Why Beginning Feels So Difficult, But Doesn’t Have to Be
What a community of writers can teach us about creative courage—and why fear and uncertainty aren't obstacles to creativity, but companions to every meaningful beginning.
July Theme: Creative Courage
Big Question: What does it take to begin, risk, and share what you create?
Week 1: Beginning Before You Feel Ready
The Question Behind the Question
This month we’re exploring creative courage, and this week we’re exploring the complexities of beginnings and the courage they take, which prompted Monday’s question: Do writers need to feel ready before they begin a new project?
The responses I received on Substack and across social media were split in half, with about half of you agreeing with some version of “Yes, preparation creates better work” and half of you agreeing with some version of “No, starting is how we become ready.” Which likely means that around half of respondents are ‘plotters’ and around half of respondents are ‘pantsers.’ And that’s not too surprising, especially when we consider the various genres and types of writing respondents dabble in.
What I did find interesting, however, is what I discovered when I asked some respondents individually what they thought the most difficult thing about starting a new project was, regardless of whether they felt prepared to begin working on it or not. And most of them replied with things like “Staring at a blank page in terror” and “Not knowing if it will be any good.”
Which leads me to believe that hesitations around beginning new projects likely have much more to do with what I referred to as ‘emotional blockages’ in Monday’s post than being technically prepared with outlines or conjuring interesting characters to follow— that feeling ‘ready’ is a much more emotional endeavor than we like to admit to ourselves or each other aloud that often. And that realization only further affirms my belief in the supportive conversations and dialogues I want to facilitate inside our community, as well as with what we read and write.
Perhaps these ‘emotional blockages’ are what give us the most insight into where creative courage truly begins. And it’s not when our fears disappear, but when we decide that fear will never get the final word.
The section that follows includes writers who offer us reminders for helpful ways to think about beginning new projects. They remind us not to think of beginnings as moments when we finally feel ready, but as moments we can meet with acts of trust, curiosity, and self-prescribed permission and courage.
And the sections after that recap my final thoughts on this week’s dialogue, then wrap up what it means to have creative courage so that we can begin.
Permission to Begin
When you’re starting a new project, it’s important to remember that you aren’t alone with whatever feelings or hesitations you might be experiencing and never have been and never will be. Not only will you have the Daily Drafts & Dialogues community to lean on now, but you’ll also have a substantial well of experience and advice from other writers to pull from. Because even they, some of the most well-adjusted and well-established writers to have ever existed, needed reminders and motivation boosts to push them through any blockages they were experiencing from time to time. We all do or will at some point. No one is immune to beginnings.
So, whenever you’re hesitant to begin and one or more of the following thoughts cross your mind, imagine an author you admire or respect telling you what you need to hear at that exact moment. Even start a dialogue with them if you have to, especially if it gets you writing.
“My first draft isn’t good enough.”
“Almost all good writing begins with terrible first efforts. You need to start somewhere.”
— Anne Lamott“The first draft is just you telling yourself the story.” — Terry Pratchett
“I’m writing a first draft and reminding myself that I’m simply shoveling sand into a box so that later I can build castles.” — Shannon Hale
“I’m not a very good writer, but I’m an excellent rewriter.” — James Michener
“You can only write regularly if you’re willing to write badly. One of the most important things a writer can do is give themselves permission to write badly.” — Jennifer Egan
“The first draft of anything is shit.” — Ernest Hemingway
“I have rewritten —often several times— every word I have ever published. My pencils outlast their erasers.” — Vladimir Nabokov
“Every first draft is perfect because all the first draft has to do is exist.” — Jane Smiley
“The blank page is terrifying.”
“You can always edit a bad page. You can’t edit a blank page.” — Jodi Picoult
“The blank page is a mirror reflecting back your own fears, but it is also a canvas waiting for your truth.” — Gloria E. Anzaldúa
“The scariest moment is always just before you start. After that, things can only get better.” —Stephen King
“There is nothing to writing. All you do is sit down at a typewriter and bleed.” — Ernest Hemingway
“The blank page is a door, but it’s a locked door until you find the key. Sometimes the key is just a single word.” — Margaret Atwood
“There is no greater agony than bearing an untold story inside you.” — Maya Angelou
“Writing about writer’s block is better than not writing at all.” — Charles Bukowski
“I don’t know where to begin.”
“Start writing, no matter what. The water does not flow until the faucet is turned on.” —Louis L’Amour
“Writing is like driving at night in the fog. You can only see as far as your headlights, but you can make the whole trip that way.” — E.L. Doctorow
“The experienced writer says to the anguished novice: ‘Just do it; get something, anything, on to the screen or page, just establish a flow of words, and criticise them later.’” — Hilary Mantel
“All you have to do is write one true sentence. Write the truest sentence that you know.” — Ernest Hemingway
“Much of what’s taught under the name of expository writing could be called ‘The Anxiety of Sequence.’ Its premise is this: To get where you’re going, you have to begin in just the right place... Why not begin where you already are?” — Verlyn Klinkenborg
“I need inspiration before I can write.”
“Amateurs sit and wait for inspiration, the rest of us just get up and go to work.”
— Stephen King“Don’t wait for inspiration. Discipline is more dependable than inspiration.” — Elizabeth Gilbert (Reflects a recurring theme in her talks and essays.)
“You don’t start with inspiration. You start with work.” — Octavia Butler
“You can’t wait for inspiration. You have to go after it with a club.” — Jack London
“Inspiration usually comes during work, rather than before it.” — Madeleine L’Engle
“I only write when inspiration strikes. Fortunately it strikes every morning at nine o’clock sharp.” — W. Somerset Maugham
“The art of writing is the art of applying the seat of the pants to the seat of the chair.” — Mary Heaton Vorse
“I need to know everything before I start.”
“I write entirely to find out what I’m thinking, what I’m looking at, what I see and what it means.” — Joan Didion
“A writer who waits for ideal conditions under which to work will die without putting a word on paper.” — E.B. White
“I have never started a poem yet whose end I knew. Writing a poem is discovering.” —Robert Frost
“I don’t want to know everything before I write because the writing is the knowing. It is the discovery of what I am capable of thinking.” — Toni Morrison
“Exercise the writing muscle every day... Writers are like dancers, like athletes. Without that exercise, the muscles seize up.” — Jane Yolen
“The first sentence can’t be written until the final sentence is written.” — Joyce Carol Oates
“I think there are two types of writers, the architects and the gardeners. The architects plan everything ahead of time... The gardeners dig a hole, drop in a seed and water it... They learn as the plant grows.” — George R.R. Martin
“What if my idea isn’t original?”
“There is no such thing as a new idea. It is impossible. We simply take a lot of old ideas and put them into a sort of mental kaleidoscope.” — Mark Twain
“Everything has been written before, but it hasn’t been written by you!” — Chris A. Jackson
“Even in literature and art, no man who bothers about originality will ever be original: whereas if you simply try to tell the truth (without caring twopence how often it has been told before) you will, nine times out of ten, become original without ever having noticed it.” — C.S. Lewis
“It’s not where you take things from—it’s where you take them to.” — Jean-Luc Godard
“If there’s a book that you want to read, but it hasn’t been written yet, then you must write it.” — Toni Morrison
“Everything that needs to be said has already been said. But since no one was listening, everything must be said again.” — André Gide
“Nothing is original. Steal from anywhere that resonates with inspiration or fuels your imagination…Authenticity is invaluable; originality is non-existent.” — Jim Jarmusch
“Write what you know. That should leave you with a lot of free time.” — Howard Nemerov
“I’m afraid of what people will think.”
“Close the door. Write with no one looking over your shoulder. Don’t try to wonder what they’re going to think about it. Just write.” — Barbara Kingsolver
“Write what disturbs you, what you fear, what you have not been willing to speak about.”
— Natalie Goldberg“An unbelieved truth can hurt a man much more than a lie. It takes great courage to back truth unacceptable to our times.” — John Steinbeck
“Write to please just one person. If you open a window and make love to the world, so to speak, your story will get pneumonia.” — Kurt Vonnegut
“If people wanted you to write warmly about them, they should have behaved better.” —Anne Lamott
“You can’t think about the audience. You have to write what you want to write.” — Judy Blume
“The only way you can write the truth is to assume that what you set down will never be read.” — Margaret Atwood
“So long as you write what you wish to write, that is all that matters; and whether it matters for ages or only for hours, nobody can say.” — Virginia Woolf
“When I dare to be powerful, to use my strength in the service of my vision, then it becomes less and less important whether I am afraid.” — Audre Lorde
“Maybe I’m not really a writer.”
“A writer is someone for whom writing is more difficult than it is for other people.” — Thomas Mann
“A professional writer is an amateur who didn’t quit.” — Richard Bach
“A writer is a person who writes. That’s it. It’s a verb, not a noun.” — Margaret Atwood
“You don’t write because you want to say something, you write because you have something to say.” — F. Scott Fitzgerald
“The biggest problem we have as writers is imposter syndrome. We feel like we are sneaking into a party we weren’t invited to. But remember, everyone else feels the same way.” — Neil Gaiman
“I think that if a writer ever stops doubting themselves, they stop being a writer.” —Shirley Jackson
“I would like to say that it gets easier, but it doesn’t. You just learn to live with the fear that you aren’t good enough.” — Harper Lee
“I’m afraid of making mistakes.”
“Get it down. Take chances. It may be bad, but it’s the only way you can do anything really good.” — William Faulkner
“The beautiful part of writing is that you don’t have to get it right the first time…” —Robert Cormier
“If I waited for perfection, I would never write a word.” — Margaret Atwood
“The only kind of writing is rewriting.” — Ernest Hemingway
“You fail only if you stop writing.” and “You’re afraid of making mistakes. Don’t be. Mistakes can be profited by... If you hide your ignorance, no one will hit you and you’ll never learn.” — Ray Bradbury
“I hope that in this year to come, you make mistakes. Because if you are making mistakes, then you are making new things, trying new things, learning, living, pushing yourself, changing yourself, changing your world. You’re doing things you’ve never done before, and more importantly, you’re Doing Something.” —Neil Gaiman
“A man of genius makes no mistakes. His errors are volitional and are the portals of discovery.” — James Joyce
“This project feels too big.”
“Lose track of the 400 pages and write just one page for each day, it helps. Then when it gets finished, you are always surprised.” — John Steinbeck
“Bird by bird, buddy. Just take it bird by bird.” — Anne Lamott
“The secret of getting ahead is getting started. The secret to getting started is breaking your complex overwhelming tasks into small manageable tasks and then starting on the first one.” — Mark Twain
“We have to be willing to grow to meet the work. Sometimes a book is too big for us, and we have to grow until we are big enough for it.” — Madeleine L’Engle
“A word at a time... It sounds too simple to be true, but consider the view from the other side. If you didn’t visualize a total of four hundred pages, if you only thought of the page you were writing today, it wouldn’t be so formidable.” — Stephen King
“First forget inspiration. Habit is more dependable. Habit will sustain you whether you’re inspired or not. Habit will help you finish and polish your stories.” — Octavia Butler
“I don’t have the courage.”
“Courage is resistance to fear, mastery of fear—not absence of fear.”— Mark Twain
“You must stay drunk on writing so reality cannot destroy you... Go to the edge of the cliff and jump off. Build your wings on the way down.” — Ray Bradbury
“Courage is the most important of all the virtues, because without courage you can’t practice any other virtue consistently. You can practice any virtue erratically, but nothing consistently without courage.” — Maya Angelou
“You have to write the book that wants to be written. And if it can be written by inside sources, it will be. But if it cannot, you have to go to the darker place.” — James Baldwin
“Vulnerability is the birthplace of innovation, creativity, and change.” — Brené Brown
“Creativity requires the courage to let go of certainties.” — Erich Fromm
“If you’re not prepared to be wrong, you’ll never come up with anything original.” — Sir Ken Robinson
“You cannot swim for new horizons until you have courage to lose sight of the shore.” —William Faulkner
“The moment that you feel that, just possibly, you’re walking down the street naked, exposing too much of your heart and your mind and what exists on the inside, showing too much of yourself. That’s the moment you may be starting to get it right.” — Neil Gaiman
Upon Further Reflection
After further reflection, I’ve come to see how crucial embracing uncertainty is to beginning new projects, and that creative courage has a lot more to do with feeling ready than actually being ‘ready’ with an outline, plan, or approach, even if those things can help us feel ready most of the time. So, the important question isn’t about whether you’re a plotter or a pantser, but how you’re able to embrace uncertainty as part of your writing process, especially when beginning new projects.
I’ve also come to see how important it is to question what we’re doing and how we’re doing it, but only as we’re working out our questions via writing and active discovery. Otherwise, we risk questioning our own intentions and value too much, which can lead to crippling self-doubt about whatever we’re writing, as well as our identity as writers. Some level of doubt is normal and healthy when beginning new projects, in other words, but only when we’re doing the writing work it takes to grapple with it and potentially unravel those doubts, one word, one sentence, one page at a time.
And most importantly, I’ve come to understand how crucial supportive writing communities are when starting new projects. It’s impossible to know how starting a new project will feel, and if you’ll ever feel ready, especially when each new project comes with its own doubts and things for us to worry about. But hearing helpful reminders and encouragement from fellow writers who have experienced what we’re experiencing at those moments can be powerful.
Dialogue Wrap-Up: Creative Courage and the Courage to Begin
Creative courage is not the absence of uncertainty, but the willingness to begin while uncertainty is still present.
Every writer, whether they outline extensively or discover the story as they go, faces the same vulnerable moment of taking the first step. Their fears may look different, but they’re not.
A plotter may worry: What if my carefully planned story doesn’t work? What if I spend all this time outlining and still can’t find the heart of the story?
A pantser may worry: What if I get lost? What if I write hundreds of pages and discover I have no idea where I’m going?
But both are navigating the same fundamental question: Can I trust myself to create something meaningful?
Plotting and pantsing are not opposites. They are two different ways of approaching the same act of discovery, which requires the same creative courage.
The plotter discovers through preparation. The pantser discovers through exploration. One begins with a map, while the other begins with a journey. But both require creative courage to begin.
“Structure does not restrict creativity; it focuses it.” — For plotters, structure can be an act of creative courage, when choosing a direction, making decisions, and creating a foundation strong enough for their imagination to flourish. A framework does not remove possibilities for them but creates a container where creativity can deepen.
“Writing without a map isn’t haphazard; it’s discovery.” — For pantsers, uncertainty is not a failure of preparation, it’s part of the process, and requires courage to step into that uncertainty. Leaving room for surprise, intuition, and unexpected turns can reveal elements of the story that could never have been planned.
Both approaches require trust. The plotter trusts the plan. The pantser trusts the process. Both must eventually surrender control and allow the story to become something beyond their original idea.
Real creative courage comes when writers stop measuring their process against someone else’s.
There is no single ‘right’ way to begin. The best method is the one that helps a writer move from imagination into action.
Beginning is difficult because every new project asks us to step into uncertainty. The outline is uncertain until it becomes a story. The blank page is uncertain until it becomes a draft. The first draft is uncertain until it becomes something worth revising.
The lesson of Creative Courage: Readiness often arrives after we begin, not before.
Writers don’t overcome fear and then start. They start, and through the act of creating, they build confidence, clarity, and momentum. Whether we begin with a blueprint or a blank page, every writer is practicing the same courage it takes to trust that something can emerge where nothing exists yet.
The question isn’t whether we should begin with a map or without one, it’s whether we are willing to begin at all, knowing that uncertainty is not a sign we are doing it wrong, but proof that we are creating something new.
Beginning is the first act of creative courage, but it is not the last. Once we give ourselves permission to start, we are invited to take the next brave step: making choices that challenge us, surprise us, and move us beyond what feels familiar. Next week, we’ll explore the courage it takes to take creative risks once we begin.
I invite you to join this week’s Dialoguers chat to share your experiences on beginning new projects with us, or any of your reflections on what it means to create beyond the boundaries of what feels safe and familiar.
Whether you join to share your responses, ask more thought-provoking questions, or connect with other writers and support their work, we look forward to your contributions as we continue to discuss creative courage this month!
Continue Exploring July’s Creative Courage Theme
ICYMI—>This week’s Posts: Beginning Before You Feel Ready
Beginning Before You Feel Ready: Writing Prompts
Do writers need to feel ready before they begin a new project?
Beginnings and endings are linked in a lot of ways…
Consider going more in depth with this month’s theme with July’s Creative Courage Writing Collection.
The writing collection is designed to help you explore creative courage from different angles: discovering your voice, strengthening your craft, experimenting with new approaches, and reflecting on the writer you are becoming.
The free Dialogues posts and Drafts writing prompts posts that will be published every Saturday this month will explore the outward side of creative courage—beginning, risking, and sharing— and should complement this collection quite well, which invites you to go much deeper into the internal work of creativity with 30 guided writing prompts and craft exercises, reflections, as well as three options for guided monthly writing challenges for those who want to go even further than that.