Overcoming writer’s block

🦊 Quick Brown Fox #37

Nov 02, 2020

Hey friends,

I hope you’re staying safe and doing well. Today’s edition is all about storytelling. A while back, I shared a draft of a short story that popped into my head late in the evening. 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.

Through writing this newsletter, I’ve learned the incredible value of working in public. Along with stories, I’ll be sharing learnings about storytelling along the way (starting today!) This week’s edition features learnings on how I unblocked myself to start writing stories. I also share stories from Anthony de Mello’s The Song of the Bird, Hundred Rabbits (a creative duo that is sailing across the ocean from Japan to Canada), and some incredible art from Ben Sack.

Overcoming Writer’s Block

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 got some traction with story writing after chatting with fellow writer and friend Ciara McVeigh. I had an incredibly inspiring conversation with her — we’ve now started to have regular chats about fostering creativity.

A few takeaways:

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.
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.
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!

Song of the Bird

I’ve been reading Anthony de Mello’s The Song of the Bird, a collection of profound short stories and poems. He includes his own commentary on each one, but recommends reading and reflecting on them deeply to derive our own interpretations. I figured that a fun way for me to do that would be to pick one story every week that resonated with me, and share it in this newsletter with my reflections on it.

Today’s story: A Vital Difference

Uwais the Sufi was once asked,
“What has grace brought you?”
He replied,
“When I wake in the morning I feel like a man who is not sure he will live till evening.”
Said the questioner,
“But doesn’t everyone know this?”
Said Uwais,
“They certainly do. But not all of them feel it.”

We often know how to do something, but don’t do it anyway because we don’t feel its wisdom in the moment. Even our hardest-earned lessons are easy to forget. When we gain insight, it feels raw and powerful as a bolt of lightning. Over time, it slowly drifts to the back of our minds as we focus on what’s directly in front of us.

I’ve written and spoken about playfulness and stillness countless times. But I’m also human. I forget the lessons I’ve already learned. I needed a gentle reminder from a friend to help get me back on track and unblock myself.

We need others to remind us of what we already know.

Tale of the Sea

Hundred Rabbits’ North Pacific Logbook is a collection of their log entries during their remarkable 51 day journey sailing across the Pacific ocean from Japan to Canada. I’m only about halfway into it and am already enjoying it more than anything else I’ve read recently. It’s so raw, and surprisingly gripping for a bunch of log entries (reminds me of The Making of Prince of Persia). It also occurred to me how much of their struggles at sea are relatable to the obstacles we hit in our daily lives. This line, in particular, resonated strongly with the story I had just read from Song of the Bird:

I want to have a good course always, I should know better. I know with sailing you can't always point where you want. The path to our destination will never be a straight line, it'll curve, zig zag and sometimes overlap itself. You can't be in a hurry. I know all of this, but I still think it, like my brain is ignoring wisdom on purpose to torture me.

If you’re not familiar with Hundred Rabbits, they are the wonderful duo of Rekka and Devine — incredible artists and programmers who created their own mobile studio on a sailboat. They create delightful software, writing, art and much more. Their lives embody the principles of finding contentment with less — even their website practices ideals like simplicity and energy conservation through low-bandwidth optimizations. I highly recommend poking around their site! It’s a palace full of treasure.