TAP033, The Case for Outlining, Outlining Pitfalls, and Overcoming Writing Obstacles

by | Authorpreneur Podcast, Fiction, habits, Outlining Your Novel, Season 3: How to Outline a Story, Writing

Hello, Writers!


I hope you are all well and are staying safe.


Before I dive into discussing how to outline a novel or the planning phase of writing, I thought it would be best to ask an obvious but nonetheless important question. Is outlining a good idea? Depending upon who you listen to, you will hear conflicting advice. To write quicker, some authors will say you need to ditch the outlining phase. While others abide by the age-old saying, “fail to plan, plan to fail.”


So which option is best for you?


In this episode, I share the things you need to consider before you decide to outline a novel, an important question that you need to ask yourself, a piece of advice that you need to keep in mind, outlining pitfalls, and my recommendations for new writers. On top of this, I talk about the downsides of creating an outline in order to give you a balanced and somewhat unbiased answer to this age-old question.


Things to Consider

Before you decide whether outlining is for you or even give it a try, there are three things you need to consider. These are how you write, any struggles you might have with your current writing process, and the story’s genre.


How Do You Write?

So, how do you write?


This question is a bit of a catch-22, especially if you are yet to finish a novel. If you haven’t written a book, consider what you are like in other areas of your life. Do you enjoy having no plans at all and going wherever the wind will take you? Or, does that scenario fill you with fear? Are you a lover of spreadsheets, planning or keeping a diary? Perhaps you identify with both of those things to a certain degree.


When you’re deciding whether you should outline or not, I believe it’s essential that you consider these things. To help you make the best decision for you, I will unpack these elements for you.


No Plans

If you don’t like having plans or feel suffocated by the concept of a tight schedule, then discovering the story as you write or writing by the seat of your pants might be a better option for you. At the moment, I’m experimenting with discovery writing because I want to give this season for the podcast a balanced view, and I’m a chronic outliner, as you’ll see in the next few episodes.


Before I started experimenting with writing into the dark, I took a course by Dean Wesley Smith on the topic. The course is by WMG Publishing, which is a company owned and operated by Dean Wesley Smith and Kristine Kathryn Rusch; the workshop is called Writing into the Dark and costs US$60, including taxes. Over on Amazon, Dean Wesley Smith has published a nonfiction book similar to the course. The ebook is priced at US$5.99. Michael La Ronn has created an in-depth review of the book on his Author LevelUp YouTube channel. If you’re on the fence about the book or course, I highly recommend checking out the video.


Writing by the Seat of Your Pants

Perhaps you already write by the seat of your pants, should you try to outline your next book? To help you discover the best answer, I have another question for you. Does your current writing process work for you? If it does, then why fix something that’s not broken. You can only write your way.; you cannot write like someone else. Stop listening to people who tell you that you have to do things a particular way. Just because a technique works for someone else doesn’t mean it will work for you. See that as a red flag. And, I hope that when you’re listening to my podcast, you realise that I’m talking about what works for me or discussing research that I need to do before I write. My advice is not set in stone, and I’m not saying that you need to strictly adhere to it.


Struggling to Write Without an Outline

I’m going to assume that you’re considering creating an outline because something in your writing process is not working for you. Now, I have an important question for you. Are you spending too much time in the revision or rewriting phase? If this is your scenario, you could try writing to an outline but tweak your current writing process before you do that. Check out the course or book by Dean Wesley Smith on Writing into the Dark. His technique is a little more involved than just flipping open your laptop and writing; it contains a series of steps that help you fix plot holes as you go along, thus reducing the amount of time you spend in the revision stages. If this doesn’t work, you could try writing to a loose outline.


Anxiety about Writing without an Outline

But what if the thought of flipping open your laptop and writing fills you with anxiety? Then you need to outline. You don’t necessarily need to outline every plot point, chapter, scene, and emotional beat in your story. But if that’s what makes you happy, feel free to write things this way.


What Are Your Writing Struggles?

Reflect on the last book you wrote. Where did you get stuck? Do you struggle with ideas or get blocked along the way and can’t write? Perhaps you love the planning phase but struggle with getting to the writing chair and keep putting it off. Or, do you love writing the first draft but hate rewriting? It’s essential that before you consider changing your writing habits, you understand where you struggle because knowing these things in advance will help you see the difference between your old habits and struggles and the issues that come with trying something new.


Document Your Writing Journey

If this is your first book, or perhaps you’re not sure about where you struggle in regards to writing, I highly recommend journaling as you write your next story. Keep track of where you get stuck, any fears, and other things that crop up as you write. Journaling is a good way of looking back and seeing where you’re getting stuck. Over time, you’ll see a pattern emerge in your journal.


Journaling for Beginners

When many people discuss journaling for writers, the advice is all about recording word count, time spent writing, and what you did during the session. Documenting this data is helpful because what doesn’t get measured cannot be improved upon because you don’t have the correct information to make good decisions. But also, you need to get into the emotional side of writing, especially if you don’t feel like writing, and you spend your writing time doing everything else but writing. A journal is an excellent way to discover why you are doing this.


Why I Put off Writing

The reasons why I struggle to get into the writing chair are complicated; it’s not just one thing. First of all, I’m lazy; I love procrastinating. If I can put it off until tomorrow, you can bet I will come up with a reason. When it comes to procrastination, I’m a genius. Perhaps I’m being a little too self-deprecating here; you get it. I’m sharing this because it’s worth knowing. Also, there’s the current health crisis. It’s impacted my mental health, and I haven’t had a vacation outside of my home in quite a long time. So, that’s in the mix as well.


Now, this is where things become painful. Since I published Missing, I have had a few experiences in my writing career that I’ve allowed to give fear a platform. I’ve become scared to publish, partly because I punish myself by reading and dwelling on my reviews. For example, my latest novella has a four-star average with seventeen reviews and ratings. Its rating is higher than the rating for Missing. I wrote this book with the lessons I learned, creating the second edition of my first novella. Readers like this second novella better than the first. Seventy percent of the reviews on my second novella are four and five stars, but I obsess over the thirty percent that are predominantly three-star reviews. These three-star reviews contain snarky comments that I’ve allowed to get to me, and I’ve let these comments take up residence in my mind. So, when I get around to writing, it’s an ordeal.


How did I become aware of all these things?



Journaling Your Way Back to the Writing Chair

If you’re stuck and don’t feel like writing, I recommend this simple journaling technique. Start by asking yourself the obvious question. Why don’t I want to write? And, just list as many reasons that your mind can come up with. Eventually, as you’re crafting those reasons, some of them will really hurt.


Sharing my habit of reading reviews and how I let it affect my writing life hurts. I let strangers dictate how I feel about my own work; it’s almost unprofessional. This is probably the reason why I’m struggling to write.


Once you’ve discovered the things stopping you from writing, you now know what you need to stop doing or cut out of your life. So, how do you get back to writing as you work on the obstacles in your writing life?


Getting Back to Writing

I’m lucky enough to have a partner who understands what it’s like to write novel or novella-length projects. My husband has a PhD, which means he’s had to write a thesis which is usually the length of a novel, defend said thesis, publish the work and hear the feedback. During these moments, when I tell him that I don’t feel like writing, he always gives me this pearl of wisdom. Just write the following sentence and write for a short amount of time. Having someone like that in my life is helpful.


So, I’m going to pay it forward.


If you’re struggling to write or haven’t written in a while, pause the podcast right here and write the next sentence in your current work in progress. Forget about writing scenes, chapters, or paragraphs; write the next line, and see what happens. Take your eyes off that grand goal of finishing your first draft, getting to the revision stage, booking your editor, publishing, daydreaming about adapting a Netflix series based on your books, or writing back to your rabid fan base. Forget all of these things and focus on the next sentence, then the one after that, because my husband is right, I have to write one sentence at a time; that’s all I do. When I get into this headspace where I can’t write, I’m making things more complicated than necessary.


What Does Your Genre Require of You?

Sometimes, your novel’s genre may impact whether you need to write with an outline or not. For instance, books with the broader romance category require a meet-cute, emotional tension, and a happily ever after or happy for now ending. If you read a lot of romance novels, you might not need an outline to start writing. But if you don’t read in the genre, you might be better off outlining the major plot elements in your story to help you write with reader expectations in mind.


What if you write a genre that has a more intricate plot, like a mystery? Then, I recommend outlining the significant elements in the story before you start writing, especially if you’re new to writing in the mystery genre. Why? A mystery requires red herrings, believable character motivations, clues for the reader to find, and timelines for the crime, victim, and perp to be planned out in advance. It’s a lot of information to hold in your head at once, and an outline can help you keep track of all of these moving pieces of the story.


But at the same time, just because I haven’t tried to write a murder mystery into the dark doesn’t mean that it’s not doable. I can only tell you what has worked for me up until now. In the reviews, a common comment is about how intricate the plot is in the novella. The majority of readers seem to enjoy the story. So, if you are writing something complicated, perhaps an outline is the right thing to do. When you write into the dark, you also need to trust that you will add all of the moving pieces in the right place. Because I’m more of a realist or pessimist. I struggle with this concept. Or, maybe I don’t trust myself to do this.


What Do You Need to Feel Confident to Start Writing?

Maybe confidence is the wrong word. Let me rephrase that, what do you need in order to feel more comfortable or less fearful before you start writing? Do you feel no fear and look forward to discovering the story? Or do you need a vague idea or loose outline before you start? This vague idea or loose outline could be an opening scene idea, concept, or an outline of the major plot points.


But what if, after creating this loose outline, you still feel anxious or fearful? This is how I feel after creating a short outline. If you feel this way, outline the entire story from beginning to end. It’s okay to do this your way. There is no right or wrong way to write a novel. As long as in the end, you create a book that your readers will love by crafting a coherent story structure and tying up loose ends in the final act. How you reach this point is up to you.


It’s a Guide, not a Straight Jacket

And most importantly, your outline is not set in stone; it’s not a straight jacket. Ideas have a way of shifting as you progress from outlining to writing the first draft. It’s okay to stray from it, as long as it serves the story. If and when you stray from your outline, you need to go back through your story and make adjustments where necessary; this is where foreshadowing comes into play.


The Downside to Outlining

While outlining has many benefits, like minimising plot holes and time spent in revisions, there are a few downsides that you need to be aware of before you decide whether it’s right for you. At this stage, I’m not going to create a pro/con list that’s obnoxiously long. That is something you can do for yourself and wouldn’t be beneficial if I created one here. But, I will focus on a pitfall that is crucial for you to know before you start outlining your first or next novel. Outlining can take the fun out of writing because there is no discovery phase; you know what’s going to happen. In fact, it can become an obstacle where eventually you don’t want to write anymore. Like in most things, preempting obstacles is the key to success.


Preempting Obstacles

What do I mean by preempting obstacles?


Earlier in this episode, I discussed your potential struggles with writing. These are the obstacles you will face along the way. If you’re unsure where you will struggle, do the journaling exercise; this will help you discover the writing obstacles you may face.


The best way to overcome an obstacle is to plan how you will react in advance. So, what are you going to do to ensure that you finish the first draft? How will you react when you feel stuck or are struggling with procrastination? What are you going to do when you see your writing obstacle floating towards you on the horizon?


If you don’t know what happens next in your story, it’s okay to take the time to think about it, maybe watch a film, read a book, take a nap, but come back to writing; don’t use this as an excuse to put off writing until you feel like doing the work. There will always be reasons why you need to do something else. Trust me, I’m a professional procrastinator. For those new to writing, it might interest you to know where I get stuck in the first draft phase. The end of the first act, midpoint and the transition into the last act are all places where I get stuck; I’m not saying you will too, but knowing this may help you. 


The Upside to Outlining

Because I’m a pessimist, it’s easier for me to start with the negatives. But it’s important to discuss both sides of an argument and give both sides equal weight. The most significant upside for outlining a novel is you don’t have to write the story in order. If you’re stuck writing a particular scene but you’re eager to write a scene that’s further on in the story, you can do that. I’ve been upfront about my lack of experience discovering a story as you write. In light of that, I can’t see how you could jump ahead in a story that you’re discovering. This ability helps you keep writing even though you’re stuck in a different part of the story. While you don’t have to write every day, keeping this momentum up is essential in the early stages of your writing journey, and outlining can help you achieve that.


Why Momentum in Writing is Crucial

The thing with creating momentum in your writing life causes writing to become a habit. Creating a habit around writing helps you put your writing life on autopilot. Consider what you do when you wake first thing in the morning. Those tasks are done on autopilot; you don’t need to remind yourself to do these things. A smart thing to do would be to attach your writing time to something you do on autopilot already. When I was a life and business coach, I recommended that my clients read The Habit Trap by Charles Duhigg if they were struggling with procrastination and wanted to figure out how to change their bad habits. Now that I’ve mentioned that book, I will add it on Goodreads and re-read the book to help me with my procrastination habits.


Recommendations for New Authors

So, what if you are a brand new writer; what is my advice to you. How do you feel about outlining? Would you rather fling open your laptop and start writing? Or, does writing without an outline fill you with a sense of dread?


With the answers to these questions in mind, I recommend that if you’ve never written a novel, then you should try outlining. Flesh out the main plot points of your story. Then sit back and ask yourself the following question. Can you write a story based upon this information?


Or, like me, are you panicking about what you should write between these plot points? If so, add scenes between these plot points into your outline. Then start writing your first draft. Try to avoid obsessing over the perfect outline because perfection is a myth we believe in when we are scared to take the next step.


Concluding Thoughts

I hope this episode gives you a few things to consider as you decide whether you should outline your first or next book? In the next two writing tip episodes, I will discuss how I go from a story idea to a fully fleshed out outline or, in layman’s terms, how to outline a novel. As always, I have a few important questions to ask. Are you on the fence about whether you should create an outline before you start writing your first draft? Or, have you found a way to write with or without an outline that works for you? I want to hear from you. Share your tips or struggles in the comments section below.


Thank you for listening, and happy reading and writing, everybody.


Your coach,

Amelia xx



Have you found the blog and podcast useful? Wish you could buy the host, Amelia D. Hay, a cup of coffee. Now, thanks to Buy Me a Coffee, you can!

Amelia D. Hay

Written by Amelia D. Hay

I’m Amelia. When I’m not hosting the Authorpreneur Podcast™️ and the Book Nerd Podcasts, I write Mystery Novels under the pen name A. D. Hay. And, I’m the author of Suspicion, the Lawn, and the Candidate.

On this blog, I help new writers to finish their first draft, prepare their manuscripts for professional editing, and when they get stuck in the first draft phase or are confused about the revision process.

Right now, I’m editing and preparing my soon to be published mystery novels, Suspicion, Duplicity, 24 Hours, and Immunity for publication.

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