Series: How to Overcome Writer's Block

Expand your life experience.

Expand your life experience.

“I’ve now written three novels, but I don’t know how to write them. Each has been the result of its own esoteric, inefficient and frustrating process, each a genuine surprise. I have yet to write the book I planned to write, yet to write in the period of time I imagined the book would take, yet to sustain one way of working through an entire book. I try lots.”

-Jonathan Safran Foer


For a writer, there is nothing quite a blank page. That first moment of opening a notebook or document to begin is an exhilarating tightrope walk between hope and fear.

At first, the blankness is an opportunity.

“That incredible freedom you have with the blank page … Writing the first draft of a book is the biggest high you can get, because there are no rules.”

-Irvine Welsh

You can share your experiences, look at them again with more objectivity, and make sense of your best moments as well as your failures. 

Or, you can create from scratch. Characters and unexplored worlds can step from your imagination into the reader’s mind. 

You can create someone you relate to, someone you’ve always wanted to be, someone you can’t quite understand—explore what motivates people, what makes them grow, decline, and change.

Writing can be limitless possibility. 

“I remember an immense feeling of possibility at the idea, as if I had been ushered into a vast building filled with closed doors and had been given leave to open any I liked. There were more doors than one person could ever open in a lifetime, I thought (and still think).”

-Stephen King, On Writing

The blankness can also transform into a brick wall. When you feel unable to write something worth reading, the white page can taunt you: Do I have nothing of value to say? 

Writer’s block can feel like nights when 3 o’ clock in morning hits and sleep still evades you. 

Each minute crawls by. Five possible hours of rest turns into four and fifteen minutes turns into three and a half. The stress of not sleeping makes it harder and harder to get to sleep. Will you be awake all night? How do you escape the cycle?

A while back, a well-meaning friend of mine asked if I’d been writing lately. 

I answered with, “I’ve been thinking a lot about writing—in other words, no.”

Then, he responded with words I’ve heard many times before: “Just write.”

This is age-old advice: just sit down, push yourself to write something, and the words will come. 

“What I try to do is write. I may write for two weeks ‘the cat sat on the mat, that is that, not a rat.’ And it might be just the most boring and awful stuff. But I try. When I’m writing, I write. And then it’s as if the muse is convinced that I’m serious and says, ‘Okay. Okay. I’ll come.'”

-Maya Angelou

In fact, there are an endless amount of successful writers who can claim the answer to writer’s block is to “just write.”

“Compel yourself to write several hours every day no matter how bad you feel.”

-William H. Gass

“I think writer’s block is simply the dread that you are going to write something horrible. But as a writer, I believe that if you sit down at the keys long enough, sooner or later something will come out.”

-Roy Blount, Jr.

“I encourage my students at times like these to get one page of anything written, three hundred words of memories or dreams or stream of consciousness on how much they hate writing — just for the hell of it, just to keep their fingers from becoming too arthritic, just because they have made a commitment to try to write three hundred words every day.”

-Anne Lamott, Bird by Bird

It’s possibly the most common writing advice there is. And, if you’re feeling blocked, it’s also possibly the most useless.

To realize you’re blocked, you most likely already tried to write. And, yes, you can force yourself to sit there weeks on end, dumping your stream of consciousness out, hoping that eventually something better appears.

But, doesn’t there have to be a more useful approach than the simple, “try again”? 

In competitive chess, when you lose a game, the best way to improve isn’t to just blindly try again at the next tournament. 

If you want better results, you prepare. You study what went wrong, looking over your losses and mistakes. You study materials (books, articles, annotated games) from stronger players, addressing the weak points of your game. Only then do you throw yourself back into competitive play.

So, I set out to find advice for struggling writers that goes beyond “just write”. 

Lately, I’ve become a bit of an addict on reading about the craft of writing itself, including interviews and memoirs by great writers of the past and present. Here is the writing advice I’ve found most effective. 

1. Expand your life experience.

“Write all the time, they’ll tell you. Write for your college newspaper. Get an MFA. Go to writers’ groups. Send query letters to agents.

What do they never say? Go do interesting things.

…So if you want to be a writer, put ‘writing’ on hold for a while. When you find something that is new and different and you can’t wait to share with the world, you’ll beat your fat hands against the keyboard until you get it out in one form or another.

Everything that is good in my writing came from risks I took outside of school, outside of the “craft.” It was sleeping on Tucker Max’s floor for a year. It was working as Robert Greene’s assistant. It was working at American Apparel, watching the office politics and learning how to get stuff done. It was dropping out of college at 19. It was saying yes to every meeting and introduction I got, and hustling to get as many as I could on my own. It was reading dozens of books a month.

It was going to therapy. It was getting into pointless arguments. It was having friends who are smarter than me. It was traveling. It was living (briefly) in the ghetto. I was able to write about the dark side of the media because I put myself in a position to see it firsthand.

All these things gave me something to say. They gave me a perspective. They gave me a fucked up writing style that makes my voice unique.”

-Ryan Holiday, “So You Want To Be A Writer? That’s Mistake #1

The craft of writing is often misunderstood in two different directions, each on the extremes. 

  1. There’s the old-fashioned impression of writing—that it’s reserved only for refined individuals who have offices full of leather-bound books and ornate pens, who exclusively consume single-barrel bourbon neat, who are full of wisdom to share about the great wars and crises of humanity. 
  1. On the other hand, with such a low barrier to entry in modern times (it costs nothing and can take as little as 10 minutes to start your own blog or upload your manuscript to Amazon self-publishing), it can be seen as an easy craft, suited for everyone. 

Both of these extremes are off the mark. At heart, the most important part of being a writer is having something to say and wanting to share it. 

To have something to say, you have to live. You have to make mistakes, lose things that matter to you, lose yourself, recover, and make brand new mistakes. 

If you stare at the screen and your mind goes blank, the first step of writing your novel may be stepping outside of your front door. 

“Keep human! See people, go places, drink if you feel like it.”

-Henry Miller, Henry Miller on Writing

“But you’ve also got to be prepared to get out and do stuff and look around and engage with people. You’ve got to engage your senses. You live your life, and that way you can bring something new to the table, because otherwise you’re just a compiler or an editor of other people’s experiences.”

-Irvine Welsh, “Failure Is More Interesting”

Experience more, but with a grain of salt:

“When I was young, I idealized writers like Hemingway, Jack London, Orwell, writers who were active in the world. There’s no question at all that when I joined the army there was a kind of literary impulse behind it. I’d learned all the wrong lessons from Hemingway and Erich Maria Remarque and James Jones, all these writers I admired—they were telling me, Don’t be such a fool as to get yourself in a position where you’re going to get shot for nothing by some other fool. And all I could think of was, Jeez, they wrote these great novels because they put themselves in danger and traveled to places where nobody cared if they lived or died. Great! That’s for me!

…the appetite for “experience” is natural to young writers. I’ve seen it often, and surely I had it, no question. But to get back to Flannery O’Connor, what kind of experience did she have, afterall? She spent, what, one year away from her farm in Milledgeville? Yet her stories are full of life and drama and real humanity, and it’s because she kept her eyes open. Experience is about seeing what’s around you, not going different places and putting yourself in danger—it’s about being attentive, seeing how things work, what they add up to.”

-Tobias Wolf, “The Art of Fiction No. 183”

This entry is part 1 of 5 in the series How to Overcome Writer's Block

Don’t underestimate your ideas.

Don’t underestimate your ideas.

“I was 22 and didn’t realise I was working on a novel, which made things easier, as there were fewer questions to force myself not to ask: is it good? Will anyone care? Do I?

I have never experienced what is often called “writer’s block” – the inability to think of what to write. But I am a chronic sufferer of “Jonathan block” – the inability to value my thoughts.”

-Jonathan Safran Foer

As mentioned in the intro to this article, writing blocks often occur because of self-doubt. Self-doubt can be extremely dangerous to ideas that are still developing. Some of the most successful works of literature required a leap of faith to see the ideas through to the finish line.

“Let’s get one thing clear right now, shall we? There is no Idea Dump, no Story Central, no Island of the Buried Bestsellers; good story ideas seem to come quite literally from nowhere, sailing at you right out of the empty sky: two previously unrelated ideas come together and make something new under the sun. Your job isn’t to find these ideas but to recognize them when they show up.”

-Stephen King, On Writing

The first draft is not the time to be too critical of your work. Seeds of ideas need a chance to grow into their potential. 

“Get the first draft done no matter what. Then the real work begins.

Too many people agonize paragraph by paragraph.

to the finish line. Then go back and walk over every step you made and see what you can do better. This is the real gift you give your reader.”

-James Altucher, “The Horrible Things About Being a Full-Time Writer”

Some of the greatest works of literature began as ideas that were nearly tossed away. I was happily surprised to find that my favorite fiction book had very humble roots:

“It started life as a paragraph scrawled on a scrap of paper very early one morning after a disastrous night on the town.

Many months later I found that scrap of paper and thought the voice was intriguing.”

-Jay McInerney on writing Bright Lights, Big City

The novel’s second person narrative is the main standout aspect of the book. Yet, even that was initially doubted.

“When I told my best friend and future editor Gary Fisketjon what I was doing he said that he hoped I wasn’t trying to write an entire novel in the second person. I was too embarrassed to tell him that that was precisely what I was doing.

the prose seemed to go a little flat; I stuck with the second person, and I have certainly never regretted it. It’s not a very versatile mode and I don’t recommend it in general, but I can’t imagine Bright Lights in any other voice.”

-Jay McInerney

Writing can be such a solitary struggle. At the end of a long session of writing, you feel excited about what you’ve created but also worried that you’ve spent too much time engrossed in your own thoughts. It can be very difficult to tell if your writing will be well-received or only end up appealing to yourself. 

“Perhaps most importantly, write for an audience of one — yourself. Write the story you need to tell and want to read. It’s impossible to know what others want so don’t waste time trying to guess. Just write about the things that get under your skin and keep you up at night.”

-Khaled Housseni, “Khaled Housseni: How I Write”

During my years as a chess journalist for US Chess, one article that was a major turning point for me was “What’s Your Goal in Chess?”. The article explored a new style of writing for me, including personal anecdotes about my own chess struggles. I spent the majority of three days straight working tirelessly to make the piece as strong as possible. I also spent most of that time excited about what I was writing. 

However, by the time I finished the article late on the third night, I re-read it one last time and felt discontent with the entire piece. I worried that the personal anecdotes I included would come off as self-indulgent. I doubted even publishing it.

I was dead-wrong, suffering the curse of too many re-reads (eventually, anything can feel banal if you read it enough times). 

“If I think something I’ve written is something I would enjoy reading, I’m pleased. I can’t wear myself out second-guessing some phantom reader.”

-Tobias Wolff in an interview with The Paris Review

When I finally pushed the self-doubt away and hit ‘publish’, the article was better received than anything I had written at that point. It went on to win the award for “Best Instructive Lesson” from the Chess Journalists of America and ranked 2nd in the 2016 Best of US Chess Top 10.

“….stopping a piece of work just because it’s hard, either emotionally or imaginatively, is a bad idea. Sometimes you have to go on when you don’t feel like it, and sometimes you’re doing good work when it feels like all you’re managing is to shovel shit from a sitting position.”

-Stephen King, On Writing

To conclude, here is a quote by blogger James Altucher that has guided me through many instances of writing self-doubt.

“I never hit publish unless I’m afraid of what people will think of me.”

-James Altucher

Why would this fear be a good thing? Because it means you’re truly putting your ideas and yourself out there. The will to express something, despite it being hard to say, means that it is all that much more genuine and essential.

This entry is part 2 of 5 in the series How to Overcome Writer's Block

Start with one small step at a time.

Start with one small step at a time.

My 11-year-old self sits at a chess board. On all sides of me, there are rows after rows of chess boards, nearly overflowing the vast chandelier-lit ballroom in Las Vegas. For the first time, I am so nervous I’m shaking at the board. 

It’s the final round of the highest stakes tournament of my young life, the finale of three days straight of nerve-wrecking competitive chess. I’ve won the first five games, and I’m tied for first place with an opponent who has done the same. 

I know that I am a single victory away from winning an inconceivable amount of money to me at the time. I am also aware that I’m a single loss away from blowing it.

What got me through this?

From the start of the tournament, one thought carried me through: “One game at a time”. 

This came with the realization of what seemed to hold me back at previous tournaments: the immensity of aiming to win every game. I realized how overwhelming and distracting this is as a goal because really—you can only ever win one game at a time. It’s a waste to worry about any of the other games until you get to them. 

This revelation made the nerve-wrecking and immense task of winning such a high stakes tournament within reach. I felt such relief at the thought that I only ever have to deal with the game at hand. That last round, I crawled one nerve-wrecking move at a time through to a messy and hard-fought victory. 

In the same way, you can’t write an entire book in one sitting. No matter how short or epic you intend your piece to be, you’ll still write it one word at a time.

“On days when the mind and the page went blank, I just kept my fingers close to the keyboard, walking distance close, just in case something would happen. I had to pay close attention. I reminded myself that a novel begins by one word following another. One sentence followed by another. One paragraph followed by another; that discipline, soldier-like discipline was absolutely necessary- as Flannery O’Connor once said, ‘If there’s a great idea somewhere out there, it knows where to find me- between 9-12 at my desk;’ By working on sentences one at a time, I realized I wouldn’t be so intimidated by the scope of the novel.”

-Helena Maria Viramontes in an interview with La Bloga

Often times when I begin a writing session, I start with the simple aim of writing one worthwhile sentence. Of course, once I have an idea that leads to one sentence, more tend to flow onto the page with it. 

It’s a useful trick. Think about it, how hard is it to write one sentence on a topic, about an experience, or for a fictional story? One sentence? That’s so reachable.

“Abandon the idea that you are ever going to finish. 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, Steinbeck: A Life in Letters

For more on the idea of starting small, check out tip #7 of 10 Tips to Writing Every Day.

This entry is part 3 of 5 in the series How to Overcome Writer's Block

Read to jumpstart your writing.

Read to jumpstart your writing.

“If you want to be a writer, you do two things above all others: read a lot and write a lot.”

-Stephen King, On Writing

Reading can be one way to jumpstart your writing, especially reading examples of the type of writing you’d like to create. 

When I first read one of my favorite books, Bright Lights, Big City, I wrote a short story of my own, testing out the unique writing style of the book (the entire novel is written in second person). Not only was this exercise fun and inspiring, I think I learned a lot about my own writing in the process. 

I believe most writers develop their own voice gradually through trial and error. By immersing yourself in many influences and trying your hand at the writing style of others, you learn what works for you and what doesn’t. You start to see what you can do differently. You find ways to take what’s been done before and add your own spin to it.

“When I read Ray Bradbury as a kid, I wrote like Ray Bradbury—everything green and wondrous and seen through a lens smeared with the grease of nostalgia.

…When I read Lovecraft, my prose became luxurious and Byzantine. I wrote stories in my teenage years where all these styles merged, creating a kind of hilarious stew. This sort of stylistic blending is a necessary part of developing one’s own style.”

…You have to read widely, constantly refining (and redefining) your own work as you do so.

…Reading is the creative center of a writer’s life. I take a book everywhere I go, and find there are all sorts of opportunities to dip in. The trick is to teach yourself to read in small sips as well as in long swallows. “

-Stephen King, On Writing

“I read everything. I read my way out of the two libraries in Harlem by the time I was thirteen. One does learn a great deal about writing this way. First of all, you learn how little you know. It is true that the more one learns the less one knows. I’m still learning how to write. I don’t know what technique is. All I know is that you have to make the reader see it. This I learned from Dostoyevsky, from Balzac.”

-James Baldwin, “The Art of Fiction No. 78”

You can also read books on the craft of writing itself. There’s a reason I’ve been heavily quoting Stephen King’s book, On Writing: A Memoir of the Craft—It’s a superb book on the writing process. It can be so encouraging to find relatable voices of other writers who have been through the same challenges and struggles and made it to the other side–to see that Stephen King too originally had doubts in works that went on to be key pieces of writing for him. Here’s the origin of Carrie, his first published novel:

“I did three single-spaced pages of a first draft, then crumpled them up in disgust and threw them away.

The next night, when I came home from school, Tabby had the pages. She’d spied them while emptying my wastebasket, had shaken the cigarette ashes off the crumpled balls of paper, smoothed them out, and sat down to read them. She wanted me to go on with it, she said. She wanted to know the rest of the story. I told her I didn’t know jack-shit about high school girls. She said she’d help me with that part. She had her chin tilted down and was smiling in that severely cute way of hers. ‘You’ve got something here,’ she said. ‘I really think you do.’ “

-Stephen King, On Writing

I love reading books about writers and the craft of writing. When I wanted to prepare myself for publishing this blog and more openly sharing my writing, I found a relatable voice from Adair Lara in Naked, Drunk, and Writing

When I wanted to strengthen my plot writing skills, Story Genius by Lisa Cron helped me write the character backstory that plot is built from. The Plot Whisperer by Martha Alderson helped me learn to create plot within my “Pantser” (a writer who writes “by the seat of their pants”, discovering the story as they write it) tendencies. 

When I wanted to learn to be a faster writer, I read 5000 Words Per Hour by Chris Fox and 2000 to 10,000 by Rachel Aaron, both of which opened my mind to how much writing you can get done with focus and practice. When I wanted to learn to write more unique and meaningful emotional scenes for my characters, I found The Emotional Craft of Fiction by Donald Maass to be immensely helpful. 

For me, reading daily has been just as beneficial as writing daily. Every morning, I start my day with reading and a cup of tea to get myself in the right headspace for my writing session.

“I wake up around 5am. I have 2–3 cups of coffee. I read and read and read for two hours. I read high quality literary fiction to be inspired, high quality non-fiction about a topic I am fascinated by in order to learn, I read inspirational or spiritual writing to feel that special something inside, and often I will spend some time studying a game. Then I might read the literary fiction some more. At some point, I get the urge or the itch to put the books away. I go to my computer and start to write.”

-James Altucher, “Want To Be The Best Writer On The Planet? Do These 27 Things Immediately”

This entry is part 4 of 5 in the series How to Overcome Writer's Block

Draw Inspiration from the Creative Work of Others

Draw Inspiration from the Creative Work of Others

It’s a Saturday afternoon. I am walking through a gallery at the Bergamot Station Arts Center during their seasonal block party when I happen upon this work of art.

Javier Carrillo, Tacos Carillo, 2023

As I take it in, the image takes me beyond the white walls of the gallery into my own memories. My twenty-something self parks on the street late night at night with a friend. One thing dominates my view: the glowing sign on the taco truck, guiding us to the next stop of the night. I can feel that moment with me, stirring memories of all the other limitless nights of my twenties.

I ponder: How did a piece of art by a stranger evoke such a meaningful personal experience? How could I bring this into my own work?

I pull out the mini-notebook that I carry with me everywhere and jot down a few thoughts:

Art isn’t the content itself. It represents the whole. It zeros in on the most poignant detail to give you the sharpest, most vivid sense of the whole.

The lights of the taco truck are the first thing you’d see in real life. They evoke the most feeling along with the shiny flames on the bottom, so those two elements are a different medium than the rest. They are designed to stand out.

I notice how the accented elements bring me closer to the real experience of going to a taco truck: The first thing I see when I’m driving or walking towards one is the light-up sign.

This realization inspires me to explore this question in my own work:

What are the most poignant moments in the story that represent my main character’s present, past, and growth?

I feel a new sense of clarity in how to take the complexity of the story I’m telling and offer it meaningfully to readers.

It also drives me to explore this question, integral to creating these poignant moments:

What drives me to create this story?

Every sentence, every word, every punctuation comes back to this question. I have been feeling a little stalled on my own writing, and I am thrilled to find clarity in such different creative works.

Another show at the event that resonated with me was Perpetual Motion by Gregory Malphurs, which had a collection of paintings, many of which looked like these:

These stop me in my tracks. I love the vividness of the colors and the way they evoke thoughts about identity. I find these to be such a beautiful expression of one’s internal experience vs. outward appearance. We see these outer shells like clothing choice, gender expression, skin tone, and body art. They can evoke preconceived notions about a person, but they don’t show us what it’s really like inside their individual mind. To me, the many colors show how multifaceted we are as human beings. The streams of motion evoke how we are always changing and (hopefully) growing. It takes time and open-minded perception to get to know the real person. 

Even after we know a person fairly deeply, the ability to continue to truly see them requires openness to how they are changing and to sides they haven’t expressed to us yet. It brings to mind a quote that’s been marinating in my mind lately:

“For things to reveal themselves to us, we need to be ready to abandon our views about them.”

-Thich Nhat Hanh

To me, this is the basis of creative thinking: taking something familiar and seeing it in a new way.

How to Draw Inspiration from the Creative Work of Others

I think there is a communal reservoir of creativity that we can all contribute to and draw inspiration from. In my upcoming posts, I’ll share some of the ways to do this based on my own experiences and advice from others. Here’s the first:

1. Explore local art galleries and events for pieces that resonate.

I haven’t studied visual art in any formal way. I’m a beginner, learning as I go. I’m usually not sure what I’m looking for. But I’ve found that, when I go with an open mind, there’s usually a piece or more that resonates with me. I’m especially drawn to spaces like the Bergamot Arts Center because it’s a collection of galleries, offering a wide range of artistic styles and mediums to explore.

The most intense exhibit I discover that day, Crude Aesthetics, is very different than the kind of creative work that I aim to create, especially in its tone. Yet, it evokes one very important aspect of my creative efforts: how art can immerse us into an idea in a unique and memorable way. 

You walk into a dark room where video footage is projected of oil pumpjacks at work, hidden in unassuming urban spaces. On the walls are photographs like the one below about the oil industry and made of oil itself. The entire room creates an experience aimed to show how prevalent yet hidden the oil industry is in our daily lives. It was eerie. I can still hear those oil machines pumping away. I can still see their haunting presence beside a McDonald’s drive-thru. 

Crude Aesthetics, 2023

Continuing the theme of different yet meaningful works of art, the unusual piece below combining technology and visual aesthetic by Mark C. Estes gave me a sense of peace to watch as it morphed in color, shape, and motion. It’s designed to never repeat.

Standard Random Digitization, 2023 

I love diving into spaces like these. While I did look up which exhibitions interested me before going, I couldn’t have predicted how it would be to experience them in person. That day turned out to be one of my most memorable experiences of the summer.

I also learned a valuable lesson: whenever I’m feeling stagnant in my own creative efforts, I can get up, get out into the world, and explore the creativity of others. We can help each other remember why we do this: why creating matters.

This article, like most of my pieces, is a part of an ongoing series. In an upcoming article, I’ll share the many ways I use music to inspire my creative endeavors.


Further

For more on all the inspiring creatives I mention above, check out:

This entry is part 5 of 5 in the series How to Overcome Writer's Block
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