30 Creative Challenges to Try (That *Aren’t* NaNoWriMo)
A meditation on the November experience as a writer
If there’s one thing I know for sure about us Substackers, it’s that we all have a NaNoWriMo war story (or ten).
Creative challenges and sprints are our kryptonite (don’t deny it 😉) and we gotta give it up for the OG. Because November isn’t just sweater weather or Thanksgiving time. It’s the season for furiously writing to cross that 50,000-word finish line.
There’s a romanticism to National Novel Writing Month. 30 days, during a dark and cozy season, to write that book that’s been in the back of your mind all year. It’s perfect, right?
But sometimes, that fantasy gives way to a nightmare. Suddenly we are stressed by the artificial pressure and the compare-and-despair that comes with watching seemingly everyone else coast through it all (and share so publicly). And then there’s the FOMO of it all if you contemplate opting out.
I’ve had a love-hate relationship with NaNo culture since high school. And it’s practically in my blood now…seeing November come around the corner and feeling the itch to start some new, bright and shiny writing project.
It’s a conflicting moment in time, as I’m looking to balance my current priority to close rings, with the draw of a fresh creative challenge.
If NaNoWriMo season has you feeling all sorts of ways, I made this post for you. It’s an expansion on one of my most-read posts — and a continued effort to make creative choices that feel aligned and intentional, rather than unnecessarily ambitious.
AKA How to Decide Whether to Join that Creative Challenge or Not
Here are three important questions for reflection…that perhaps one day I’ll expand into a decision tree :)
Do you have time and space in your day to commit to this challenge? This is the moment to be lovingly realistic with yourself. Do not pass go if you are already feeling filled to the brim.
Follow-up questions: What can you release to make the time? If you think you have a little bit of time, what level of creative output feels realistic for that window of opportunity?Can you set yourself up for success before it even starts? Sure, it’s never too late. But getting ahead of the curve will help you keep on track and focused on the process.
Follow-up questions: How can you best set up your environment for your writing (or creative activity)? What other systems can you have in place to make the weeks ahead go smoothly? What decision-making (like planning, outlining, plotting, etc.) can you tackle ahead of time?What is ultimately motivating your desire to embark on this challenge? Again, this is a moment to be lovingly realistic with yourself about the why behind your decisions.
Follow-up questions: What do you envision at the end of this challenge? What are you going to be most proud of? What is going to feel like the ultimate reward for your efforts? Are your thoughts pointing more to extrinsic or intrinsic motivations?
For those looking to organize, simplify, and wind down:
Dedicate 30 minutes each day to close your 2024 “rings.”
Find 10 items each day to declutter from your home or digital life.
Brainstorm four ways to update your creative space and/or systems for focused action. Engage one each week in November.
Write out 30 creative boundaries (one a day!) to commit to in 2025.
If you’re still itching to write:
Draft a haiku a day.
Write thirty 100-word stories.
Revisit previous work and update one piece each day (great for blog posts or Substacks!)
Genre mix! Write a love story in recipe format. Your memoir in poems.
If your creative well feels depleted:
Crack open a new-to-you poetry book and read a poem a day. (Check out
’s routine and perspective for more on this 🙂)Create and edit a new Pinterest board each day.
Listen to a new-to-you album from beginning to end each day.
Choose a tiny topic you’re curious about (the more random the better). Become an armchair expert in 30-minute research sprints a day. Follow the breadcrumbs of curiosity. Keep a log of your journey.
Take 30 minutes each day to learn something new. (Check out Duolingo or Masterclass.)
If you want to be creatively challenged:
Learn to draw something new each day.
Film a minute of your life every day.
Make one small collage every day.
Think up an invention each day — go for niche and mundane!
Take a photo of the same subject from a different perspective each day.
If you’re trying to get out of your shell:
Publish a Substack note a day.
Choose your favorite Substack read each day and post a comment.
Each day, choose someone you admire and reach out. Send a quick note of gratitude (and perhaps a gift or invitation to collaborate!).
Try out a new social media format—not for building a following, but for the practice in itself :) Post daily.
Create in public. Choose another challenge from this list and publish your findings/reflections/creation each day.
If you’re feeling introspective, reflective, or nostalgic:
Jot down one memory from the past year each day.
Create a soundtrack of your life by choosing one meaningful song daily.
Make space for a creative altar. Each day, collect one item (around the house, from outside, from downtown, etc.) to include in your altar.
Document one family tradition or recipe each day (anything you don’t want getting lost in time!).
Write 30 lists for 2025 (tiny goals, resolutions, things to say no to, places to go, things to try, etc.).
Now, I’d love to hear from you! If you enjoyed this week’s issue, please consider:
A quick tap of the 🖤 icon below
Tapping the 💬 icon and sharing whether, why, and/or how you are navigating NaNo season this year!
Pick your favorite NaNo alternative and hit restack 🔄
Love these inspirational invitations! Thank you!