Generating Ideas, Plans, and First Drafts

Getting started with a larger writing task can often feel like trying to climb a mountain in one step. Luckily, there are a long list of activities one can try that help make the process feel more manageable.

General Overview

You may have already dismissed activities like mind mapping and outlining as inefficient–why bother with extra tasks when you can just get started writing? For some writing tasks, this instinct makes sense. When writing an email to a friend, it would seem silly to brainstorm a bunch of ideas first. You probably know exactly what you want to say when you open up the email app. However, if you’re writing a longer essay or research paper, it’s likely that you don’t know what you want to say in every part yet. Maybe an idea for the next paragraph will come to you when you reach the end of the one you’re writing, but maybe it won’t. Or maybe a better idea for the middle section of the paper will come to you after you’ve written the whole paper, and it will seem like too much work to change things around to add it in. If doing a little planning now could be made easy, and make things easier down the line, maybe that makes sense too.

This guide is based on the idea that most of the work of planning is done while you’re doing other things–walking around, eating a meal, talking with friends. Every so often you take out your mind map or your notebook of ideas and add a few things that just popped into your head. If you use an app on your smartphone, you can do this wherever you carry it–in line at the cafeteria, walking to class, on the bus. By creating a planning document you tell a part of your mind to get to work coming up with ideas and then you can just go about your day while it keeps churning things out. The more you can capture these throughout the day into your notes, the more ideas your mind will serve up.

Often, these ideas don’t come to mind in any particular order and they might not always even be relevant. That’s why it can be more efficient to use a mind map or outlining app rather than just a notes app where you can type. Mind map and outlining apps make it easy to move ideas around in chunks, so you can quickly reorder topic ideas or add some structure, making one idea a main category and another an example that fits into that category.

Once you get some practice with this kind of activity, you may be surprised at how straightforward the next parts of writing can feel. Sure, you could sweat it out from scratch the night before the deadline while staring at the assignment sheet in your dorm, but it might feel better to be rearranging 10 or 20 idea chunks you wrote down over the course of a few days earlier in the week. You might feel more confident knowing that you’re not going to run out of ideas because there’s already a plan, even if it is a loose one. You might even feel impressed looking at the ideas your past self made and improved over the planning period.

Capturing Ideas Everywhere

The key aspect to the kind of planning activity discussed in the previous section is being able to write down ideas frequently. One version of this might be to get a dedicated app for ideas on your phone or a small notebook and pen that you can carry around in your pocket. If that’s not appealing at this point, you might also try just sitting down with a mind map or outline for five minutes 2 or 3 times a day for several days. Again, if you write down these ideas more frequently, then the part of your mind working on this in the background will trust that it’s doing a good job and keep serving them up.

The next main section will cover mind mapping, outlining, and other practices for this kind of work, but first a brief overview of tools and the various pros / cons of different choices.

Digital vs. Analog

If you’re used to taking out your smartphone frequently, it makes sense to try out an app for this kind of planning. By connecting this new writing habit with an existing habit (checking your phone), the new habit is more likely to stick. You might take out your phone out of habit to scroll Instagram, only to find a bunch of ideas pop into your head for you to write down first, as your mind starts to associate getting out your phone with capturing ideas. You can even use the dictation features to speak your ideas instead of having to type them out. This can really get things flowing.

However, if you’re not so hooked on a phone or maybe you are actively trying to use your phone less, a notebook might also be a great idea. In fact, this method is quite popular as you can see from the zillions of options available for writers–from different notebook sizes, bindings, and paper types to different pen sizes, functions, and ink types.

Moving Text Between Apps

If you’re going the digital route, you’ll want to make sure you can get your text out of the planning app you choose in an easy and useful way. That is, if you want to start writing your paper in Word or Google Docs, if might be nice to have the outline you’ve made in your app pasted into that document first to get you started. Or you might want to start with a mind mapping app, then move to an outline app once you’re ready to really organize the structure.

Most mind mapping and outlining apps (whether they are separate apps or web apps you visit in a browser) will be able to read and write an OPML file (“Outline Processor Markup Language”). When you are trying out a new app, look for options to “save as” OPML, or to “export” or “import” an OPML file. These files allow you to open your mind map or outline in another app, so you can create a mind map, then see how it would look as an outline. Additionally, some specialty writing apps will open OPML files and create a writing space for you based on that outline.

Screenshot demonstrating how to export an OPML file from iThoughts. Screenshot demonstrating how to export an OPML file from Dynalist.
These screenshots depict exporting OPML files from a mindmapping app and an outliner web app.
This video demonstrates importing an OPML file into the writing application Scrivener, showing how the hierarchical structure of the mind map in the image above is re-created in the Scrivener outline in the left panel.

However, you can’t open OPML files in Word or Google Docs. To get text from an outline or mind map into these applications, a different process is needed. Each app will have its own mechanisms for this. Some will allow you to “save as” a Microsoft Word Doc format, others will allow you to “export” as .docx. Some might not create a Word document, but will export “text” or .txt, files which can be opened in Word or Google Docs. As a last resort, you might be able to select all the text in an outline, copy it, then paste into Word. (For more on different file types and dealing with them, see the file format guide.)

No matter which software apps you are checking out, you’ll want to test this ability to save/export text before you get too attached. It would be fairly annoying or worse to construct a full and detailed outline in an app and not be able to save that into your writing app if that’s how you wanted to work.

Notebooks and Pens

Small notebooks and pens can be picked up at nearly any store with school supplies. However, if you’d like to try something more specially suited for this kind of practice, there are many options available.

In terms of notebook, Field Notes are often highly rated in reviews, as are Baron Fig notebooks. You’ve probably also seen Moleskine Notebooks around, with their elastic straps on the cover (but these can be difficult to lay flat and you can’t fold the cover around when writing standing up, and they aren’t reviewed well by pen fans.) For a more functional and DIY approach, the Hipster PDA can work well (essentially, just a stack of index cards held together with a binder clip). Writing ideas down on individual cards lets you later sort them in a stack or on a large table.

[Photo of a hipster PDA]( by [bamse16](
Photo of a hipster PDA by bamse16

For pens, there are more options to choose from than can really be discussed in a guide like this. Many Hipster PDA users swore by the “Fisher Space Pen” because it could write upside down and was small enough to fit in a pocket easily (or, of course, you could use a pencil like a Russian astronaut). If you’re curious about pens, here are two reviews to start your journey down the rabbit hole: Best Mini Pens and The Best Pen.

Generating Ideas

A key rule of thumb for creative work is to suspend judgement while generating ideas. Instead, you’re looking to tap into creative and associational mindsets. This means finding ways to list ideas quickly and draw connections between them rather than deciding whether any of them are “good enough.” After you’ve generated five times more ideas than you think you’ll need, you can then go through them–improving them, making more connections, adding even more new ideas as you see patterns or make insights. It’s important to generate a large number of ideas here because if you are trying to be efficient and just come up with the ideas you need to write your paper, you’ve slipped back into the judging mindset. The creative voice in your head won’t trust that you’re really looking for good ideas until you’ve written down a few that seem irrelevant or silly.

Mind mapping can be a great method for generating and connecting ideas quickly. After the map is made, you can re-arrange the ideas on the map (if you’re working digitally), use the map to construct an outline, circle the best ideas in a particular marker color, or just get started drafting. Instead of mind mapping, outlining (discussed in a subsequent section) can also work here as long as you’re mindful of generating a bunch of ideas at first rather than trying to create a perfect structure for your paper on the first attempt.

Mind Mapping

While there are typically many similarities between pen/paper writing and computer writing, with mind mapping the differences are more stark. Drawing on a large sheet of paper on a table with 10 or more marker colors is a dramatically different exercise than typing on a keyboard or poking at a screen with your finger. Many people find it is easier to get into a creative flow with the paper, where they can write anywhere and draw connections however they see fit. Most mind mapping software only allows for certain kinds of connections (namely, hierarchical connections where each idea has “parents”, “siblings”, and “children”). And yet, mind mapping on paper in this way is more difficult to do frequently over the course of several days. Furthermore, it is much easier to list a bunch of ideas quickly and then move them around to try different organizational patterns using an app. Rather than deciding whether you’re a “paper” or “digital” person, it might make sense to consider what methods work best for any particular project you’re working on. Maybe you start on paper, then transfer the ideas to an app on your phone so you can keep working on it over the course of another week or two. If you have less time, maybe paper makes more sense. If you aren’t feeling the need for a creative flow so much as a place to record ideas over time, maybe a digital mind map or outline makes more sense.

What Can You Do?

Generate ideas quickly

Both pen/paper and apps allow you to add ideas quickly, but the experience here can be quite different depending on your preferences. It’s worth trying both out to see how you respond.

When using pen and paper, you can add written labels as fast as you can write. After you’ve written a bunch of labels, you can pause and draw the connecting lines between them (either between each label and a central hub, or something less linear, whatever you want) or draw some doodles to represent the ideas. This pause can be a great opportunity for you to switch tracks mentally–while you focus on drawing, the background part of your mind can keep cooking up ideas and be ready to serve them up to you when you’ve finished drawing.

[A hand-drawn mindmap]( by [jean-louis zimmermann](
A hand-drawn mindmap by jean-louis zimmermann

Working digitally, you can add new “nodes” to the map (a node is simply each “bubble” or “note” on the map) as fast as you can type. Most apps make this very easy–not requiring any mouse clicks, just press the “enter,” “return,” or “tab” key to get a new node. After you’ve typed a bunch of ideas, you can typically select several and adjust their color, or find some images online to attach to them. Depending on the app, you may also be able to draw associational connections between nodes or move them in a more free-form way on the map.

This video demonstrates how quickly new nodes can be made in the app iThoughts, so that your ideas will be captured as soon as they arrive.

Capture ideas anywhere

While you could use a small notebook to add nodes to a hand-drawn mind map, that may be too cramped to be useful. However, many mind mapping apps have phone and tablet versions. The phone versions of mind mapping apps aren’t really less cramped than a notebook, but it’s a lot easier to quickly add a bunch of ideas by typing on the phone keyboard than trying to draw creatively in a small notebook.

Screenshots of the iPhone versions of three mind mapping apps: MindMeister, MindNode, and iThoughts.
Screenshots of the iPhone versions of three mind mapping apps: MindMeister, MindNode, and iThoughts.

Make connections between ideas

There are several different types of connections that can be made between ideas on a mind map.

  • Hierarchical / Branched: Nodes in a mind map often radiate out from a central hub and branch out in a hierarchical way from there. This creates an easy way to relate items that belong together, but it can be limiting if you don’t know what the central idea is yet or you’re not sure of the main categories. Most apps make these kinds of links the default, as new nodes will be created either as “children” or “siblings” of the current node. Hand drawn maps can also introduce further meaning in these kinds of links by making the branches thicker or thinner to indicate strength of connection.
Screenshot of two branches in a digital mind map.
Screenshot of two branches in a mindmap.
  • Associational: Any two nodes can also simply be connected by a line, regardless of whether they are on the same branch or not. When hand drawing, these are simple to make. Apps may not always include this feature, but typically it involves selecting both nodes then pressing a toolbar button. However, these lines can quickly make the map difficult to read, so if you find yourself making a lot of them it may be worth considering other ways of making connections (like colors, icons, or images).
Screenshot of associational link between the *general overview* node and the *digital vs. analog* node.
Screenshot of associational link between the general overview node and the digital vs. analog node.
  • Color: Color can be used in a variety of ways to indicate connections or relationships between nodes. Obvious coloring options include the branches and the nodes themselves. You can also, when hand drawing, use a new color to circle individual nodes or to circle entire areas of the map. Some apps allow you to specify an “interior” color for a node as well as an “outline” color.
Screenshot of colors in the mind mapping app iThoughts.
Screenshot of colors in the mind mapping app iThoughts.
  • Icons / Images: Icons, emoji, or images can be used to indicate connections between ideas as well. These can help link ideas that aren’t on the same branch, but still allow you to quickly group them when looking over the map as a whole. For example, you might use a microscope (🔬) to indicate nodes that need more research, or the gem (💎) to indicate valuable ideas.

Use images and other means for making the map attractive

In addition to using emoji for broadly categorizing nodes on the mind map, you can also use images of any kind (including doodles, photographs, or images copied from a web search) to make your map attractive and help stimulate more creative juice.

Screenshot of a photograph added to iThoughts node.
Screenshot of a photograph added to iThoughts node.

Convert your mind map into an outline

As described above, you can use the OPML file format to convert your digital mind map into an outline. Branches translate to sections of the outline. However, if you have more than one central topic, this process may lead to unexpected results in different apps.

Of course, you can also simply use your mind map (digital or hand-drawn) as a guide for creating a fresh outline. Because your mind map (hopefully!) has many more ideas on it than can fit in your paper, you will want to pull out the best ones, do some combining, and probably draft some new material as you work. Starting “fresh” in this way can encourage you to continue working toward the best version the project, rather than remaining attached to your first take on it.

Draft paragraphs or ideas within a mind mapping app

Because digital mind maps emphasize hierarchical, branched connections between nodes, you can use these as outlines themselves–no need to create a separate outline or use another app. Most apps allow you to select a node, then open up a separate text field where you can type whole paragraphs or more. The “label” of the node on the map can stay short, while the note contains more text. You can then export or copy all of this text into a word processor or other writing app and have a good deal of the text already written, thereby avoiding the dreaded blank screen.

Screenshot of drafting paragraph text in the iThoughts mind map app.
Screenshot of drafting paragraph text in the iThoughts mind map app.

When you’re finished generating ideas, you can use your mind map in a variety of ways. You may just want to move on to an outline or to drafting without looking at it again, but you can also continue to use it for tracking progress, or to provide inspiration, or as a reference. Some more full-featured mind mapping apps allow you to attach various bits of “metadata” (or information about the node) to each node. This could be a due date, a pie chart representing how much progress you’ve made on that part, a checkbox, a link to a web page, etc. Using due dates, check boxes, and pie charts could be useful for a large-scale writing project or something collaborative where the map can help you see the overall plan and how to move toward completion.

Screenshot of iThoughts mind map with nodes that have task information assigned.
Screenshot of iThoughts mind map with nodes that have task information assigned.

What Apps Should I Try?

  • iThoughts: Mac, Windows, iOS. Create mind maps in a variety of different layouts and customize colors and links in endless ways. Simple to use, but also many advanced features as well–such as adding due dates, check boxes, or images to nodes. Can view the mind map in outline form in the app as well. Exports to a variety of formats. Be sure to use the education discount.
  • MindNode: Mac, iOS. Very similar to iThoughts, but fewer features and increased focus on “simplicity.” Can customize layouts, colors, links as well as adding images and check boxes to nodes. Can also view the mind map in outline from within the app. Exports to a variety of formats.
  • FreeMind: Windows, Mac, Linux. Free, open source software. Less focus on simplicity, more focus on advanced features and ability to create diagrams via the mind map. Seems less focused on generating ideas and more on displaying complex information. Also check out the related project Freeplane, which has been updated much more recently than FreeMind.

Free Form Support

These apps don’t operate like the ones above–they don’t organize nodes hierarchically and instead allow you to group nodes more creatively, as if you were drawing them by hand.

  • Scapple: Mac. Instead of automatically linking nodes to a central hub or through branches, this app allows you to basically place notes anywhere on the screen, connect them however you want, and organize them in a variety of ways (through links, by stacking them, by simply placing them near one another). Can also export in a variety of formats, but could be hard to get a coherent outline from this since the nodes aren’t connected hierarchically.
  • Canva: Online, Free. This app is all about design and can help you design infographics and posters, as well as mind maps. You can make mind maps that are much more free form than branches with a central hub.
  • Tinderbox: Mac. This app is expensive, but does much more than visually display notes in a mind map style. Best to check out the website to see all the possibilities.

You can also just use a drawing app as well–anything like Photoshop or Illustrator will work, or on the iPad with the pencil, Notability and Concepts are good choices. However–these won’t export to outlines because they are just drawings, not “nodes.”

Online Web Apps

  • Free. Very simple node creation, but fewer additional features. However, can easily collaborate with others and also exports to Word file or basic text outline.
  • MindMeister. Free. Very full-featured, like iThoughts and MindNode above. Additionally, easy to collaborate with others and exports to Word files, text outlines, or other mind mapping apps.


Outlining can also be a free-wheeling process akin to mind mapping, and digital tools in particular facilitate rapid addition of new ideas and make it easy to move them around. Or more conventionally, outlining can be a place to transition from generating broad ideas to starting to write sentences and paragraphs for a rough or first draft. Because of these fluid aspects of outlines, using pen and paper for this activity has more drawbacks because it is more difficult to rearrange sections.

As described above, you can typically open a mind mapping file in an outlining application when you’re ready to view the structure in a more linear way. If you’re interested in this kind of process you’ll want to double check that the apps you’re using support the same kinds of files before you get too far along.

You’ll also want to be sure that you can move from outlining to drafting in the way that you want. If you prefer to keep your outline as a separate document or a printout, then you’re set. You might instead want to paste your outline into a writing app and use the outline as headers indicating the structure of the paper. You might even have already started drafting some sections of the outline in the outlining app and want that text added to the writing app. Nearly any app will let you copy and paste the text between them, but you might double check the particular applications you choose for any more advanced features, or to be sure that the copy/paste process doesn’t mangle formatting too badly.

What Can You Do?

Add ideas anywhere

With an app or a small notebook, it’s easy to add ideas to an outline wherever you’re at. This makes it easy to have your mind generate ideas in the background, while you just write them down whenever they pop up while you’re doing other things.

With an app, the experience can be even better because it’s easy to add items anywhere on the outline without having to scratch things out. You can also quickly rearrange items if that seems necessary.

Screenshot of the outlining app Workflowy on the iPhone.
Screenshot of the outlining app Workflowy on the iPhone.

Word Processors

Before diving into features available from different applications, it’s useful to see what you can do with apps you already have. Microsoft Word, of course, has an outline mode that can be invoked in any document. In this mode, it’s easy to create new branches and move them up and down the structure.

Screenshot of a Word document in Outline view.
Screenshot of a Word document in Outline view.

If your outline becomes very long, you can also change the view in different ways, so that you only see the top level headings, or only the top two levels. This is useful if you start drafting paragraphs in, say, level 4. Once you have several paragraphs drafted it will be difficult to see the whole outline in one screen on a smaller laptop, so invoking this feature to see only top level headings will give you a view of the whole structure at once. However, as we’ll see below, most outlining apps have a more flexible feature called “folding,” which allows any branch to be shown or hidden, not just all level 3 branches or all level 4 branches.

This video demonstrates hiding outline branches in Word.

One trick if you want to start writing paragraph text (as opposed to headings) in Word’s outline mode is that you need to set the text style as “body text” in the menu bar.

Screenshot of changing text formatting from an outline level to regular paragraph text in Microsoft Word.
Screenshot of changing text formatting from an outline level to regular paragraph text in Microsoft Word.

Google Docs now provides a useful outline panel for documents with headings, but there is no way to go into an “outline” creation mode as with Word.

Beyond word processors like Word and Google Docs, however, there are a host of specialty outlining tools that offer useful features for idea generation, especially for managing projects with research or other material you’re looking to collect.

Folding and focusing headings

While Word allows you to only show certain levels of headings (like only the top level headings), most outliners allow “folding” and “focusing” (although these features may have different names in different apps). Basically, “folding” means hiding any levels under a particular header. In the animation below, you can see one section of the outline being “folded” or hidden, while the other sections remain visible. This way, you’re not limited to hiding all the headings of a certain level, but instead can choose exactly what to hide and what to show.

This video demonstrates folding and focusing outline levels with the web app *Workflowy*, then with the Mac app *FoldingText*.

“Focusing” goes a step further in hiding and showing. When you “focus” on a heading, that heading becomes the new “top-level” heading and all you see is the content under that heading. For example, if you focused on the second main heading of an outline, you would only see content in that second section–you wouldn’t see anything from the first heading, obviously, but also you wouldn’t see anything from a third or fourth top-level heading. That material hasn’t been deleted, only hidden from view until you “unfocus” the outline. Sometimes this feature is called “hoisting,” because whatever level you choose is now “hoisted” up to the top of the screen.

One of the great ways to use folding and focusing for writing a paper is the ability to dive into the details of a section (by focusing on it, or folding away other sections) without worrying about the other material (i.e., getting into that creative non-judgmental state). Then, you can reset the outline to show everything and start thinking about how those new details fit into the structure of the whole document. Folding and focusing different sections of an outline for a complex paper you’re writing is the most immediately obvious use of these features, but they are also great for managing different kinds of information or multiple papers at the same time.

For example, you might use the first top-level header to store quotes from research you’ve done, then fold this level to hide it when you’re working with the rest of the outline for creating the structure of the paper. Or, you might focus on that top-level header while you’re doing research to have a clear space for adding more quotes. Or you might store reference URLs or citation information under each heading and fold them up to maintain a clean view of the structure.

The web app Workflowy makes heavy use of focusing (which it calls “zooming”) because each user only gets one outline to work within. If you want to create multiple outlines in Workflowy, you need to “zoom” in on heading and then create the new outline there. If you’re taking a bunch of classes all focused on the same broad area, it might be nice to have all that information accessible from the same place. Further, because Workflowy also makes heavy use of tags (described in more detail below in the Project management section), when you search a tag you see results across all your content at once. This might help you make connections between disparate projects that you might have missed.

Project management

When you’re working on a larger or more complex paper, it might be worthwhile to frame it as a “project” rather than just a writing task. Putting “write the essay” on your “to do” list won’t cut it when what’s required is a months-long process of research, drafting, responding to feedback, revision, and editing. A project has multiple tasks, some of which are happening at the same time and some of which are dependent on previous tasks being done first. These various tasks might have separate deadlines or milestones. If you’re working collaboratively, different people might be assigned to different parts. Furthermore, you might want to keep track of where each part of the project is at any stage (maybe the fourth section is finished and polished, the third section needs editing, and the introduction still needs to be drafted).

A dedicated outlining application will typically offer features to support project management. For example, using Workflowy you can add tags to represent what stage each topic is at (e.g., #needs-editing, #needs-research) or to represent who is responsible for what (e.g., @elizabeth, @julian). With the web app Dynalist, even more options are available in addition to tags. Each item in the outline can also have a checkbox (check the item off once it’s finished) and a date (for managing deadlines or milestones). With Dynalist, it’s also possible to link to other outlines–so you could have one outline represent the project plan and link tasks in that outline to various sections of the paper’s outline.

Screenshot of the Dynalist web outlining app with checkboxes, due dates, and links to multiple documents.
Screenshot of the Dynalist web outlining app with checkboxes, due dates, and links to multiple documents.

With an application like OmniOutliner, on Mac and iOS, even more customizability is available. Each item in the outline spans multiple columns, and users can assign whatever information they wish to each column. For example, one column might hold URLs for webpages, another might hold a due date for that topic, and another might hold traditional citation information. OmniOutliner can then create a Microsoft Word outline file, but this Word file will not contain the custom columns from the OmniOutliner document.

Screenshot of OmniOutliner with two extra columns depicting the status of each chunk and a deadline.
Screenshot of OmniOutliner with two extra columns depicting the status of each chunk and a deadline.

Lastly, even some mind mapping applications can toggle between mind map and outline and offer these project management features. iThoughts, available on Windows, Mac, and iOS, allows for each item to have a due date, a priority, and a checkbox. Each item can also be assigned a “percent complete” number. The view of the map or outline can then be filtered to only show items that meet certain criteria, such as only those that are in progress, or only those that are due soon, or only those that are less than 50% completed.

Screenshot of iThoughts mind map with nodes that have task information assigned.
Screenshot of iThoughts mind map with nodes that have task information assigned.

What Apps Should I Try?

  • Workflowy: Windows, Mac, Linux, iOS, Android, Web app. Fully-functional free version. Minimal-looking outliner, but has many useful features. Works on the concept of a single outlining space where you can “fold” and “focus” headings to show exactly what you want to work on at any given time. Makes use of tagging as well for organization across all the information.
  • Dynalist: Windows, Mac, Linux, iOS, Android, Web app. Fully-functional free version. Somewhat similar to Workflowy, except Dynalist allows you to have multiple outlines organized like conventional files. Additionally, Dynalist offers more features, including creating checklists, links between different outlines or different sections of the same outline, support for adding images, and others.
  • NoteCase Pro: Windows, Mac, Linux, Android. Fully-functional free version. Multi-windowed outliner, meaning that the outline appears in a column on the left side of the screen, and the content for each section of the outline when selected appears in a main writing window in the center of the screen. Supports images, checkboxes, tagging, and many other advanced features.
  • cherrytree: Windows, Linux. Free software. Like NoteCase, a multi-windowed outliner. Can import many different types of files as well as export, so useful for when you are working between mind maps, outlines, and word processor documents.
  • OmniOutliner: Mac, iOS. Two different versions with basic and advanced features available. Don’t forget to use the education pricing discount. With OmniOutliner you can make basic and minimal outlines, and then keep adding features for whatever you need–extra columns, notes for each item, audio clips and other file attachments, and automations. You can also export the outline to other file formats, like Word files, Powerpoint, Excel, or OPML.

Less Conventional

  • Gingko: Web app. Fully-functional free version. Gingko asks you to imagine your outline as a stack of cards that you can rearrange easily and spread out to see how everything fits together. To really get a sense of how fluid it is to see varying levels of the outline you should watch the promo video on their site.
  • Scrivener: Windows, Mac, iOS. Don’t forget to use the educational pricing. One of the key features of Scrivener is the ability to view the same information in a variety of ways. It’s possible to create an outline in Scrivener and then view it in a way that resembles OmniOutliner’s multiple columns, or a way that resembles Cherrytree’s multi-window view. You can even view it as a set of index cards that can be re-arranged as if on a big table. Scrivener is also a flexible and useful writing environment, meaning you could outline and compose using the same application. See the “managing longer projects” guide for more on Scrivener’s capabilities.

Getting Started Writing

Even after generating a great outline or mind map, you may not be ready to write polished text. Maybe you find yourself staring at the plan and you’re not quite sure how to get started. At this point, it may help to just start typing.

Some people prefer to stay in the mind mapping or outlining application and do some initial drafting there. Mind map apps like iThoughts provide a text box to write in when you to click on a topic.

Screenshot of area to write in when a node is selected.
Screenshot of area to write in when a node is selected.

Again, if this seems appealing to you, it’s best to test out how the app you’re using exports or saves this text. You don’t want to find out later that there’s no easy way to get it into a Word file, for example, and end up needing to copy/paste each topic separately.

With outlining applications, it’s typical to just create a new “child” topic and start drafting there. Usually then you can just fold that up to see just the outline again.

However, you may prefer to do your initial drafting in a more conventional writing application, leaving your outline or mind map open to guide your writing.

What Can You Do?

Starting a writing task can be daunting, which is why so many popular writing guidebooks advise that you just get some words out without worrying too much about what it sounds like or how polished it is. If you start judging every sentence word by word as you write it, you might only write a sentence or two before you run out of time for that session or you run out of interest in writing. Writing more freely at first lets you build up some momentum, and once you’ve got several pages written, you can go back and start revising.

But writing freely can be a difficult habit to develop! Especially if you’ve had a lot of criticism focused on “correct” sentences and using only the best words. (These aspects of writing are important, but not when you’re just getting started.) Fortunately, there are several techniques to help you get into the groove.


If you’re not used to handwriting, this can actually be a huge benefit when trying to develop the habit of writing without judgement. When you’re handwriting, it’s more tedious to erase what you’ve just written and start over, so you’re more likely to just keep going. In fact, you can make it a kind of game–don’t pick up your pen for 10 or 15 minutes at a stretch. Just keep writing! If you can’t think of something to write, just write about that and sometimes that pops you out into a new line of thinking to write about (e.g., “And now I’ve run out of things to say because this is a boring paper to write because the topic really needs to be connected to this other idea that’s way more interesting and maybe I should just do that in this paper, hey, great idea”).

One other great aspect of handwriting is that you’ll need to type the paper up afterwards and you won’t be able to just fix a few misspelled words in your messy draft and turn it in. Some people may see this as a drawback to handwriting, but it’s really a huge benefit. Lightly editing a bunch of text that you wrote in a mad dash is not really what revision is about. Free writing, when it works best, provides you with a strong sense of what you want to say and how. Then, you can start writing the paper with this in mind. You might use a few phrases or even a sentence or two from your free writing, but it’s not too valuable typically to transcribe your handwritten paper into the computer. Just use it as a guide to write the paper itself.

Computer Games

Over the last decade, several folks have created applications that turn free writing into a kind of game. These games help motivate you to keep churning out words rather than going back to edit or sitting in your chair staring off into space trying to think of the “right” way to say what you’re thinking.

The most notorious of these games is Write or Die, which in one configuration will start deleting what you have written if you pause your writing for a few seconds. There are other modes that you can set, however, so it’s not necessary to be this drastic. However, sometimes if you’re feeling stuck, the deletion mode can really get your heart racing and help you fill up the page.

Rather than focusing on consequences, other games emphasize rewards. Written? Kitten! gives you an image of a cute kitten (or puppy, or bunny) after every 100 words (or you can set the bar higher). Fighter’s Block provides a whole role-playing game backdrop, so that every time you reach your word goal, you level-up your character and/or defeat the next boss villain.

Focus Modes

Another way to encourage yourself to just keep writing instead of going back and tinkering with what you’ve already written is to restrict your focus. Several new writing applications allow you to “dim” or even completely hide any existing text except for the line, sentence, or paragraph you are currently writing.

Screenshot of the paragraph focus mode in the iA Writer app.
Screenshot of the paragraph focus mode in the iA Writer app.

Different applications use different names for these modes. iA Writer and Typora call this “focus mode” and Ulysses calls it “typewriter mode.” Some applications also have a “distraction-free” writing mode, which they might also call “focus mode,” where no text is hidden but instead the screen goes black except for the writing space. For example, Microsoft Word now has this feature, which it calls “focus mode.”

Screenshot of Microsoft Word interface button to turn on focus mode.
Screenshot of Microsoft Word interface button to turn on focus mode.

Lastly, you might achieve a similar effect manually using the outlining “folding” and “focusing” features described above. After writing a paragraph, you could fold it away and begin the new one, or each time you start a new paragraph you could “focus” on it, or “hoist” it up, depending on what the app you’re using calls this feature.

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