Tech Life Why are we making this harder?

Everything Goes in a Context Bucket

The easiest way to improve your information consumption practices is to watch someone you trust to do their work. I get glimpses every day. At the beginning of meetings during the traditional inane five minutes of wondering why the AV never works, I eagerly await your shared screen on the room’s monitor see how you work.

Apoplectic adequately describes my reaction when I see one or both of the following situations on the screen: a desktop cluttered with unorganized icons and/or a browser with forever tabs. My concern: how much of your day is spent finding things?

Your Random Pile of Important Junk

I’d like to introduce you to your future desktop1:

If your reaction to this blissfully blank canvas is anything but delight, I have questions. If your desktop is a lovely clutter of things, I have more questions. Let’s start with: “What are you using your desktop for?”

I drop stuff there.

What stuff?

Stuff I’m working on.

All the stuff?

No, stuff I’m currently working on.

Right so, the most important work of the day got thrown into a random pile of junk?

Rands. Just. Chill. Ok?

Ok, I’ll chill. I get it. It’s just before lunch, you’re at peak coffee and jamming on a document during a meeting, you’re capturing deep thoughts, and now it’s time to get to the next meeting, so you quickly save your document to the place of least resistance. The place is sitting right in front of you. The visually obvious place. Your desktop. It’s sitting right there. Now is not the time for best of breed organizational strategies, now is the time to capture the thoughts whilst getting to the next meeting as quickly as possible. The same strategy works for your endless parade of tabs in your web browser. You’re not done with whatever reason triggered this web page, so you leave it open Along with the next tab. And the next. Aaaaand the next.

This is not the problem. The problem occurs at 5:23p when you have free time to sort through your day’s thoughts and think, “Oh, that document… … I need it now.” 37 second later, you’ve cleared up the four web browsers cluttering your desktop, mentally scanned your desktop, and finally found the document.

Again, how much time are you spending finding things?

Everything Goes In a Context Bucket

Whenever I perform a save or equivalent preservation action, I stop and spend a second determining the context that needs to be associated with this artifact. Every single artifact has a bit of context. Examples:

  • A web page with a useful thing that I think need to read at some point. This is saved to the “Scrub” browser folder. This folder is scanned and purged regularly. This is the only folder that gets random web content.
  • An in-progress Keynote goes in the Presentation folder in Dropbox.
  • An in-progress article is a new page inside of Bear. I used to save the TextEdit articles in an “In Progress” folder in Dropbox, but as we’ll see in a moment, Bear both removes a saving step while automatically providing context.2

The point. Later when I need to find a thing I’ve forgotten, I don’t need to remember the thing, I remember the context. Over the years, the tools I use on my desktop are designed for lightning fast context selection.3

The Desktop Toolset4

  • Whenever you need another window, never ever ever use the mouse. Use Cmd-Tab. Attempt to figure out the algorithm they use to sort the Cmd-Tab application list. Scratch your head. Move on. It’s not worth it.
  • Purchase and install LaunchBar5. Ignore the plethora of configuration knobs and dials and realize that LaunchBar out of the box will greatly accelerate your finding of the things by using the keyboard to jump straight to the proper context. CTRL-SPACE-Ch == Google Chrome. CTRL-SPACE-Dro- == my Dropbox folders. CTRL-SPACE-Wi- == every Wikipedia article ever.
  • Purchase and install the window manager SizeUp. I rarely see my desktop because I’m constantly expanding windows to fill as much visual real estate as possible. Right now, my iMac monitor screen is right-half Chrome (four pinned tabs, one tab open with the prior article for handy reference) and left-half is Bear. With these applications loaded, getting to this efficient layout was simple. Select Chrome via LaunchBar and CTRL-OPT-COMMAND-LEFT ARROW to move Chrome and fill the left half the screen. Select Bear, CTRL-OPT-COMMAND-RIGHT ARROW and we’re done. Done with a window? CMD-H and it’s hidden. Oh hey, there’s my pristine and clean desktop.
  • Finally, purchase and install Bear. As I wrote about in How to Write a Book, I need my primary writing application to write beautifully. No fuss. Very little options. Strong typography. Simple multi-document navigation Bear is my scratch pad, my temporary task list, and chosen tool for all writing. It automagically saves to iCloud, and the mobile app is equally lovely and usable which means every single one of my scribbles follows me everywhere.

A win condition: Any artifact you regularly need is three to five seconds away via the keyboard.

Honor Sharon

I like to watch how humans surf their computers because there is always more to learn. See, for every single piece of software, there is Sharon and Sharon’s job is to design the software to make your life easier. This is Sharon’s only job, and she’s stunningly qualified. She sweats the details, she puts herself in your shoes and tries to think how you think and how you work, and she speaks up in the meetings six times a week to say, “Why are we making this harder for our users?”

When an operating system or application misbehaves or straight up crashes, you have every right to be angry. The developers of some piece software or hardware failed. When you’re using an operating system or application and find it unintuitive or otherwise inefficient, you can get angry, or you can honor Sharon.

Sharon is looking out for you. She is working hard for you. Sharon designed the software in a way to make you efficient, but there is work on your part to find Sharon’s hard work. Yes, I want my software to read my mind, but it doesn’t yet, so I when I find a piece of software working against me, I remember Sharon. I examine each menu item. I carefully walk through preferences. I search online for other’s who have captured and documented Sharon’s hard work.

How you work is a small collection of readily available actions. You readily call on these actions without thinking hundreds of times a day. Some of those actions are your clever concoctions, but others are the unending hard work of Sharon. Whether you want to each working minute count or not, she’s looking out for you.


  1. Same disclaimer as the prior piece. One or more of these suggestions will give you rage. We’re cool. Just trying to help. 
  2. If an article needs editing by another human, it will land in Google documents in a conveniently named “Editing” browser folder. 
  3. As also mentioned in the prior piece in a footnote, channels in Slack are great context. It’s one of the reasons I’ve dumped all productivity tools since going all-in on Slack. 
  4. Unlike the prior articles, I will not offer non-Apple application equivalents. I’m certain they exist. Maybe you should write that article? 
  5. I’ve tried Spotlight search multiple times over the years. It’s fine. 

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2 Responses

  1. Xianhang Zhang 2 weeks ago

    Ah yes, the eternal messy person/tidy person debate in which the tidy person endlessly scolds the messy person. Messy people just have a different way of organizing information in their brain, it’s not arbitrary, it’s not inefficient, it’s not poorly thought out. It’s the system that works for them and if you bother actually delving in and learning about each messy person’s system, its as sophisticated and thought out as any average tidy person’s system.

    Next, will you write an article about how night owls are just lazy and if they only woke up earlier, they would be a bajillion times more productive?

  2. Alex Broquet 2 weeks ago

    “If it is a human thing to do to put something you want, because it’s useful, edible, or beautiful, into a bag, or a basket, or a bit of rolled bark or leaf, or a net woven of your own hair, or what have you, and then take it home with you, home being another, larger kind of pouch or bag, a container for people, and then later on you take it out and eat it or share it or store it up for winter in a solider container or put it in the medicine bundle or the shrine or the museum, the holy place, the area that contains what is sacred, and then the next day you probably do much the same again—if to do that is human, if that’s what it takes, then I am a human being after all. Fully, freely, gladly, for the first time….” – The Carrier Bag Theory of Fiction by Ursula K. Le Guin