Sydney Allen is a journalist from Indianapolis, Indiana who currently lives in Yogyakarta, Indonesia. She works as a journalism teacher, writer, and editor and is passionate about all things communication. When she’s not working, you’ll find her attempting to surf, diving down YouTube rabbit holes, and zipping around on her motorbike.

As a burgeoning freelance writer and editor, my inbox is full of newsletters and stories about other writers and editors who’ve reached the level of success I’m working towards.

“Here’s how I published 100 stories in one month.”

“Top 10 tips for being a top-notch freelancer.”

“Meet the top 30 under 30 female journalists.”

When I’m feeling confident, these emails buoy, inspire, and motivate me. They help me find my creative flow, push me to work harder on my current projects, and give me a list of action items that I can apply to my own career.

But when I’m feeling low… let’s just say they have the opposite effect. 


What happens when you fail to act like a top-notch freelancer? When you miss your deadlines, turn in half-baked work, and fall short of your creative goals?

I’m interested in writing about self-compassion when you fail in creative spaces. And I’m going to start by talking about my own failures — as embarrassing and shameful as I may find them.

Last year I was contracted for a freelance writing opportunity for a magazine I greatly admire. The magazine asked for around 2,000-words — lengthy, but not entirely out of my wheelhouse — about sexual education in Indonesia, where I live. 

The truth was, I wasn’t the best person to write that piece. I wasn’t excited about the topic and didn’t have the background or inspiration to really make it shine. But I was so determined to get my work out there and driven to succeed, that I figured I could overcome those barriers. 

The following months were filled with a vicious cycle of procrastination and writer’s block. 

First, I had some health problems that kept me in bed for a couple of weeks. Of course I couldn’t complete the piece then; I told myself I’d do it when I recovered. Then Christmas came. I had to quarantine to travel, and after that, I postponed the piece in favor of family time. The whole month of December passed. Then I had to return to Indonesia and deal with a frustrating assortment of travel restrictions and COVID tests. I told myself I couldn’t possibly write under those stressful conditions. 

By then, it was February, and I was facing the terrifying reality that I was overdue, uninspired, and unmotivated to complete the piece. I was dodging texts from my editor and feeling a near-constant low-level panic. 

My paltry notes were sitting in an open Word document on my desktop. My To-Do List had an all-caps reminder to WRITE YOUR ARTICLE, which I conveniently looked past when I marked off my daily tasks. Whenever I considered starting the piece, I was ambushed by intense feelings of self-anger and guilt. I started getting stomach pains. When I tried to write, I’d feel my eyes prick and my stomach cramp and would immediately search for something else to do to distract myself. 

In the end, I didn’t complete it. Despite the guilt, dread, anxiety, and self-loathing I simply could not do it. 

I ended up passing the opportunity on to a friend and connecting her with my editor. I simultaneously felt intense sensations of failure and relief. I could breathe easily for the first time in months. It was such an obvious solution — I couldn’t do it, so I made way for someone who could. But it was also one of the hardest professional choices I’ve ever had to make. 


Letting go of this assignment taught me a valuable lesson about self-compassion: that sometimes it’s healthy to fail. While I’ve heard this line over and over throughout my life, it failed to truly sink in until I was faced to confront my failure head on and acknowledge that I had gotten in over my head. 

After I gave up this piece, I found myself in a much better headspace, able to focus on a multitude of other projects and creative ideas. I was able to complete other assignments that actually excited me — topics that I was passionate or curious about, which didn’t feel fraught or impossible to overcome. 

As a writer, I typically only see the finished products that my friends and colleagues produce. I don’t see them struggle. I don’t see them throw away drafts. I don’t see which pitches get rejected. No matter how successful someone is, they will have experienced failures, but those challenges are often invisible — and rarely make it into inspirational blog posts and top-ten lists. 

I know I personally would have appreciated some feedback about failure when I was waffling with my writing. At the time, I thought not completing an assignment was the worst thing in the world. Afterward, it became quite clear the worst thing was actually being stuck in a limbo, unable to complete the piece and unable to move on.

Choosing to fail — choosing to welcome failure, learn from it, and use it to improve the next time around — was the best action I could have taken.


I want to make more space for compassionate, honest conversations about the downsides of working in a creative field. Failures should not be a shameful secret, but rather experiences writers and creators can collectively learn from and use to support each other. 

With that in mind, I’d like to open a discussion about creative failure. Where have you fallen short of your creative goals? What have those experiences taught you?

In my case, I thought that not completing a single assignment signaled some type of long-term personal failure. If I couldn’t do this job, I must not be a real writer, a real journalist. But I see that that’s not true. Just because I struggled, and failed on this particular assignment, doesn’t mean my identity or competency are permanently devalued. It’s simply a sign that I should be more intentional about the work I choose. That I need to work on protecting my time and creative energy.

Let’s continue this conversation in the comments — because the more we know about the struggles involved in creative work, the better we can work together to overcome them.

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