Five Ways to Conquer Crippling Self-Doubt and Get Writing

5 Ways to Conquer Self-Doubt

Sylvia Plath once wrote, “The worst enemy to creativity is self-doubt.” It’s a lesson all aspiring writers know to be true, and yet so many of us still struggle to apply that universal truth in our writing. For a long time, I’ve tried to figure out what it is about writing that feels so distinctly torturous. Even when the ideas are there, when a rough outline has been sketched, each word carefully typed on page feels like it’s being wrung out of you. Paralyzing self-doubt crawls out of whatever hellhole it’s been hiding in to sit firmly on your shoulders, whispering again and again, “not good enough.”

But here’s the thing about self-doubt—it’s not all bad. In fact, there’s a perfectly good reason why we’re all hardwired to doubt our decisions and actions once in a while. The truth is self-doubt is an integral part of self-preservation. Think about it. Our ancestors needed that nagging voice to remind them to be cautious when approaching large prey or sampling the surrounding foliage. Their very survival was hinged on equal parts of bravery and self-doubt. Today, in its simplest form, self-preservation may take the shape of something as rote and innocuous as making sure your car’s in tiptop shape before embarking on a long drive or doing a sniff test before consuming last week’s leftovers.

Self-doubt also pushes us to do better. It teaches us humility, and consequently, open-mindedness. Imagine if we were all gifted with supreme and unshakeable confidence that bumbled into arrogance. We’d all be convinced that we’re always right and experts at everything. It would be disastrous. We’d either be foolhardy daredevils putting ourselves and other people in constant danger with our reckless behavior, or we’d be argumentative fools furthering mediocrity with the belief that everything we do is nothing short of absolute perfection.

The truth is, people who think they’re the best hardly ever want to get better—and that’s a tragedy in itself. You may be the best at something now, but if you let your skills stagnate, someone willing to work harder or do better will eventually surpass you. This is why it’s important to maintain a modicum of self-doubt. It keeps us in check.

So, if a little self-doubt is good, why am I writing an entire post on how to vanquish it? Well, see, healthy self-doubt has an ugly, hyper-inbred cousin, that’s just as bad as supreme arrogance—Crippling Self-Doubt.  Self-doubt ceases to be healthy the minute it stops you from trying to achieve your dreams.

As Shakespeare puts it,

“Our doubts are traitorous and make us lose the good we might oft win by fearing to attempt.”

Crippling self-doubt is the windmill masquerading as a giant. Now is the time to unleash your inner Quixote and drive that lance into that monster’s heart. After all, some monsters may be invisible or even imaginary, but if they cause you visceral terror, then these monsters are worthy foes that must be crushed. That being said, here are five ways to finally conquer crippling self-doubt so you can get started on your writing.

1. Get in with the right crowd.

We all know that saying from Jim Rohn that “You are the average of the five people you spend the most time with.” Now, there’s a lot of debate online when it comes to the truthfulness of that statement. But I do think that at the core of things, Rohn did get it right. It is important that you surround yourself with people who can help make you better. People who you admire, people you can learn from, people you believe in and who believe in you in return—or, as Aristotle puts it, Friends of Virtue.

As a writer, it pays to have friends who are writers or creatives too. Since you’re embarking on the same journey, it makes it easier to learn from each other and help each other become better at your chosen craft. But beyond having friends with the same interests and goals, I can’t stress enough the importance of surrounding yourself with positive people who will inspire you to keep reaching for your dreams. You need to be around people who will uplift you during moments of debilitating self-doubt, but will also be honest enough to provide real and helpful feedback when it comes to your work.

2. See failure for what it is: an opportunity for growth and learning.

“The test of whether or not a writer has defined the natural shape of his story is just this: After reading it, can you imagine it differently, or does it silence your imagination and seem to you absolute and final? As an orange is final. As an orange is something nature has made just right.” – Truman Capote

There’s a gorgeous article from Buzzfeed called 20 Brilliant Authors Whose Work Was Initially Rejected. It’s a great read if you’re an aspiring writer struggling with fears of rejection. Without giving everything away, the list includes J.K. Rowling’s Harry Potter, rejected 12 times, Madeleine L’Engle’s A Wrinkle in Time, shelved 26 times, Stephen King’s Carrie, turned down 30 times, and Robert M. Pirsig’s Zen and the Art of Motorcycle Maintenance, given the ‘no thanks’ a whopping 121 times! Ouch!

Now, I recognize that there are two ways to take this information. If you’re prone to negative self-talk and catastrophizing (like me), then you can slide into a snowball of panic and say, “Shoot. If these literary giants couldn’t cut it, I have no chance in hell!” Cue the self-pity party for one.

But there’s another way to interpret that data, and that’s to see the one quality that binds these authors together. (I mean, aside from the fact that they’re all bona fide geniuses of the craft, of course.) Some call this quality, persistence. Others may call it grit. But I prefer the word faith. You need to have faith in your work and your ability, not just to write well but to adjust to rejection and see it as an opportunity to do better, try harder, or try elsewhere.

Rejection is a big part of the writer’s life. I honestly can’t think of a single famous writer who hasn’t struggled at least once in his/her career. Whether it’s agonizing over writing something of value or having trouble finding a publisher, it’s always going to be a harrowing and painful uphill climb. But you don’t become a writer just because you want the spoils that success will bring. I mean that’s a pretty hefty bonus, but that’s probably not the reason why you’re torturing yourself day-in and day-out trying to squeeze out one good page or a single great line.

You write because you have a story to tell. You write because there’s a voice inside you that won’t shut up until you put pen to paper and try to capture even the slightest glimmer in the treasure trove of ideas locked up in your head. You write because writing may feel like torture but it’s the one thing that you’d rather be doing for the rest of your life.

So have faith. Don’t let something as natural and paltry as rejection derail you from your life’s purpose. See rejection for what it is. A roadblock. A chance to recalibrate, to review, to revise, or to stand your ground and say, “My work is an orange, and if you don’t like it, I know somebody else will.”

3. Write in Solitude.

“Writing is a solitary occupation. Family, friends, and society are the natural enemies of the writer. He must be alone, uninterrupted, and slightly savage if he is to sustain and complete an undertaking.” – Jessamyn West

In an interview published in The Paris Review, Maya Angelou described her writing process, which was essentially checking into a hotel by herself and working for about six hours every day. J.K. Rowling is said to have written Harry Potter in various cafes in Edinburgh, with her baby sleeping beside her. Haruki Murakami, Stephen King, and Henry Miller meticulously set aside a chunk of their day for writing. Ernest Hemingway wrote early in the morning to avoid any and all distractions. He also wrote standing up, because, well, he’s Ernest Hemingway. And then there’s Jack Kerouac, who liked writing from midnight until dawn… by candlelight. Again, because Kerouac.

For the most part, it seems like all writers have their rituals. Some had very specific rituals like Maya Angelou, Ernest Hemingway, and Jack Kerouac. Others, like J.K. Rowling were content with carving out some semi-quiet space in a coffeeshop.

As I’m writing this, my husband sits across from me, pen in hand with a notebook open. He’s coming up with ideas for his next social media campaign. And apart from the occasional smile from over my laptop, we’ve pretty much left each other to our own devices. See, writing is mostly a solitary craft. You need time alone and aplenty to get in the zone of writing. You need ample stillness to listen to your thoughts and to have that inner dialogue with yourself that will help you build your work, word per word.

But what about collaborations, you might ask. Well, even when collaborating with other writers, there’s always a period wherein you need to stay quiet and focus on your side of the work. I remember watching a video of Neil Gaiman talking about writing Good Omens with Sir Terry Pratchett. He talked about how they divvied up parts of the book based on the characters and how most of their planning was done via phone. And look how well that book had turned out. It probably would’ve been very difficult for them to create Good Omens if they were peering over each other’s shoulders the entire time.

4. Resist the urge to compare yourself to other writers.  

“This is not a novel to be tossed aside lightly. It should be thrown with great force.” – either Dorothy Parker or Sid Ziff

Let me start this section off by saying there is absolutely nothing wrong with reading other writers’ works, especially if the end goal is enjoyment or to learn from their writings. Humility is an important part of the writing process—especially if you’re just starting out. Plus, there’s always something inspiring about really good prose. I’m sure you know what I mean—that energized feeling you get when you encounter a particularly great idea. You know, when you read something that is so moving that it becomes a fulcrum for your own writing. When you feel that way about other writers’ works, then it’s a win-win situation. The writer earns a fan and you get motivated enough to do something great too.

I suppose the problem starts when you read something and end up with a completely different takeaway. If the piece is so good it’s just too good, feelings of inadequacy may bubble up, tipping you over into the state of insecurity and self-pity. This happens to me quite a lot. In fact, one of my unhealthiest habits as an aspiring writer is to look up every author of every single book I love. That alone isn’t too bad, except I zero in on the writer’s age upon the book’s publication and if the writer happens to be younger than me, I agonize over this detail for a while. Oftentimes I end up on Google with the following search terms: “Is 33 too old to become a writer,” “writers who started in their 30s,” and “Is it too late to start over in your 30s.” I used to do this every single time and honestly, that little routine has done me no good whatsoever. It doesn’t inspire me to write. In fact, it does the complete opposite. I end up plagued by crippling self-doubt. Totally unproductive.

Another unhealthy takeaway you might have is jealousy. It’s when you read a bestseller that you think is so mediocre or so bad that you start thinking you can do better. Again, let me come clean. I get that sometimes especially when perusing the contemporary poetry section of the bookstore. But as soon as feelings of jealousy and resentment come bubbling up, so does a little bit of shame. Just because the book is not to my liking doesn’t mean it isn’t good or that I can’t learn from it. Here’s one way to reframe the entire experience: books we don’t like become bestsellers because the writers must’ve done something right. Whether the writers are excellent at marketing their work or they speak the voice of the current generation, there’s a lesson to be learned from these writers. Don’t miss out on this opportunity to improve your writing, or at the very least, your attitude.

5. Set aside your editing cap and write your sh*tty first draft. (SFD)

“Almost all good writing begins with terrible first efforts. You need to start somewhere. Start by getting something—anything—down on paper. What I’ve learned to do when I sit down to work on a shitty first draft is to quiet the voices in my head.” – Anne Lamott

Two months ago, I was having lunch with one of my closest friends who also happens to be a really good writer. I was bemoaning the fact that I couldn’t get started on my writing because I couldn’t get past editing and revising the first line. I asked her what her secret was. How was she able to churn out so many articles so quickly? She laughed and told me, “The first five drafts are terrible. The sixth draft is okay, but I do most of my editing on the seventh draft.”

That was really reassuring to hear. It also presented a bit of a challenge. See, ever since I started writing, I’ve always been the type to edit as I go. That’s why I’ve always been a bit of a slow writer. I believe the record was 13 hours to write a 400-word press release. I would go back and forth, changing this, erasing that, hitting delete on an entire document, all the while thinking “This is crap.” And I don’t have to tell you how quickly “this is crap” can turn into “I am crap.” By the time I reach the final line, I’d be so sick of my writing and hating myself so much that I would give the article a once over, send it out, and never read it again.

But this is one lesson that I’m determined to learn, and hopefully it’s one that will help you out as well. Don’t be afraid to write a sh*tty first draft (SFD) or a couple or even seven bad drafts. As Anne Lamott said, almost all first drafts are terrible. Just for today, embrace the terrible and just get that page done. Have faith in your idea and trust your own skill to create something that can be made better later on.

Keep the writer and the editor in you separate. If you write in the morning, set aside an hour to go over your work in the afternoon or the evening, à la Maya Angelou and Joan Didion. Sure, you might have to scrap a sentence or even a page, but hey, you’ll be writing! And that’s a terrific start to getting things done.