The Tell Your Story Challenge by Sarah Fay starting in:
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A 21-Day Substack Challenge
Tell. Your. Story.
I’m going to teach you the art of telling your story—so people listen.
- 21 Notes and 2 posts on your Substack that expertly tell your story and are you
- A repeatable system to help you consistently show up as you with no imposter syndrome (which is what it actually takes to have tens of thousands of subscribers and become a top-ten bestseller)
- Command of your voice and what makes you real to a reader
- The chance to be featured on Substack Writers at Work and get your Substack in front of 37,000 people
In 21 days.
My clients are doubling, tripling, and 10x-ing their subscribers. I’m going to show you how.
The challenge: Tune out the noise and focus on yourself 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.
I’m going to teach you to capture people’s attention with the story of you and become the kind of writer whose emails people open, read, engage with, and pay for.
You’ll learn the art of telling personal stories, plus how to:
- Stop doubting yourself and your Substack
- Stop feeling like a fraud and show up as you
- Stop procrastinating on your posts and growth
- Go from throwing spaghetti at the wall to knowing what sticks
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.
The Substacks with huge audiences and making tons of money give us a person—and they deeply enjoy doing it.
No one can compete with you if you’re bringing yourself to what you do here instead of trying to be like everyone else.
For 21 days, I’m giving you the personal storytelling prompts that have made Notes and posts go viral, posts be featured by Substack, subscribers convert, and my clients be cited in The New Yorker.
You’ll use them to tell your story and become an utterly compelling writer in the process.
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.
Day 1: FRI SEPTEMBER 25 · 2:30 PM CT
KICKOFF + MASTERCLASS: THE ART OF TELLING YOUR STORY
+ The chance to meet your fellow TYS challengers
Live with me on zoom · Replay forever
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 do it. 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.
Even when you’re convinced no one will like it.
Even with the voice in your head telling you no one will care.
Even when you feel the ick of putting yourself out there.
BY OCTOBER 15:
- 21 live Notes telling your story
- 2 Substack posts where you show up as yourself
- 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 15 · 1 PM CT
CELEBRATION + MASTERCLASS: UNCOMPLICATING SUBSTACK TO TELL YOUR STORY AND BUILD YOUR AUDIENCE IN 2027
We celebrate! In this 60-minute live Zoom celebration and send off, I show you how all this leads to growth and revenue.
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:
- My full Tell Your Story (and 10x your subscribers) System
- What I’m telling my clients to focus on
- What I’m insisting they stop wasting time on
- How to uncomplicate Substack
- 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, 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 produce two posts on your Substack
STACKED BONUSES.
BONUS 1
MASTERCLASS: THE POWER OF STORIES THAT DRAW SUBSCRIBERS ON NOTES
SPECIAL GUEST: DARIEN GEE
FRI OCTOBER 2 · 1 PM CT
Live with us on zoom · Replay forever
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 9 · 1-2 PM CT
Live with us on zoom · Replay forever
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
The foundation we build on day 1:
- 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 to mine your posts for Notes gems 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
THIS IS NOT A “GO VIRAL” CHALLENGE.
That would be a waste of your time.
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 trying to figure out how to get likes and restacks.
You may despair over Notes and go into a slump when it feels like you’re writing into the void.
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.
Why is this so expensive?
If you commit to one thing this year, let it be this. Personal storytelling is what gives your Substack value. If we looked at all the top bestsellers, all the biggest Substacks, it's not how often they post. It's not all the silly things that people think that some of the Substack growth people tell you it is. It's because they are in their Substacks. They know how to tell their story. They know how to show up as themselves. And enjoy it. Substack posts are valueless if people can get the same thing, or some sort of similar thing, from ChatGPT. What's the one thing ChatGPT can't give you? A true personal story.
It can make it up, but it will never be true. 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.
I can hardly keep up with Substack as it is.
This isn't just one thing to add to the things you "have to do" on Notes on Substack. 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 my personal life.
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. →