The State of Instant Messaging

Apple's iMessage was the warning shot that things were changing. Some embraced it and didn't look back. Some didn't know they were embracing it -- for them it was just a matter of having a blue text bubble versus a green one. Others saw it as a way to get out from under the thumb of greedy cellular carriers who charged outrageous prices for text messages. However you look at it, iMessage affected everyone who uses text messaging or instant messenging -- and it is proprietary.

Microsoft's purchase of Skype is finally changing the face of their instant messaging backbone. The popular MSN Messenger is widely used, especially among businesses, due to its ubiquity on the Windows platform but recently Microsoft announced that they were forcing all users over to Skype for voice and text chat -- and it is proprietary.

Google, after having a huge success with Gtalk, has just introduced Hangouts. It is a souped up combination of Gtalk and Google+ hangouts and has the promise to be the best of both worlds with synced conversations across all of your devices (a la iMessage), best in class video and sound conversations (a la Skype) and integration with Google's ecosystem (a la they get all of your usage data for free) -- and it is proprietary.

The big three seem to be circling the wagons in an attempt to lock their faithful users in to their platform of choice. While there is solid logic behind this, it is the users who are the ones made to suffer for their choices. Over the last few weeks, I've been trying to build a comprehensive view of the instant messaging landscape in an attempt to pick the best tool for the job (and then attempt to push everyone I know onto it).

What Features Are Important, New and Useful

With such a wide reach among tools, I felt it was best to start by boiling down what features I wanted in an instant messenging application. Deciding what was important would naturally push some of the choices out of the nest, making it easier to make a decision.

Here's what ended up being important to me:

  • Synced conversations across devices - This was something that I didn't know I needed until iMessage made it a reality.
  • Reliability - it sounds like something that would be an easy-to-add feature to an IM designer's list of features but the latest crop of IM applications often drop the ball here in a big way.
  • Interface clarity - Seems like this would be high on the list for designers, but try and find a specific Hangout on the Google+ page and get back to me. Some folks clearly forgot to add "interface clarity" to the whiteboard in their brainstorming session.
  • Accessible to people I care about - Whatever the choice eventually is, I will need to convince people I know to use it or this entire exercise is pointless. Having friends scattered across four or five services is bad, but given the state of IM, this is about to get a lot worse.
  • History search - This needs to be toggled for each user for security reasons obviously, but having the ability to search through certain conversations later or use them to excavate notes from a chat session is a great feature.
  • Group chats - The ability to have a chat with more than one person can be helpful on projects or with certain groups of friends. These little group conversations echo the functionality of a small IRC private network when done right.
  • Open protocol - I know this is "a bridge too far" at this point but a non-proprietary network would greatly encourage innovative interface designs and competition for the mantle of "best app". In the end, this means the user would win.

The Contenders

There are a lot of choices out there. I'm only going to list the good ones. I am not going to waste time on things that are platform-dependent[1]. I am also not going to waste time on the "text message replacement" apps like What's App, HeyTell or Kik because making a friend pay a dollar to talk to you seems like a bad idea. I'm definitely not wasting my time on anything with the word "Facebook" in the title.

So what's left? Not much, that's for sure. Here's the rundown.

Trillian/Adium - These apps are very similar and they entail creating an account on AIM, Gtalk, ICQ and the like. They function as a multiprotocol client that shows all of your contacts, and manages all of your conversations, in one place. Of the two, I find Trillian more capable because it has an iOS client which allows you to continue synced conversations between your Mac and iPhone/iPad. It is very powerful and it is one of my most-used apps. No group chat though.

iMessage/Messages - This is Apple's entry into the scene. The Mac client builds on the old iChat model and tries (and ultimately fails) to combine the old paradigm with the new. It supports cross-device chat for iMessage conversations but if the user is on one of the other protocols or devices (like Android), you're out of luck. I love that Apple completely routed around the text messaging monopoly held by the carriers and the way it falls back on text messaging if the device has no data connectivity is a work of genius. The Messages app has a serious bug that causes it to re-order entire conversations randomly. Continuity issues aside, the conversation sync feature is powerful and useful. If your devices are registered with iMessage/iCloud, a conversation can be continued seamlessly across all of your devices or machines. Facetime is integrated as well for voice and video chat. It is Apple-centric however and I doubt Apple will make it an open protocol anytime soon. If they fixed the message-reorder bug, this would be a major contender. It is so comprehensively powerful I'd gladly shun my Android friends (more) to consolidate on the platform. Group chat is well-implemented and I use it daily.

Google/Gtalk/Google+/Hangouts - Google, as usual, has made a mess. Gtalk was built on an open protocol (XMPP) and was easily integrated into chat clients like iChat, Trillian and Adium. As Google marches forward with Google+, it waves goodbye to consistency and convenience, replacing them with a Creepy Uncle hug to the integration between its half-baked, proprietary Hangouts effort and Google+ interface design fiascos. Google has decided to start pushing its closed protocol and combine it with its Gtalk "product". I wouldn't be surprised it if moved users over to their closed protocol in the coming months and shut down their XMPP service. Hangouts does support group chats and seems to aim squarely at making that a focus. Today, after extensive testing with Hangouts, I noticed that all of my Circles are now mashed up in my normal Gtalk user list on all clients[2]. Some of these faults could be redeemed if the Hangouts app was good, but it isn't. At times, the chat delay is pronounced, I had issues with lack of sound during some video conversations, the interface lacks some very basic options and the iPad app is a stretched-out version of the iPhone interface. It is a shame. After a few minutes, I thought the app held promise. After about an hour, I was slightly frustrated but bemused. After a few days of use, I couldn't delete it fast enough. The tech press was trumpeting "Google wins with voice chat and synced messages" last week while Apple users have been using these features since the release of iOS6. The state of Google chat is bad, folks. Really bad. "Open always wins" though. Yup. Ok.

Skype - Out of the Big Four, Skype has the worst chat interface. It is a trainwreck.[3] Admittedly, its voice chat is very good; it is practically a standard across all of the businesses I work with day-to-day. Most of the time, however, I just need to send someone a quick text message and this app isn't the one I'm going to do it in.

Social Networks (Twitter and ADN) - Twitter and ADN have private (or "direct") message capabilities. Unfortunately, both of these are at the mercy of two different potential issues. The first potential issue is the social network's ability to handle and support direct messaging. Twitter has downplayed its direct message capability and even floated the idea of doing away with it at some point (hard to feed ads to direct messagers, I guess). It clearly isn't a focus for them so I'd rather avoid getting caught out by building a reliance on it. ADN has a rich direct/private messaging capability but it seems dependent on the quality and consistency of the client. As ADN relies heavily on the support of third party development, they also rely heavily on the developers understanding and ability to exploit the full potential of the protocol. So far, in testing, I've had spotty results. While you can successfully send messages back and forth to a user, it doesn't seem to work very well for conversations that stream back and forth quickly. Twitter's implementation is the inferior of the two but it is also the most ubiquitous so its a case of "pick your poison". ADN has some interesting efforts like Project Amy which integrates ADN with Apple's iChat/Messages app. I tested it but have yet to put it through heavy paces. In a cursory test, it seemed to work surprisingly well. ADN supports group conversations you can use apps like Patter to take advantage of them. If ADN were more universal, its great third party developer support coupled with smart considerations from its attentive owners would make this a nice contender. No voice or video chat though (yet).

Goodbye Status

One thing is clear -- user status is going away. In the old days (last year), the ability to mark yourself "Away" or "Extended Away" was seen as a key feature for a chat client. These days, with device-synced conversations coupled with the fact that we are now used to disjointed and discontiguous text messaging, it seems less important than ever. I am happy to see it go since it was easy to forget to change your status. I gave up trying years ago.

Conclusion?

There is no clear winner here. As I mentioned before, the user is the real loser because the pitched battle for users and a lock-in model serve to create a wide range of favorites with each user deciding on what is their most important feature and then trying to convince all of their friends that their solution is the best. Out of all of them, Apple has the most comprehensively thought-out messaging model but it is plagued with a few serious bugs. Facetime serves the voice/video spectrum and the iMessage protocol (with its smart switching between text messaging and online-based chat) does an admirable job of syncing conversations amongst all of your Apple-based technologies.

And there is the problem -- what about people who use Windows all day at work? If they can't access chat on the desktop easily and take those conversations with them, it presents a large hurdle to building a consensus. This is the main reason why I end up using Trillian so much -- it spans desktops, platforms and devices for users who aren't me. After all, if you had the best chat client but no one to talk to, what fun would that be?

For now, my solution is going to be the Gtalk XMPP protocol via Trillian in order to span my desktop and iOS devices regardless of my chat partner's choices. For friends who have Apple devices on both the desktop and devices, it makes sense to consolidate on iMessage, despite the occasional bugs in message continuity. The bugs will eventually be fixed but what will remain is the best platform from top to bottom. The real challenge will be convincing all of my friends to use it. For my Android-using friends, there's always email...[4]

  1. As much as I think my friends who use Android make bad choices in life, it doesn't mean I never want to talk to them. ↩

  2. What was a once a manageble 20 users is now up to 108 people I almost never talk to. Nice job, Google. Thanks for letting me know this was going to happen. ↩

  3. I do have to praise its consistency however as it has the worst chat client on all platforms, without exception. ↩

  4. Have fun with that. ↩

The Later Box

There have been quite a few email applications introduced into the iOS ecosphere in recent months.

Mailbox, Mail Pilot and Triage are three of the apps that I've tried. Each has a focus on managing your email in new ways -- primarily they present ways to wade through your Inbox quickly and efficiently with a focus on action.

Mailbox has the ability to flag emails for later, set a timer or date for them to appear again, archive etc. It is an elegant and fast way to do things and I liked it a lot. Mail Pilot takes the same tack but takes Mailbox a step further, working with IMAP mail services beyond just Gmail. Truthfully, I loved Mailbox. If it worked with mail accounts other than Gmail, I would still be using it.

I found that Mail Pilot, despite the premium price compared to its compatriots ($15), delivered a spotty implementations. It was sluggish, slow to refresh and moving a piece of email often left it in a state of limbo. Moving email to an archive and searching for it later, was a crapshoot. Sometimes the email was just gone, only to show up later without any explanation. I'm sure it was related to syncing everything back and forth between the iPhone/iPad, the IMAP account and my mail client (in this case Mail.app). It also used a folder/filing structure that ended up getting quite Byzantine after a few days of use. This was hidden from the user on iOS but I go back and forth between my iPhone, iPad and MacBook Air and having to search through a dozen folders to find out where Mail Pilot decided to file something was less than ideal. Eventually, I would be able to track down the wayward email but it was a lot of wasted cycles and worry.

The aforementioned Byzantine file structure presented another problem in that it left my email account cluttered with empty folders. Maybe it eventually cleans them up but I didn't stick around long enough to find out. I'll check back on it after a few updates.

Triage was something I heard about on ADN. I was pointed to a Viticci article (as I often am) and I got me interested enough to try it. Triage is simple. You hook it up to your IMAP account and you have two gestures to work with - Up (mapped to Delete in my case) and Down (mapped to Keep). Flicking up will throw the email into my Deleted Items folder and flicking down will leave the email alone, unread in my Inbox. Conveniently, it no longer will show up in Triage when marked as Keep. Why they don't allow user-mappable gestures to the cardinal directions I'll never know. If it did, my problems would be solved and this post would be over. Still, it comes close to what I need.

What Mailbox pointed out to me is that I need is a Later box. A place to stick emails that I don't want jamming up my Inbox but I really do need to act on "later". Ideally, the number of emails flagged in this way should be relatively few. If it is more than a handful, it is probably pointing to a different kind of problem -- the last thing I need is an interim archive. I need two things -- a place to hold emails until I return to my Mac and the discipline and discernment to act on them when I get there.

To solve my problem, I employed a mishmash of tools and techniques (as I do). First, I created a Later folder on my Fastmail IMAP account. If an email came that I couldn't respond to immediately, I would use Sparrow on my iPhone and move it to that folder. Sparrow thankfully makes this painless and fast. Problem solved? Not quite.

The new problem was that I never checked the Later box. Things would go into a limbo state and I'd only remember to check it every few days. It ended up causing more friction than it was meant to solve. What I needed was something that did what Mailbox did so well; when a trigger event occurred, it would move the email back to the Inbox. This move was essentially flagging the email to indicate that the email needed to be dealt with again.

As so often happens, Keyboard Maestro offered a solution. On my Mac Mini "mail robot" (if you don't have a Mac Mini home server, you're missing out -- those things are really useful), I set up a Keyboard Maestro macro that selected anything in the Later box and moved it to the Inbox every day at 7:30PM. The result is a flexible and extensible workflow that simulates what Mailbox does except with my Fastmail account. Problem solved for now.

My mail setup isn't perfect yet. If Triage had a left and right swipe action, I could map them to "Later" and "Archive". That would be quite convenient but, alas, this will have to do for now.

Here's how it works -- mail comes into my Inbox throughout the day and I quickly delete the stuff that I don't care about using Triage. After deletion, there are usually just a few emails in here. The rest of my processing happens in Sparrow when I have a bigger chunk of time. If an email shows up that I need to hang on to (like a receipt) I can quickly send it to my Archive. If it is something I need to reply to, I do it right then and there. If it requires more thought or will take more than a few sentences, I send it to my Later box for when I get home. Every night, all of the things I deferred throughout the day appear in my Inbox at 7:30PM.

It is not elegant. In fact, its annoying and kludgey. There are too many steps and it involves too many apps. The main advantage the whole messy process confers, however, is that I have a clean Inbox throughout the day which allows me to speed through my email quickly when I get a spare moment . It also wastes a minimum of brain cycles thinking about how to deal with each one. That should do for now but I'll still hold out hope that Mailbox will one day work with IMAP accounts or that Triage will eventually support a couple more speedy gestures.

Follow Up 5/10/2013:

I changed the automation to just call some simple Applescript which was more efficient and runs more consistently. Here's what I used.

tell application "Mail" to move messages of mailbox "INBOX/Later"  of account "Fastmail" to mailbox "INBOX" of account "Fastmail"

Put that in a time-triggered Keyboard Maestro macro and you're golden.

Switching From Google

When Google announced that they were shuttering Reader it made me take stock of how I felt about the company and how I interacted with them. I looked around and saw how heavily invested I had become and, over time, had been completely reliant and reservedly trusting of their services -- specifically Gmail and Google Calendar.

The Reader shutdown is the last in a line of events that underlined the fact that Google's interests and mine were diverging. When they were innovating with interesting technology like Google Wave[1] or Google Voice or taking the lead with a centralized and better solutions like Google Reader, Gmail or Gchat, they always seemed to be pushing the boundaries of what could be done on the web and focused on making it better.

But somewhere during the rise of Facebook, things began to change. Google's focus was on ad revenue and how to monetize these great base technologies they had helped create and foster. Their focus shifted subtly at first and I was forced to ask the question more and more "I am willing to give up access to my personal information for this product? Is it really that good?"

In most cases, the answer was "yes". Gmail really was that good. It was a killer app. Reader really was that good. It centralized hundreds of newsfeeds into one place and a burgeoning ecosystem was built upon it making it easy to read things in one place and have them stay marked as read in another.[2]

My move away from Google has been one borne out of the fact I no longer see them heading in a direction that I want to support. Their products seem confused and ill-focused. I see the main reason being that they no longer are concentrating on just building a great service and sorting out the money bit later; they need to fold that in upfront and it is diffusing their focus on serving people who use their tools and it putting it squarely on serving the companies buying ads to serve to the users of those tools. I understand that companies need to make money, certainly. But since Google's ability to make money is directly proportional to how much access they have to me and my data, this direction change didn't sit well with me.

I started taking steps to extricate myself from their products as much as possible. This wasn't going to be an all-or-nothing thing. I wasn't about to post some indendiary "I am so done with Google!" rant and stop using everything associated with them all at once. This was going to be a reasoned, sensible approach to minimizing my exposure to being disappointed by their current (and no doubt future) product decisions. I didn't want to close the barn doors and burn the barn down. I just wanted to use only the services that were truly helping me. I also wanted to consider the price of taking the path of least resistance with regards to my personal data and the fact that, while in the Google ecosystem, I wasn't using a product -- I was the product.

Calendars

At first, I switched my calendering over to iCloud. It had obvious integration with OS X and Fantastical and the switch was completely painless. In some ways, it was better than dealing with Google Calendar because it is one of the few things that iCloud seems to get right. I still use Google Calendar for shared calendars for specific purposes because it is simply easier when collaborating with others. When it ceases to be easier, I'll probably stop using it in those cases too.

Mail

The second switch was more painful -- mail. I have been a Gmail user since it first launched. I have gigs of data on the service and having access to my archive of communication, combined with Google's fantastically efficient search, has saved my bacon many times.

I couldn't help feeling that I wanted to have more control however. And as much as I used to not believe it, Google's idea of "free" was quickly coming with a price as services I loved went away and services with marginal use were pushed to the fore in ways I found obtrusive and ugly.

After some asking around on ADN for some mail services people like, a name that kept coming up was Fastmail.fm. I did some research into Fastmail and sites like it and ended up thinking Fastmail was a pretty good choice. IMAP support, good security, excellent help documentation, setup guides, and their tech support (I later came to find out) was top notch.

I set up my Gmail accounts to forward to the new Fastmail.fm account and added Fastmail as my main inbox in Sparrow on both iOS and my Macbook Air. Everything went smoothly, the mail started flowing and all looked good.

There were a few things that were a worry when moving away from Gmail though. Looking through my Spam folder, it was clear that Gmail does a great job of trapping most garbage from hitting my inbox. Fastmail has touted anti-spam algorithms but I thought it might be good to take matters into my own hands on this one.

I bought an app called SpamSieve and installed it on my Mac Mini, which serves as a home multimedia/download server among other things. Using the Mini as a mail server drone took some fiddling and testing but I got SpamSieve's Applescripts to work, allowing me to remotely train the Bayesian filters from any of my devices.

After a few weeks of testing, SpamSieve has been nothing short of miraculous and I couldn't be happier with how clean it is keeping my inbox. It has saved me a lot of time in just deleting the marginally-spammy mails. I left the main spam filter running on Fastmail to catch the "v14grA" level spam, but the email equivalent of sales circulars and such are now heading to the Spam filter too. I peruse it daily to make sure thing important is stuck in there but very little has been mis-filed. If it ever is, I just throw it in a "TrainGood" folder and SpamSieve knows to let them through in the future and if junk ever gets into my inbox, I drop it in a "TrainSpam" folder. Both of these actions help tune and train the Bayesian filters in SpamSieve and it just keeps getting better and better.

I shelled out for Mail Pilot on iOS and was hoping to include it in my review of this whole process but Mail Pilot launched having issues with Fastmail IMAP settings. I'm eagerly awaiting a new App store release to try it out since it will apparently address these problems. It has felt like a long wait but with the likes of "invite throttled" apps like Tempo.ai and Mailbox lately, I guess should be used to delayed gratification by now.

Google search is the best. There's really nothing close, although engines like Bing and DuckDuckGo are coming along. In order to give one those other servies a try, I set up DuckDuckGo as my default search in Alfred and Safari on my Mac. The results from DDG have been mixed. Sometimes it is spot on, but other times it is nowhere near as much of a mindreader as Google. I am never sure if that is because it has been scanning my personal life in such detail for so long that it has built a profile that guides the tuning of my results or if I am giving too much credit and they are just generally better at deducing what people are looking for.

Whatever the reason, Google just finds what I want faster and with less spurious links in the result set. I am still going to keep using DuckDuckGo for a while though. I don't think its fair to base my opinion a small sample size of just a few weeks. It is something I'll keep my eye on in the ensuing months.

Social

Google+. What can I say? I tried to like it. I set aside my distaste and distrust when it launched as it tried to create a "better Facebook" but it became apparent quickly that it sucks in all of the ways that Facebook sucks but also sucks in new and different ways as well. In a strange way, the more people that used it, the worse it got. The comments were less thoughtful and more reactive and the anti-Apple vitriol seemed to be the main focus when reading technology-related posts. I kept it around for a while to see what the crowds were saying but when I realize the answer was "nothing", I checked out.

Right now, my main source of social-related activity is ADN. The conversations are far better, the people are more inclined towards civil (and interesting) discourse and there are fantastic apps out there that make use of it (Riposte and Felix are the two best on the iPhone and Kiwi the standout on the Mac).

Twitter is fun too. The main reason I enjoy reading my stream there is Twitterific. It's the best way to read Twitter right now, although Tweetbot on my Mac does yeoman work as well. I wish there was a stream-marker system that crossed apps and platforms that worked consistently but, for now, I just scroll to the top and try not to care so much about what I "missed".

Work in Progress

I realize I have a contrarian streak in me a mile wide and I need to be mindful of that fact as I make decisions like this. Some decisions I've made in the past about apps and services have been impulsive but still were no-brainers[3]. I leave those behind with no regrets. Other decisions however carry some weight that require a bit more introspection. In the scope of things, calls like this seem minor but they bring up serious ideas like digital security, archiving, accessibility, integration and future-proofing. These are the ideas that are worth putting some thought into.

  1. I wish Google Wave was still around. I am still thinking up uses for it. It was hobbled by a slow infrastructure and somewhat inscrutable design but overall it was an entire platform waiting to provide solutions to problems that hadn't taken shape yet. ↩

  2. You can say it killed an ecosystem in doing so but the result was so compelling and useful it hardly mattered to me at the time. ↩

  3. Any app or service that merges with Facebook is something I'll no longer use. Any app or service that requires Facebook in any way (to find friends or integrate "socially") is something I delete immediately. ↩

Putting Things In, Taking Things Out

Most of the things I do to stay organized are to reduce friction and have something at my fingertips when I need it. I collect a lot of things that ideally I'd like to get to quickly -- a running list of books I'd like to read, meeting notes from a month ago, ideas for a story I'm working on, brewing notes, tasks, reminders, scanned paperwork or bills, product manuals, game rules, in-progress blog posts -- the list goes on and on.

Leave aside the question of why I care so much about this (that's probably the topic for another lengthy post), the simple truth is that technology has taken over as a form of outboard brain for me. I'm not alone in this. Others have mentioned this concept in their own lives in much better posts than this one. The worthiness of the goal aside, we spend a lot of time to deciding how to put information into all of these systems but have we really given adequate though to getting it back out again?

Putting Things In

When I really look at it, I have what I'd refer to as a "meta-system". The system itself is a group of applications that collect data and put it in places that I can get to easily. The system doesn't just deal with notes; it also governs my task management, reminders, and contact and password management. I have distilled the process of putting things into this meta-system down to the essentials. While I'll often try out new apps and tweaks, new things that come into my orbit of activity have to be really good to dislodge the processes that are already working.

I guess you could say I'm done with the tinkering that comes with getting these systems tuned up and doing what you want them to do. Wait... let me rephrase that -- "doing what you need them to do", not "want them to do". If these processes you are taking the time to build or the apps you are buying aren't needed, then they need to be dropped.

The key to all of this is to keep things simple but not too simple; as complicated as it needs to be, really. The boundary of what "complicated" is will be different for everyone and the boundary can change along with job changes, life changes or family changes.

Here are the apps I use to put things into my meta-system of content creation/content gathering and remembering/reminding.

Writing

Dropbox is key to my writing workflow for any task. It is essential to pretty much everything I do involving words (plus a whole lot more). A quick search through the apps and applications below will show that everything in the list has deep Dropbox integration.

On The Mac

On the iPhone/iPad

  • Drafts for general text entry
  • Nebulous Notes for editing, searching or viewing things created in Dropbox
  • Fade-In for screenediting
  • WritingKit for writing blog posts on the iPad (and writing in Fountain markdown format)
  • DayOne for journals
  • Textastic for writing Python stuff

Contacts and Calendaring

There have been some exciting advances on the calendaring front recently. While I love Fantastical and use it for all of my meeting entries on both my Mac and my iPhone, Tempo has taken over the task of daily calendar viewing on the iPhone and I find myself interacting with it in meaningful ways throughout the day. Other than that, it's Fantastical all the way.

Email, Task Management and Reminders

On The Mac

  • Sparrow for general mail use (which is mostly Gmail)
  • Apple Mail for accounts that I don't want cluttering up my regular email
  • OmniFocus (duh!) for task management
  • Sticky Notifications for things I need to "post" onto my desktop
  • nvALT for list management, reference files and notes via text files stored on Dropbox.

On the iPhone/iPad

  • Mailbox is certainly something to celebrate. Finally something is better than Sparrow, which was incredible.
  • Mail.app for work email
  • OmniFocus for task management and reminders

Other Apps

On The Mac

  • 1Password for getting new passwords or sensitive information somewhere where it's safe and I don't need to remember it
  • Last.fm for getting songs I listen into a searchable format. Nerdy but interesting.
  • My paperless system for getting bills and other documents into a searchable, backed-up format. It has saved my bacon more than once already.
  • Droplr for getting pretty much anything to people on the web.
  • TextExpander helps me get text into my system in a consistent format which helps with the second part of this article -- finding things when you need them.

On the iPhone/iPad

Integration is Key

The best apps are ones that are integrated with your devices so seamlessley that they add the data you want to save transparently. For instance, if I had to log every song I listened to I would never bother. But Last.fm has a conduit (called a "scrobbler" -- worst name ever) that just reads what you're playing and sends the data to their site. It is integrated with apps like Rdio so no matter what device I listen on, the data is still saved.

I created a series of Pinboard bookmarks that quickly add links, but Pinbook can also make use of clever bookmarks on the iPhone so, again, the data gets into the system quickly and easily. Almost all of the "data consumption" apps I use have Pinboard support (Reeder, Twitterific, Riposte). Funneling all of that information to the same place reduces friction a lot.

Eventually you find that you are choosing apps because they integrate in ways that reduce friction too. Drafts (iOS) is one of those conduit-type apps, helpfully shuttling information into a variety of surprising places. The more apps you can harmoniously integrate into the process, the easier it will be to do the next part of the process.

Taking Things Out

What is the point of putting all of these things into places if you can't find them when you need them? Getting data or information back out of these systems, knowing where to look, and searching with the least amount of friction is a key to getting any system like this working.

There's nothing more frustrating that not being able to find a note you made a week ago. You look where you'd expect to find it but its not there. Confused, you start constructing alternate search strings, scanning your brain for other snippets of identifying text. Next you start looking through other apps, thinking of ways you could have confused yourself about mis-filing. Not finding what you need after a meandering search like this is demoralizing, especially if you spend so much time putting things where you expect to remember them.

Most of the things I put into my system are text-based. There are generally three places I have to look when I want to find something.

  • nvALT
  • Pinboard
  • Gmail

nvALT has changed the way I work. It required some shifts in how I thought about things like notes, plain text, file creation, cloud storage and such, but the benefit has been massive. All of the weekly notes I wrote in FoldingText are catalogued in the same folder as everything else on Dropbox. I can't count the number of times I have heard someone in a meeting mention something that didn't sound quite right so I just bring up nvALT, search on a keyword and find the meeting in question and refresh everyone's memory. It's extremely important for stressing accountability but also reminds people I'm not just checking Twitter behind the screen of my MacBook Air.

But it is that way for everything. nvALT and my Dropbox folder act as an outboard memory, a repository for scratch files containing ephemera to jog my memory, a place to archive my writing. It is the most useful workflow I've come across in years.

For web bookmarks and saving things to read later, Pinboard and Instapaper both serve their purpose. I put pretty much everything straight into Pinboard these days. I used to make a big distinction between articles to read later and just a bookmark I didn't want to forget but lately I just dump it all to Pinboard. Once or twice a day, I'll roll through Pinboard to tag bookmarks for later search and retrieval but I'll also star things (which will send them to Instapaper).

Pinboard is one of those things that accrued more use over time. I got it just to store a few bookmarks but it has become a hub of how I work and live on the web. I pay for the $25/year tier which also archives everything offline. I find it an incredibly useful service and I'm more than happy to pay given how much I use it and given how other bookmarking services are in the control of Google or a free service (and we all know how those turn out...).

Gmail is my other text-based archive. I am a long-time user and have email archived back to 2005 and beyond. It has been surprisingly useful to have the ability to pull those emails up at a moment's notice and it is one of the things that has made me most hesitant to leave Google behind (the subject of an upcoming post). I'm not about to throw the baby out with the bathwater yet. Soon, maybe...

I view my calendar in Tempo. It is an incredible consumer, data miner and presenter of calendar data. It also coalesces various sources of information to build a very complete view of each calendar event. Things like map locations, phone numbers, pertinent emails and documents (even attachments). When it works, it appears to be magic. Highly useful on the road as well.

Making use of the task items I put into my system is obviously going to involve OmniFocus. Having one place to look for that stuff, in the end, makes things easier and reduces a lot of friction. Apps like Checkmark and Drafts can conveniently hold some of that information for you but finding it again becomes an issue and this is all about "taking things out". Having more places to look just means more wasted effort. Reducing options and simplifying really helps here.

There are a few other little tools that extract meaning from the bits of data accumulated over time. Last.fm has an API which has spawned services that tweet your top three artists of the week or help visualize the vast oceans of data making up your shifts in musical tastes over the years.

We live in a time and place where we can accumulate, track, store and access our data from wherever we are. I love that it is all ubiquitous and electronic. I never have to scan for a pen and paper, or wonder which notebook I scribbled a nonsensical scrap of text into. Keeping things simple, accessible and organized with a minimal number of applications has taken a problem I have had all of my life and reduced it to something manageable and useful. I am so glad I no longer carry around a paper notebook and pen. It is surprisingly liberating.