Writing a Real College Essay: Part 3 - Outlining


This is Part 3 in a our series of videos where I demonstrate a structured approach to essay writing by working through a real college essay assignment.

In Parts 1 and 2 I showed how I use Scrivener to organize information about the assignment and my research materials and how I take notes, and took a first stab at a topic proposal and a working thesis statement.

Since then I’ve gone and done more research and spent some time working on an outline. In this video I’m going to show you that outline and talk about the thought process behind it.

I strongly recommend watching the first two videos if you haven’t already, because I’m going to cut right to the chase and pick up where we left off at the end of the last video, and it’ll be confusing if you’re jumping in right here.


Our topic is whether it’s worth it to go to art school if you want a career as a visual artist. And more specifically, whether the value of a degree from an art college offsets the costs.

Private art colleges in the Unites States are notoriously expensive, and it’s not like medical school or law school where you might expect your earnings after graduation to compensate for the cost — typical art school graduates earn much less, and the debt they incur can be debilitating, so there’s a real issue here and it’s a debate that many people are having.

At the end of the last video I had decided to use an essay by Noah Bradley to set up the issue and frame the initial position, which is strongly opposed to art school — he thinks it’s just not worth it, unless you’re getting a free ride and can graduate without going into debt.

So at this point I needed to do some more reading and research, and try to produce an outline of some kind to organize the essay.

Instead of working in Scrivener, for this part of the process I decided to use a web-based outlining tool called Workflowy.

WorkFlowy is a zoomable outlining and list-making environment that is super flexible for organizing ideas. I use it almost every day. There’s a free version and a paid version. I’m using the paid version, which gives you unlimited lists and some options for the visual look of the environment. This wood-grain theme, for example, is only available in the paid version, otherwise it’s just a plain white background.

Let me just quickly show what’s inside this Workflowy document, and then we’ll back up and work through it from the top down.

When I started this document I was thinking okay, let’s try to make the strongest case we can in favor of Bradley’s conclusion, that art school is not worth it. Then we’ll try to think through the most obvious objections and see how a supporter of Bradley’s view right reply to those objections.

The third item in this list, the one called “Outline”, is reserved for final thoughts on how I want to approach the organization of the actual written essay. The first two items, where I’m working through the arguments themselves, isn’t necessarily intended as a model for how the final essay is structured.

The goal here is to help me think through the issues, and at this point I’m still not really concerned about how I’m going to organize things on the page. I’m trying to figure out what I want to say, not necessarily how I want to say it.

Now when I open up this first level there are three sub-levels. These titles correspond to different thoughts I had about how to think about the issue, based on the research I had done.

"Is art school an irrational choice?" Is this how I want to frame the critical position? If so, then this has implications for how the argument is going to be structured.

“Art school and preparation for success”. This section is devoted to the claim, made by Bradley and other critics, that art schools don’t adequately prepare students for success. So I have a whole section devoted to the issues surrounding this claim.

And the third item here is about the moral dimension of the critique, whether art schools are guilty of exploiting students, or of false advertising of some kind. I wrote quite about this, but in the end I decided not to pursue this angle in the final essay, for the sake of space.

There’s a lot of content inside these three sub-headings. Once I’d spent some time on those, I created this heading called “Objections and Replies”, where I tried to organize my thoughts on how defenders of art schools might respond to this argument.

I identified two types of objection, which I labelled “A” and “B” here.

“A” has to do with whether the critique of art schools really only applies to some types of artists and professional work. So it’s about criticizing the scope of the argument.

The “B” objection has to do with the idea that certain kinds of artistic practice really are well-suited to an art college setting, and that for these areas of art, there really isn’t any viable alternative to going to art school. There’s a lot of content inside this section too, but first let me just show you the notes I eventually wrote on the final outline.

This is the last thing I wrote. I decided I would use the Bradley article to introduce and frame the question, and that I would frame the issue as a rational choice issue, rather than as a moral issue. Under what conditions would it be irrational for a person to choose to attend an expensive art college?

Then I’ll present the case for why it is very likely irrational for certain kinds of aspiring artists to attend art college. Here I’m anticipating the objections and qualifying the claim in a way that makes it more reasonable.

My final note is that, rather than have a separate section devoted to objections and replies, I’ll integrate the objections and replies into the main presentation, so we’ll deal with them “on the fly”. I say this because I already have in my head a good idea of how I want the essay to read, and I think this organization will be natural and engaging.

Now before I show you any more, I want to return to a point about the writing process that I talked about in an earlier unit in this course.

Remember this diagram? We were talking about writing for discovery versus writing for presentation. In the discovery phase we’re working out what we want to say, in the presentation phase we’re concerned with how we want to say it with a specific audience in mind.

The writing that I’m doing in this outline document is part of the discovery phase for me — I’m trying to get my head around the issues and exploring the logical relationships between claims and arguments and objections and replies.

I do a lot of writing in this phase, as you’ll see, but I’m not writing for presentation yet — I’m writing for me. I’M the audience.

One of the advantages of using a good outlining tool like Workflowy, where you’re forced to write in lists and bullet points, is that you don’t get hung up on your choice of wording and making it sound pretty. You can focus on concepts and relationships of ideas, and that’s very liberating.

So when you see all the writing I’ve done at this stage, just remember that I’m not writing for presentation yet. I can certainly USE some of this language in the final draft, but I don’t have to.

Okay, let’s open up this first header - “is art school an irrational choice?”

You can see a bunch of numbered sub-headings. These correspond to premises of an argument that I’m trying to reconstruct. I’m trying to frame the decision to go to art school in terms of cost-benefit reasoning. If it turns out that, when all factors are considered the costs seriously outweigh the benefits, then there’s a case for saying that the decision to go to art school isn’t just unfortunate, it’s irrational in this restricted sense of the word.

Now, whenever you see a bullet with a grey shaded circle around it, that means there are more bullet items nested inside that item, so I’m not even showing you the whole thing. I’ll come back to this section again.

If we jump down to the second section, you’ll see that the discussion here is about whether, and why, art schools fail to adequately prepare students to create professional quality art, or how to make a living as a professional artist. These two claims are part of the strong critique that Bradley and others make.

For each of these claims I wanted to look in more detail at the motivations for making them, so there are a lot of sub-headings here where I try to reconstruct this reasoning.

For example, if we unpack item 5, “art schools do not teach students how to produce professional quality art”, what you see is my attempt at an analysis of what is actually being said in this statement, and why it’s being said.

If you were writing this up in proper essay format you’d have the raw materials for several paragraphs here, where the nesting structure may well mimic the structure of the final paragraphs, with topic sentences up front and supporting details within the body of the paragraph, but you don’t have to view these as paragraphs in an essay — these kinds of notes stand on their own, they express logical and evidential relationships that reflect your thought processes as you think through the issues.

It’s the same for this section, which analyzes the statement that art schools fail to teach students how to make a living as an artist.

What I’m trying to emphasize here is the kind of intellectual work that students often fail to do when they start writing. They make statements without really thinking about what they mean, or they reproduce statements from a source or an author without understanding the broader context in which they’re made, and as a result their writing isn’t focused and cohesive, it just jumps around from one assertion to another without paying attention to the logical flow of ideas.

That’s what we’re trying to avoid with all this pre-writing that we’re doing.

Now, I want to switch directions a bit and talk about how this kind of outlining is helpful for identifying sources and the need for supporting evidence and documentation.

Remember that this is a research essay assignment, and one of its goals is to have students demonstrate an ability to do research, identify relevant sources and cite those sources in appropriate ways in their essay.

For example, an important issue in this essay is how much students pay to attend art school. So it’ll be important to have some way of backing up any claims I make in the essay that aren’t common knowledge.

So as I started unpacking this element of the argument, I did a Google search for tuition for art schools and found a couple of helpful links, which I copied and pasted into my outline document here so I can refer to them again later on.

You can see that tuitions really are substantial; these are tuition fees for a single year.

In the essay I also make claims about typical salaries of art school graduates, and I’d like to substantiate those claims, so I’ve got some links to sources on this too.

As you can see, from this survey, average starting salaries are around the $40,000 per year mark.

One of the things you want at this early stage of your writing is the freedom to follow up on sources and links, because they’ll inevitably lead you to other sources that couldn’t have known about at the beginning.

Like this source, for instance. I was searching for information on the percentage of art school graduates who actually work as artists or in art-related professions, and came across a blog post that linked to this report, titled “Artists Report Back: A National Study of the Lives of Arts Graduates and Working Artists”, which was an absolutely perfect source for this project.

Here’s the link, and it opens up a pdf of the report that includes these helpful charts and quotes like this — “out of 2 million arts graduates nationally, only 10 percent, or 200,000 people, make their primary earnings as working artists.”

The recommendations section of the report also includes this quote:

We acknowledge that some arts graduates are happy to work in other fields, but we hope to show that the fantasy of future earnings in the arts cannot justify the high cost of arts degrees. We know that expensive art schools leave arts graduates with high overhead in the form of student debt, making risk-taking and innovation after graduation more difficult, if not impossible. Still believing in the power of arts education, we point prospective art students toward low-cost and tuition free arts programs and we defend the liberal arts as integral to higher education nationally.

And as I noted when I typed this note, this is Noah Bradley’s thesis in a nutshell.

So this is very helpful as a reference document that helps to support many of the claims that otherwise I would have to take on authority from people like Bradley, or anecdotal reports based on testimonials, which can be biased.

And the point I want to make is that the process of finding references like this is part-and-parcel of this kind of structural outlining, where the focus is on identifying chains of reasoning and asking yourself, how would I justify this claim to a skeptical audience?

Is it obviously true, is it common knowledge, is it a statement from a reliable authority? If it’s the sort of claim that needs backing up, that’s my cue to do some searching and see if I can find a reliable source. Then when you find a good source you’ve got a reference you can use in the essay, but you’ve also got the potential for additional quotes and leads to other sources.

This is another reason why you need to block off lots of time for this stage of the writing process, well in advance of your deadline, because it takes time to work through your ideas and follow-up on references. If you wait too long to get started you’ll short-circuit this discovery phase of your writing, and the final result won’t be nearly as good.

To wrap up this video, I’ll show how I get this outline back into Scrivener where I can use it to help with the actual writing of the essay.

You can export any Workflowy outline at any level of the hierarchy just by hovering over a title on the left hand edge, and a menu of options will appear, which includes the option to export. Click this and it’ll give you some options, but the easiest is just to copy the contents to your clipboard.

Then you can go back into Scrivener, and I’ve got a text document open where I’ll paste these notes.

And that’s it, now I’ve got a full copy of these notes, which I can use as reference while I’m writing. So for example I can open a text document and put the notes up side-by-side and I can type in the document while referencing my notes.

The kind of outlining that I’ve shown you here is important for working out your own thoughts on what the issue is, how the relevant arguments are supposed to work, and to fill in the gaps in your understanding so that you’re confident that you know what you want to say when you get to the stage where you’re actually writing for presentation.

This kind of outlining is primarily an exercise in writing for discovery. Because you’re not worried about presentation it can be very liberating. You can write in point form and incomplete sentences and lists and drop in links and parenthetical comments and you can rearrange the order of things and add sections with no pressure.

The way I’ve done it here isn’t the only way of doing it of course, but however you do it, you want to include a stage like this in your writing process.

Now I’ve got to go and write a proper draft of this essay. But I’m in much better shape now than I was before I started this outlining phase.

So in the next video I’ll let you see what I come up with.