How to Overcome Self-Doubt in Your Writing

What to do when the little voice in your head tells you you’re not good enough.

“The counterfeit innovator is wildly self-confident. The real one is scared to death.”- Steven Pressfield, The War of Art

Four years ago, I decided to become a writer. I’d just graduated from law school and was so repelled by the idea of being a lawyer that I moved to New York City and began pursuing my life long dream of becoming a writer. I’d written a (very bad) draft of a sci-fi novel while in school, but I wasn’t singularly focused on that project. Really, I just wanted to make a living from writing anyway I could.

In the beginning, I was writing every day, and within a year, I’d published two articles and ghost-written another. However, after pivoting to a career in academic consulting to keep the lights on, my writing schedule became increasingly erratic. Three years later, I felt like I was back where I had started, trying to build a whole new routine. By that time, however, the pressure to succeed was greater and my ability to produce writing on a consistent basis had totally withered.

Of course, I knew what I was battling. The War of Art by Stephen Pressfield calls the obstacle between us and the pursuit of any creative calling Resistance. I’ve known resistance in most of its forms, but the most pernicious for me were procrastination and self-doubt.

Even when procrastination didn’t stop me from writing on a given day, self-doubt would stop me just as I’d started. It would tell me that I needed to do more research, that my plot lines and headlines were dumb. That I wasn’t doing the kind of writing I was supposed to be doing.

The fact that I had given up a legal career for writing only exacerbated the power of self-doubt. I saw my friends making five times what I was making as big-time law firm associates, clerking for prestigious judges, changing the world as public defenders and legal aid attorneys. I couldn’t help but wonder whether I’d made a terrible mistake. Maybe I really wanted a stable, soul-sucking career and a 50th floor apartment in Hudson Yards. No matter how often I told myself that I wanted none of those things , no matter how much I reminded myself that my friends at firms had miserable hours while I had the freedom, daily, to enjoy the wonders of the city, the voice of self-doubt would creep back in.

Photo by Teslariu Mihai on Unsplash

“The most pernicious aspect of procrastination is that it can become a habit. We don’t just put off our lives today; we put them off till our deathbed.”- Steven Pressfield, The War of Art

The more I gave into the two-headed beast that was procrastination and self-doubt, the harder it became to get anything out on paper: a chapter a day, a scene a day, a blog post a day, an instagram caption.

I tried overcoming procrastination using a myriad of strategies: checklists, morning routines, quarterly planning, and breaking my tasks down into itty bitty pieces. Yet, the more I tried to break down my tasks, the more I struggled and the worse I felt for not accomplishing them. Rather than bolstering my self-confidence by completing extremely simple tasks, I added more resistance. My failure was proof that I was not good enough, that I would not be able to accomplish any of the writing I wanted to.

Studies have shown that the root of procrastination is the avoidance of negative emotions: the kind of negative emotions one feels when a task takes longer than it’s supposed to, is more difficult than you thought it would be, or is just plain painful to complete.

Yet, what happens when you successfully avoid that negative emotion by simply not doing a task? You build a pathway. Your body knows it can resist, and the resistance is strengthened.

Three years into my writing career, I had stalled myself out and didn’t know how to recover. I would wake up every day, sit down for five hours before I had my first tutoring session, and plan to write a scene, or a blog post or even just a few hundred words. And I’d fail. Or, worse, some days I would succeed, but my goals were so small that my scattered successes meant little in the way of progress.

It was the same feeling I’ve often had when having a stand off with a bug in my kitchen. You flip on the lights and it stops in its tracks. It’s frozen and you’ve got to trap it. This is your only chance, the perfect chance. What stops you from bringing that plastic dome down? What holds you there, gripping the plastic cup tightly in mid-air, just as frozen as the bug?

For me this feeling is the essence of resistance — an invisible force holding your hand back against all of the mental force telling you “Go, it’s now or never.”

Photo by Clark Van Der Beken on Unsplash

“Never forget: This every moment we can change our lives. There never was a moment, and never will be, when we are without the power to alter our destiny. This second, we can turn the tables on Resistance.” -Steven Pressfield, The War of Art.

So, how does one overcome that force? Stephen Pressfield argues that it is by “turning pro.” “Turning pro” doesn’t mean making money, it means showing up every day, no matter what, staying at your desk until the day is done and sticking with a project until you see it through. More importantly, “turning pro” means sending your work out into the world. As Pressfield states, “We receive praise or blame in the real world.”

Making a commitment to publish everything I write (or, more importantly, write things with the intention of publishing them) has had a profound on my writing: my writing output has soared. Recently I’ve found myself with a stack of new ideas for blogs, short stories and more — I’ve even made significant progress on my novel.

Still, the last hurdle of resistance for writers, and the most crucial to overcome, is getting stuff out into the world. That’s what I plan to do through Medium and other platforms. I’ve committed to blogging, posting, and submitting with abandon, and with the express purpose of receiving feedback.

I’m betting on the fact that publishing on platforms like Medium will hold me accountable. Every time I hit the publish button, I will chip away at the mountain of resistance I’ve built these past four years. I may be met with a barrage of responses about how I’m an imbecile for giving up a good career like law to be a bad writer. But, whether my ventures refute or confirm my own doubts about writing, I will ultimately overcome Resistance.

Freelance writer, editor, and tutor. I write about politics, health, NYC and other things

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