We writers are really kind of a whiny bunch. Our Facebook and Twitter streams, our blogs, sometimes even our books are full of discussions about how hard it is to to be writers. There’s a lot of (mostly) good-natured woe-is-me-ing; sharing of commiserative quotes from our patrons, St. Hemingway and St. Plath; and so, so much of that fantastically cathartic black humor we all love so much about how hard it is to take risks with your writing.

There’s a reason the #YouKnowYouAreAWriter hashtag is popular. There’s this sense within the community that “only another writer could understand.” Non-writers glaze over in the face of our whinging. Even if they’re too polite to say it, there’s this sense they’re thinking: “What’s so hard about writing? Anybody could do that. I wish I could stay home in my pajamas and play on the computer all day.”

In all fairness, there’s a certain justice to that. I’ve talked before about what I call “the myth of the suffering writer.” We definitely can take ourselves too seriously—our melodramatic existential blocks, our laziness in the face of the the blinking cursor, and our insistence that the process of writing will never be easy, can never be easy, should never be easy.

I can attest that the process of writing gets easier with time, patient practice, and gradual mastery.

So why are we still whining?

Because the difficult intricacies of the craft aren’t really what scare us witless, are they? The scariest part of writing—the part that never really gets less scary—is the inherent risk of writing our guts out every single day.

And yet, if you want to write anything worthwhile, on either a technical or thematic level, you have to be willing to take risks with your writing.

The Riskiness of Good Art

Art that is safe is art that doesn’t matter.

Safe writing doesn’t challenge the reader, and it certainly doesn’t challenge the writer. This is true on so many levels: personally, socially, even commercially. Safe writing is stagnant writing. Where the art is stagnant, so too is the society.

Even just stating that feels a little scary, a little risky. Writers are just humans, after all. We like to be safe. We like to be able to control our worlds, our lives, our beliefs, and other people’s beliefs about us. For many of us, our writing is our safe spot—or started out that way. We started writing in private, perhaps for fun, perhaps for catharsis, but in the understanding that our words were sacred secrets held between us and the page. No risk involved.

But time goes on. People begin to read our words. They begin to learn about us through our words. More than, that we begin to learn about ourselves through our words. The page is no longer a silent receptacle. It is a reverberating challenge to ourselves: be honest, be brave.

You can either stop your ears to that challenge and close off the call of life itself. Or you can rise to it and seek to take risks with your writing that may leave you feeling unsafe but that will also spur you to greater growth as individuals—and, by extension, give you the opportunity to share that growth with your communities.

5 Ways to Take Risks With Your Writing

Sounds exciting, right? But… how do you do this? What does it mean to take risks with your writing? Does it mean dramatizing your most embarrassing moments? Villainizing problematic family members? Spouting only your most radical ideas and beliefs? Choosing vulgar language and situations just for shock value?

Light the Dark edited by Joe Fassler (affiliate link)

Maybe. But probably not. Taking risks with your writing is actually a pretty precise science. Hanya Yanagihara put it all in a nutshell in his essay “Writing for Right Now” in the anthology Light the Dark:

Whether it’s plot, or characterization, or structure, or a voice, or the language, a book has to take risks with at least one thing.

1. Be Honest: Question the Narrative—Your Own and the Story’s

The riskiness of good writing begins and ends with honesty. It’s the truth that scares us—the truth about the world, the truth about ourselves as people, and the truth about ourselves as writers. We’re endlessly afraid that none of these things will measure up to our own hopes and ideals.

Frankly, sometimes they don’t. But as the science of character arcs teaches us so clearly, the only way to move forward in life is to be willing to abandon the comfortable Lies in favor of the oft-painful Truths.

Being honest on the page begins by being honest with yourself. I am coming to see that, really, this is the whole journey of life. Could it be that in giving us life, God also gives to each of us a great gift—a great mission? That gift is ourselves—and that mission is finding ourselves.

Your job on this earth is to find yourself. No one else can find you. Others can see you, learn from you, love you, use you as a mirror in finding themselves. But no one else can find you. You are here to find yourself. It is one of the most important things you can ever do, because you are the only person who can do it.

The only way to do this is to be honest with yourself—about who you are, what you want, why you want it, and what you believe.

Your view of life is the single most important thing you bring to your fiction.

From that springs the further honesty of telling honest stories. Choose your narratives, your premises, your genres because they are yours, not because they are familiar and easy. In these days of commercial pressure to conform to popular genres and narratives, this in itself can sometimes feel inherently risky. And that’s just the beginning.

2. Be Innovative: Never Write the Same Book Twice

I used to say that I never wrote the same book twice. On the surface, this seems true. Up to this point, my published books are wildly varied in premise and even genre. I’ve written everything from a straight-up western to a medieval love story to a portal fantasy to a crazy historical/dieselpunk mashup to a historical superhero story. But actually, they are all, in a way, the same story. I have a theory that we all go on writing the same story over and over, just in different ways.

So when I say “never write the same book twice,” I’m not saying you have to reinvent yourself with every new story. You like writing procedural mysteries? Keep writing ’em.

But don’t settle for the familiar. You should be risking something new with every book. If you’re taking the same risk in this book that you took in the last, you’re not pushing yourself. Even as you try to satisfy readers, you want to be putting them ever so slightly off their guard with each new book. Don’t ever give them exactly what they expect.

Curiously (or not), a majority of the books and movies I love most passionately were those to which I initially had a knee-jerk negative reaction. And yet with a little time and re-reading/watching, I not only learned to appreciate the unexpected in these stories, I came to love them. In his Light the Dark essay “Music for Misfits,” Mark Haddon observed:

I think it was Jean Cocteau who said fashion is what seems right now and wrong later. Art is what seems wrong now and right later. Great art has the slight discomfort to start with. It takes you a while to think, Yeah, this is right. I just didn’t realize that it was right at the time.

It feels this way because good art is innovative art. It is not what we initially expect. It takes time for us to adjust our expectations. “Bad” art, on the other hand, is what we initially expect, in the sense that we’ve been there before. It’s familiar and therefore often cliched. It’s not risky. It’s very, very safe. And as a result, it’s ultimately forgettable.

3. Be More: Look Beyond the Mere Gratification of Fiction

I write for pleasure. I write for gratification. I write for escape. I write for catharsis. If I didn’t get these things from my writing, perhaps I wouldn’t write at all. They’re important. But if I lose myself too deeply in them, I risk writing stories that are not only self-indulgent but probably vapid.

You must challenge yourself to consciously seek a higher level of writing, a higher purpose. Please: write fun, entertaining stories. But don’t write just fun, entertaining stories. Use that simply as a launchpad for stories of greater depth, meaning, and honesty. This requires guts. It requires bravery. But it’s the doorway through which all great art enters.

In his New York Times essay “Writing Is a Risky, Humiliating Endeavor,” David Gordon acknowledges:

Writing then, must feel risky in order to feel like life. I used to cringe when people talked about “brave” writing. I’d think, calm down, it’s not like you’re a fireman or a Special Forces commando. If the mission fails, just toss it in the wastebasket. But I do think, upon reflection, that there is a need to generate emotional risk, a sense of imminence, of danger, in order to transmit that aliveness to the page. This needn’t mean personal revelation or offensive language. Sometimes quiet, dense writing is the most deeply and complexly honest. Sometimes intellectual discourse is brave in our Twitter culture. Genuine and sincere emotion can be risky in a world of snark and irony. So can making silly jokes about matters our society regards with sanctimonious seriousness. Sometimes it is just a matter of a writer doing what she does not yet know how to do, speaking about something he does not yet understand. The risk of ambitious failure.

4. Be Rebellious: Never Follow the Rules Blindly

I pledge allegiance to the writing rules. I love them, and they love me back. But our relationship is not that of a dictator to his slave. It is a vibrant, evolving relationship of constant interchange, a dialogue of learning and refining.

In short: it’s a good idea to follow the rules, but never follow them blindly. Questions are our greatest tool in this life. Question the rules and keep questioning until you find the right question that leads you to the right answer—a full and personal understanding of your craft.

Where have the principles of story theory come from? Why is it that the patterns of structure and character arc are the way they are? (Or are they?) How do you see story? What patterns, archetypes, and symbols are most powerful and pertinent for you? Why?

Occasionally, I watch Michael Tucker’s great YouTube channel Lessons From the Screenplay. Recently, he posted thoughtfully about why it is that some writers reject the idea of classic structure, find it confining, even condemn it as formulaic. The answers he came up with were deeply personal to him and, as a result, usefully honest to everyone else who watched his video. Although he more or less ends by confirming the same ideas of story theory, he did it in a way that was intensely personal to him. He’s a perfect example of a writer who embraces the “rules” from a place of understanding rather following them blindly.

5. Be Committed: Don’t Give Up

Sometimes the riskiest part of writing is just doing it. Showing up at your desk every day, going to that raw honest place inside yourself, putting words on paper with the utmost of your own ability—that takes guts. That takes commitment.

In the course of writing our lengthy first drafts—before anyone else even sees them—we face down our own doubts about the worth of what we’re doing. We struggle with our inadequacies. We admit our fears about sharing these dangerously vulnerable parts of ourselves with others.

And then we let others actually read what we’ve written—and some of them love it and some of them hate it. We have to deal with the fallout. In the harsh light of new realities, we face new truths about ourselves—as people and as writers. We pick up the pieces, we try again, we fail again, we fail better.

It is a life of risk. But we do it because we must. It is the only way to reach for our potential, the only way to live our lives to the utmost, the only way to give all we have to give to our world.

Perhaps it is impossible to write and not risk. Perhaps even if we are trying our best to protect ourselves and only write what is safe, we are still inevitably risking something—some part of ourselves that trickles around the edges of our defenses.

But today I challenge you—I challenge myself—to write every word with honesty, innovation, bravery, awareness, and commitment. Let’s risk.

Wordplayers, tell me your opinion! Which of the above do you think you could do more to take risks with your writing? Tell me in the comments!

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