Overcoming Writer's Block

In this note, I share how I overcome writer’s block and wrote my first fictional short stories.

A while back, I shared a draft of a short story in a newsletter. I really enjoyed the process of writing it, and I wanted to work on it more to expand and flush out the story. But my other projects kept filling up my time. The story sat idle, like a half-assembled toy, waiting to be played with.

I decided it’s time to bring this toy to life! For the past couple of weeks, I’ve been diligently working on the story. I expanded and edited the draft into a more complete tale. I’m now incorporating the feedback I’ve received from the original as well as this expanded version. I plan to share it with you in an upcoming newsletter very soon. Stay tuned!

I’d like to write at least a handful of stories like this. I don’t have a specific goal in mind for them — perhaps I’ll publish them as a book (!), they could form a collection on my site, or just be a fun project I work on for a while. I want to give myself a real chance to focus on writing them, and see what happens. Inspired by stories like The Little Prince, I dream of writing stories as approachable as a children’s fairy tale that give readers lessons to ponder along the way.

I know it won’t be easy, but I also know I’ll never succeed if I don’t try.

In my (brief) experience, writing stories feels quite different than writing essays or blog posts. Normally I rely on my notes or research to found the basis of a post. Stories don’t really work that way for me — the first story I wrote just appeared in my head one day. I was a bit terrified that I wouldn’t be able to repeat that process.

I finally started getting a little traction with story writing once I spoke with fellow writer Ciara McVeigh. A few takeaways:

1. Don’t take it too seriously: I formed all these ideas in my head about what these stories were going to be. I built them up too much, and got myself stuck in a cycle of overthinking. I needed to take them less seriously, and embrace the ideals of playfulness that have served me well. Once I became more casual about the story writing process, I became far more productive.

2. Find more stillness: The nuggets that form a story are often rooted in our own experiences. To unlock them, we have to give ourselves the mental and emotional space to let them emerge naturally. I knew this from experience, as I recently wrote a poem (without having the intention to write one) after going through an exercise in meditation while at my writing desk. I sat down to quiet my mind for a while, and voila! My inner creative voice finally had a chance to speak. Stillness breeds creativity.

3. Prioritize and focus: Another challenge I have with writing stories is making room for it in my schedule. If every week I spend my time writing a packed weekly newsletter, essays, digital notes, videos, Twitter, and so on… there’s little room for anything else. I allowed myself to write a shorter newsletter and ease the gas on other creative outlets. The freed bandwidth is crucial while I’m trying to write these stories. Interestingly, last week’s shorter newsletter got a lot more positive feedback than most of my longer ones. It was a good reminder of the importance of quality over quantity.

I’ve now almost completed one story, and already have ideas for a couple more. Excited to see where this new arc in my writing journey takes me!