The Tell Your Story Challenge with Sarah Fay
A 21-Day Challenge
Tell. Your. Story.
I’m going to teach you the art of telling your story—so people hang on every word.
- 21 Notes that compellingly tell your story
- A repeatable system to help you show up consistently as you
- Confidence (not imposter syndrome) every time you click Post
- The ability to captivate with stories, not post into the void
- The chance to be featured on Substack Writers at Work and get your Substack in front of 37,000 people
In 21 days.
I’ll give you the personal storytelling skills and prompts that have made my clients' Notes and posts go viral (for them), their subscribers convert, and their writing be featured by Substack and cited in The New Yorker.
The challenge: Tune out the noise and focus on yourself and your story for 21 days to do the same.
Doors close September 24 ⏺ We start September 25
37k
active subscribers
Featured Substack
Top-10 bestseller
Featured in:
The New York Times, NPR
ON SUBSTACK, YOUR STORY IS CURRENCY.
The thing that matters most is you showing up as yourself with a story to tell.
Your personal perspective and storytelling is the one thing that gives your Substack value.
If we look at all the top bestsellers, all the biggest Substacks, what do they have in common? It's not how often they post or the length of their posts. It's not all the silly things that people think that some of the Substack growth people tell you it is.
They are in their Substacks. They know how to show up as themselves. They know how to tell their story.
And they do the one thing ChatGPT never can: Tell a true personal story. It can make it up, but it will never be true. (If ChatGPT can give someone what we're posting, it's valueless.)
ChatGPT will never taste, feel, see, or smell. It will never actually travel to Greece or Des Moines. It will never actually be nervous to step on a stage. It will never pet a cat or miss the green of the trees in winter.
You and your story are the most valuable assets you have as a writer or creator in the age of AI.
I’m going to teach you to capture people’s attention with the story of you.
Even when you’re convinced no one will like it.
Even when the voice in your head tells you no one will care.
Even when you feel the ick of putting yourself out there.
The Honest Part
I CAN’T CONVINCE YOU THAT GROWTH AND REVENUE COME FROM YOU AND YOUR STORY.
That’s up to you.
Know this: Every other strategy, feature, branding, blah blah blah matters not at all if you can't captivate readers with your story.
Once you can you:
- Stop procrastinating when it's time to click Article on the Create dropdown menu
- Don't spin on every word in your post, trying to make it perfect in the hope people like it
- Go from feeling like you're throwing spaghetti at the wall on Notes to knowing every Note you post is a gift
That’s the whole challenge. I’ve helped thousands of Substack writers do it. Now you do it too.
Here’s exactly what you get
THE OFFER.
01
GET IN NOW.
KICKOFF + MASTERCLASS: THE ART OF TELLING YOUR STORY
+ The chance to meet your fellow TYS challengers
Live with me on zoom · Replay AVAILABLE
The 60-minute live Zoom session to give you what you need to start
This is where you get all my expertise as your Substack Strategist, USA Today bestselling author, and Northwestern creative writing faculty member to help you craft the Notes and posts you’ll write during the challenge.
We’re covering:
- Why most viral Notes are personal stories
- Why your human story is the most profitable skill you have as a writer and creator in the AI age
- What makes people restack, lean in, keep reading, comment, and pay to read you, not your Substack topics
- How to tap into your own voice
- The neuroscience of humans as storytelling animals
- How to move through perfectionism and imposter syndrome
YOU’LL LEAVE WITH:
- Confidence in the value of who you are (because you’re way more amazing than you think you are), your perspective (which is way more interesting than you believe), and the compelling (yes, it’s compelling) life you've led
- Your first compellingly told personal story on Notes
- The restack support of your fellow challengers
02
DAILY DROP + WEAVE
Days 2–21
20 DAYS OF EXACTLY HOW TO TELL YOUR STORY ON NOTES PROMPTS
Delivered daily September 25 – October 15
For the remaining twenty beautiful days, you will tell your story every day, once a day, in short form on Notes and long-form (if you choose to) on your Substack.
I’m guiding and inspiring you to tell your story.
You’re just writing it down and posting it.
EVERY MORNING IN YOUR INBOX AND OUR PRIVATE SUBSTACK
A pep talk from me and your daily prompt.
You’ll know:
- What part of your story to post that day.
- The exact structure to do it.
- The psychology behind why it draws people in.
You wake up. You're inspired by my prompt and 2-minute pep-talk video. You post.
Then you join the restack thread that gets your Note seen and read.
Even when you don’t feel like it.
Even when you’re too busy.
Even when you dread it.
BY OCTOBER 15:
- 21 live Notes telling your story
- Confidence in your work and your voice
- The view of yourself as a “real writer”—or at least someone who can entertain, captivate, move, and reach people with their story
03
YOU DID IT.
Day 21: FRI OCTOBER 16 · 1 PM CT
CELEBRATION: UNCOMPLICATING SUBSTACK TO TELL YOUR STORY AND BUILD YOUR AUDIENCE IN 2027
Live with me on zoom · Replay AVAILABLE
We celebrate! In this 45-minute live Zoom celebration and send off, I show you how all this leads to growth.
I share how I help my clients quadruple and 10x their subscribers by showing up as themselves, telling their stories, and stop getting in their own way.
WE COVER:
- The full Tell Your Story on Substack Notes System
- How to keep telling your story when you don’t feel like it, are too busy, dread it, are convinced no one will like it, with the voice telling you no one will care, or you feel the ick of putting yourself out there.
04
BE FEATURED ON SW@W (37,000 SUBSCRIBERS)
Be featured in my Substack Writers at Work "Tell Your Story" Roundup post and get your Substack in front of 37,000 subscribers.
Tell your story all 21 days, participate in the restack thread, and complete the form and testimonial.
STACKED BONUSES.
BONUS 1
MASTERCLASS: THE POWER OF STORIES THAT DRAW SUBSCRIBERS ON NOTES
SPECIAL GUEST: DARIEN GEE
Self-paced · October 9
We dive into how to write compelling tiny stories on Substack Notes, short posts, in micro-essays, or at cocktail parties—anywhere you want to craft a narrative that compels readers to read more, including: how you can learn from Notes that go viral; the importance of white space, the five w's, being specific, creating emotional arcs, and tapping into universal experiences; the power of being shareable; the difference between storytelling Notes vs. idea Notes; how to be funny, even if you think you aren’t. Plus! The storytelling blueprint PDF for telling great stories on Notes.
$397 → INCLUDED
BONUS 2
MASTERCLASS: WRITING THE PERSONAL
SPECIAL GUEST: JEANNINE OUELLETTE
FRI OCTOBER 2 · 1-2 PM CT
Live with us on zoom · Replay available
A very rare opportunity to learn from award-winning author, master storyteller, and creative writing teacher Jeannine Ouellette of Writing in the Dark, a Substack bestseller with tens of thousands of subscribers, and writing in the WITD: The School. Jeannine recently landed a book deal for her impeccable teaching on helping writers dive into the crevices and cracks to pull themselves out and into their writing.
$397 → INCLUDED
BONUS 3
YOUR PERSONAL STORY DONE-FOR-YOU POSTING PLAN
Your repeatable editorial calendar for Notes
- Your Substack DNA and topics
- What obsesses you
- Your audience
- Your voice
$97 → INCLUDED
BONUS 4
PERSONAL STORYTELLING DONE-FOR-YOU NOTES TEMPLATES
A fillable PDF with my teachings and prompts all in one place
- All 21 days of viral storytelling Notes structures
- Prompts you can use again and again to generate new Notes
- Strategies to repurpose your posts for Notes gems and vice versa so you don't have to be writing more Notes
$97 → INCLUDED
Bonuses total value
$988
Here’s the math
ADD IT ALL UP.
The Core
- Get In Now Kickoff + Masterclass: The Art of Telling Your Story
- Private Substack to help each other do this and know you’re not alone
- 21 Daily Drops + 21-Day Restack Thread
- Masterclass: Uncomplicating Substack To Tell Your Story and Build Your Audience in 2027
- Feature on SW@W (37,000 subscribers)
$1,997
The Bonuses
- Masterclass: The Power of Stories That Draw Subscribers on Notes
- Masterclass: Writing The Personal
- Your Personal Story Done-for-You Posting Plan
- Personal Storytelling Notes Done-for-You Templates
$988
Total value
$2985
Your price today
$297
Doors close September 24 · We start September 25
THE POINT ISN'T TO “GO VIRAL.”
The truth: Going viral tends to bring unengaged subscribers who don’t ever upgrade.
The Tell Your Story (TYS) Challenge is about becoming yourself as a writer and creator on Substack and to stop pandering (even a little) for likes and restacks.
It's hard to trust yourself and your story, especially when it feels like no one's out there.
Good.
That’s what it takes.
If Substack were easy, everyone would have a gazillion subscribers and be making tons of money.
Not having what you want is the price of getting it.
21 days is just the start.
I can’t guarantee you’ll get subscribers. That’s not the point of the challenge.
Most people are flailing around on Substack desperately trying to go viral by doing what they think people want. Don’t be like most people.
Show up as yourself and tell your story until even you believe it’s amazing, interesting, compelling, and utterly worth paying for.
WHAT YOU MIGHT BE THINKING
I definitely don’t have the time to do this.
The way it’s set up, it doesn't matter if you're traveling or have 10 kids who need all of your attention, or if an aging parent has disrupted your schedule. You can tell your story in 10 minutes a day.
I can hardly keep up with Substack as it is.
This isn’t yet another Substack “to do.” For 21 days, you’ll ignore the Substack noise, new features, etc., and focus on yourself and your writing.
I'm an introvert and don't like sharing about my personal life.
When you know how to tell a great story, you never feel like you're talking about yourself too much. Even if you don't like talking about yourself, the way Substack grows, the way to build a platform and make money on Substack is to focus on bringing yourself to your subscribers. The challenge will push you in the gentlest, most supportive, funnest way to show up every day as yourself for yourself, with my expert guidance on writing and how to tell your story.
THE PERSON TEACHING YOU THIS–
Hi there! I’m Sarah.
Here’s what happened: In 2021, I had a memoir coming out. I was a writer and knew I was a good writer, but I had so many doubts. I never felt like I was good enough. No matter the awards, the bylines, the publications, the agent, the book deal, it was never enough. I definitely didn't think of myself as a great storyteller and envied those who were.
HarperCollins told me to start a Substack to promote my book, so I did, and I didn't grow by a single subscriber in a year. This was before Notes and before even Recommendations.
Flash forward four years and my agent introducing me to Substack's head of writer relations, me growing my Substack to 6,000 subscribers one year, me realizing that I understood Substack on a deep level, me getting to know the people at Substack and them setting me up to help people 1:1, and me becoming the world’s leading Substack Strategist with a multiple six-figure business and expertise based on pattern recognition from over 1000+ private clients and tens of thousands of subscribers.
I know Substack. I never meant to be “the Substack whisperer” or expert, but here we are.
I did mean to become a national bestselling author and writer with bylines in The New York Times, The Atlantic, The New Republic, and The Paris Review (where I was an advisory editor) with awards and fellowships from the McDowell Colony and Yaddo and an award-winning teacher at the University of Iowa, Northwestern, and elsewhere, so here we are.
The one thing you need to be a Substack writer with thousands or tens of thousands of subscribers is to be yourself and tell your story.
Because people subscribe to you, not your Substack.
Take that in.
READ THIS BEFORE YOU BUY
Precedence
I have a deep understanding of Substack, perhaps deeper than almost anyone on the planet. I understand how it works.
In 2025, I launched the Notes Boost Challenge because I knew how to help people go viral with that algorithm. That challenge was wildly successful:
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“My subscribers grew by 42% in the last 90 days, from 2620 to 3729, and that is much higher than the previous 90 days, which had crawled along with a 5% a month growth rate. I got 700 new subscribers in March which is a record for me. I had two notes go viral (thousands of likes) and quite a few get into mid-high hundreds. An amazing lift.” —Ros Barber
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“I nearly doubled my subscribers in the last 70 days. But more than the numbers, it’s the connections that matter—writers who’ve become real friends. That’s the part I never expected. And the part I’ll never take for granted.” —Heather Hausenblas
I know how to help people grow on here, and I have a sixth sense and a deeply researched understanding of the algorithm, especially the Notes algorithm, and how posts and Notes are shared and get visibility.
More importantly, I know how to help you use Notes to grow and not use it against yourself.
The TYS Challenge will give you priceless opportunities to get followers and subscribers and use Notes as a sandbox to cultivate the most valuable skill for writers and creators and visionaries (and just about everyone else): the ability to tell your personal story.
Questions
What if I can't make the kickoff, the bonus masterclasses, or the final celebration?
What if I dread the idea of writing about myself? What if I feel burned out by Substack?
What if I don't feel like I have anything to say?
Is there a community/coaching?
What if I fall behind?
Can I get a refund?
Will there be another round?
Last call
YOU CAN KEEP TRYING TO DO WHAT YOU THINK PEOPLE WANT.
OR YOU CAN TELL YOUR STORY.
Three weeks from now, you'll either have:
- 21 Notes and 2 posts on your Substack that tell your story and are examples of you showing up as yourself
- a profound understanding of what it actually takes to have tens of thousands of subscribers and become top-ten bestsellers
- a keen grasp on the psychology of storytelling and what makes people read and want to keep reading more
- command of your voice and what makes you different
- been featured in Substack Writers at Work and gotten your Substack in front of 37,000 people
Or you'll be skipping dates you meant to post, stewing in imposter syndrome, haphazardly posting on Notes that make you cringe, reading more posts on "how to do Substack," and still not having the audience you deserve.
Get in. Now. →