I don't like outlining

is there still a way to do it?

I just printed out the third draft of the first draft of my latest feature screenplay. It’s sitting on my desk as I type this, hot off the Brother HL-L6200DW presses.

Wait a minute. What exactly do I mean when I say “third first draft?” What is this, Alice in Wonderland math?

Well… usually, when I’m writing, I will end up with at least a few different passes of a first draft. There’s the very first sort of “speed draft” that I’ll write as fast as I can, from an outline. Then I’ll sit down, read that one, notice all the holes and things that don’t make sense and will force myself to re-break the outline. Then, I’ll write another draft. Then I’ll do this again. I save all of these drafts in my “FIRST DRAFT” folder even though that first draft will end up with anywhere from 1-5-7(?, sometimes I lose count) drafts.

Then, I’ll get notes from friends (or producers, or my friends who are the producers). The next draft that responds to all the notes will be the SECOND DRAFT.

Why am I telling you this? Well, this is my newsletter, I’ll tell you whatever I like. Personally, I always appreciate hearing from other writers how much of a grind it can be — and it can be! — just to get to something good enough. AND, I recently got a writing process question that I think really nicely pairs with my current headspace as I ponder: “I have a decent draft but is it decent enough?”

Here’s the (abridged) question:

“I REALLY STRUGGLE WITH OUTLINING. Nothing makes me feel less like a writer than my inability to outline effectively. I know every writer’s process is different, and some even choose not to outline at all, but I just cannot find something that works for me. My current process goes a little like this: Concept/logline --> blue sky brainstorm –> very rough shorthand bullet point outline (indecipherable to anyone but me) --> spend weeks trying to force myself to write a more detailed outline or treatment --> get nowhere --> give up --> go to script with those meager bullet points as my guide.

…I’ve had moderate success with this process… But the day has finally come where the gaps in my process are catching up with me… My issue with the freewheeling method is that it becomes really easy to convince myself that good enough = good. I’ll paint myself into a corner and end up settling for whatever I’m able to convince myself is the best combination of convenient and plausible to get me out. For a cold reader (including myself after some distance from the project), the scale tips PAINFULLY in favor of convenience. I can even occasionally detect this hacky problem-solving method while I’m writing. But I’ve mastered the art of muting that critical part of my brain… a skill that, I’m sure, is much more useful when writing from a real outline. I also know that, paradoxically, true freedom in writing often comes once the outline is solid.

… Any tips or tricks for outlining and writing treatments?”

Huge shoutout to

Aidan Kilpatrick

for this VERY GOOD question! And as a reminder to you all, my DM's here (and on instagram and TikTok) are always open for good questions.

This is a doozy to answer, but before I start writing a LONGWINDED technical answer, I want to be sure I get to the reassuring part… I too find outlining to be very hard. And very tedious. And I often find myself with an outline that’s insufficient, so I’m flying by the seat of my pants a little bit as I draft something.

All of that to say… A normal and very relatable problem. Now let’s try to solve it.

it really does feel like this at some point during the outline, every time

How do you write an outline and/or treatment that actually works and, better yet, is good?

If I knew the answer I wouldn’t also struggle with this! But here’s my experience of the problem so far, and some of what has helped me.

The process you’ve detailed above for coming up with a movie idea isn’t all that dissimilar from my own workflow, which I’ve written about before.

Idea > Brainstorm > big bag of material > force that into an outline > write a draft.

But how exactly does one go from “create a big document of a bunch of different ideas” to “outline that is decent?”

Here’s how I try to do it.

First thing I do (once I have my big bag of brainstorm material) is create a brand new document, separate from my “BIG BRAINSTORM DOCUMENT.”

This will be called “PROJECT OUTLINE.” Then in PROJECT OUTLINE I will start to put down the things I absolutely know I want and need, the superstructure of the movie.

I usually do this in a kind of “skeleton first” method, putting in the headings whether I know what actually happens there or not:

The Bare Minimum Outline Template

STATUS QUO
INCITING INCIDENT
END ACT ONE

ACT TWO
FUN AND GAMES / PROMISE OF PREMISE
MIDPOINT
ALL IS LOST

BREAK INTO ACT THREE
CLIMAX
CONCLUSION / SYNTHESIS

This isn’t exactly three act structure, the hero’s journey, nor “save the cat” structure, but a weird remix of the terms used in all three (plus a little bit of the story circle) that sort of gives me (and this is just me) the bare minimum signposts that I feel like I need to know to be able to start to fill in the rest of the project. Basically I’m just trying to get the major turns of the script down on paper.

Then I start to do what you’ve described above, get some more fleshed out beats to happen between each of these big things, to help drive us from one turn to the next. I’ll pluck stuff from the big bag of ideas, start tossing it in here, and seeing where (if anywhere) it fits. If it doesn’t fit, I need new connective tissue to get from a to b to c.

That will usually get me, if I’m doing a decent job of outlining, somewhere between 4-6 pages of bullet points. And I’m with you, a bullet pointed outline isn’t that useful, nor is it that interesting to share. I never share a bullet pointed outline with anyone anymore. Under any circumstances. Because they usually look like this…

• Charlie confronts Claire about what she did last night.

• I think this is a scene in which she’s trying to solve the problem, but it’s not yet a crisis?

• Now it’s a crisis. Calls Charlie.

• They hit the road.

• ACT TWO

Yawn!

How do we write something more detailed, and more useful?

What I have begun to do, in recent years, and after writing for television, is then take that outline and begin to do a “Scriptment.” This is just a portmanteau of the words “Script” and “Treatment,” and it has been (in my TV writing experience) the document that comes between breaking the episode on the board in the room, (the bullet pointed outline, just on note cards) and then writing the first draft. And this step is usually where you start to see all the structure and story issues really stand out.

How does a scriptment work? Basically you write the outline into your screenwriting software, with a little bit more detail, so that every single scene actually gets spelled out. It’s a bit more fun than a prose treatment (IMO) and it gives you a leg up when you then do send yourself to write the script because… it’s already in your document, waiting to be expanded upon!

So instead of the bullet point “Charlie confronts Claire” it becomes…

INT. CHARLIE’S APARTMENT - MORNING

Charlie confronts Claire about what she did last night. She’s upset that he didn’t just bring it up last night when it was happening. “You always do this, get mad when it’s too late.” He storms out of there, says not to expect him home. She says, “Good, I’ll do it again tonight, this time by myself!”

It’s going to be a great scene. Clearly.

Here’s why I like and advocate for a scriptment, especially for people (like me) who hate outlining.

Writing the scenes without actually writing the scenes is a good way to a) scratch the itch of “I just want to start figuring this out” while also, and more importantly b) starting to identify for yourself where things might be going off the rails structurally.

If you force yourself to write out all the major scenes in this format, you’re going to start to see which scenes do or don’t feel interesting, which scenes do or don’t feel propulsive, and which scenes start to feel like you’re simply settling into “What Would Happen Next Syndrome.”

Identifying where you’ve gone wrong is really one of the key skills we can hope to develop as writers. But it’s hard to do sometimes, because you are looking at a lot of material. Giving yourself less information to sift through in order to see where you’re going wrong can be very useful. In the scriptment phase, you won’t be able to fool yourself with a clever line or clever scene work. You’ll be staring at the fundamentals of each and every scene. What does each character want from the other in the scene? What do they do to get it? What stands in their way? What changes by the end of the scene?

This should make it a bit more glaringly obvious when nothing interesting actually is happening in the scene as proposed.

Not to mention, this has the added benefit of making it A LOT easier to start to cut and re-work and re-order stuff that doesn’t work. You won’t have written a 90 page screenplay that loses steam around the midpoint, you’ll have a 15-20 page scriptment that starts to lose steam.

As for how to motivate the sitting down and outlining / writing the treatment?

Well… I actually find writing the scriptment part to be fun, in a way that writing a prose treatment, or heaven forbid, a bullet pointed outline, isn’t.

So if you really feel like you’re pulling teeth on the outlining stage and want to skip ahead, this might be a comfortable middle ground to skip to.

You can still “discover” without needing to “just write the whole thing to see.”

How do you avoid the boring / rote connective tissue stuff?

Skip it! Just skip it! Only write the interesting scenes! I’m serious.

If you’re getting bored with a sequence of the movie, skip it. Go to the next part that’s interesting to you! You don’t have to write any of it in order.

And if you do start to skip around, rather than write it all in sequence, you’ll tend to be able to better weigh for yourself what exactly you will need to connect the two interesting scenes you’ve figured out. Sometimes you will find you don’t need any connective tissue at all. The connective tissue or the “what next” can be inferred.

Another way to think about this same challenge:

Don’t think about “what would happen,” think about “what do I want to see?”

“What would happen” tends to get us in trouble, because that’s where we’re pulling from the obvious. “What do I want to see” gives us somewhere a little more interesting to aim.

If you have something you really want to see, you can reverse engineer a way to get there, and make it happen, rather than settle for what would probably happen given certain circumstances. The crazier the thing you want to see, the harder it is to get to, the more interesting it will probably be getting us there as an audience.

Supposedly (according to

Blank Check

, great podcast, great newsletter, highly recommend) The Coen Brothers made Inside Llewyn Davis because they thought it would be interesting to see a folk singer getting beaten up behind the club. They just had to write an entire movie to make that scene they wanted to see make sense. And it turned out to be pretty good.

[I’ve been rewatching all their movies, as I listen to Blank Check’s series about their filmography, and I actually think they are the Kings of skipping past “what would be next” and instead shaping their movies however the heck they want]

And… after I’ve done all that, and I’ve taken the treatment and gotten it to a place where it feels good, I’ll write the movie. Then I’ll end up needing to rewrite the entire outline based on what doesn’t works, and start the whole process all over. On to the second first draft and then the third first draft, and so on.

Hopefully, at the very least, this long winded breakdown of process has been reassuring that it is simply, quite hard! You’re not alone!

I recognize that this was a scattershot and long post about a very important and very complicated part of the screenwriting process! So I’m curious…

How do you all outline? How do you all keep it interesting for yourself? Let me know in the comments! Maybe we can collectively solve this problem once and for all!

And let me know if you want more about outlining, or any of the other equally challenging parts of getting a first, second, third, or even third first draft completed.

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Previously on Hollyweird…

So you want to scare a screenwriter

Announcing my directorial debut "The Comedy Hour"

This isn't easy