I use Dropbox as the nerve center for all of my digital goods, keeping data, configurations, histories, log files, and anything else I need access to centralized and available from my Mac or iOS devices.

Here are a few of my daily tools or information trails I want to keep synced up, so anything here can be a few clicks or a search away:

• Instant message chat history
• iTunes library
• Histories + log files
• OmniFocus backups

Chat Archiving

I use Messages on the desktop for all chat conversations with my Jabber and Google accounts. I access the transcript history daily to find things I told people in chat conversations, look up links I sent, and other things. So much of my communication happens via instant messaging that I rely on it to keep logs of interactions (albeit securely).

Backing up chat transcripts is simple with symlinks. For me, I want all chat logs to be archived into a Dropbox directory continuously, so I don’t have to remember to back them up. Messages stores its transcript files here:

~/Library/Messages/Archive/

Since I want my chats to all be instantly backed up to Dropbox, I symlink the directory into a ~/Dropbox/backups directory, like this:

ln -s ~/Library/Messages/Archive ~/Dropbox/backups/chats/

Linking those files to a Dropbox directory will automatically sync them to your account in real time, if you have syncing enabled. These files are then backed up for good, in case I need to search later. A downside with Messages is the transcript files are .ichat files, not plain text. So they can’t be searched from the Dropbox iOS app or mobile text readers. The in-app search works okay, but hopefully we’ll see some performance improvement there in the upcoming OS X Mavericks release. This piece from Glen Fleishman has some other good tips on instant messaging with Messages.

iTunes

My iTunes media is mostly secure at this point, with iTunes Match and iCloud, but I still like to keep a backup of the raw XML library data. This contains a ton of stuff I don’t want to lose, like playlists, ratings, and other metadata. ID3 tags and album art are safe with the MP3 files. A couple of symlinks make it so every time I close iTunes, the latest changes to my library get backed up. The .itl file is the primary iTunes database, and the XML file adds a software compatibility layer for other apps that read from your library (like Garage Band and others):

ln -s ~/Music/iTunes/iTunes\ Library.itl \
  ~/Dropbox/backups/iTunes/iTunes\ Library.itl

ln -s ~/Music/iTunes/iTunes\ Music\ Library.xml \
  ~/Dropbox/backups/iTunes/iTunes\ Music\ Library.xml

History + Logs

On a daily basis, I’m all over the place with my machine — working with data in Postgres or SQLite, writing Ruby scripts, and just generally working on the shell doing tons of different things. I love having my command history for anything that has a CLI archived somewhere, so when I need to pull up some command or see how I had built a package from source, it’s as simple as searching a history file. Many Linux & Mac applications keep themselves a history file inside your home directory, typically hidden, like .bash_history for the bash shell environment. I use zsh, with the awesome oh-my-zsh environment framework, highly recommended. Here’s a few I keep around for posterity and convenience, in a “histories” backup¹ directory:

• ~/.zsh_history
• ~/.irb-history
• ~/.psql_history

With those backed up, I can always search the logs for when I installed something with Homebrew:

history | grep "brew install mapnik"

As for OmniFocus, backups are cake. Just check the preferences for the database backup location and frequency settings, and change it to somewhere within your Dropbox folder.

In addition to the convenience of keeping this stuff linked into a secure, synced place like Dropbox, using an online backup service (like the fantastic Backblaze) is a no-brainer for keeping your stuff safe. You should be using one. Even though Time Machine is super simple to get going to an external HDD, I don’t trust the hardware enough to rely solely on that.

Through a number of recommendations around the web, I’ve started using Drafts, an iOS app with an interesting workflow model that’s helping me replace a number of input channels for capturing different pieces of information while on-the-go.

It’s positioned primarily as a text editor or note-taking app for iOS, but it introduces a fundamentally different approach to the capture → process flow than most other solutions I’ve tried, even ones that I like. Like most heavy mobile users, I have a suite of apps I use constantly to capture different inputs: OmniFocus for task management, Mail for email, Byword for notes and Markdown content, Fantastical for calendar items, and others. I love each of these apps for what they do, but speed is paramount for capture to be truly ubiquitous, at least for me. And I sometimes find myself swiping around looking for the right app to put something.

The way Drafts handles input is novel because it puts the content first, and the action second. You can jot something down, then decide how to process it. Sometimes it’s a to-do, sometimes a draft of an email, and sometimes just a quick note. I love the idea of starting with a bit of text, then picking the chute down which to send it in step two. Open the app and its ready for some text; no need to add titles to text files, create a new document, or any other hurdle, just start typing. It’s my new method for throwing things in the OmniFocus inbox¹.

Depending on the exact wording of the quick note, it could end up as a to-do in my OF inbox:

• Set up phone call with John → Add to OmniFocus

Then later become an appointment for the calendar:

• Conference call with John 4/16 at 2pm → Parse in Fantastical²

One of my favorite features is the ability to write emails in Markdown. For quick replies I still use Mail (and most replies are quick from my iPhone, anyway), but for longer-form messages, I’ll open Drafts where I can include inline links and formatting using Markdown, then use the “Markdown: Email” feature to convert it and send as HTML email.

There are tons of actions supported for processing your input once you’ve entered it — Sending the text to email, Reminders, Messages, clipboard, printing, Dropbox — as well as the third-party app support. Things get really geeky once you dig into the customizable URL and Email actions.

This app is changing how I capture information from my iPhone, helping me strike a better balance between ubiquity of capture and the all-important correctness of processing. Highly recommended.

I’ve gotten interested recently in how people and businesses communicate ideas, in the contexts of work, project management, product marketing, education, et cetera. Late in 2012 I read a book called Made To Stick, a study on what constitutes sticky, viral ideas. While the book is about the communication of ideas in a marketing context, it struck a nerve and got me thinking about how we communicate in general, whether as individuals or companies.

The book postulates that “sticky” ideas have six core properties: they’re simple, unexpected, concrete, credible, emotional, and they tell a story. There are dozens of great examples of ideas that have lasted for decades or centuries, things like urban legends, proverbs, and countless meme-like advertising campaigns. The book makes a very compelling case, replete with examples to demonstrate the point. But what I’m interested in more than viral nature of ideas is what makes some interpersonal communication so effective, and some so ineffective. Much of theory in the book is relevant to everyday communication, too, not just marketing. I think bad communicators struggle mostly with clarity and simplicity.

I recently watched a talk given by Supreme Court Justice Clarence Thomas at Harvard, and he nails what it means to communicate clearly, in his case when publishing opinions of the court (around 58:30).

The entire talk is fascinating, but this part stands out — on editing for clarity:

“The genius is not to write a five cent idea in a ten dollar sentence, it’s to put a ten dollar idea into a five cent sentence. That’s beauty, that’s editing, that’s writing. The editing we do is for clarity and simplicity, without losing meaning and content. And without adding things. You don’t see a lot of double entendres, you don’t see wordplays or cuteness in the opinions. We’re not there to win a literary award, we’re there to write opinions that some busy person, or someone at their kitchen table can read and say ‘I don’t agree with a word he said, but I understand what he said.’”

Care and attention like this is missing from a lot of communication. It’s sometimes difficult to understand who the audience is for a piece of information — employee, customer, boss, citizen, spouse — and to tailor the message so that it connects with them in a way that’s comprehensible. If the message we want to convey is important enough that we want it to sink in (when is it not?), it takes more care and mindfulness to hone it to its fundamentals.

One of the stories in Made to Stick involves the idea of the “Curse of Knowledge” as a contributor to these common disconnects between communicator and audience — meaning the conveyor of information (whether it’s your boss, your client, or the Supreme Court) holds a body of knowledge about a subject that the recipient does not. Think of times when company leaders talk about bottom lines, synergies, or corporate strategy — terms with completely ambiguous meanings to a regular employee. If we remove the layers of abstraction and insert common everyday language, it might not sound as pretty, but people certainly get the point.

Take the book’s example of JFK’s 1961 address to congress in which he made his famous call to put a man on the moon:

“But why, some say, the moon? Why choose this as our goal? And they may well ask why climb the highest mountain? … We choose to go to the moon in this decade and do the other things, not because they are easy, but because they are hard.”

Few words, but tons of concreteness. There’s no confusion about his intent, “we’re going to the moon, and here’s the deadline”. The author provides a contrasting example of how an American big business CEO would probably put it:

“Our mission is to become the international leader in the space industry through maximum team-centered innovation and strategically targeted aerospace initiatives.”

That’s absolutely something you would see on a Fortune 500 company website. There’s far too much of this abstractness in the working environment today, and I think it hurts young people coming into the workforce. It creates poor writing and lures people into wordsmithing only to maximize the buzzword count.

A quality I admire most in people is an ability to be articulate, to clearly express a point or intent in few words, and to get to the point quickly. It’s frustrating to have someone tell you something, or ask a question, to then find out they haven’t thought through the point. The burden is then on the audience to figure out the intent, and then to respond. The notion of Commander’s Intent can be helpful in understanding the value of clarity and articulation. In order for the listener to take your information and respond appropriately, goals, purpose, and a clear picture of what the successful “end state” looks like are critical to clear understanding.

I highly recommend Made to Stick to anyone interested in improving messaging, particularly in the context of products or business. It certainly helped me to get outside of my own head and think about copywriting and messaging around products with a more objective viewpoint.

If you enjoy hearing stories from visionaries, listen to this talk that Gabe Newell (founder of Valve) gave at UT Austin:

“It seems fairly obvious that the Internet does a better job of organizing a bunch of individuals than General Motors or Sears does. Corporations [with hierarchies] tend to be pre-internet ways of organizing production.”

In it he discusses economies within Steam, where Steam is headed as a central core of APIs for game publishing, and a good bit about how the company operates.

I relish the opportunity to hear stories about really smart people doing work and making things. Gabe definitely fits into that category: He left Microsoft in their crazy lucrative years during the mid-90s to found a video game company with his own money, with a flat structure, and no job titles that now generates hundreds of millions in revenue.

For the last month or so, I’ve been readopting the GTD methodology for organizing my work, personal and business. I read David Allen’s book back in 2007, and attempted to adopt the workflow. This was before having any sort of smart device, so workflow systems were much different back then. My system when I initially jumped in involved pens and pads, inboxes, folders — most of the recommended elements from the book. I didn’t last long, and since then I’ve only dabbled around really getting back into it. Merlin Mann and Dan Benjamin’s recent podcast series on the subject spurred me back into giving it another serious go.

Without getting into the weeds of the system, I’ve always seen three pillars to GTD that are critical to reaping benefit:

• Ubiquitous capture
• Breaking down your work into discrete, actionable tasks (processing)
• Weekly review of projects and actions

There are more elements to the total system, but these are the core functional components of GTD that I’ve adopted, eschewing the parts about the 43 folders and some of the other fiddly things like labelmakers and lettered reference file cabinets. I think a contributor to my initial dropoff with the system was not appreciating that you can adopt only some elements of the total system, as long as you’re closing all the loops.

Here’s a snapshot of how I’m reintegrating GTD into my daily flow:

Capture

I’m a heavy user of OmniFocus for everything task-related. The notion of “ubiquitous capture” is the first step to getting the thoughts, ideas, and tasks out of your brain and into the flow. For me, ubiquity means it needs to enter the river of material to be processed either through my Mac or my iPhone, one of which I’ll have at fingertips at all times. I love the tangibility of pen and paper, but I’m not trustworthy enough to have that at all times. There are OmniFocus versions for Mac and iOS, so that gets that piece out of the way. Plus they stay in sync over the air. If something you need to do something about enters your mind, there needs to be a frictionless way for it to enter the pipeline.

Processing

This is probably what I struggle with the most. This is where the majority of the thinking comes into play; What project is this action part of? Should I just do it right now? How many smaller actions does it need to be broken into?

Effective processing requires regular attention. If you just load up the inbox for weeks on end without sorting through each item and determining the next action (which could be deleting it), you end up working through tasks right out of the inbox. I can sort through the cruft in my inbox with vigilance — e.g. “finger on the delete button” — but where I tend to fall off the wagon is with keeping the processing frequent enough not to get behind. I’ll find myself after a few consecutive hectic days cherry-picking actions to tackle right in the inbox, instead of hitting things from a higher level based on project importance or context. This can lead to wheel-spinning and procrastination, and put you right back to thrashing around with all that data in your head.

This time around, I’m putting more energy into the processing steps. Failure there is a large part of why I fell out with GTD some time back.

Reviewing

The weekly review is processing’s older brother, meant to walk you through each of the projects on your plate, reorganize them, enter any missing actions, and just generally get a “control tower” snapshot of all the runways in front of you. OmniFocus has an awesome “review” mode designed to handhold you through looking at each and every project in your OmniFocus database one by one. With a full force inbox dump, plus effective processing, it’s insane how many projects end up in the system. A good, regular review is a healthy way to clear the decks and make way for the projects that you’re actually going to do. This is another area I’ve struggled with in the past, it’s one of the last steps in truly closing loops and making sure your task database isn’t filled with garbage to fight with.

The unspoken “fourth pillar” in all of this is, naturally, doing. Inboxes, apps, text files, and folders aren’t going to actually accomplish those next actions for you. Many blog posts out there neglect to mention this most-critical piece of the flow (it seems obvious, right?), but it’s important. Making sure that the actions are as mindlessly straightforward as possible in the processing phase is critical to making the actions so easy, you hardly have to think while you’re cranking. GTD mostly serves as a method to create order from chaos. My personal objective is to get comfortable enough to make the system second-nature. I don’t want to think while I’m doing, at least not very much.

Related links:

• David Allen’s talk at Google, 2007
• Getting started with GTD

I wrote a blog post last week about the first few months of usage of Pushpin, the mobile app we built for editing OpenStreetMap data.

As I mentioned in the post, I’m fascinated and excited by how many brand new OpenStreetMap users we’re creating, and how many who never edited before are taking an interest in making contributions. This has been an historic problem for the OpenStreetMap project for years now: How do you convince a casually-interested person to invest the time to learn how to contribute themselves?

3 months of OSM edits with Pushpin

There are two primary hurdles I’ve always seen with why “interested users” don’t make contributions; one technical, and one more philosophical:

1. Editing map data is somewhat complicated, and the documentation and tools don’t help many users to climb over this hump.
2. It’s hard to answer the question: “Why should I edit this map? What am I editing, and who benefits from the information?”

To the first point, this is an issue largely of time and effort on the part of the volunteer-led developer community behind OpenStreetMap. GIS data is fundamentally complex, much moreso than Wikipedia’s content, the primary analog to which OpenStreetMap is often compared — “Wikipedia for maps”. It’s an apt comparison only on a conceptual level, but when it comes time to build an editor for the information within each system, the demands of OpenStreetMap data take the complexity to another level. As I said, the community is constantly chewing this issue, and making amazing progress on a new web-based editor. In building Pushpin, we spent a long time making sure that the user didn’t need to know anything about the complex OpenStreetMap tagging system in order to make edits. We picked apart the wiki and taginfo to abstract the common tags into simple picklists, which prevents both the need to type lots of info, and the need to know that amenity=place_of_worship is the proper tag for a church or mosque.

As for answering the “why”, that’s a little more complicated. People contribute to community projects for a host of reasons, so it’s a challenge to nail down how this should be communicated about OSM. There are stray bits around that tell the story pretty succinctly, but the problem lies in centralizing that core message. The LearnOSM site does a good job of explaining to a non-expert what the benefits are of becoming part of the contributor community, but it feels like the story needs to be told somewhere closer to the main homepage. Alex Barth recently proposed an excellent idea to the OpenStreetMap mailing list, a “contributors mark” that can be used within OSM-based services to convey the value of free and open map data. This is an excellent idea, with a nice presentation, that addresses a couple of needs. For one it communicates what the project actually is, rather than just sending the unsuspecting user to a page about ODbL, and it also gives a general sense of how the data is used by real people.

In order for those one million user accounts to turn into one million contributors, we need to do a better job at conveying the meaning of the project and the value it provides to OpenStreetMap’s thousands of data consumers.

We’re headed to Weeki Wachee this weekend to do some scalloping, kayaking, and diving. We’ll be hanging out up at the springs and (hopefully) catching our limit in bay scallops out on the sea grass. On Sunday I was up in Dunedin helping my dad get the engine ready to put back in his boat. He’s got a Shamrock, and has been putting together a new Chevy 350 to install before we head up for the weekend. There was a little fiberglass work that needed doing on the center console, too, to shore it up from water damage.

I’ve built several apps in Fulcrum for capturing different sorts of data while we’re out and about: for bird sighting locations, one for marking scalloping spots, and another for aids to navigation and other marine features for eventual contribution as OpenSeaMap features — and I also built a catchall for capturing “geonotes”, blobs of text with a photo for some general comment. Can’t wait to do some real field collection.

I pulled down some DOQQs from Florida’s LABINS site, built some nice high-resolution offline maps with TileMill, and downloaded them to my phone in Fulcrum. There are tons of creeks and canals running through the wetlands near the mouth of the Weeki Wachee River, and I’ll be able to catalog which ones are navigable by kayak at high or low tide.

Graham Hawkes has a fascinating approach to undersea research and exploration. Rather than focusing on deep ocean submersibles (which he’s built plenty of), his company is currently building underwater airplanes, craft that fly through the water with hydrodynamic wings and thrusters, capable of flying alongside dolphins and manta rays. Hawkes is obsessed with the ocean, and is fond of saying to space explorers that their “rockets are pointing in the wrong direction”. It’s amazing how little is known about the ocean floor, and how relatively little funding we roll into hydro-exploration.

The R&D work Hawkes is doing is amazing, focusing more effort on underwater flight than deep ocean dives. While they have built craft for the purpose of superdeep dives, that doesn’t seem to be Hawkes’ passion. They’ve designed and built several craft to study hydrodynamics, provide research platforms for scientists, and modes of transportation for recreation or studying the seafloor. The Merlin and the Challenger are two vessels funded by Richard Branson, under the moniker Virgin Oceanic.

I found myself obsessed with Hawkes and his work, and spent Sunday morning trolling the internet reading interviews and backstories, and watching videos of his projects. The notion of underwater flight is fascinating to me, and makes me wonder why the technology hasn’t caught on and become a popular attraction for divers in the tropics, to allow divers to fly through reefs and wrecks. I imagine flying over the Great Barrier reef for hundreds of miles sightseeing, stopping along the way for closer looks. Or diving to depth between the Cayman Islands, soaring over the bottom with sea turtles and schools of fish.

His company is running a Kickstarter campaign to fund a field test expedition to Lake Tahoe with his two-seater, Super Falcon, to perform “hydrobatic” maneuvers in the deep parts of the lake. If you’re as interested as I am in this stuff, here are some other links to check out:

• Run Silent, Run Sleek, Popular Mechanics.
• Race to the Bottom of the Sea, Men’s Journal.
• Just Don’t Call it a Submarine, Outside Magazine.
• Graham Hawkes flies through the ocean, TED Talks.

(In my browsing yesterday, I also read about the Aquarius Reef Base, an undersea research station operated by NOAA since the 1980s. It sits on the bed of Conch Reef off the coast of Key Largo. The project is in danger of being shuttered soon, so they’ve launched a funding campaign to try and save the project.)

Jeff Lawson of Twilio gave this talk on SaaS pricing at the Business of Software conference last year:

Everyone in the SaaS product business should watch this. Great approach to thinking through putting prices on your SaaS service. What’s always been difficult for me in doing pricing analysis (which I think is fairly common for people with technical backgrounds, who aren’t business people).

It’s key to understand all the facets of your product, and what things cost you as the creator, in addition to slicing and dicing options for your customers to buy what they need. Facets like:

• Quantities (How many gigabytes? What kind of bandwidth is allowed?)
• Features (Can I do push notifications and alerts? What about management dashboards?)
• Support (24 x 7 phone support?)

These things on their own are even sometimes difficult to figure out — what are all the variables you can tweak and change about your offerings? And those are thing that you can control, properties of your own product. I still maintain that the hardest part, bar none, of building pricing models (though it seems obvious) is understanding what your potential customers are willing to pay for your service, and then making sure you can serve them a product cheaper than that.

Bruce Sterling on storytelling and the art of computer game design, from GDC 1991:

I don’t think you can last by meeting the contemporary public taste, the taste from the last quarterly report. I don’t think you can last by following demographics and carefully meeting expectations. I don’t know many works of art that last that are condescending. I don’t know many works of art that last that are deliberately stupid. You may be a geek, you may have geek written all over you; you should aim to be one geek they’ll never forget. Don’t aim to be civilized. Don’t hope that straight people will keep you on as some kind of pet. To hell with them; they put you here. You should fully realize what society has made of you and take a terrible revenge. Get weird. Get way weird. Get dangerously weird. Get sophisticatedly, thoroughly weird and don’t do it halfway, put every ounce of horsepower you have behind it.

Don’t stick to tradition, and don’t go halfway.

I Instapaper’d this over a year ago and ran across it while reading some old stuff.