How to deal with self-doubt when you’re a creative entrepreneur

By Brittany Taylor

work + Life

How to deal with self-doubt as a creative entrepreneur

4 professional creatives sound off on how they handle periods of creative self-doubt

by Brittany Taylor

published November 15, 2017

updated May 30, 2018

In the book publishing world, authors are either pantsers or plotters. A “pantser” is someone who writes by the seat of their pants, going wherever their imagination takes them with little forethought or preparation. A “plotter” does the opposite; it’s an author who lays a solid framework for their book before they begin to write.

I am a meticulous plotter. It extends to every facet of my life, whether I’m buying a book or scribbling fan fiction or considering a trip or deciding where to have lunch. Before I got a smartphone, I wrote out directions (complete with mileage and road markers) on sticky notes and stuck them to my steering wheel.

Some people say I spend too much time planning and researching. I say there’s no such thing.

Planning doesn’t mean you’re set for life

The thing about planning is that you spend ages figuring out where you’re going…and then you change your mind. Maybe you make a wrong turn, maybe you buy the wrong thing, maybe your tastes change, maybe you’re just not feeling it. Whatever the reason is, there are always plans that go belly-up. For me, that’s every single creative project I’ve ever started, whether it’s a business or a book or a painting.

I always begin with the best intentions. I have systems to keep me organized, calendars and schedules to follow, goals to meet and actions to take that will help me achieve those goals—on paper, I’m all set. It should be a no-brainer: follow the plan, launch a solid business, reap the rewards.

And for a while—maybe a few weeks, maybe a few months—I’ve got my head down and I’m working away. I’m enthusiastic. I’m on-message. I’m checking off my to-do list day after day.

Then, something happens. I start to wobble, and at first, I recover. I get myself back on track. But then I fall. I wipe out. I lose track of my path forward and my work becomes vague and inconsistent. I stop hitting my goals and I stop caring about them. After that, it’s no surprise that the plan I crafted so carefully falls apart.

What causes creative wobble

I’m a highly sensitive person, so it’s not surprise that I’m an emotional boss. My instincts tend to drive my business decisions, which leads to excellent results when it comes to client projects and my own writing. But that same instinctual push in a certain direction is also what gets me into trouble, because sometimes, my instinct is to freak out.

I can feel the anxiety at the base of my spine. It’s like when you’re sick with the flu and you’ve got chills, but you’re not sure if you’re too hot or too cold. You know, a subtle shiver that you can’t get rid of. That’s what my business panic feels like.


How to survive being a shy, introverted, or anxious boss.

The wobble is this feeling. It’s this gut instinct that something is wrong, but you’re not sure exactly what that wrong thing is. It makes you falter and lose focus. It’s creative self-doubt, it’s Imposter Syndrome with a twist.

And it turns out that it’s an absurdly common problem creative people face, but we never talk about

The wobble is real. Here’s how a group of professional people deal with creative self-doubt

I spent a recent Saturday cloistered with thousands of other young adult book lovers and our favorite authors. In a panel directed at aspiring writers, someone stood up and asked what Leigh Bardugo, Kami Garcia, Margaret Stohl, and Soman Chainani do when their brains freak out on them mid-story and insist that they need to change some huge part of their idea.

The authors got what the person was asking immediately. And from my perch in the back of the packed, 500-seat auditorium, I could see that the rest of us did, too. We all leaned forward. We all quieted down. We all waited to see what Leigh and Co. would say.

This is the gist:
It’s OK to let your instinct tell you a change might be necessary, but it’s not OK for you to let your instinct make decisions on the fly. Don’t let creative self-doubt derail you.


Hey, creative boss! Business got ya freaked? Here's the Big List of Boss Fears...and how to get shit done even when you're shaking in your sneakers.

About me

Brittany Taylor

My name is Brittany, but my friends and clients call me "Britt." Online small business owners hire me to create content strategies and write their blog posts, email newsletters, and social media updates. I work with bosses around the world from the marshes of Charleston, S.C.


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