Braindump: Managing Documents

Braindump: Managing Documents

Happy Monday! Today I am thinking about my document management practices. It’s on my mind because I have quite a mixed list of writing assignments to tackle today, from strategic documents to training primers to process definitions. For some reason it’s really bothering me this morning that I don’t have one place where I keep everything, nor do I have a preferred writing application. So I think I’ll just think aloud here in this post, and see if some clarity comes to me.

My Writing Method

I write fairly conversationally, which means I write the way I talk. As I am writing this, the sentences are just appearing in my head and my fingers are automatically transcribing them at approximately 60-70 wpm. I can type faster than this if I am merely transcribing, but thinking as I go (with the occasional pause to ponder what I am going to type next, as I did in this parenthetical) is the way I write.

What I like about writing blog posts, at least the way I write them, is that I don’t have to cross reference any material…I just write. Generally I am just writing what I’m thinking, perhaps thinking ahead to some point I want to write about, but mostly just seeing where it goes. I started this blog post with an unexplored idea—the desire for better document management—and then arbitrarily picked the “method” as a starting point. This works out pretty well for a wide variety of the writing I do, which is thinking in words. The strategy document I need to write later will fit into this process, as will the process documentation.

After I’m done writing this blog post, I may review it in its entirety and see how I feel about it. Is it too wordy? Is there a point? Is there a topic that readers will readily grasp at the very beginning of the post so they can decide whether to read the entire post? Did I drop words as I transcribed my thoughts, or use the wrong plural form or switch tenses mid-way through a sentence? Did I wrote “seah” when I meant to write “sea”, or write “area” instead of “are”? These are the perils of writing on the fly; sometimes I zone out and something else flies out of my fingers than what I was thinking.

After I get a few sentences of writing done, I may have a better idea of where I’m going, so I’ll go back and rewrite/reorder sentences. I just inserted this sentence! This goes on until the entire article is written, chunk-wise. As I don’t enjoy reading my own writing, I have a tendency to just publish it to the site, though lately I’ve tried to force myself to take a break and come back to the words later.

There are a few major contexts in which I write, which I’ll review now.

Blog Writing

One of my preferred writing formats is Markdown, John Gruber’s main technical claim to fame beyond his sublime punditry on the state of technology. Markdown is a plain text markup language that looks like this:

Once upon a time there was a **bobcat** named Jonathan. Jonathan _loved_ being a bobcat, because:

* "Bobcat" is a cool word
* Why wouldn't he?

So there. 

In the parlance, Markdown is a “light markup language” that allows you to insert text formatting like bold and italics, bulleted lists, and other sundry text conventions using a very readable format. It certainly beats the hell out of using HTML:

<p>Once upon a time there was a <strong>bobcat</strong> named Jonathan. Jonathan <em>loved</em> being a bobcat, because:</p>
<li>"Bobcat" is a cool word</li><li>Why wouldn't he?</li>
<p>So there.</p>

My eyes are bleeding! These days, WordPress users have the option of using the “visual” editor, which works more like a word processor with point-and-click, or optional shortcuts like CTRL-B to BOLD and CTRL-I to ITALICIZE. But I really despise the visual editor because it often gets confused, inserting mysterious extra spaces and carriage returns that can’t be deleted. They are also more sluggish in response than pain text entry, and I am highly-attuned to speed of interactivity…if I feel a lag greater than 50milliseconds, I will start to get grouchy. When you are typing at the speed of thought, any perceived hitch in the think-write-read cycle feels awful.

Shared Documents

When I’m writing documentation or files that are for projects, the simplicity of Markdown-in-a-blog goes out the window. Markdown works well for blog posts because it’s automatically converted to HTML, but it’s a little more difficult to find a satisfying way to use it in a shared context. These are the ways I share my documents with other people:

  • Through Basecamp, which has very limited / awful text format control. The Writeboard / Text Document feature is where I store some writing. I use the file storage options only for deliverables, though some clients like to append stuff there.
  • Through Google Docs, which has a passable online word processor that stores documents in the Google Cloud. I have my own domain account for, which is easy enough, but it gets trickier when I am accessing other people’s documents in their domain accounts. It’s a pain in the butt.
  • Through Dropbox, which creates a special file folder on my computer that is automatically synched with all my other computers AND others who I am sharing with. It’s great. I use a number of different document types that are shared, which I’ll get to in a bit.
  • Through Google Drive Desktop, which is like Dropbox but also is linked to Google Docs in a somewhat confusing manner.
  • Through GitHub or BitBucket, version control repositories where I can track changes to documents and sets of documents. Mostly I use source control for managing programming projects, but there is often documentation included.
  • Through Email, which I try to avoid as much as possible. Docs that are sent through email get copied to my coded project folders.
  • Through Skype, when people send me documents for quick review. I almost always delete them after I’m done; if it’s really important, I’ll save it somewhere else.
  • In Scrivener, which I use for journaling and occasional blog post development. I’ve fallen out of the habit of using it because I don’t really like the word processor in it. It doesn’t feel very consistent in its font sizing, and its cross-platform formatting compatibility with the Windows version is not very good. I need to find a good cross-platform font solution and then fix styling so my documents look GOOD and format the same everywhere.

There are multiple kinds of document formats I deal with:

  • Plain Text. I often use text files for notes, and save them…somewhere? This is part of the problem.
  • Markdown Text. These are text files saved with the .md filename extension, which I can open with a text editor like Sublime Text or preview with a Markdown processor like Marked.
  • Google Word Processing and Spreadsheet documents. These are in Google Docs / Google Drive.
  • Microsoft Word and Excel documents. These are in DropBox, sometimes in Basecamp. I don’t really like using Word anymore, though I still like Excel.
  • InDesign documents. When I need to use a column or block-text format, InDesign is pretty handy even without adding fancy formatting. Sometimes I’ll also use Illustrator for this, if the amount of text is small. They are a pain to set up to get the formatting working well.
  • PDF. Mostly these are “final versions” intended for distribution, converted from one of the other formats. HTML is sometimes a format I will share, but only within the context of a web-based project.
  • Proprietary Online Formats. Basecamp has editable text documents. WordPress posts stored in the blog.

The Great Big Pain in the Ass

So there are a lot of different formats I’m using, stored in multiple places. It seems like I should be able to systemize this. Right now I am feeling paralyzed because I don’t have places to put the following project output for the day:

  • Mobile App HTML files, leftover work from GiveCamp
  • Beginning Web Strategy for an NPO, for coordination
  • Training Documentation for using Basecamp for non-technical users
  • Primer on using a CPA as an Independent Creative
  • A blog post (like this)
  • Marketing strategy for and related stuff

In my ideal system, I would have ONE PLACE where I would put these files. However, due to the different sharing requirements, I currently can’t do that. Here’s how it breaks down:

  • The HTML files will go into a Git repository that will be shared on Bitbucket, with the local repo either /dev/web or /users/dseah/desktop/hg on the laptop or D:/HG/ on the PC.
  • The web strategy and training docs are both for the same NPO, and I could store Word files (which they favor) in my Dropbox @Projects folder, or the organizations unused Google Drive account, or store it in my Google Drive account and share it with them. They’re also starting to use Basecamp, so that’s yet a third option.
  • The CPA primer is for my CPA, so he can understand the kinds of financial requirements a business like mine has and tune the next round of service toward that. I could create this in my Dropbox @DAVE-Projects folder, but the problem with that is I don’t often see those folders enough.
  • Blog posts generally go into WordPress as blog post drafts, though for my journaling I have used Scrivener. I’m not journaling very much these days, so I’ve just been writing in my WordPress admin section.
  • Marketing strategy probably will go in my @DAVE-Business folder, under Marketing or something.

So that’s a lot of places. Every time I switch to a project, I have to remember where it is, then click a whole bunch of times to find it either on (1) my computer or (2) the cloud. Then I need to open the file with the right application, which may not be the same on the Windows machines as it is on the Macintosh. It’s very tedious and it makes the start of a new task feel like a chore.

Pain Points to Address

I want ONE PLACE to go to find my in-progress files, but the solution has to be cross-platform. Likewise, I’d like to have ONE PLACE to share my files, but I don’t think that’s possible. I almost want an “documentation integrated design environment” that can gather all these disparate sources into once place, set it up once, then use that as a launch pad.

Ok, that’s enough brain dumping!

(decided not to proofread…gotta post and run to a meeting)


  1. C.L. 10 years ago

    Sounds like an app or a startup. We all need better no-think organization. What of using some sort of book-marking/tags combo to provide a TOC of sorts?

  2. Ron 10 years ago

    One thing that can help minimize the number of clicks you need to wade into your folder hierarchy is a good consistent file naming convention and a search program. I started using better file names a few months ago. I still use a folder hierarchy but I designed it to be as flat as possible. So I have a long list of favorite folders up front and only a few levels deep.

    I have one active projects folder with a subfolder for active projects. I store all project support material in that folder. The only exceptions are images that are stored in a reference library because I don’t want to break indesign links. Deliverables that are ready to share go into the appropriate dropbox folder, with a version stored in the project folder that is moved to an archival folder called work, organized by client.

    For example, if I were writing a marketing strategy document I would create a project folder. . When I was finished I would move the entire folder to my business/marketing folder. The active project folders are my project list in the gtd system. It is easy to access, easy to review and It is integrated into my work so I don’t have to create a separate list just for productivity sake.

    For continuity I keep a process journal. Two sentences at the end of the day about what I’m working on is easy to read the next day and helps get me back into the work flow.

    If you create a software solution, please make it cross platform.

  3. Vincent 10 years ago

    Ever try emacs + org-mode ? changed my life !

  4. Holly 10 years ago

    Hi David,

    It sounds like someone needs to come up with a version of Scrivener that is made for coders. Good luck finding it, and let us know what you come up with.

    In the meantime, you could always use Ifttt to send things to Gmail and from there to Google Drive, Box or Dropbox. I didn’t see any recipes going to Amazon AWS but that would also be a good place to put everything.

    Good luck and let us know if you find a solution!

  5. Andrew Steele 10 years ago

    You might be intrigued by Jolidrive has hooks into several of the services you mention above, including Google Drive, Dropbox, etc.

    Still no bitbucket or github integration, but like Holly suggested, IFTTT can help shore up some of those holes too. ;)

    If you can’t have one app for everything you need to do, why not one app that ties all the others together? ;)