Tackling The Freelancing Slump of Self-Doubt

Why does writing success make you feel like a fraud?

Hello, perfect strangers. It’s been some time since I published any writing — six and a half months to be exact. Before my hiatus, I felt like I had a handle on writing on Medium. Not only was it an outlet that I thoroughly enjoyed, but I was also finding more success on the platform than I ever imagined.

And just as suddenly as I started blossoming in my blogging career, I faltered and then abruptly stopped.

It took me about three months of consistent writing to achieve my first four-figure month on Medium. Once I found that success, writing got a lot harder. I couldn’t bring myself to publish more than a couple of articles a month. For the amount of work I was putting out, I was earning really well. And yet the more money I earned, the more difficult it was for me to produce content that I was proud of.

And so I stopped publishing altogether.

So, what changed? How’d I go from a newbie writer earning pennies for my articles with all the confidence in the world, to earning hundreds of dollars on my articles and feeling like a completely unqualified writer?

The feeling of inadequacy is a strange thing, and it can show up in many forms. I personally didn’t feel like I wasn’t cut out for the world for freelance writing until I started seeing success. Once I had a viral article, a fear of never being able to write anything near as quality as my previous piece led to procrastination.

I can’t tell you the number of hours I’ve spent working on the dozens of drafts sitting in my stories. They sit nearly finished, but just not quite ready to publish because I always found a reason to say they weren’t good enough.

But now I’m determined to get back on the “write” track and overcome my feelings of self-doubt. Here are a few things I’m going to focus on as I continue my freelancing journey; perhaps a few of these tips will resonate with you too.

Call It What It Is

It’s taken me the better part of six months to admit that the only true challenge I was facing in my writing was my own self-doubt. I used to try to blame my busy schedule or a shift in my passions for my lack of publishing.

But once I started to acknowledge that I was neglecting my passion to write because of my own irrational fears of failure, I found myself with a newfound motivation to start publishing.

So if you find yourself unable to pull the trigger on the publish button, be completely transparent with yourself. You’re likely limiting yourself with self-doubt.

Let Yourself Screw Up

You know something ironic? Part of my writing slump has been caused by a fear of making mistakes, yet my most successful article to date has a typo in the opening sentence. That article has earned over $1,300 because it’s a good quality article, not because it’s the epitome of perfection.

I’ve thought about fixing that opening sentence typo, but I’m going to leave it as it is to show myself that just because something isn’t perfect doesn’t mean it can’t be successful.

Now, I’m not saying throw all caution to the wind and neglect basic editing and proofreading. Rather, don’t chase the impossible standards of perfection. If you find yourself re-reading your drafts dozens of times and still refraining from hitting that publish button, then you’re limiting yourself.

So, I’m challenging myself to limit my proofreading and editing to two passes. If I don’t catch an error during those two phases, then it’s good enough to publish.

Figure Out What Real Writers Do

I had myself convinced that I wasn’t a “real writer”, so I challenged myself to figure out exactly what it was that “real writers” do. Did I need to create my own website to be considered a real writer? Maybe I needed to be publishing content on a regular schedule. Or perhaps I couldn't consider myself a real writer until I had at least 10k followers.

And no matter how extensive my list of qualities of a real writer grew, I kept coming back to the same thing — all real writers had to start somewhere. And I’d never get to a place where I felt like a real writer if I didn't just start writing.

I know my self-doubt has been holding me back from doing something that I enjoy; having a creative outlet to write without constraints. And although my self-doubt and feelings of inadequacy in writing have cost me a few months of blogging, I’m grateful for the kickstart it’s given me to taking action.