Finally, the Perfect Outliner

Maybe because of the way I think, I have trouble working in a flat document to put down my creative ideas. They come in a haphazard fashion, and at the moment I'm not sure where they fit into the global structure I'm trying to create. In the past, most of my newsletters, sermon preparations, teaching plans have all taken place on a nice yellow legal pad. But no one else would be able to interpret the end result. There'd be whole paragraphs crossed out, lines drawn from one paragraph to insert in another place, and then on page 4 I would probably start from scratch and recopy everything over so even I could interpret it. But now my craving for legal pads has been left in the past.

At first, I tried numerous outlining programs that would allow me to drag and drop sections of the outline as my thinking got more formulated on the topic. But all of these systems have flaws that proved to be debilitating. My requirements were rather simple, or so I thought, but technology just wasn't cooperating. The ideal outlining system had to have the following:

  • The ability to drag-and-drop sections of the outline elsewhere on the page
  • Automatic numbering that would adapt when a new section was introduced
  • The ability to easily print the outline
  • Easily exportable text into Word or PDF formats
  • And the tough one: the ability to sync with my mobile device


I started out with PocketThinker which worked on my Windows Mobile PDA, but that software was eventually abandoned. One thing I really liked about it was that it used an open XML standard for outlines, OPML.

When Google documents came out--also having the ability to collaborate with multiple team members on a single document, I got my hopes up. You could do an outline in Google documents, and you could drag and drop. But if any of you have worked with numbered lists in a Google document you'll know that they are terrible! The numbering system gets messed up with even minor changes in the text and it is a nightmare to try to correct. We would have hoped that there was an intelligent XML beneath the surface but it looks like Google traded off for easy HTML coding.

At some point, I hit upon Microsoft OneNote. I think I got a free license for it with my Dell Axim PDA based on Windows mobile. But Windows mobile went away and good riddance. Its heavy reliance on the stylus with teeny tiny buttons and controls on the screen made it a very difficult operating system to navigate. I ended up just using Microsoft OneNote on my laptop. It worked great and had the most robust features of any outliner I had ever tried. You could drag and drop to your heart's content and the numbering or outline structure would never get confused. But then to major changes took place that revolutionized the technology.

First, Microsoft got smart and built-in android app that runs OneNote. I don't know if they have an iPhone app yet, but they most certainly have an app for the new Windows mobile phones. So now I was able to do my outline on my laptop, but then walk up to the podium with just my cell phone and be ready to roll.

Secondly, with the advent of, Microsoft added an online version of OneNote. If you think Google docs is cool, wait till you try out OneNote on Somehow, the web interface mirrors the functionality of the desktop program perfectly. You can create the outline in the desktop version, synchronize it with your free Microsoft account, and then send the link to anyone you wish who can collaborate with you on the outline. In fact, they can choose to work in their browser or to open the document in their version of OneNote. In any case, additions that they make are marked with their initials in my copy of the document.

Honestly, there is some amazing code under the surface that is able to manage the merging of two outlines when whole sections get rearranged. I haven't had a whole lot of experience with the collaboration part just yet, but the tests I've done so far are very promising.

From now on, I'll probably be developing all of my training materials in OneNote first, and when they are fairly complete it'll be time to move them to a wiki site.

I'm thankful to God for the day and age that I was born into.  So many exciting things that can help us build His Kingdom!