What Makes a Classic a Classic?
A question from our Substack live that deserves a real answer
Someone asked this during our live Q&A session, and honestly? It’s the best question I’ve gotten all week.
What makes a classic a “classic”?
Here’s the answer nobody wants to hear:
A classic is a book that enough powerful people decided was important.
That’s it. That’s the answer.
But Here’s the Longer Version:
A book becomes a “classic” when it:
Gets taught in schools - If it’s on curricula, it becomes generationally reinforced
Survives academic gatekeeping - Scholars write about it, which legitimizes it
Addresses “universal themes” - (Which is code for “themes that resonate with the people who decide what’s classic”)
Is old enough to feel “timeless” - Usually 50+ years, but Shakespeare gets bonus points for being dead longer
Gets repeatedly republished - Publishers keep it in print, libraries keep it on shelves
The Uncomfortable Truth:
Most “classics” are:
Written by dead white men
About experiences of privileged people
Published when certain voices were systematically excluded
Canonized by institutions that valued some perspectives over others
Does that mean they’re bad books? No.
Does that mean they’re the ONLY important books? Absolutely not.
What SHOULD Make a Classic:
My hot take? A classic should be a book that:
Survives time - Still resonates decades/centuries later
Influences other writers - Changed how people write
Captures something essential - About human experience, culture, or a moment in time
Rewards rereading - You notice new things every time
Provokes thought - Makes you see the world differently
By these standards, plenty of “classics” aren’t actually that classic.
And plenty of books that SHOULD be classics aren’t recognized as such.
Your Turn:
What do YOU think makes a classic?
And more importantly: What book do you think SHOULD be a classic but isn’t recognized as one?
Drop your answers in the comments. Let’s build a better canon.
📚 SUNDAY EXCLUSIVE FOR MEMBERS: Your 14-Day Classic Love Story Challenge
Speaking of what SHOULD be classics...
This Sunday, paid subscribers get exclusive access to something special:
A complete 14-day reading challenge featuring 14 classic short stories—all about love.
But not the fairy tale kind. The real, messy, complicated, sometimes-beautiful-sometimes-devastating kind.
Here’s what you’ll get:
✅ A complete reading schedule - One story per day, Feb 1-14
✅ Free links to every story - All public domain, ready to read
✅ Discussion questions - For each of the 14 stories
✅ A theme tracking worksheet - To spot patterns across authors
✅ Daily reflection prompts - To deepen your understanding
✅ 10 bonus stories - For when you finish and want MORE
The Stories Include:
O. Henry’s “The Gift of the Magi”
Chekhov’s “The Lady with the Dog”
Poe’s “The Tell-Tale Heart”
Hemingway’s “Hills Like White Elephants”
The Yellow Wallpaper, The Lottery, Cathedral... and 7 more
By Valentine’s Day, you’ll have read 14 COMPLETE classics. Not started. FINISHED.
And here’s the thing: These stories challenge everything we think we know about love. Some are romantic. Some are horrifying. Some will break your heart. Some will make you rethink your own relationships.
Together, they answer the question: What IS love, according to the writers we call “classic”?
Why This Challenge Matters:
Remember how I said classics are books that “survive time” and “capture something essential about human experience”?
These 14 stories do exactly that.
They’ve influenced every love story written since. They’re still taught in schools. They still make us feel things a century later.
And you can read ALL of them in just 14 days.
No intimidation. No guilt. Just one short story a day, with a guide to help you understand why each one matters.
This Sunday, paid subscribers get:
The complete guide with all links
Discussion questions for every story
Printable worksheets to track your progress
A community to discuss the stories with
Plus, you’ll be joining us for:
Weekly deep dives into classic literature (without the academic BS)
Exclusive reading challenges and guides
Behind-the-scenes thoughts on writing and reading
A community of readers who actually GET IT
🎁 Special February Offer:
Sign up this week and get immediate access to:
This Sunday’s 14-Day Challenge Guide
The entire archive of Sunday-only posts
All future weekly exclusive content
Because if we’re going to talk about what SHOULD be classics, we might as well actually READ the ones that earned their place.
See you Sunday. Bring your coffee and an open mind about love.
P.S. The challenge starts February 1st, but you can jump in anytime. The stories aren’t going anywhere—that’s kind of the point of classics. 😉
P.S. Thanks to everyone who joined the live! Your questions are always the best part.I hope to see you at the next one!
Nice…gotta sneak in that “white man bad” injection somewhere 🙄