Storytelling Tips I Stole from Friends, Therapists, and Taylor Swift

Stories that connect most aren’t the polished ones. They’re the ones with cracked edges.

Let’s start with a confession: some of the best storytelling advice I’ve ever received didn’t come from bestselling authors, award-winning screenwriters, or Substack gurus with perfectly organised bullet points.

It came from:

• An intoxicated friend at a house party who couldn’t remember how her story ended but sure as hell remembered how it felt.

• A therapist friend who asked me, “And what was the story you were telling yourself?”

• And Taylor Swift, queen of turning emotional breakdowns into Billboard hits.

This trifecta, tipsy friends, professional listeners, and emotionally raw pop stars, taught me one undeniable truth about storytelling:

The stories that stick are rarely the most polished. They’re the ones with cracked edges and visible seams. The ones that feel like they were yanked from the middle of someone’s messy, beautiful life.

And if you want to be a storyteller who connects deeply, makes people feel something, and leaves them better than you found them, you need to stop obsessing over perfection—and start writing like your drunk, oversharing, beautifully flawed self.

Here’s how.

But before that, a story that has been brewing for the last week.

---

Over the past few days, 24 people have joined the 90-Day Write-Grow-Monetise System—because they’re ready to stop spinning their wheels and start building real momentum.

They saw what I saw: writing great content isn’t enough. You also need to grow the right audience and have a simple, aligned way to earn from your knowledge.

I created it after studying the top creators in our space and realizing they were all working across three pillars: writing with clarity and consistency, growing their audience intentionally, and monetising with purpose.

So I built a system I could stick to—working at least 15 minutes a day. No overwhelm. No burnout. Just small actions that stack up to big results.

Now, I’m inviting a small group to go through it with me. If you’re tired of guessing and want structure, strategy, and support, I’d love to help you too.

Use the link below to join and get 20% off.

---

Lead with the emotion, not the moral.

Let’s talk about friends for a second.

They don’t start their stories with, “Let me walk you through the key takeaways from this pivotal life event.”

No. They slam their drink down, lean in too close, and whisper, “OK, listen—this is gonna sound insane but—”

And suddenly, you’re hooked. Why?

Because they lead with the emotion.

They’re not trying to teach you a lesson. They’re reliving a moment. A real, chaotic, heart-thumping moment—and inviting you to come along.

Great storytelling does the same thing.

Before you rush to explain what the story means, let your reader feel what it felt like.

Did your stomach drop?
Did you laugh so hard you snorted?
Did you cry while pretending it was just allergies?

Put us there. Emotion first, insight second.

Nobody wants a lecture. They want a ride.

Don’t over-edit the messy middle.

There’s a weird thing writers do: we polish our stories so much, we lose the fingerprints.

We round off the edges, delete the awkward, and overthink the hell out of it until what once had a pulse now sounds like a TED Talk in a robot’s voice.

The problem?

People don’t connect to perfect. They connect to real.

And “real” often lives in the messy middle of your story.

Therapists know this. They’re professionally trained to live in that liminal, uncomfortable space where you don’t know what happens next.

Where your voice shakes. Where you say, “I don’t know why I did that,” and then quietly realize the exact reason ten seconds later.

So when you’re writing a story, resist the urge to skip straight to the resolution. Sit in the mess a little longer. Write from the part where you were confused, scared, guilty, relieved, or in love with the wrong person, but convinced it was fate.

That’s the good stuff.
If you think it’s, please share so that others can find it too.

The more specific you are, the more universal it feels.

Taylor Swift doesn’t say,

“He broke my heart, and I was sad.”

She says,

“I left my scarf there at your sister’s house / And you’ve still got it in your drawer even now.”

And suddenly millions of listeners start checking drawers in their ex’s houses.

Why does this work?

Because specificity is what makes your story real. And the more real it feels, the more people will see themselves in it.

This goes against the grain of every “generic motivational content” article you’ve ever read. You were taught to generalize. To broaden your message. To keep it “relatable.”

But real relatability doesn’t come from being vague. It comes from being vivid.

So instead of:

“I felt stuck in my job.”

Try:

“I used to cry in the office bathroom between Zoom calls, then fix my eyeliner before logging back in like nothing happened.”

That’s the line your reader will remember.

Because they’ve done that too. Or they’ve been close to it. And they’ll never forget that you were the writer who said it out loud.

Use structure, but don’t let it choke the life out of your story.

There’s a place for structure: hero’s journey, three-act arc, conflict-climax-resolution, before-change-after. All good tools.

But remember: a story isn’t a worksheet. It’s a felt experience.

Drunk friends don’t worry about arcs. They jump all over the timeline, interrupt themselves, change voices mid-sentence, and still somehow manage to keep your full attention.

Why?

Because they’re committed. They’re emotionally in it. And that makes you want to stay in it, too.

Use structure to guide your story, not to sterilize it.

Start in the middle if you want.
End with a question if it feels right.
Let your voice crack open if the moment deserves it.

Nobody’s grading you. They just want to feel something real.

Don’t protect yourself so much that we can’t find you.

There’s a fear, especially with personal stories:

What if I say too much? What if I sound weak? What if people think I’m a mess?

Spoiler: you are a mess. So am I. So is every person reading your story.

And the biggest disservice you can do to your reader is to protect your ego at the expense of their breakthrough.

You don’t have to share every detail. You’re allowed boundaries. But don’t sanitize your story until it’s emotionally hollow. Don’t hide your fear, your failure, your guilt, your tenderness—because those are the things your reader is quietly aching to see in someone else, just to feel less alone.

So be brave.

Show them your cracks.

That’s where the light—and the connection—comes through.

End with something true, not just something neat.

Writers love a clean ending. The epiphany. The mic-drop. The “and that’s why you should believe in yourself” button.

But the best endings don’t always tie everything up.

Sometimes, the most powerful way to end is with:

• An unresolved feeling.

• A quiet realization.

• A single image that lingers.

Like:

“I never saw him again. But every time I walk past that bar, I still check the window. Just in case.”

That sticks. It doesn’t tell us what to feel—it lets us feel it.

Trust your reader. They don’t need everything explained. They just need to know that what you shared was true.

The best stories feel like a whisper, not a shout.

If I’ve learned anything from listening to tipsy confessions, therapy sessions, and emotionally devastating bridges from Taylor Swift, it’s this:

The stories that change us are never shouted. They’re whispered into the parts of us that thought no one else felt that way.

So write stories with cracked edges.

Leave the polish for your floors. Your writing should feel like a late-night conversation. A slightly embarrassing voice note. A lyric you’re scared to admit still makes you cry.

Don’t aim to sound impressive.

Aim to sound like yourself—on your most honest day.

That’s the kind of storytelling people don’t forget.

And the kind they come back for.

Again and again.

If you’re ready to stop winging it and start treating your Substack like the powerful platform it can be, become a paid subscriber and get access to the 90-Day Write-Grow-Monetize system—starting now.

---

That’s all from me today.

As always, thanks for reading—I don’t take your time for granted.