my Dropbox for me. Easy.

Drafts: Quick capture and instant dumping into a variety of iOS apps. I keep a “Drafts” folder hooked up to Dropbox and have it set to capture text notes that I intend to file away in my large note file. Hazel watches this folder and drops .txt files into the other one for me.

TextExpander: Super time-saver. TextExpander takes snippets of keys you assign and drops giant chunks of text in their place. I keep the settings synced with Dropbox between my systems.

Paper: My favorite sketching app. Although I don’t use Paper all that much, when I do, it exports my journals right into a Dropbox folder. I end up using this to quickly diagram things for clients sometimes. It helps to have a picture to go with what I’m saying, and if we’re all in agreement, I can save it, export it and refer to it when I go to create a formal wireframe document or something like that.

Software: I keep a master repository of all kinds of .dmg files and installers in Dropbox. I’ve been a Pro customer for years, and recently had my storage space doubled to a massive 200gb, so this is even less of a problem now than before. Super convenient when you’re managing multiple systems in an office environment and the Mac App Store isn’t how you plan to do it.

System: I keep a folder called System in my Dropbox, and the purpose of this folder is to preserve app settings and things like that. If I can, I’ll install an app and configure it so that its settings automatically go there, but if not, I can always manually copy/move some things around or set up Hazel rules to duplicate these settings/files. Alfred is a good example of an app that runs out of this folder – all my extensions and tweaks are synced between my Macs into Alfred from here.

What else?…

Sharing: throw things in a Dropbox folder, get a quick link. Better than email for giant files, and usually works ok for everyone.

IFTTT: there’s all manner of cool automated things you can do with IFTTT, a web service that aggregates other web services to do some nerdy heavy lifting for you. I’m currently pulling all my Instagram shots in automatically, as well as Facebook pics I’ve been tagged in. I also have something set up to automatically forward a document from my iPhone to a folder specified by me in Dropbox, but I don’t really find myself using it. Still, it’s cool and it’s just scratching the surface.

iPhoto: I wouldn’t recommend trying to point multiple machines’ iPhoto installs to one library you keep in Dropbox (seems to have issues, YMMV) but if you only have one machine on which you use iPhoto, it’s an easy way to back that giant file up (if you have the space).

I could go on and on. When I record podcasts, they dump directly into a Dropbox folder from Audio Hijack. I keep a folder just to sync stuff between my MBP and my Mac mini server at home if I need to. A different folder to share things with my wife and her MBP. The possibilities are nearly limitless, and growing every day. It’s a fantastically reliable and functional tool I’ve grown to rely on. I’d hate to go back to computing without it.

If you’ve got a great way to use Dropbox, I’d love to hear it.

Twitter | App.net

Un-simplified, and happy.

I recently talked about my intentions to simplify my workflows by using the default Apple apps on iOS and the Mac (Notes, Reminders, etc.) as replacements for the many apps I like to jump between. My goal was to see if by just letting go of my need to tinker with the connective tissue between parts of my workflows I could improve both my base anxiety level (derived not from fear, but from a constant feeling of “could I be doing this more effectively?”) and my ability to focus more on the “work” and less on the “flow” overall. I stuck with it for several weeks, and the results are in.

It’s… not for me.

The short version: between heavy-handed interfaces and iCloud flakiness, I gave up because I felt that I was neither gaining relief from the productivity improvement demons nor was I focused on my work. Instead, I was waiting for the other iCloud shoe to drop (data loss) and talking myself into the idea that this was good enough for me, when the truth of the matter was that it really isn’t.

I’ve been reliant on Dropbox for so long I can’t even remember or imagine a world without it. Many apps take great advantage of the APIs Dropbox has in place to both sync settings and data with moderate to high levels of success based on the app and its implementation. There are two reasons I feel better about this path:

  1. Dropbox exists in a tangible way on multiple computers I own as well as in the cloud
  2. Flexibility between interfaces

The first one is easy. I don’t trust iCloud fully yet. Every time I saw three copies of a single note appear in the Notes app or a reminder re-add itself to a list after completion, I added a tiny tick mark to the wall in my mind. Which is not to say that Dropbox sync services are without folly; certainly they can and do fail from time to time, however I always have the opportunity to throw my data into another app and test the waters elsewhere. I can easily see my data in Dropbox, which is important not primarily for sync settings, but for things like my plain text notes, which might be transitory and not long-term in nature as I’d discovered, but important to see and preserve as I saw reason to take the information down and capture it. Seeing duplicate notes appear was the flip side to the coin where notes suddenly vanish, and I’m not comfortable with that.

Second: Apple’s UI choices are polarizing if nothing else. There are many choices I enjoy and find delightful, and many at which I continually level disgust and contempt. With the relief provided by giving up my tinkering ways to Apple’s choices comes a compromise I’m unwilling to make right now – I’m stuck looking at yellow paper that formats plain text in obnoxious ways and parchment lists that while functional, are hardly the optimal way to organize (in my mind, at least) the tasks and efforts I need to complete. By using apps that plug into Dropbox, I’m afforded a variety of ways to look at the exact same data. Sometimes I need that variety, and it comes at the price of my inability to sometimes stop myself from exploring other apps and interfaces. I look at these screens entirely too much each day to be unhappy with what’s staring back at me. I can work at leaving well enough alone with regard to fiddly bits, but I can’t work at liking a UI I simply don’t.

The fundamental truth I learned about myself, which I mentioned in the first sentence of that other post is that I am a tinkerer. I like to try different things, break stuff, put it back together, and start from scratch. It’s something I can’t really turn off entirely, nor do I want to. It’s a curiosity I’ve had since I was a kid, and I hope my daughter expresses the same interest in exploration, whether it’s with software or any other interest she’s passionate about. I try new apps and add layers of complexity because I need to. It’s an evolving little puzzle I do with myself, like a game of Jenga in reverse. Occasionally I find something rock solid and leave it working, but there’s always something else to move on to, some new thing to play with, some new web service to leverage to make the mental machine run a little more smoothly. Understanding this about myself means I don’t feel guilty anymore about trying a million different ways to do a simple thing because I can rest a little easier knowing I’ve ruled out the ways I didn’t know before.

So, back to plain text, back to Dropbox, like a favorite pair of jeans. Sometimes you buy new jeans, sometimes you wear a suit, and sometimes the jeans sit in your drawer for a few weeks. But they’re there, and you know it, and it makes you happy.

Simplified.

I’m a tinkerer. I’ve always been a tinkerer, I’ll always be a tinkerer. I fiddle, I test, I try, I look up, I download, I delude myself into thinking it’s all in the goal of figuring out some better way to do things. In some cases, it happens that it’s true. More often than not, I realize that I’ve gone down a road I didn’t need to, but the journey of discovery usually pays for itself.

I love this stuff. I really do. But time is fleeting lately, between craziness at work and a new tiny person with some serious demands on my time waiting for me at home. I started to wonder: can I strip away small bits of complexity from my workflows and actually enjoy what most people would consider the “Apple experience”? I’ve long crafted elaborate workarounds to avoid using the default apps that ship with OS X and iOS, but they’ve matured to a point with 10.8 and iOS 6 that I’m entertaining the idea of giving them a shot again. The place that sees the most impact (unsurprisingly) is with productivity apps, traditionally my most fiddly bits. It took some intestinal foritude to take these first few steps, but in the interest of personal self-discovery, I suppose it’s worth it.

I’ve tried dozens of task/to do apps. I go through them like tissues in cold season. I landed on using OmniFocus for tasks a few months ago. I was initially impressed with how flexible it is as a product (I’m a big Omni Group fan), and how you can adapt it to how you wish to use it. What I came to realize is that I personally wasn’t using more than a few of its terrific options, which made it akin to killing a mosquito with a rocket launcher. So I’m giving Reminders another look. With the release of Mountain Lion, a dedicated app ships with the OS, and it’s on iOS already. So far, it seems to be doing an extremely servicable job for what I need, and Siri integration is really nice.

I’ve used plain text files stored in Dropbox for basic note-taking for a long time now. I’ve long preached the flexibility of plain text as well as the fun of plugging multiple apps into a single stored location and being able to try all kinds of things. As it turns out, about 60% of the notes I take are of no value to me after a certain period of time, and so I deleted a bunch of them. This freed me up from the mental burden of thinking I needed to keep everything around. Once I cleared that hurdle, I decided to try Notes again. As with Reminders, OS X ships with a dedicated Notes app now, and I wanted to see if I could get by with it. I’ll still compose anything more than a transitory note in plain text and keep it in Dropbox, but for basic capture, I’m sticking with this for now.

I just got brutally honest with myself and realized that I never actually do cool things like converting my plain text captures into Markdown and then emailing myself HTML snippets while automating task generation. I love the idea that so many apps allow you to do so much more than the basics, but if I’m being honest, then I can’t pretend I use all that stuff. So if the Apple apps are good enough, then why the question at all?

My main hangups center on how much I trust iCloud. I feel like maintaining folders of .txt files that I can easily point to and drag somewhere else *feels* right to me. I know I can dig out the Mobile Documents folder buried in ~Library, but it’s not the same. And I could back up my OF database in Dropbox and have days’ worth of copies to fall back on should the app fail for any reason. With iCloud, I basically have to put my trust in Apple that these bits of information, upon which I rely for my daily organization are going to be there when I need them. I’m not super comfortable doing this, but at the same time, I’m trying really hard to let go of my need to grip everything so tightly. Partly because I’m tired of the endless tinkering with my workflow, and partly because I’m envious of people who don’t even have these thoughts. It’s a sickness, you know. A beautiful, enriching, crippling sickness.

The experiment’s underway. All my short-term text is in Notes, and tasks in Reminders across my devices and Macs. It’s a strange feeling, using apps now that I’ve long derided as “not enough” and realizing that they are in fact, just fine. I don’t know if I’ll stick with this – it depends on my neuroses about this data and how long I can keep them at bay – but it feels oddly freeing. Like a weight has been lifted. Fewer moving parts, fewer options and switches, and a focus on something else.

Actually doing stuff.

(to be continued, I’m sure…)

Putting on my big boy pants.

I started using OmniFocus about a week ago. I’d avoided it for a while because it seemed way too complicated for me, but I decided recently that while I’m able to manage my tasks and to-do items, I need to step up my game and start becoming serious about the loose ends. The goal was to finally push all the disparate buckets of capture into one meaningful place, and to more accurately gauge how well I’m doing in terms of completion. I’d just been making lists, and lists don’t exactly provide the context or the motivation I was looking for with this process.

From my cursory understanding of it, I’d always thought that the GTD mentality was overkill for what I needed. When I waited tables in college, I would remember detailed orders, from multiple people, easily. People would try to mess with me and quiz me, but as I rattled them back their orders, they quickly acquiesced. So keeping stuff in my mind has not really been a problem for me. But when I actually started to throw things into the OmniFocus inbox with the purpose of methodically clearing my head, I noticed a weird kind of comfort that came from not having to remember all those things. Some people feel overwhelmed by this process, the remembering, I never really did – but not doing it feels so much better, I wish I’d tried this earlier.

It’s taking a little while to fully embrace the entire philosophy, because I’m still finding a way to apply it to my workflows, but it’s interesting to be sure. I definitely see value in it, although I don’t know that I’d ever become a GTD zealot the way some people end up. It’s fairly complex and a lot of people don’t need this level of complexity. However, there is a certain freedom in being more serious about the lists I was previously making and applying a new level of rigor to them. I feel like I’m putting a little more pressure on myself to actually complete things by being more realistic about what I can accomplish and when I can do it. It’ll be an ongoing experiment, but I’m feeling pretty good about it.

I love finding better ways to do things. Wanna talk about it?

What does Gatekeeper mean for jailbreaking on iOS?

The sudden (at least to most people) announcement of OS X Mountain Lion this week came with many new features and talking points. One of the most talked-about involves security and the Mac App Store, called Gatekeeper. Gatekeeper is a new feature in ML that allows the user to select levels of security for his/her computer. The default setting is to allow Mac App Store apps and apps by identified developers who have opted to sign their apps with Apple. The two other settings are Mac App Store only and “allow everything”.

For the entire lifespan of the Mac, third-party software has been a driving force in its success. With the arrival of the MAS and the sandboxing restrictions Apple put in place for applications, many developers were either unable to include their apps in the Store or chose not to because it would have required hobbling functionality to achieve Apple’s goals. However this new feature connects a developer’s identity with the trusted status of the application, which essentially bridges the middle ground between outright malware and the sanitized App Store experience, providing many devs with a sense of relief. How it plays out remains to be seen, but the idea is that devs would no longer have to make the choice of App Store or go it alone, and can offer a high level experience on par with Apple’s expectations in their own way.

But as Apple moves to unify iOS features and OS X features as we’ve seen with the inclusions of apps such as Notes and Reminders this week, it begs the question: will Apple ever allow Gatekeeper to function in the same way on iOS? And if so, what does this mean for the jailbreak community? Apple has quietly taken both inspiration from, and (presumably) umbrage with the moves that the jailbreak community has executed in the past few years, but with the exception of closing exploits to ensure a more secure system has done little overtly to quell the actual jailbreak process itself. It’s mostly a “no comment” situation for Apple, and when comments come, they are aimed squarely at securing the platform first and foremost, not stifling innovation.

There are many legitimate and extraordinarily talented developers working on jailbreak apps that simply can’t exist in the iOS App Store. But what if Apple allowed them the same privileges it will allow OS X devs? I’d love to see a world in which not only do fantastic apps like LockInfo and SBSettings exist, but in which they can be installed with the equivalent of Apple’s blessing, provided that the dev signs the code with Apple and the user is savvy enough to change the settings in the OS. This kind of a move would definitely show that Apple is serious about enabling creative development on iOS outside of the App Store walls, while still preserving the notion that security is a paramount concern for the platform. It’d be a bold answer to the cries of iOS being a closed system to Android’s open one (a tenuous claim if there ever was one) and in one fell swoop obviate the need for jailbreakers to cling to security holes to run apps and enhancements they’ve grown to love. A more secure platform for Apple, and the freedom to really own your device’s functionality even more seems like a huge win for everyone.

Plenty of people have called for “expert settings” on iOS for years now, so this is not a new idea. But the existence of Gatekeeper in OS X and the strive to unify the platforms experientially leaves at least a little hope that Apple’s getting the message.

How to fix the Mac App Store’s licensing issues.

A lot of people, myself included, are excited about the arrival of the Mac App Store, but there’s a few issues still outstanding, some of which I spoke about yesterday. After a little bit of thinking, I came to some conclusions on how Apple might be able to deal with one of the bigger ones, namely helping users who have already paid for software transition into the App Store without having to repurchase it.

I see two possible solutions. The first is that Apple allow developers to issue “transfer” codes, similar to promo codes in the iOS App Store. Currently, as I understand it, there are limits to how this works in iOS, but in that case, we’re talking about a software ecosystem that didn’t exist prior to the device allowing it. In the case of the Mac, there are years of investment on the part of users, and loyalty built upon certain developers and their work.

The second might even be easier. Developers have lists of registered users and their associated email addresses and licenses. Just like there’s a “Redeem” section of the iTunes store, create a “Transfer License” area. Allow developers to upload a database of all their registered users to Apple. Customers who wish to transfer their licenses to the App Store can then fill out two fields: their email address on file with the dev and the license code they’ve already been issued. We’re probably mostly talking about power users here, so this two-step process shouldn’t be too difficult. Once the license is transferred, no one else can repeat this process (just as with the current iOS redeem codes). Furthermore, once the database was uploaded to Apple, the dev would in fact be implicitly agreeing to move all future purchases to the App Store, alleviating the need for two purchase channels. The existing user list goes in, and that’s it. After a while, this could even be phased out entirely.

I don’t think either of these would be too difficult to implement, especially in an effort to ease the transition from the web to the App Store for Mac purchases. It would be an extremely favorable position for Apple to take, and engender a lot of goodwill among users and devs, and would probably avoid polarizing the massive potential user base for the new store. I know I’d be more inclined to move toward it, knowing everything I’ve purchased thus far wasn’t completely negated by the new retail channel’s expectations.

The Mac App Store is live, but not perfect.

The Mac App Store was unveiled earlier today with the 10.6.6 update, and while for a great many Mac users, it heralds a new, easy way to grab interesting software you might ordinarily have missed, it’s not without its foibles too.

For a regular user who just wants a way to browse for things like they do on their iPhone or iPad, it’s a great thing. Get all your apps in one place, get notified when they’re updated automatically as in iOS. But for power users, who are accustomed to the modicum of effort it takes to seek out and find apps, there are a few downsides. Already there are rumblings that certain popular apps had to remove pieces of functionality just to be included in the store. That could be a deal-breaker for someone who’s been using a piece of software and wants the unified benefits the App Store offers, but can’t give up a function he/she relies on.

Apps already installed on your Mac show up as installed, but as of now, won’t be updated through the App Store either, which can cause confusion for users. It’s probably because they don’t want people to purchase apps they already own again, but it’s a confusing UI choice. Could be a bug, could be a real pain further down the line when version numbers don’t quite match up, functions are different between two seemingly identical versions of the same app, and users have questions about what they have and why it isn’t like the other things they have.

Furthermore, before the iOS App Store, there really wasn’t a super easy way to get apps on and off your device. The ease of instant downloads and instant deletions made it perfect for not having to think too much about those impulse buys. But the Mac is very different. As of right now, I can’t find a simple “tap-and-hold” delete function for Mac apps like on iOS, and people are going to want that. Soon. Within the App Store app, I don’t see any mention of uninstallation. Just a purchase history. And considering that the Mac is not sandboxed the way iOS is, it could lead to problems and confusion in the future.

Considering Apple’s aiming this squarely at the standard user and not so much at the power user who understands where .plist files are stored and why they might be crashing your app every time you open it, they have a lot of work left to do to make it exactly the same kind of experience the iOS App Store has become. It’s a great first effort, but be prepared for some quizzical expressions here and there as we go along. Perhaps 10.7 will address some of these issues. I hope so, because as it stands, it’s just not the same fluid consumer experience people are used to. And that may be a bigger problem for Apple than they realize.