Writing Challenge: One Month Update

Reflections and learnings from my weekly writing challenge so far

I’m one month into my writing challenge and I wanted to share my reflections and learnings so far.

I have a bad case of ‘what-will-people-think-about-this-itis’

When I embarked on my writing challenge a month ago, I catalogued the writing process into 7 steps in an effort to figure out what it is about writing that makes me want to fling my phone across the room with every post.

1. Coming up with the idea

2. Draft or outline of the essay

3. Revising the essay

4. Getting the art, assets, links ready (production)

5. Hitting publish on the essay

6. Promoting the essay on social media

7. Reading comments and stats afterward

I asked myself: What part is easy and where am I getting stuck? The early steps are easier. While I used to get stuck at step 3 in endless revision hell, the decision to cap the revisions at one pass has helped a lot. Now the hard part is all in the steps at the end: 5, 6, and 7. Why are they so hard? If I had to put it into words: What will people think about this? What if someone reads this and thinks it’s just self-serving drivel?

Likewise, when I promote my writing, it feels deeply personal to put it out to people I know. I’m worried about what they’ll think. While it’s still hard and not super fun, the good news is that framing this as a challenge has been so helpful. Not only do I have a structured schedule, but I also feel like I’m giving myself permission to write.

What I’m doing about it: I’m still working on it, but one hack I use is scheduling my publish time a day in advance. Pressing schedule feels easier than publish, and I’m often in a meeting when the post actually goes out. Last week’s post, How to Help an Anxious Child, never got promoted on social media because if I’m really honest I was just dragging my feet. I’m going to try pre-scheduling the social posts as well.

Myth: Great writing just comes naturally
Fact: Real writing is hard work

It’s kind of ridiculous to see this written on paper, but I’ve been telling myself a story. The story is that great ideas come out of writers onto paper, fully formed and complete, and that’s how writing works. This is also because I know writers who outline a post, punch it out in 45 minutes, and hit publish.

As I wrote this story down, it helped me look for the data and start to recognize what my logical mind knows: writing well is hard work. There’s that quote that comes to mind, from Michaelangelo: ‘I saw an angel in the marble and carved until I set him free.’ Writing feels a little bit like his stone sculpting- there are these great ideas and concepts floating around, and we’re trying to capture the full dimensions of that idea in words.

I started looking for content about how to write, and found a lot of great videos and essays from contemporary writers like Tim Ferriss, Deb Liu, Julie Zhou, Brandon Sanderson, etc. One point comes across loud and clear: get disciplined about writing and treat it like a job. Write and write and write. Edit with a careful eye toward clarity and structure. And be intentional about what you’re reading and study what makes writing good.

It is a good reminder that the work to produce good writing is invisible to the reader, and gives me some grace that well of course my writing is not great- I haven’t had the practice!

What I’m doing about it: I’ve improved my writing setup: clearly marked off time on the calendar, all windows minimized, notifications off. I’ve also been reading more literature (current read is Steinbeck’s Tortilla Flats) and I’m also working my way through the book On Writing Well.

I haven’t found my writing voice yet

Once I started actually paying attention to writing, I realize how every writer has such a unique style. Some of them are very factual and research based, and others are very colloquial and opinionated. They’re also writing on all kinds of different topics. The combination of style and topic is their writing voice. What is my voice? I realized I have no idea.

How do I find my voice? What comes up is advice from a watercolor art class I took recently. Someone asked about art style and the teacher told the class, ‘Don’t worry about figuring out your style. Start by copying the work of others, and then over time as you paint more, your own style will emerge.’ I’m beginning to feel that writing is just the same, and what I’m missing is that I haven’t yet had the opportunity to find my style because of the ‘what-will-people-think-about-this-itis’ holding me back from the full range of exploration.

Last week’s essay was actually the most anxiety-inducing of all my recent essays because I was putting out a parenting essay. Who will take me seriously? I felt like I’d gone off the rails and I feel very reluctant to promote it. I even found myself searching how to track Substack unsubscribes to validate how I felt.

What I’m doing about it: I had to remind myself of the principles underlying this exercise: write and write and write, and experiment! The parenting essay being difficult is good because it means I’m stretching myself. Today’s post is unique for the same reason. Instead of doing more of the same, I’m going to try to change it up over the next few weeks.

Thank you

I’m really grateful for those of you who have reached out or hit reply on these essays to let me know you’re reading, or sharing some feedback along the way. I especially love that I’ve inspired a few of you to start writing on your own, too! Thanks for following along on my journey.

This is essay #4 in my series to conquer my fear of writing.