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Pros and Cons of Writing With and Without an Outline

Continuing my evaluation of large language models (LMs), I gave GPT4 the same prompt as I gave Copilot. Here are the results.

(As a reminder, I believe writers must create their own content using their own brains. Using LMs for ideas and examples are acceptable uses for breaking through blocks, brainstorming, and conducting research. Copying and pasting results of prompts is never a good idea. But for the purpose of comparison and demonstration of the remarkable abilities these LMs have, I am doing exactly what I caution against.)

CM Strawn 7/11/2025

Chat GPT4 gave me a choice of two different writing styles. One voice is more academic, and the other is more casual. I prefer the second, simply because my approach to writing is a more relaxed style.

I have poste the response GPT4 gave with some formatting tweaks. This post may be TL;DR. 😉

Prompt: Write a blog post on the pros and cons of writing with and without an outline.

Response from GPT4:

You’re giving feedback on a new version of ChatGPT.

Which response do you prefer? Responses may take a moment to load.

Response 1

Sure! Here’s a blog post that explores the pros and cons of writing with and without an outline:


Writing With vs. Without an Outline: The Pros and Cons

Whether you’re drafting a novel, penning an essay, or outlining a blog post like this one, one critical decision you’ll face is how to begin. Some writers swear by outlines — carefully plotting every chapter, argument, or point before typing a single sentence. Others dive in headfirst, letting creativity guide the process. Both approaches have their merits — and drawbacks.

Let’s unpack the pros and cons of each to help you decide what works best for your writing style and goals.


Writing With an Outline

✅ Pros

  1. Clear Structure and Direction

An outline gives your work a roadmap. You know where you’re starting, where you’re going, and how to get there. This is especially helpful for complex projects or academic writing.

  • Efficient Use of Time

Outlines can make writing faster. With the major points and transitions mapped out, you’re less likely to get stuck or veer off track.

  • Fewer Revisions

A well-structured draft from the start often requires less restructuring later. This saves time in the editing phase and reduces frustration.

  • Helps Stay Focused

Outlines help prevent tangents. You’re more likely to stick to your main argument or storyline, which makes for a tighter, more coherent piece.

❌ Cons

  1. Can Feel Restrictive

Some writers feel boxed in by an outline. It may stifle spontaneity or make the writing feel formulaic if followed too rigidly.

  • Overplanning Can Lead to Procrastination

You might spend too much time perfecting the outline and delay the actual writing. It’s easy to fall into “planning paralysis.”

  • Limits Discovery

Some of the best ideas emerge in the process of writing itself. An outline might keep you from exploring unexpected but brilliant paths.


Writing Without an Outline

✅ Pros

  1. Encourages Creativity and Flow

Writing without an outline can feel more organic. You may stumble upon insights, themes, or characters you hadn’t considered at the start.

  • Frees You From Perfectionism Early On

Without the pressure of fitting ideas into a pre-made structure, you can write more freely and worry about coherence later.

  • Better for Exploratory or Personal Work

For journaling, creative writing, or reflective essays, discovery is the process. Not knowing where you’re going can be part of the magic.

❌ Cons

  1. Risk of Getting Lost

Without a plan, it’s easy to lose focus or write yourself into a corner. The piece might lack clear direction or require major revision later.

  • More Time Spent Editing

What you gain in initial creative freedom, you might lose in the editing phase. Restructuring a disorganized draft can be time-consuming.

  • Harder to Stay on Message

Especially in persuasive or informative writing, it’s easy to drift from your core message or theme when writing without an outline.


So…Which Should You Choose?

It depends on:

  • The genre or purpose: A research paper? Outline it. A poem or personal essay? Maybe not.
  • Your personality: Are you a planner or a pantser? (A “pantser” writes by the seat of their pants.)
  • The stage of the project: Some writers draft freely, then create a reverse-outline to check structure later.

Ultimately, many experienced writers blend both methods — outlining key points but leaving space for creativity along the way. Try both approaches and tweak until you find your ideal process.


What’s your writing style? Do you swear by outlines, or do you prefer to let the words lead you? Share in the comments!

I prefer this response

ChatGPT

Response 2

Here’s a draft for a blog post on that topic:


Should You Write With or Without an Outline? The Pros and Cons

Every writer eventually faces the question: Do I need an outline? Some swear by them, insisting they’re the secret to clarity and speed. Others ditch them entirely, trusting the process to lead them where it needs to go.

The truth is, there’s no single “right” answer. Both approaches have strengths and drawbacks—and the better you understand them, the easier it is to choose (or combine) what works for you.

Let’s break it down.


✅ The Pros of Writing With an Outline

  1. Clarity and Focus

An outline gives you a roadmap. You know where you’re starting, where you’re going, and how you’ll get there. This reduces the chances of wandering off-topic or missing critical points.

  • Saves Time During Drafting

Because you’ve already made major structural decisions, writing the actual draft often feels faster and smoother. You’re less likely to get stuck wondering “what’s next?”

  • Easier to Spot Gaps and Weaknesses

Outlining helps you see the big picture before investing in full paragraphs. If something feels thin or off-balance, you can adjust early—before you’re knee-deep in prose.

  • Helpful for Complex Projects

For long-form content (like books, reports, or technical guides), an outline can keep you organized and ensure all the moving parts fit together.


❌ The Cons of Writing With an Outline

  1. Can Feel Restrictive

Some writers find outlines stifling. They lock you into a structure that might not fit once you’re in the flow of writing.

  • Might Kill Creativity

If you’re someone who discovers ideas as you write, an outline can short-circuit that process. You might skip over surprising tangents or emotional depth because “it wasn’t in the plan.”

  • Time-Consuming Up Front

Building a detailed outline takes effort. For smaller or more informal pieces, that extra prep might not be worth it.


✅ The Pros of Writing Without an Outline

  1. Frees Up Creative Flow

Starting with a blank page allows you to explore ideas organically. Many writers feel this is when they do their most inspired and original work.

  • Surprising Discoveries

Without an outline, you’re more likely to stumble upon unexpected connections or insights that you wouldn’t have thought of during planning.

  • Great for Short or Personal Pieces

If you’re writing a journal entry, a poem, or a quick blog post, diving straight in can feel more natural and engaging.


❌ The Cons of Writing Without an Outline

  1. Risk of Rambling

Without a plan, it’s easy to meander, lose your point, or end up with a structure that feels chaotic.

  • Harder to Spot Weaknesses Early

You might write several pages only to realize you’ve taken a wrong turn—and now you need to rewrite large sections.

  • Can Take Longer Overall

Although skipping the outline saves time up front, the drafting and revision process can take longer as you figure things out on the fly.


📝 So… Which Should You Choose?

The decision depends on your goals, personality, and project type:

  • If you’re working on something long or highly structured, an outline is probably worth the effort.
  • If you’re writing a creative or exploratory piece, going without an outline may give you more freedom.
  • And if you can’t decide? Try a hybrid approach: sketch a loose roadmap with key points but leave space for detours and discoveries.

Ultimately, writing is not about rigid rules—it’s about finding what helps you produce your best work.


Would you like me to:

✅ Rewrite this in a more casual, conversational style (like a personal blog)?

✅ Or make it longer and more detailed, with examples and tips for hybrid outlining techniques?

✅ Or keep it concise for a LinkedIn-style post? Which audience are you aiming for?

I prefer this response

It’s amazing how smart these LMs are. They are wonderful tools, and I have watched my writing improve since I have been using them.

It would be easy to get lost in the convenience of allowing the bots to do my work for me. But I would lose my voice as a writer. I will continue to use them as tools and not as ghost writers.

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