OmniOutliner is an outlining app. Let me wait while you pick your jaw up off the floor. Yet if you're not shocked that this is what an app of that name does, I truly am astonished at how much this single piece of software has changed my work. How much it has changed me. For before I used this, I could've stood up on a soap box to argue against outlining.
Two years into using it, though, I think I finally understand why I was so much against outlining then and why, if my heart still prefers exploring instead of planning, my brain understands the benefits. More, my fingers do too: I've realized I will now unconsciously turn to OmniOutliner for many, many things beside conventional document planning.
The reason for the loathing, I now see, was Microsoft Word. Let me tell you a parallel example from back when Word was in DOS. I was required then to write in Word, and I was required to use its Styles feature. I don't know why this is true, but at the time I couldn't understand this Styles feature. It doesn't matter what the feature is, what's relevant now is that I could tell you what it did and I could tell you why you'd use it, but it's as if I didn't really comprehend it for myself.
Until for some reason I had to write a book in MacAuthor, a long-gone word processor which, if it's known now at all, is known for being what Douglas Adams wrote on sometimes. MacAuthor, if I'm remembering this correctly, also had this Styles feature, and what I do most definitely recall is the moment I understood it. So that's what Styles are. It was obvious when you know, and as I moved back to Word, I now understood and so could use Styles there too.
I just think now, a lot of years later, that there was something similar going on with outlining. Word has a feature-packed outlining section, and I didn't get it. I could tell you what it did and I could tell you why you'd use it, but it wasn't for me.
Until I became so addicted to
OmniFocus, a To Do app. You'd be surprised how common it is for people to get hooked on that, so much so that they then go off looking into what else the same developer makes. I honestly tried OmniOutliner, just because OmniFocus is so good. Also because you could download a trial version of the OS X app; I'm not crazy.
I think it's a 14-day trial, I'm not sure now because I didn't wait the whole period: I knew after using it for a short while that I would be keeping it, so I bought the app. Specifically, I bought version 3 for the Mac -- and never used it again.
For within an hour or two, certainly no more than a day or two, The Omni Group released a beta of OmniOutliner 4, and I tried it. I tried it thinking that I was a being a fool: if there were things in this new version that I liked, I was going to end up buying it. There was plenty that I liked, and when version 4 finally shipped, I was wiling to pay again -- but didn't have to. I got it for free for having bought OmniOutliner 3 so recently.
You can see why I'd like the company, and you've gathered that I like the software. It's harder to explain exactly why I like it so much, though: it is certainly easier to use than Word's clunky version, it is certainly well made with great features. More than the specific features, though, it is the OmniOutliner environment that I like. It is an enjoyable app to use. That is partly because I feel it doesn't get in your way, it doesn't require you to learn feature lists before you can do any actual work. It's just there, giving you what you need, when you realize you need it.
I did have one very specific early project that meant I tested OmniOutliner in anger. I was pitching to write on a particular TV show and while it didn't happen to work out, during the months-long process, I was asked to lob in some ideas. Of course I agreed: not only because anyone would, but because they were just ideas, I could rattle off a one-liner idea or two with ease. I think it ended up being about 20 ideas and that's fine, I'm using some of them in other projects now, but what was less fine was how they couldn't be one-line thoughts. I was required to deliver fully worked out stories and write, I think, about 1,200 words on each.
There was also a rush to do them, of course. Very quickly, I found I was opening OmniOutliner to jot down a single line of an idea. Then I'd look at it and think, well, that would work best with this character, so I'd write their name down. What needs to happen to put that character in this idea? Then if they get into this plot, what's the first thing they would do?
Very soon the one line would become about 15 lines, and as this is OmniOutliner, I could drag the lines around and experiment with their sequence. Soon I'd have what felt like the best order, the most dramatically satisfying order, and then I'd just write it all out again in 1,200 words of prose.
My heart tells me that this is not the way to write stories, at least not for me, but I wasn't really writing stories there, I was proposing them in detail. OmniOutliner helped me crank out these things very quickly and, okay, that project failed -- but three or four of the ideas are really good, and I'm off writing them for other people. Outlining and planning is a mechanical process, to my mind, but doing this in OmniOutliner made me create drama ideas I simply would not have thought of otherwise.
If that isn't story writing, it is at least what you'd traditionally expect an outlining app to be used for. Let me just check something, though. I'm counting. Okay, right this moment, I have exactly 100 OmniOutliner documents on my iPad. Many of them are drama ideas, a huge number are production plans: events, workshops, talks. All planned out in OmniOutliner. Plus, I know the 100 don't include the many that I create and throw away. It doesn't include the couple of times I slogged through a plan that was chaos incarnate at the start, and at the end was something I could paste directly into OmniFocus as a clear To Do list.
OmniOutliner works well with OmniFocus, and it plays nice with just about everything. While I'm more a text man than a visual one, I've recently enjoyed mind-mapping out a problem, because I know OmniOutliner will take that map and turn it into an outline.
OmniOutliner also plays very nice with ... OmniOutliner. I have this now on my Mac, iPad and iPhone with outlines automatically shared between them. It is routine now for me to finish up a workshop plan on my Mac, and then head out to the event knowing that plan is already on my iPad.
I like that very much, and you'd have to be wilfully awkward by now to pretend you aren't sure whether I'm keen on this app. There is just one thing: this could well be me, I hope it's just me, but I could not find a way to search for an outline on OmniOutliner for iOS. I have to scroll through those 100, with apparently only the option to list them by title or date.
I still wish there were a way to do it, or that you'd tell me what I'm missing, but this is the one criticism I have, and it is also one thing that has recently changed. As of now, you can search for OmniOutliner documents in iOS 9. Come out of OmniOutliner to the home screen on your iPad or iPhone, swipe to the side to begin a search, and type something you know is in an outline document somewhere. Apple's iOS 9 will find it.
That's obviously as much the work of The Omni Group as it is iOS 9, and while I'd rather search within the app itself because then I might remember it, the company is very hot on new Apple features. I was doing a Keynote presentation from my iPad when I accidentally swiped and brought up OmniOutliner in Slide Over. Frankly, I will never again bother with Keynote's presenter notes feature when I can just have my outline right there in front of me.
OmniOutliner is on the home screen of my iPhone and iPad, it's in my dock on my Mac, and I probably use it every day or at least every other day. I am shocked, actually shocked, how my ferocious anti-outline stance has changed. If you'd told me five years ago that I would now be using this software, well, I'd have got it then instead.
OmniFocus 4 for OS X costs $50 for a standard version, and $100 for a pro version that adds features I've personally not found a need for yet. While the software is on the Mac App Store,
get it direct from the The Omni Group instead. You get a trial version and better, easier deals on upgrades, like the one I had going from version 3 to 4. OmniFocus 2 for iOS is a universal app that
costs $30 for the standard version.
-- William Gallagher (
@WGallagher)
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