Summer explorations, part three: Resolution and refinement.

Parts one and two of this series are here and here.

I know this all seems like a tremendous waste of time, and in some ways I’d agree. I get a little sad when I think about how many other ways I could have spent the time I’ve sunk into task management and this kind of thing. Moving from one app to another. Thinking about perspectives, and filters, and tags. Talking to friends about what they do. Experimenting, tweaking, and returning to the starting point.

But if you’ve read this far, you’re likely the kind of person who sees some value in the process. And that’s part of my point.

I see two things very clearly now. The first is that this really has become a hobby, which is a little weird, but whatever. My hobby is playing with task apps and organizing information. This should come as no great surprise to anyone, given my previous statements. And for all the hand-wringing it causes me, I do like it. It’s fun. It’s like doing a jigsaw puzzle over and over again, but the pieces’ shapes change ever so slightly each time, so it’s familiar, but not exactly the same. It’s oddly delightful.

The other thing is that for better or worse, the way I feel about myself is intrinsically tied to how I feel about the information I manage in my life. I’ve discovered (re-discovered?) that I feel great about myself when I think I’m completely on top of things and not so great when I feel like things are slipping through the cracks. I suppose this is slightly better than tying your feelings of self-worth to something like your personal appearance or fiscal status, which may not be as easily managed.1 At least this way, I have a relatively manageable way to climb back out of whatever emotional abyss I find myself in from time to time, and can reason out why I might be feeling that way at that time.

I’ve found there’s something almost Konmari-esque about switching task apps after a certain amount of time. Each time I do this process, it takes less time than before, because I get serious about pruning things that have been floating around in my system that I have no intention of ever really getting around to. I shed a handful of things that were being maintained and adding to the overhead and re-prioritize some other things, forcing myself to take a good look at what I want to get out of the switch. It feels… cleansing, if we’re being honest. And I like that feeling a lot.

After all this, what have I learned?2

  1. I’m not going to feel guilty about doing this stuff. It’s fun, and it serves a purpose.
  2. I have great friends for humoring me as I go through this. Of course, they’re as bad as I am.
  3. Splitting work and personal data, while initially somewhat challenging, has yielded some interesting things both in how I use apps, but also in how I think about getting things done.
  4. If this is what I have to do to make me feel good about myself, things could be a whole lot worse.
  5. I should spend more time with my kids.

That last one pretty much applies to all aspects of adult life, but as you crest over the hill of “yay, I feel like I’ve settled into my new task app” it starts to kind of assert itself a little more.

So that’s it. Summer lovin’. Happened so fast. See you in about a year when I manage to get myself knotted up all over again about something else. Or the same exact thing. Either way.

  1. “No offense if that’s your bag, it just isn’t as important to me,” he said as he ate a third helping of dessert and drove away in his modest five-year-old mid-size vehicle. 
  2. The other thing I’ve learned is that it’s tremendously helpful to read my old blog posts. It’s like talking to myself in a private (except that it’s published publicly on the the internet) therapy session. 

Summer explorations, part two: The serpentine path of satisfaction.

Part one of this series is here.

As I said in the last post, splitting task data was something I’d not done before, and it became a very interesting scenario. I toyed with the idea back in July, but it was purely a theoretical thing, a thought technology and not much more. It didn’t stick then. In fact, it took seismic shifts in my daily routine and workload to precipitate the change and have it remain intact. But that happened in the past few weeks, and now I’m using two separate apps for work and personal tasks as opposed to filtering those things in a single app.

Once that decision was made, the next thing that happened was a realization that the way I think about “work” and “home” are drastically different–but I was managing them the same way, with the same overhead, filtering, tagging, etc. It didn’t make sense anymore. When everything is in one app, you start playing with filters and views to separate things you don’t need to see in reasonable ways. Eventually you hit on something that works, and you’re happy. But what I realized as I broke this data apart was that the things I want and need to accomplish in my personal life are vastly different from the things I need to accomplish at work. More importantly, the way I think about these things and the way I set about trying to do them really ought to be different too.

So I stepped back, with two disparate data sets, and thought about it. Todoist is a perfect tool for work, with team collaboration, web integrations, and cross-platform support. But what’s the perfect tool for everything else?

I’d been using 2Do for the past few months, and I’m a big fan of the app. It totally changed the way I think about information, how I organize it, and how I access it. I was late to that party and I’m far from the only fan, so if you’re interested, I encourage you to read these other great posts.

But 2Do started to feel (as flexible as it is) like more than I needed for this. So I did what any rational person would do in this position. I tried 47 other apps.

I began with redefining the things that happen in my personal life: there are “reminders”, which are things I need to remember, usually at a certain time. And there are “tasks” which can be things that need to get done but have no date—or things I’d like to get done, whether tactical or aspirational. I took anything without a date and created individual lists in Notes. I told myself I’d refer to them on a regular basis.

Mm hmm.

I went back to Reminders, like a gentleman. Built-in, deeply integrated, and simple as can be. Set up a few lists. The perfect place to store the things I need to be reminded about. Even does those cool deep-link things between apps as of iOS 9. The Notes idea, however, quickly became a weak spot, so I pulled those items into a single note in Drafts, which I am in all day, every day. Figured if it’s right in my face, I can see it and take action. I would look through that list each day and if I saw something I needed to do that day, I would highlight it and send it right to Reminders for attention-grabbing. It was flawless! Until it wasn’t.

Reminders is great because of what it does, which is exist on all your devices without a bunch of extra effort and mostly capture things in a reasonably expedient manner. But what it doesn’t do is allow you to make changes to those items easily and quickly. Or sometimes sync reliably (I had weird duplication of tasks, and stuff marked as done come back from the dead multiple times). All it takes is a few cracks in the facade, and I’m running. So while in principle, having all those unchanging things (bills, medication alerts, household stuff) always available on any new device via iCloud, it just didn’t feel like enough to take the throne.

More disappointingly, even though I adore Drafts more than life itself, it really isn’t the place for me to house my tasks and take action on them. The idea of a single Markdown list of the things I want to do was intoxicating, but it didn’t fit with my mental model of how I manage things I actually need to do.

Then I went back to Wunderlist, which I’ve used in the past. Wunderlist is cool because like Todoist, it’s web-based, so you can do some cool stuff with it. The app’s come a long way and features excellent things like natural language capture now. But between some syncing weirdness, some UI glitching on the iPad, and general malaise, I decided within a few days that it wasn’t going to be the winner either.

Then I snapped entirely and put everything back in 2Do. I wiped all my previous data one Sunday morning and decided it was the right place. I told myself I would change the way I think about organizing things (more capture, more action, less fiddling, less overhead) and I was convinced I was done.

Until about 45 minutes later, when I re-downloaded OmniFocus, installed it, and put everything in there too. OmniFocus, my longtime on-again, off-again girlfriend, with whom I share history, with whom I am not truly complete, despite my weary wanderings.

For the next 36 hours or so, I had all of my personal life in those two apps. And then I just freaked out. No, seriously, I did. I had a baby anxiety attack, quickly righted the ship, realized I’m a total asshole, thanked the heavens that this was my biggest problem right now, and just said fuck it, it’s going to be OmniFocus again, and that’s that.

The more I thought about it, the more I realized that the way OmniFocus organizes and displays information is what I was looking for right now. It does bulletproof reminders and due times. And with what I learned about not using due times and surfacing things at the right time when I need to see them, I figured out what I needed to do.

If you’ve made it this far, I truly am sorry. And thankful. We should hang out.


Anything that either has to happen at a certain time or should happen by a certain time gets a due date in OmniFocus. Everything else sits across a handful of projects. Flat hierarchy (for now), no folders, no sub-projects, none of that. Simple. Barely any contexts. Contexts are a luxury now. I only create one when absolutely necessary. I have four perspectives: “Today” (due and flagged), “Available” (everything without a due date), “Wait Up” (stuff I’m owed or stuff I owe – good for work and personal life), and “All” which is just everything, in case I ever need to dive in. I can use Drafts and Siri for capture everywhere, and things like MailDrop and calendar integration as well.

The idea is: things I need to do each day (due) show up no matter what. In addition to that, I comb through “Available” each morning and choose one or two things I really want to get done–and think I can during the course of that day–and flag them so they show up. I have to be brutally honest with myself, and only pick those one/two, but it’s made me start to plan around how I want things to get done a bit more, instead of just making lists and never actually doing them. Last week alone, I cleared about four or five little things that had been hanging around just because I pushed myself.

And therein lies the big lesson.

This isn’t about apps, or systems, or UIs, or web integrations. It’s about getting serious and allowing myself both the flexibility to do things, and not do things as life dictates. It’s about changing the way I think about work projects and the way I think about my personal goals, so that both get accomplished in the best way possible. By changing the way I visualize and organize, I’ve been able to reset what my actual goals are, and start clearing items out. But it wasn’t the apps. It required a serious mental shift, and I had to be ready to do it. I wasn’t before. Things changed, and conditions became favorable, I acted on it, and I’m pleased with the results. I still have lots of work to do to move through some longtime lists I’ve been carrying around, but the new ideals I’ve created will lay the foundation for how I manage those things going forward.

Final chapter: after all this nonsense, what does it all mean? I realize some things about myself (again) and crystallize how I want to think about things for the future.

Summer explorations, part one: A feeling of relative control.

Summer traditionally seems to be a great time to muck around with my systems and workflows. Lots of people are away, so the office gets these nice little lulls where I can sit quietly for bits of time and ruminate. We’re on the cusp of a new iOS release–and new hardware–but nothing is happening quite yet, so I’m thinking about it, but also can’t act on anything. Year after year (if I read back through blog posts and journal entries), I end up tugging on threads in my setups over and over again, exploring things I’ve used for months or years, trying new things, generally comfortable with upending everything, knowing in September I’ll be wiping everything and installing iOS fresh.

This summer’s been no different, apart from me being way busier than normal at work. But ironically, it’s been this shift that’s precipitated probably some of the biggest changes and realizations about the way I organize and deal with information in my life. In fact, the changes in my responsibilities have triggered a chain of events that will likely alter the way I deal with information for a long time.

It came in phases. Phase one involved creating a calculated division between my work and personal worlds, which didn’t exist before. Phase two built on phase one and is all about how I think about doing things in my personal life, and how I structure the things I need to remember, the things I want to accomplish, and just about everything else that makes its way into my brain.

But I’ve come out (what I think is) the other side now, and the crazy part is: sure, I’ve played with some apps and done some reconfiguration of tools, but in doing the things I’ve done this time around, I’ve uncovered some things that I didn’t expect to.

We’ll get to that.

This is all probably too long and meandering to walk through in one post, so I’m going to break it up. Gotta get those 16 page views somehow. Fair warning, this is some nerdy-ass stuff.

Let’s begin.

Since joining a much larger company, the things I need to do–and subsequently keep in my mental RAM–have changed dramatically. I interact with many, many more people, on a global scale, across time zones, in different disciplines, and with greatly varying agendas and goals. It’s actually been an incredibly good experience for me as a person because it’s opened me up to thinking about things in new ways, and given me the opportunity to work with lots of personalities I might not have been exposed to otherwise. All good things.

Along with this comes a lot of new stuff I need to do and think about. I lead a small team doing interesting projects, but I also play roles in other parts of the company as well. I have to span a lot of different activities in the course of any given day, and I may not have time to cover everything I need to. I have had to learn to delegate and share some of the load, which honestly was a challenge for me, but utterly necessary in order to keep my sanity. Luckily for me, my team is amazing and is more than willing to help out with anything.

So instead of keeping my tasks in a silo by themselves, we’re all using Todoist together now. It has been transformative, mostly because I’ve never used it with anyone before. 1 I’ve used it extensively myself, but the service begins to take on a whole new life when you use it with other people. So we all have the app installed, and the team has access to just about every project in my personal list. This way, they can see everything I’ve got going on, can jump in and handle things if they see an opportunity to do so, and I can assign tasks to them as I work through setup of projects on calls and in meetings. I get notifications when things get done, and we can comment on tasks, attach files, and chip away at large bodies of work all at the same time. It’s been terrific for feeling like we’ve got a handle on everything we need to do, and I’m glad I kept my premium account active, because it’s really been quite handy.

However, now that I’m sharing all this stuff in Todoist, I’ve discovered that I want to have the things I’m tracking in my personal life somewhere else. The other part of joining a large company is stuff like IT policies and compliance, and I’ve found that having a clean separation of work and personal data on my company-provided laptop is the most comfortable way for me to work. It also gives me another reason to bring my iPad to work every day, which is essentially my personal laptop now anyway.

So I’ve split my world: email in different apps (Mail for work, connected to Exchange, Airmail for personal), files (Box for work, Dropbox for personal, along with my Synology), and tasks (Todoist for work and a million freaking things in the last month for personal stuff). For some reason, my calendar is the only thing I don’t mind blended, although I tried that too for a while (Calendar for work, Fantastical for personal).

I’ve never done this before; work and personal life was always together, and not in an unhealthy way. When you help start a company, it kind of happens. You don’t draw those boundaries the same way you might when you’re not personally invested in something. It never bothered me to see that stuff all mashed up–in fact, I really liked figuring out how to filter and sort in creative ways. Some of my best tinkering has been around how to use my favorite tools to show me exactly what I wanted when I wanted it. Now I’ve realized with all the things I’m tracking, the best way to do that and accommodate my personal wishes to keep work and personal life connected but separate means I take that information and split it right down the middle.

With certain data, like email, this was easier than I’d expected. I always thought having a unified inbox was wonderful, until I was sifting through dozens of work emails to lift out the actually important personal email about my mortgage that I absolutely couldn’t afford to miss. So I bought Airmail and haven’t looked back. It got a great update right around the time I was making this change, so it was rather fortuitous.

Files were easy too. I keep one folder from Dropbox on my work machine called “Sync” and it only contains a dedicated 1Password vault I use for work stuff, and my Alfred data. Everything else on that machine is work stuff and so it lives in Box.

Tasks. That’s where things take a real turn. Big surprise, I know.

Next post: the clouds part, I go a little crazy, and land right back where I always start, a little more enlightened for the journey. As it should be.

  1. Federico has written quite a bit on using Todoist with his team at MacStories, and they do some very cool stuff over there with it and a few other tools. 

Ain’t no party like a network-attached storage party.

I’m a relative overachiever when it comes to complicating things in my technological life. I like tinkering. But I’ve always kept local storage a little on the basic side, with a few external hard drives cloned to one another using Carbon Copy Cloner. When one of these drives started to go recently, I finally decided it was time to take the plunge on a NAS setup in my home. I asked for recommendations on Twitter.

The answers were overwhelmingly in favor of the Synology family of products. A quick trip to Amazon and several hundred dollars later, and I had my ticket to board the train to NASville.


Anyway, my needs are fairly straightforward: I just want a big drive to store a bunch of stuff, and I want redundancy. After looking over the different models, I went with the DS414j as my entry point to this brave new world. I coupled it with two WD Red 3TB drives to start (leaving two bays free for later).

Holy hell, this thing is cool.

It took about 10 minutes to set up. I was prepared for a protracted land war, and it was more like a game of laser tag. The box opened up, the drives went in the box, the box got closed, it did some magic, and then I had a web interface to see the box. It was so easy, I was convinced I did something wrong for a minute.

The web dashboard has a ridiculous amount of options, most of which I’ll never even use or look at again, but it’s crazy how much these boxes can do. I got about 1.3TB of data copied over the LAN in 10-11 hours, and I was done. I can’t remember the last time I had a big computery task to do that was this easy and non-enraging.

I’ve barely scratched the surface, but I plan to play with it and explore a bit more soon. In the meantime, if you’re thinking about something like this, start your search with Synology. So many people recommended it without hesitation, and now I can see why.

A week with the Pebble Steel.

Prior to the announcement of the Apple Watch, I had little to no interest in wearables of any kind. The closest I came previously was a year-long dalliance with my Fitbit. Even today, I’m still not wholly convinced of the overall utility of wrist computing, but I’ve begun to think about it more seriously and as such wanted to dip into the current market so I’d have a way to make a comparison when the Apple Watch does finally arrive.

So last Saturday, with some birthday money in hand, I went to the nearby Best Buy and left with a Pebble Steel. At first, I figured I would just get the cheaper plastic model, which is half the price, but it was so ugly that my modest personal style sensibilities immediately overrode that decision. The Steel is actually a pretty decent looking watch anyway, and not so far afield from what I might ordinarily consider. The goal of the experiment was the following:

  • get a little experience with some kind of wrist-based computer thing in advance of the Apple Watch to understand what it’s competing against
  • decide if having notifications on my wrist was even something in which I was even mildly interested
  • explore the apps and functionality the Pebble line currently offers, having matured a little since its introduction

I’ll quickly address the hardware itself. The Steel is a nice watch, but I always have issues with metal watches with leather bands that are waterproof. I realize the casing can take it, but who wants to get leather wet? And I’m far too lazy to spend the time treating and waterproofing the stock band. It’s just not that nice. The black leather that comes standard is less than stellar, and I immediately replaced it with this, which is a vast improvement and feels more like one of my beloved G-Shocks. I know there’s a steel band you can buy as well, but it also looked sort of lackluster and I wanted something that felt more sporty. The Shank is a great product, and I’m really enjoying it. Now I don’t care if the watch gets wet because it’s metal and silicone and feels more durable as a result, even if it’s all in my head. I think Pebble should have offered a band like this themselves, as it still feels high end, but adds a resilience to the overall design.

On wrist-based computing: The first day I wasn’t convinced this was for me. Little stuff like controlling music/podcast playback is nice, but my best use case so far was viewing a shopping list on my wrist in the zoo that was Whole Foods on the day before Thanksgiving. That was actually super convenient, especially now that I have the 6 Plus. So I think a device that can do more than this (e.g. respond in some way to notifications) could be useful in a hands-free scenario.

On notifications: A bunch of buzzes on my wrist, telling me all kinds of things happening on my phone that I found I mostly didn’t care about. A little tweaking of settings, and I can definitely see the value of having little blips here and there when you don’t want to or can’t take your phone out of your pocket. I’ve always kept a lean notification profile on my phone, but I trimmed it down to only the stuff I want to see on my wrist and it’s pretty useful. Calls, messages, support tickets for Stringer, and only a few more things are what make it to the watch, and it’s working out pretty well.

On the Pebble experience/apps: Most of the “apps” that I found in the Pebble ecosystem were pretty goofy. Proof of concept stuff, things that overreach with what the watch can actually do, etc. There are some interesting things happening, but overall it feels pretty half-baked. Speaking of which, the Pebble app on iOS is an abomination. I think it’s just a wrapper for a web app, and it performs horribly, with a high percentage of your taps not registering, the app freezing, and you generally just losing interest in the whole process. When you actually install something, it’s a fairly janky process, the settings for the apps are stored in web pages on the phone with varying functionality and complexity, and you can only manage eight slots on the watch at any given time. It’s… less than ideal.

Understanding that you need the phone to do anything with the watch, it’s really disappointing how terrible it feels. It’s also (as of this post) still not optimized for the new iPhones, which is really annoying, but that’s just me being petty, I suppose. Still.

All that said, I’m a believer in having something on my wrist to use this way. I wasn’t just over a week ago, and now I am. So I can thank the Pebble Steel for getting me on board with the concept. I thought the Apple Watch looked cool when it was introduced, but I was skeptical as to whether or not it was for me. I think it definitely is, and the Pebble’s just made me look forward to it more. For all my criticism, I am actually enjoying the Steel, and I’ll continue to wear it and use it until I can upgrade this satellite experience next year.

Moving from Evernote to Dropbox.

On this week’s Connected, there was a hearty discussion about some choices that Evernote is making with its product, namely the addition of “Context”. Offered as a Premium feature, the goal of Context is to surface additional useful information to the user as a note is being created, viewed, or modified.

Stephen voiced some very reasonable concerns about the direction in which Evernote seems to be moving, and how this type of feature can feel intrusive. In the absence of more information, Federico shared some of those sentiments, while Myke argued on the side of the business, namely that it’s a seemingly innocuous change that we could have expected this company to have made to increase its viability at some point (and everyone marveled that Google hasn’t done this yet). I don’t know all the facts about Evernote’s investors and fiscal plans, but even before this, I was considering moving away from it for different reasons.

First, let me start by saying I have been an Evernote user since 2008. I am a Premium subscriber. I love the service. I love Phil Libin’s focused and honest approach to the company. I love that it works almost all the freaking time, even when I do something dumb that should have broken it. It’s truly great. But I’ve started to realize that it’s also in direct conflict with the way I want to think about, store, and access my information.

I’ve never been a fan of GMail because I am an old-school IMAP guy. I like making folders, I like using folders, I like taking forethought and putting things in places. I don’t like the “leave everything in the inbox and just search” mentality. It’s never worked for me. And while Evernote allows you to create notebooks and stacks of notebooks around those, I found myself dumping voluminous amounts of information into it, organizing it, and still not really having an idea where my stuff actually is. Luckily, its search is tremendous and I can usually find what I need. But it still didn’t feel right to me, the way my brain works.

In addition to this, I have a long-standing affinity and love for plain text. But I also take pictures of things. And scan documents. And create PDFs all the time. How will I find all this? How will I search and have it make meaningful sense? Where is my context?

So I’m shifting gears. This week I manually created plain text copies of all my blog posts from this site. I wanted a local copy of everything, and I did some housecleaning while I did it. I used Editorial, because it was actually easier to do it–my hand to Federico–from the iPad with workflows than on the desktop. And yesterday I began migrating data out of Evernote, one note at a time.

I created this hierarchy in a top-level “Notes” folder in Dropbox:

It works like this:

Audio is for any kind of aural snippet I might capture and not have a specific place for yet. This could include funny things my daughter says, a conversation, a song idea, whatever. I have Dropvox set up on my iPhone to start recording the instant the app opens, and put its files directly here.

House is a folder I share with my wife. In it are ideas for renovation, pictures of interiors and exteriors we like, and documents we both need access to.

Lists is just casual stuff I want to keep track of: books to read, music to download, etc. Managed via Listacular on iOS.

PDF is any file of that type that contains information I want quick access to, or that has no relative home elsewhere (say, in the “House” folder). Evernote allows you to convert notes to PDFs easily, so a lot of things in this folder are series of images that ended up as one PDF. Handy.

Photo contains any kind of photo note I might grab with my phone. Wine we like, the type of paper towels I’m supposed to get, the back of my router. You get the idea.

Scans is for anything grabbed via Scanbot, Scanner Pro, or my ScanSnap. Yes, these could probably live in PDF in most cases, but I like the idea of a separate folder, because I will almost certainly remember scanning something. I do it infrequently enough, although I want to start doing it more. And chances are these are “documents” as opposed to say, the very first issue of Nintendo Power that I have also stored as a PDF, in the PDF folder.


Sketches: any hand-drawn notes via apps on iOS, using whatever app I feel like.

And text is just the library of .txt files that make sense as straight up text. I’m using my longtime favorite nvALT on the desktop, and I found the incredible Jottings last night, which is as close to nvALT on the iPhone as I’ve seen yet.

All my files are named in a readable natural fashion (Wine – Chianti – Birthday Party.jpg) so I can scan for what I want quickly. I use Alfred and Spotlight to find them instantly on my hard drive. I’d tried Alfred workflows for searching within Evernote, but they always felt kludgy and slower than a fast file system search. This feels good.

I’ve set up a great set of Launch Center Pro actions to help with all this too:

They’re all pretty self-explanatory, and they’re working really well so far. “Checkbook” is a little prepend action so I can keep track of the handful of times I actually have to write a check, since I haven’t kept a proper checkbook in about a decade. And I can open the Dropbox app itself and browse all these files really easily. It’s great.

So that’s pretty much it. I’m out of Evernote in less than 24 hours (about 550 notes) and I have an accessible, lightning fast, and extensible micro-file-system. The idea of having a tangible handle on my data, visibility into it, and the ability to move it easily (not to mention switch between apps that handle all these standard file types) is a breath of fresh air. Nothing against Evernote, I still think it’s great, but it was time for a change, and this feels like the right one for me.

11-15-2014, 9:12 AM
A few people on Twitter brought up the idea that I’d be losing rich features like annotation, notes with both text and images, etc. Not really. Notability has excellent Dropbox support and provides a variety of format export options. I have mine set up pointed to my PDF folder, saving in that format. Changes sync to the folder instantly. It’s pretty great.

11-28-2014, 10:17 PM
In using this system for almost two weeks, I’ve added other functionality and condensed some actions within LCP. My notes group has been augmented by a Drafts action to send text to iCloud Drive for quick access from the Mac (this is still in beta, hopefully coming to the App Store release soon!), as well as with NoteBox. It’s a cool app that can merge bits of text together easily, which I learned about from this post on MacStories.

Now instead of a bunch of individual icons, I get this nice menu when I need to perform an “add” action of any kind. Cleans things up nicely.

Obviously, I’ll continue tweaking, maybe forever. Such is my curse. This is how it stands today.


Part 1, Discovering Time Where There Was None

I guess it started around the time iOS 8 came out.

I knew I was going to get a new iPhone a few days later, so when I restored and updated my iPhone 5 (I didn’t buy the 5s, so this was to be a big upgrade) to the production version of iOS 8, I purposely decided to keep my app count light. I saw no reason to spend a ton of time reinstalling everything and logging back in to a bunch of accounts. I never restore from backups, always doing clean installs, and while I have my process down to near-science, it still does take at least a little while. Then there’s the week afterward in which you discover all the little tweaks and settings adjustments you forgot to do on day one. But I was skipping all that. Keeping it simple. On Friday, I’d have a new phone and I could go nuts then.

But Friday came and went, and I didn’t have my new phone. I didn’t get up in the middle of the night to upgrade because I usually manage to get one at our local Apple Store on launch day. Not the case this year. I wanted a 6 Plus, and they only receieved a handful, selling through them almost immediately. I’d have to wait, or order one at this point, and bear the interminable 3–4 weeks of shipping/tracking number-hounding misery that would follow. No, I’d take my chances with the store. I’ll grab one eventually, hopefully within a few days. I was certain. How long could it be?

As of this post (9/30), I’m still waiting. It’s cool. I’ve made my peace with it.

I continued to use my iPhone 5, trusty warrior that it is. I installed only the most necessary of apps to do my day-to-day work. No games, no fluff, nothing extraneous. My home screen was a mere handful of apps, mostly default iOS, and a few third party favorites. I stuck the rest (bank, credit card, other necessities) in a folder and I was done. Signing into everything took me less than a half hour, and I was fully functional. I wasn’t fiddling with a litany of URL schemes and settings, constantly checking the App Store to see if I had any updates (no, I don’t do automatic updates, I’m old-fashioned and like to see what I’m installing before I do), or doing any of the million other time-wasty things I would ordinarily do with my phone to kill a few minutes dozens of times throughout the day.

I discovered something unexpected: I was picking up and using my phone in short bursts to catch up on the stuff that seemed worth catching up on, and then putting my phone down. Or I was chipping away at the tons of good content I’d saved in Pocket and then doing something else. Namely, spending time looking around at other things: my kid, my wife, trees, other people, etc. Earlier in the summer I’d read this post on using a distraction-free phone and while I enjoyed it, I had a very “great story, but not for me” kind of reaction. Yet here I was, unknowingly backed into just such an experiment by the simple fact that it was new iPhone season and I was just stuck waiting for the specific model I wanted. I didn’t go as far as the author of the post did, but it was far-removed from the way I have always used my phone.

It’s been almost two weeks at this point, and I don’t miss most of the apps I used to have on my phone at all. There are definitely a few that I’ll put on the new phone that aren’t on the current one, but I think I’ve turned a corner in how I think about this always-present, always-beckoning device. I can’t say it’ll last forever. Hell, this might all be over when I finally get that glorious giant glass beast that’s just out of my reach. But I think I’ll try to keep this up. I truly feel a change internally, on some tangible emotional level that was not only unexpected, but that I welcomed as it became revealed to me, which speaks volumes about how I felt before without realizing it. My phone remains my digital Swiss Army knife, but like the multitools that I love, I only take them out when I need them–I don’t play with them all day long, looking for reasons to use them.

Part 2, Changing Habits and Revealing New Things

I’ve always loved third-party apps on iOS. They can offer things that the stock apps simply can’t, for a variety of reasons, and the freedom of interface design and variety of different takes on the same problem always excited me. In some cases, I’ve even been resistant to use the default/first party offerings both on the phone and from various services because of some real or perceived weaknesses or flaws that I had identified. A great example of this phenomenon is how I think about Twitter.

I was a huge Tweetie fan from the start. That app was the perfect blend of simplicity and functionality, and pioneered some UI conventions that we now take for granted. Twitter is something I do every day, and I’ve enjoyed and used most of the apps on iOS over the years, settling on a few favorites, namely Twitteriffic and Tweetbot. I love them both for different reasons, just as you wouldn’t love one child over another. And that may seem like an asinine thing to say about Twitter clients, but I think a lot of you will just nod and move on anyway, so let’s leave it at that.

Twitter acquired Tweetie back in the spring of 2010. It proceeded to make some minor changes to the interface, along with a series of poor decisions, most notably this one. Overall, I lost any interest I had in the app itself, as what I wanted from the app and what Twitter wanted me to want seemed to be on divergent paths. Ads in my timeline? Heresy. Favorites made public? Balderdash. Twitter making choices for me that I should be making myself about what I see and how and when? Good DAY, sir! I exclusively used third party apps, even as they came under fire at various times from the company, as the business moved forward and choices were made to keep the experience focused on user acquisition and marketing. The nerd circles I travel in all agreed; the official app wasn’t worth even considering. Indie devs could always do a better job. I accepted this without contest, it was written, it was true.

Recently I noticed several of my friends both in real life and on the internet using the app, and this weekend I finally posed the question. It spawned a lively discussion that revealed to me quite a few things of which I wasn’t aware. I had a ton of great feedback from all kinds of users and decided to put the app on my phone again (it’s not installed by default, but if you sign into your account in Settings, it asks you to download it so it’s pretty close). What happened next surprised me.

Giving myself over to the new experience, I surrendered my preconceived notions about how Twitter was supposed to work. My timeline–which had gone from a place I loved to be to another number to clear–became a shallow pool of information that I chose to dip in and out of without consequence. My timelines stopped syncing, which meant I stopped caring about seeing every tweet coming in. Even the things I thought I would despise–the Discover tab, the promoted tweets–don’t bother me at all, and in some cases provide a new way of looking at a tool that I’ve been using every day for the past six years. My eyes are open differently to how I process and interact with this information, and that has, in turn, forced me to reexamine a lot of other things I’m doing.

Shifting perspective can be invigorating, it can be upsetting, and it can be net neutral. I pride myself on trying new things and gaining the lay of the land accurately, but in truth, I was actively avoiding keeping my mind open to the possibilities that there was something out there I hadn’t seen–or more importantly, that I would like something I was sure I wouldn’t. Along with revisiting a simpler phone setup and some of the simpler stock apps, this process is re-shaping the way I think about what I’m doing, and what other normal people (i.e. potential customers who may one day buy a product I release) do and want from their devices as well. I may not stick with the app long-term, but it’s been an extremely valuable exercise.

It’s worth reminding myself that no matter how perfectly architected the things in my life may feel, there’s something to be gained by breaking them down and starting over. I’ll be doing my best to keep this thought close to the front of my mind.

The sickness of efficiency.

I suffer from a strange affliction that I’ve lived with for some time now. I’ve spoken to others in my circles and I take some solace in knowing they share either symptoms of it, or experience it full-blown. It’s a sneaky sickness that manifests itself in an all-consuming urge to deconstruct patterns, methods, and expectations in my life in a constantly self-doubting and brutally examined way.

I am, of course, referring to my addiction to task management applications.

We joke about it, those of us who know. Here’s a new one, anyone tried it yet? I’m back on Reminders (again). Screw Reminders. When is the update for [App] coming out? This doesn’t do custom repeating alerts? (Do I need custom repeating alerts?) YO GUYS you can totally hook up Drafts/Launch Center Pro/etc. to grab stuff and pass it in. Swoon. I’m always looking at, trying, evaluating, and otherwise just exploring the landscape. Sometimes that exploration leads me back down familiar roads.

Yesterday I re-re-re-downloaded OmniFocus again and dumped all my things into it. I do this every summer, it seems, although the constant tinkering is a year-long battle. I keep as much of this from my family as possible, for I fear they’d stage an intervention for this behavior as clinically speaking, I’m sure there’s a buried DSM-5 classification for it, or at least some heading under which it could be placed. So I’m finally going to try to break this into what I believe to be its component parts to try to understand why I’m this way as a person, why I’m forever chasing the last high of streamlining data input and retrieval for things as complicated as multi-stage projects and as mundane as taking out my trash on the right day.

I see the never-ending shift between these apps as an interplay between the following things I’ve identified in myself:

  1. An inherent need, despite the fact that something may be working, to explore, experiment, and generally try different kinds of software and see new ways to solve similar problems
  2. A desire to change the UI of whatever it is I’m using since I spend so much time in it every day that I tire of it, notice its shortcomings, etc.
  3. An internal nagging to always be assessing the state of my workflows and methods to determine if they are actually the best possible ways to do my work
  4. An ever-present doubt, that coupled with item 3 insists that I’m missing steps, forgetting things, dropping threads (which is sometimes manufactured and sometimes very real)

So let’s break these down. I’m not talking about specific apps from here on out, because it’s utterly irrelevant in the math here.

  1. I help to design and develop software almost every single day that I’m awake. On weekends, I download and try things, help friends with interface questions, find bugs, and generally fool around with personal projects if time permits. I know that there exists in my life a finite set of productivity problems that I need to solve for, and sometimes the thing that sets my mind off in a new direction actually helps me think about something else unrelated to what it is I’m focused on at the moment. If I never tried new software, I wouldn’t see how other people solve for the same problems, just the same way that you don’t get a pizza from one place and never eat another slice anywhere else. Life would be so boring without that kind of exploration, no matter how simple.

  2. I’m a super-visual person. I need to see things in front of me to make sense of them. I have a really hard time with audiobooks because my mind will wander and I’ll lose the story for my own thoughts and so read on my Kindle instead. My eyes are the way into my brain and my brain tells the rest of me how to feel about things. There are certain aspects of my daily experiences that I simply can’t change (easily–I know I could hack just about anything if I wanted to). The look of the operating system can’t really change. The interface of Mail is what it is. The Finder is windows and lists, and it’s fine. I don’t need those things to be different, because they’re all tools like my garden hose–I use them, I move away from them. I don’t care how my hose looks, I just want water to come out in varying degrees of force when I turn it on. I don’t need Finder to blow my mind, I need it to move my files around the same way, every time. But since I can easily change the look and function of my task lists, I’m tempted to do so and offered the opportunity almost every week. It’s an embarrassment of nerd riches. As I continue to design interfaces, I notice things I like in apps and things I really don’t, and they help me make better decisions in the work that I do. It’s valuable to me to keep my eyes fresh, and task apps are a weird, easy way to do that without a ton of disruption in my life.

  3. Ever since I was a kid, I’ve had a problem with keeping things the same for too long. I would endlessly rearrange my bedroom furniture, often in the middle of the night without my parents knowing. They’d wake up and see a completely different room than the night before. I had a limited kid-bedroom canvas to work with, and I was always looking to maximize the space I had to move around as well as the storage and access of all my stuff. This is but one example of this kind of behavior. As an adult, I don’t have the time or energy to move furniture all the time (and my wife would likely divorce me should I decide to make this a focus in my life again), but I look for other small efficiencies in my life that I can optimize. Rearranging the silverware drawer to gain access to the stuff we use the most. Same for the kitchen cabinets, putting things within reach and moving other things further away. The garage. My desk at work. My car. Shall I go on? Anywhere I see a repeatable task or a friction, I find a way to make it perfect (or as perfect as it can be within the limits of reality).

  4. This one’s the toughest. The fact of the matter is that I get everything done that I’m supposed to. I’m pretty good at it. I base everything against dates, and I’m brutally honest with myself about when things need to be accomplished. A former procrastinator in my youth (in stark contrast to what I just revealed in the above paragraph), as I got older, I realized that honesty and planning are better for me mentally than avoidance. However, I do capture things without dates, or without an immediate need. And they sometimes linger, or I forget about them. Sometimes it’s fine, and they never really needed to get done in the first place, and sometimes it’s dinner with a friend from six months ago and I’m a horrible person and let’s finally finally get together sorry man. Some of this dropping creates doubt in my systems and nudges me into new directions. Some of it is completely true and I find I’m not managing things as well as I think I’d like to–with little ill effect, other than a desire to improve as a person. But it’s there. Real or not, the thoughts are there and they need to be addressed.

All this considered, it’s worth noting that when I’ve got a lot to do, and people are depending on me, I don’t mess around with my system. I focus, get my stuff finished, and move on. I’m not a monster, after all. Work is work, and all this fiddling doesn’t matter at all when things are on the line. And I haven’t touched on it, but I absolutely, unequivocally realize the irony in wasting time trying out productivity software. Some people take it to extremes, and it just becomes farcical.

The last point I’ll make is that if I’m being honest, I have to say that my needs sometimes actually do change too. I might use Reminders between iOS and OS X and it’ll be just perfect for a few weeks or months, but then I realize that I actually do need a feature it doesn’t support for something. And not a manufactured need, but a real, honest-to-goodness need. It might even be a temporary need, but once I recognize it, it starts me thinking and the machine spins up all over again. Then I wrestle with some feelings–truly–about how and why I am the way I am. Why can’t I just leave well enough alone? What am I hoping to gain by engaging in this activity for the third time this month? I’ve become comfortable with my shortcomings, real, perceived, or otherwise and I just want to do good work. If a little dicking around with tasks makes me feel better and isn’t hurting anyone (and I’m still actually doing the things I need to), I guess I’m fine with it. I could have worse habits, I suppose.

But when time permits, and my mind wanders, or my eye tires, or the little kid in me really wants to move his bed and dresser again because maybe, just maybe he could fit some more stuff in here somehow… now I just open the App Store. It’s a wonderful time to be a lover of software, and we often forget just how great things are.

Now if you’ll excuse me, I have some data entry to do. Again.

Data loss and noble truths.

I don't remember the first time I lost data. I don't even remember what it was. I do remember the feeling of utter despair though, and the declaration that I wouldn't let it happen again. Since then, so much of my time and mental energy has been spent thinking about ways to prevent this from happening and creating layers of redundancy around my data and in many cases the data of those close to me.

Of course, no matter how careful you are, things can happen. All you need to do is listen to any recent episode of ATP and it becomes apparent that I could still be adding layers, checking backups, making sure. Checking disks. More. Verifying. I could always be doing more.

But I've started down a path that calls into question – or at least forces me to examine – the ways in which I think about the preservation of data. It began when I was in our kitchen, absent-mindedly staring at my wife's small box of recipes – written on index cards, as is often the case in many of our homes. Certainly she's always using the devices around our house to look up new recipes online, but this box contains things from her mother, her grandmother, relatives, and friends – things given to her over time. And it suddenly dawned on me:

This is the only place where this information exists.

I immediately began developing a strategy. We will digitize the recipes. We both use Dropbox–no. She has an Evernote account; I would simply have to get them in there somehow. Probably take photos of the cards, let them sync that way. That would be the easiest. Yes. I would talk to her about it later that night, and such it was set in my mind as I drove into work.

And then I stopped myself and began an attempt to trace back in my thinking to a point at which I could see the inception of this obsession with redundancy. I thought about what might happen if that box were lost. I suppose she'd be upset, but she could probably retrieve many of the recipes again from the folks who provided them. It would be work, but it was possible and certainly not the end of the world. Then I extended this to all the other places where I obsess about data. What were the things I truly couldn't live without? I have spent so much time actively creating elaborate architectures for the preservation of my personal data, that everything has fallen into this bucket of “must retain”. Certainly things like pictures of our daughter's birth are worth saving and having in many places. But I sometimes feel like I've taken the preservation of data to a strange new place.

For example: It all starts with Dropbox. Copies of all my files, online and on multiple machines. I can't trust iCloud, but I use it for contacts, calendars, and reminders – so I individually back each one of those up with manual exports. I love Evernote, but once a week, I manually export and save a complete set of my notes in Dropbox. When browsing for apps, I often won't even give an app a chance if there's no Dropbox sync or backup component. It's partially because I want to save time in the future with setup tasks, but there's also a voice in my head always reminding me how transient these bits I'm pushing between my devices truly are. I'm writing this on the iPad in a text editor hooked to Dropbox, but I'm not sure exactly how often it saves my document, so I stop every paragraph or so and move the view around to see that it is in fact, updating and saving. All our music and movies are available for streaming whenever we want, but I always download and store (and back up) a local copy of everything I buy. Stuff for the business? No brainer. Of course. Cloned copies as far as the eye can see. It's sort of a sickness, and sort of a well-oiled insurance policy, but it's already saved me countless hours of aggravation.

There's a large part of me that's proud as hell that I do all this. There's another part that wishes I could care a little less and just be more relaxed about things. I am by no means a practicing Buddhist, nor would I claim to be a student of it in any regard. But I do find reading about it to be very interesting, and I find myself doing it from time to time. One of the tenets of the first of the Four Noble Truths of Buddhism involves the individual's inability to let go as part of the cause of suffering – the anxiety or stress of trying to hold onto things that are constantly changing. This is an idea that is core to the religion, but this concept also exists outside of Buddhism as well. I accept the inherent impermanence of the things with which we often concern ourselves, and realize that all my efforts are but a fleeting stab at self-placation. I try to always remember this when I find myself perseverating on small issues and physical objects (not an easy task for someone who is always eager to play with new electronic toys). This idea however, is in direct opposition to my philosophies on preserving my data, which border on good-natured zealotry in the eyes of most of the people who dare engage me on the topic.

Which brings me to the core question: is data – and the memory, time, and emotion we etch into it in our lives – more valuable than the physical objects with which we surround ourselves? Can we draw a line of distinction between the two that squarely places an iPhone below the photos I took with it of my newborn child? Attachment to anything is the key factor. I often wonder how life would be different if I were to lose all the things to which I ascribe value. Life would certainly go on if we were safe, but all our things were gone, so how important are these invisible, psychically tangible things? I would be lying if I said that I haven't stayed up in bed thinking about backups at one point or another, mulling over my machinations, unsure of just how good they were. I suppose it's more of a theoretical debate than something one can put into practice, but I can't stop thinking about it. I suppose as with most things, there's a balance to be struck between managing data and preserving what is necessary or important to you, but understanding at a deep level that it's another thing tying you to a potentially stressful obligation in your life.

I hope I don't sound like some nitwit who would put his family in jeopardy and throw away a mortgage and a home to run free among the flowers unencumbered. Nor did I want to take a fundamental precept of one of the world's major religions and apply it to a triviality like where my phone numbers are in iCloud. We all take on various levels of responsibility and as providers to those we love, we shoulder the burdens that come with those choices. That wasn't the point of the thought exercise. I just happened to reflect on this concept and follow it to this point. I plan to continue backing up and safely retaining all my data, just as I am today. I may even become more neurotic about it. I haven't gotten around to the recipes yet, though.

But I probably will.