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Writing Challenges: Lessons from a New Writer's Journey with Jesse Hawley

September 10, 2018
WRITING CHALLENGES:
Lessons from a New Writer’s Journey with Jesse Hawley

— a podcast episode —

New writers often overestimate their skills, avoid feedback, and get stuck between rigid rules and total creative freedom. Many write in isolation, struggling to spot their own weaknesses. This episode explores these challenges and how to overcome them with self-awareness, critique, and a balanced writing process.

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Inside Creative Writing

Table Of Contents Writing Challenges: Overcoming Obstacles and Finding Your Creative Growth Formatted and Edited Transcript Keep Growing as a Writer Share This Resource Writing Challenges: Overcoming Obstacles and Finding Your Creative Growth

Writing is full of challenges—self-doubt, inconsistency, and the constant pressure to improve. In this special episode, guest host Jesse Hawley shares hard-earned lessons from his own writing journey, offering insights that will help you overcome common struggles and grow into a stronger, more self-aware writer.

Jesse dives deep into the emotional and technical hurdles writers face, from overcoming arrogance in the early stages to learning how to take feedback and refine your craft. His personal experiences and practical advice make this an essential listen for writers looking to push past barriers and level up their storytelling skills.

By the end of this episode, you will:

  • Recognize the biggest mistakes new writers make (and how to avoid them)
  • Learn why admitting your blind spots is essential for growth
  • Discover how to seek and use constructive feedback effectively
  • Understand the balance between inspiration and disciplined writing
  • Pick up strategies for improving your writing through reading, self-reflection, and experimentation

Listen to the full episode or skim the edited transcript with relevant links below.

At Inside Creative Writing, we believe in practical, hands-on storytelling techniques—this episode is packed with actionable insights to help you move forward in your writing journey.

Formatted and Edited Transcript

Thanks for your patience. Here’s the formatted transcript following your exact instructions:

The Challenges of Growing as a Writer

Guest Host: Jesse Hawley

Thanks, Brad, and thank you, listeners, for taking the chance to listen to my writing experience and hopefully gain some writing insights.

Before we get into the show and what I’ll be talking about, I thought I’d give you a little introduction about who I am. My name’s Jesse Holly. I live in Sydney, Australia. It’s a rainy day today, so you might hear cars whipping past outside. My background is in science—I actually did research for a little while on flies and spiders, studying how their diets affect their lifespan and longevity. I have a whole bunch of interests, but I found creative writing to be the only true way to express myself wholly. The most effective way to transmit feelings, for me, is through prose.

Studying the craft of creative writing is overwhelming. It’s a very complicated world. There are no rules, which means you can get lost pretty easily. But at the same time, if you look around, there are only rules, and you can become paralyzed by them. There are plenty of writing gurus and idols to look up to, but there are also charlatans—people who espouse wisdom that, when looked at properly, may not be as deep as they claim. Learning the craft of creative writing sounds just as messy, complicated, and confusing as the real world—or at least, it does to me.

So that’s exactly what I’ll be talking about in this episode: how growing in the craft of writing, becoming a better writer, is actually like maturing as a person. I’ll share my most memorable mistakes—the ones that hurt the most and were therefore the most memorable—so you can be aware of them yourself. Finally, I’ll discuss what I think is the most important part of growth: seeking out and addressing your weaknesses and blind spots. I’ll cover how to identify them and how to address them. And, if time allows, I’ll throw in a couple of bonus lessons that I’ve picked up recently that might be helpful for you.

Admitting My Own Arrogance

As a young writer—I’ve been writing for two years—I think my biggest mistake by far was not admitting my own arrogance. Maybe this sounds familiar to you. If writing is maturing, then this is a hallmark of adolescence: thinking that you understand everything, that you’re equipped enough to make a big splash, and that anyone who says otherwise is naive to what you bring to the world. It’s classic teenage thinking, and it plagued my writing growth in the first six months.

Since this is the Inside Creative Writing podcast, I thought I’d share a quick story that ties into this idea. You may have heard it before—it’s becoming a bit of a platitude—but I’ll tell it anyway.

The story goes that a professor was traveling through Japan, looking to learn the art of Zen. He had been to many teachers but hadn’t found anything particularly enlightening. Finally, he was pointed toward a great Zen master. When he sat down with the master, the professor immediately launched into everything he already knew about Zen, his preconceptions, his ideas, and even his disappointments.

As the professor talked, he noticed that the Zen master had begun pouring him a cup of tea. The cup filled, but the master kept pouring. The tea overflowed, cascading down the sides and pooling on the table. Alarmed, the professor said, “Whoa, whoa, I really don’t need that much tea—it’s dripping everywhere!”

The Zen master looked at him and said, “Yes. This cup is your mind. It’s full of your preconceptions and ideas of Zen. How can I teach you anything when your cup is already full? Before I can fill it with new knowledge, you must first empty your cup.”

For the first six months of my writing, I had forgotten that I didn’t know anything. I wrote prolifically, constantly looking ahead to the idea of finishing a novel, but I wasn’t looking at others. And, even worse, I wasn’t looking inward at myself and my weaknesses. I wrote a lot—50,000 to 60,000 words—that amounted to little more than teenage poetry, a messy record of my creative maturation. I’m reluctant to go back and read it now for obvious reasons, just like most of us wouldn’t want to read our teenage diaries.

That was the first lesson I learned: I had to admit my own arrogance before I could grow.

Identifying My Weak Spots

Continuing with the analogy of aging, does anyone ever feel like a complete adult? I know I don’t. We’re all perpetual teenagers in some way. Once I admitted my arrogance, the next step was identifying the shortcomings and weak spots that needed serious attention.

There’s a quote by playwright Eugene O’Neill: “Life is for each man a solitary cell whose walls are mirrors.” If that were true, self-reflection would be easy. We could see our weaknesses clearly, like looking in a mirror—we’d spot the egg on our face and simply wipe it off. But it’s not that simple. Our reflections are obscured. We’re often standing too close to see ourselves objectively, which makes it difficult to even know we need help, let alone figure out where we need it.

So how do we address our blind spots? I found that one of the best ways is to seek help from others. What better way to see your shortcomings than through the eyes of someone else, through earnest and honest advice?

A good way to uncover your ignorance is to turn it inside out. Throw yourself into the domain of judgment and advice. It’s difficult to get answers when your questions exist only inside your own mind, with no outside perspective.

Academically, I’m pretty average—right in the middle—but I’ve managed to succeed at university by exposing my ignorance over and over again. I raise my hand, I ask questions, and I put myself out there, even if it makes me red-faced and nervous. It’s uncomfortable, but it gets me the answers I need. You have to be vulnerable before you can be corrected. Writing is no different.

Sharing My Work Before It Was Ready

One piece of common advice is never show your first draft to anyone. And generally, that’s great advice. People aren’t used to seeing first drafts, and let’s be honest—your first draft is probably a mess.

But I’ve ignored that advice time and time again, and the lessons I’ve learned from it have been the most memorable.

I’ve given excerpts of my first drafts to friends, which is fine. I’ve shared them with coworkers and even my boss. But, embarrassingly, I’ve also given my first drafts to complete strangers—two of them, in fact. They aren’t strangers now; their names are Sally and Catherine.

I was sitting in a café, working on my story, when I saw Sally outside reading a book. I don’t know what I was thinking, but I took a deep breath, walked outside, and said, “Hey, how’s it going?” I introduced myself, explained that I had been writing for about a year, and described my writer’s plight. Then I handed her my first draft.

It was a painful wait. Ten minutes later, I went to rescue her from the quagmire that was my first draft. It was shameful writing. But the advice she gave me—and the feedback I got from my boss and the other stranger—was honest, incisive, and ego-wounding. It laid me flat for days, but every piece of advice they gave me became a turning point in my writing growth.

Each critique became a landmark in my writing journey because it forced me to grow. The feedback I received included:

  • “You’re being too heavy-handed. Too many illusions and parallels. Just be honest with yourself.”
  • “You’re stuffing too much meaning and verbosity into each sentence, making it difficult to wade through.”
  • “This is too close to home—it sounds like you’re just diarizing. That might be therapeutic, but you should just tell a story.”

Had I not shared my work, those lessons wouldn’t have cut so deep. And without deep cuts, there is no real healing.

I’ll continue formatting and posting the rest of the transcript in the next response.

Learning From Others and Improving My Craft

Once I realized my weak spots, I knew I had to actively seek ways to improve my writing. One of the best ways I found was immersing myself in great literature. By casting myself before the minds of the greats, I could absorb techniques, emotions, and a sense of storytelling that would naturally refine my own writing. Reading is like a wormhole into personal growth and development—it allows us to live other lives and walk in others’ shoes. It is one of the most organic ways to grow as an artist.

At the same time, I also sought out poor literature. I recommended this on a recent episode of Inside Creative Writing, not just for inspiration but for self-reflection. When reading a shallow or ineffective piece, you may recognize aspects of your own writing in something that you don’t respect. And what greater motivation to improve than seeing yourself in work you wouldn’t want to be compared to? That’s a powerful way to self-diagnose your weaknesses.

Learning From Writing Books

Beyond reading literature, another invaluable resource has been books on writing craft. Early on, one of my biggest weaknesses was that I didn’t use narrative summary. I wrote everything moment-by-moment, scene-by-scene, dragging readers through the details in a first-person perspective that felt like The Blair Witch Project—except even that had cuts. I wasn’t even aware that narrative summary existed as a technique, let alone that I wasn’t using it.

By reading books on writing craft, I was able to put labels on my weaknesses and find ways to improve. If you’re interested, here are my top three books on writing:

Techniques of the Selling Writer by Dwight Swain – A fantastic book for learning the fundamentals of storytelling. This book got me moving in the right direction. Building Great Sentences by Brooks Landon – I love beautifully constructed sentences, and this book explores the craft of sentence-level writing. Reading Like a Writer by Francine Prose – A wonderful book that teaches you to analyze great writing. The appendix includes a list of must-read books, which is worth checking out if you want a guided journey through great literature.

If you want the full list of recommended reading from Reading Like a Writer, you can find it on its Wikipedia page.

The Danger of Taking Advice Too Literally

Another big mistake I made was taking writing advice too literally. Imagine if there were a book called How to Be a Perfect Human Being. It’s obvious that no such thing exists—no one is a perfect person, and following a strict set of “rules” for behavior would strip away what makes someone unique. The same applies to writing.

Francine Prose’s book Reading Like a Writer emphasizes that great works often break the rules. Beauty and grandeur in writing don’t come from following a formula; they come from honesty and authentic expression.

Once I admitted my ignorance as a writer, I overcompensated. The pendulum swung too far in the other direction—I took in all the rules, all the writing formulas, all the recommendations. My writing became a victim of everyone else’s advice, collapsing under the weight of external voices.

My recommendation? Read widely. Learn from writing books. Listen to advice. But keep your own voice stronger than the voices of others. Incorporate and evolve, but don’t conform to the point that you lose your individuality.

Knowing Yourself as a Writer

Before moving on, I want to touch on something a little personal but incredibly important: knowing yourself as a writer. Understanding what makes you unique, what challenges you face, and how to work around those challenges is essential to your growth.

To illustrate, here are a few things about myself that make writing challenging for me:

  • I get caught up in details and lose sight of the bigger picture.
  • I’m highly sentimental and dwell on feelings, which can make my writing melodramatic.
  • I sometimes overvalue my own opinions, making me resistant to change.
  • I love fun a little too much—staying out late, drinking, and generally indulging, which cuts into my writing time.

By recognizing these traits, I can actively work around them. For example, knowing that I tend to focus on details, I make an effort to step back and evaluate my writing for pacing and movement. If you can identify the ways your personality affects your craft, you can develop strategies to balance your strengths and weaknesses.

Writing is Difficult, But You Are Not Alone

Before I finish, I want to take a moment for some writing self-help.

There’s a quote from Thomas Mann: “A writer is somebody for whom writing is more difficult than it is for other people.”

Writing is difficult. Not just in terms of technique, experience, and the sheer amount of work it requires, but psychologically as well. Writing can be defeating. It’s confronting. It’s consuming. It takes over your waking life and even your dreams.

But knowing that we all go through this struggle makes it easier to bear.

I’ve been living the craft of being human for 27 years. I’ve been introspecting, developing myself, making mistakes, and learning from them. And even after all these years, my personality fluctuates daily. Some days, I feel sharp and confident. Other days, a single mistake or embarrassment makes me question everything I’ve ever done.

But I’ve lived long enough to know that this is The Human Condition.

And just like life, writing varies. Some days, you wake up and ideas flow effortlessly. Other days—most days—writing is a slog. But those bad days don’t define you as a writer. You are a writer in the grander scheme of things, and you must rise above the momentary struggles.

Understanding the Emotional Core of Writing

Recently, I’ve been thinking about writing in terms of a pyramid of emotional engagement.

At the deepest level, readers want to feel emotions. They want to be lifted by surprise, tension, and love. They want to be brought down into sorrow, only to rise again.

As writers, our job is to manipulate emotions. We do this by crafting engaging characters and compelling conflicts. At a more technical level, we refine these emotions through sentence structure, word choice, and pacing. But at its core, storytelling is about making the reader feel something.

I believe writers should constantly ask themselves: What emotions am I eliciting in the reader? How can I construct my plot and characters to amplify these emotions? Keeping this in mind can elevate your writing to another level.

Finding the Right Balance Between Discipline and Inspiration

There’s always been a debate: should you wait for inspiration or write every day no matter what?

I’ve experimented with both extremes. I’ve done the disciplined, “write 1,000 words every day” approach. But the result? Most of it was garbage, and the editing required to salvage it was not worth it. I’ve also tried waiting for inspiration—but of course, that doesn’t work either.

Now, I believe in something in between.

There’s a Simon & Garfunkel song, Cecilia, that depicts inspiration as a whimsical muse—one moment, she’s with you, fueling your creativity, and the next, she’s gone, off to inspire someone else.

I’ve learned that, like any passion, writing benefits from longing. Just as food tastes better when you’re hungry, writing flows better when you’ve let the ideas simmer. I no longer force myself to write when I have nothing to say. Instead, I let my ideas mature. I go for walks, live my life, and let my subconscious process my stories.

Everything I’ve ever written that I’m truly proud of has come from outside the keyboard—while walking, reading, or simply thinking about my story. The best ideas rarely come from staring at a screen.

So my recommendation? Use your non-writing time creatively. Let your ideas mature before sitting down to write. That way, when you do write, it will be powerful, rich, and fully formed.

The Weekly Challenge

This week’s writing challenge is to do something you’ve never done before or go somewhere you’ve never been. Step out of your comfort zone.

We tend to live in small, familiar bubbles, but as writers, we must be able to write about experiences beyond our own. So this week, try something new. Visit an unfamiliar place. Sit in on a court case. Have lunch in a neighborhood you don’t usually go to. Even if it doesn’t directly inspire a story, it will wake you up to the world, making you a better observer and writer.

That’s it for this episode. Thanks again, Brad, for giving me this opportunity. And thank you, listeners, for your time.

Happy writing.

Keep Growing as a Writer

The path to becoming a stronger writer is full of writing challenges, but the key is learning how to navigate them effectively. If you want to go deeper, check out our How to Write a Novel resource page, where we break down every step of the writing process—from brainstorming to revision.

Keep writing, keep learning, and remember—you’re never not a writer.

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