Outlining Like a Boss, Part II
Software and Tools for Outlining Effectively and Efficiently
The weather has not taken on the lamb-like qualities I had hoped it would over the last several days. It’s been very chilly and overcast and not at all conducive to righting my internal clock, which is off by one hour for some reason. Even the dogs adjusted to the time change faster than I did, this year, and that’s saying something.
I hope you enjoyed Tuesday’s article, because I have more of the same coming your way today. Earlier this week, I talked about strategies and techniques for getting thoughts out of your brain and into an outline format. Today, I will talk a bit about outlining tools and software that are available and some of the pros and cons of each, much as I recently talked through some mind mapping tools.
To refresh your memory on what I’m looking at when I evaluate software—or any tool, really—to help me in my writing, here are the most important criteria to me:
Available on every platform I use
Cloud-based storage to sync across platforms
Solid value proposition at the price point
More or better features than whatever I’m already using
Ease of taking my files with me when I leave
I’ll elaborate just briefly on each before I introduce you to a few of my favorite outlining tools and walk you through what makes each special.
I like to do writing tasks at my laptop, which is running Windows 10. That’s where I do most of my drafting, at least. But when it comes to outlining and other writing tasks, I am just as likely to be using my Android tablet or smartphone or even using a couple of those tools at once. And complicating the situation further, I want to be able to access my stuff from any laptop or tablet or phone—not just my own personal machine that has the application on it. So I’m always looking for tools that allow me to use them on mobile, with an app on my computer, and in a web browser if neither of the previous two are handy. (I know a lot of people use Apple products so I’m looking out for tools that are available for Android and iOS as well as Windows and MacOS).
I want any application I use to store my materials in the cloud and not on the hard disk of the device the app is on. This speaks directly to the above provision of being available on all that platforms I use—no matter what platform I am working on at any given moment, I want the most up-to-date version of my stuff available as soon as I click. If I close a file on my laptop and open it on my phone ten seconds later, I want to see a file that was saved 10 seconds ago. I can live with pushing a button to force a sync, but if the application stores files locally I’m just not going to bother with the program. I have left “emailing files to myself” behind along with “printing out mapquest directions.”
The price point for any software purchase or monthly subscription charge has to be right. Before I will even consider purchasing any software, I need to be able to try out all of the features I intend to use. I strongly prefer software that is indefinitely free to use with a limited feature set, with a premium version that enables the full feature set. I will generally not waste time trying out a tool that is free for a limited amount of time after which it becomes unavailable until I pay for it. The price point I think is reasonable for software depends on the type of software it is and how much I intend to use it. Since I’m always outlining things—both for writing and for other purposes—this is already a type of tool that I’d consider more worthwhile to pay for than, say, a mind mapping software.
But before I’m willing to pay anything at all, I have to satisfy myself that the tool works better than what I already have available to me. There’s no point in paying for software—or even taking the time and effort to learn a new software—if what you have is already serving your purpose well. For me to be willing to switch to something new, I either need to be satisfied that it has features I want to use that my current setup doesn’t have or I need to see that it integrates better with other tools I use. Otherwise, there’s no point.
Finally, the old Scrivener gotcha. I dislike Scrivener and I especially resent how difficult it is to port your files out of Scrivener if you reach a point where you no longer have the software available. I had to reinstall Scrivener one time to try and recover some materials that had been saved as its native file type and I think I ended up having to copy text out of a PDF and paste it somewhere. Whatever I’m using needs to be compatible with industry-standard file formats for me to be willing to use it. Saving and exporting my work as an easily portable file type is a must.
Those are the criteria I’m applying to the tools I’m looking at today.
I’ll start with Microsoft OneNote because it’s software that almost everybody has access to. If you have Windows it’s on your computer already, and if you use a Mac you can get it for free. It’s available for mobile platforms and offers a web interface. It saves all your materials in the cloud so you can access them anywhere you are by opening the app or logging into your Microsoft account in the web app.
OneNote is great for all kinds of things and it makes outlining really easy: You open a notebook (or make a new one), start a fresh page, and type the numeral 1 and then your top level idea. Hitting enter will take you to the next line and format your first line as a list item. If you keep going on that way you’ll get a list, but if you tab OneNote will automatically take you to the second level. You can go on adding levels in that fashion eight unique levels of label deep before the program starts again with the numeral “1” (indented eight times). You can easily make a new line indent further with tab or outdent a level with backspace. Fast and easy.
You can expand and collapse your outline at any level by mousing over the beginning of any line and double clicking the little gray arrow that appears, which is very helpful for getting a treetop view when you’re working with a big project that has many levels of depth. Helpfully, you can also grab any item and change it’s indent or outdent level and you can also expand your selection to indent or outdent all of its nested subitems relatively.
OneNote also lets your record audio and video directly into it and will take dictation (speech to text) if you prefer getting your ideas out that way and then organizing them in type. And if you like to use a mix of analog and digital notetaking, it has optical character recognition (OCR) support to import your handwritten notes.
On top of everything else, OneNote is a Microsoft product so it integrates seamlessly with the most common word processor out there (and can also export to PDF). OneNote’s big competitor in the notetaking arena is EverNote. For outlining specifically, though, EverNote doesn’t do nearly as well as OneNote. OneNote is basically the gold standard for me for outlining. It ticks all the boxes I said I was looking for and has some features you won’t find in your word processor (probably). So why bother looking at any other ones?
I’ll go ahead and give you a spoiler alert. OneNote is probably the best all-around package on the list and it’s totally free. However, there are a couple other products out there that perform comparably for outlining and have some outstanding features that you might find useful depending on your specific circumstances. If you need a little extra help with your outlining in one area or another, each of these is a standout in some special way.
My next favorite outlining software is Workflowy. This bad boy is purpose-built for outlining and really does that bit just as well as OneNote does, in my opinion. You can get it for Windows, Mac, Linux, iOS, and Android or use the web interface, and all versions sync up. It’s intuitive to use, with enter taking you to a fresh line and tab taking you to a deeper level of outline (backing up a level can be more challenging, depending on what platform you’re working on). The bullets collapse and expand with double clicks, and the software helpfully highlights (in light gray) any collapsed bullet with items nested underneath to quickly show you which ones can be expanded further. You can drag bullets around laterally or to higher or lower levels of the hierarchy.
What really makes Workflowy shine is its tagging function. You can tag any item with a #hashtag. For instance, if you have a character named Jane you could tag any item that relates to that character with #jane—for instance, you could use this to tag any scene in which Jane appears. You can then search for #jane in your Workflowy environment to see every single place you’ve tagged her, and in the search bar at the top of the app you will now see #jane as a potential search vector. You can develop a very deep tagging and indexing system that I personally have found very helpful for quickly navigating around information about a very complex project.
The only downside to Workflowy is that unlimited access is $4.99 a month. That price point feels reasonable to me, but it’s tough to beat “free.” My only issue with the free access version is the limit of 250 list items per month. This is ample except when I’m in the ideation phase of a complex story, during which time I have seen myself hit the 250-item limit in two hours or less. The good news is, if you hit that hard limit and you want to take your work someplace else, Workflowy makes it very easy for you to export plain or formatted text that you can simply paste elsewhere.
If Workflowy doesn’t tickle your fancy but you’re not already married to OneNote, there’s Cetacean to check out. Cetacean is a fully featured writing suite that you access through a website. While Cetacean doesn’t have desktop or mobile applications, you can access your work through the website on any device. After creating a project, you’ll have access to four views: brainstorming, outlining, writing, and revision. I have more to say about the suite as a whole in a coming article on writing software, but the outlining function has an interesting twist that I haven’t seen elsewhere.
The outlining tool in Cetacean has a handful of well-known story structures already built into it as templates, such as Joseph Campbell’s Hero’s Journey and Blake Snyder’s “Save the Cat” Beat Sheet. If you have the shape of your story in mind but you aren’t sure how to turn it into a plot, you can follow a preset template with prompts that correspond to these storytelling methods. (You can instead choose to start without a template and create a freeform outline, if you prefer not to work with any of the above.)
As you work, the outline tool also allows you to add characters and settings associated with each plot point from a drop-down menu populated by characters and locations you’ve added to the Cetacean project in the planning phase. If you’ve populated the character sketch tool with your cast, then you can attach them to each scene or plot point in the outlining tool to keep track of who has been where, and when.
Cetacean has a lot of the same functionality as Workflowy, but created with writers and storytellers in mind. It’s a nice writing suite with free limited use (you can only create one project with a free account), and if you decide you like it the monthly cost is the same as for Workflowy—$4.99 per month. If you’re interested in trying outlining a writing project but you’d like a little guidance through the process, Cetacean is a great free tool to check out.
I hope this week’s articles have brought together everything you need to get started outlining your next story (or series!) like an absolute pro. When I sit down to write, I know that I don’t need to outline every story in order to write it well. There’s a threshold of complexity that a story crosses, though, that has me thinking to myself, “If I don’t get this organized it’s going to intimidate its way to the bottom of my to-write list.” If you’ve ever had a story you want to tell but it just felt too big to get your mind around how and where to start, mind mapping and outlining together can get you to The End.
I’ve got a short list of fun topics I’m eyeballing for next week so I hope you will meet me back here on Tuesday to see what I’ve got in store for you. In the meantime, I hope you’re looking forward to a pleasant weekend ahead! Enjoy the rest of your Thursday!
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