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    How to tell stories on Twitter (even if you’re not an expert)

    By Kieran Drew
    This is an edition of my old newsletter Digital Freedom.

    It's lightly edited but otherwise untouched. I've kept them on the site to show how the journey has evolved.

    Today we’re going to discuss storytelling.

    But not ‘once upon a time there was a dentist going bald’ kind of storytelling. That was last week. Today we’ll talk about how to deliver small, magnetic stories using Twitter. It'll help you stand out in your niche, build a loyal fan base, and get paid to do what you love.

    This one’s a 7-minute read.

    Let’s dive in.

    Stories are digital assets

    I don’t think there’s been quite a rush like the first time I went viral.

    It was August 18, 2021, and I’d just posted a story thread that had been gathering dust for months. I felt stupid. I didn't enjoy writing about myself, nor did I think anyone would care.

    I went to bed that night with no clue what I’d started.

    Because before that thread, I had nothing to show for the previous 12 months of work. A tiny audience. No business. No unique message.

    But I woke up with an extra 2,000 followers and hundreds of DMs.

    More importantly, I had hope.


    That thread was the catalyst for my creator career. 3 months later, I quit my job to go all in. Not just because my audience growth had accelerated, but because I felt confident in how to make an impact.

    I'd had my first taste of storytelling, and I wasn't going back.

    “Marketing is no longer about the stuff that you make, but about the stories you tell.”

    - Seth Godin

    Here's the truth my friend.

    You can’t build a creator business by hiding in the shadows.

    A personal brand is like a puzzle.

    Your audience is trying to piece you together, one sentence at a time. Platitudes and listicles might go viral. But it’s stories where the magic happens.

    Think about it.

    If everyone posts generic ideas, but you share mistakes, fears, doubts, wins, and losses - who do you think they’ll remember? Who do you think they will relate to more? Who do you think they'd be willing to invest in?


    Stories are how you build trust at scale.

    But you don't need to be a master storyteller. Nor do you need to break your neck (although it certainly helps). In fact, you don't even need to write a thread. If you want to tell compelling stories, all you need is 280 characters.

    Introducing: The StoryTweet

    For almost 3 months now, I've shared a story a day.

    If that sounds a little daunting, don't worry. It's actually more simple than you'd think.

    The key is to set constraints.

    So today you'll get a framework to follow to make storytelling simple, then I'll give you a few examples to chew on.

    StoryTweet Structure

    Most stories follow a traditional 3 act structure - setup, rising action, and conclusion.

    And so does our StoryTweet.

    1. Introduction: the hook
    2. Explanation: the meat
    3. Action: the climax

    We'll write one together now...

    The introduction should be short, sweet, and instantly interesting.

    Open with sentences like….

    • When X,
    • Last year,
    • X years ago,
    • I used to believe…
    • I always thought that…
    • My biggest worry/fear/mistake etc.

    Here’s our example:

    I used to be terrified of telling stories.

    Can you see what happens here?

    It opens a loop. There's implied change and a potential lesson. This creates tension, and that's what keeps people reading.

    • What did Kieran learn?
    • Why was he scared?
    • What does he know now?

    Next up, the explanation.

    I worried about being judged. But the truth is people follow people, and stories are the best way to stand out. So I set a rule to share one a day, and now business is great.

    Twitter is great because you don’t have the words to mess around.

    Explain your idea. Share your realization. Touch on your audience’s pain points (if you want to be a great storyteller, know who’s listening).

    But the secret to impactful storytelling is how you finish.

    The call to action.

    Or what I like to call, the sexy final sentence (I have far too much fun writing).

    Stories are magnetic. Don't be afraid to share your own.

    The sexy final sentence relieves tension, giving your reader a little squirt of dopamine (easy tiger).

    You'll see me write a tweet like this every single day. Constraints let you get creative. Next up, you just need to plug and play with ideas.

    5 sources of StoryTweet inspiration

    These are the stories you can tell over and over:

    1. Realisations
    2. Mistakes
    3. Fears
    4. Wins
    5. Experiences


    Lessons are everywhere if you choose to look.

    This is why I love writing. You build an awareness of what happens around you that's often lost in the modern day blur.

    For example.

    As I write this, I’m in first draft mode. I used to HATE this part. I’d see Dickie Bush talk about bullets and structure and feel bad because mine's more like brain vomit. Even after Ship30.

    But emergent writing is a technique. Some of us need to free flow to find ideas.

    So I posted this:

    Within a minute, 10 people agreed and shared their own experiences.

    I'm not screaming platitudes from my podium. I'm having a conversation. I'm treating my audience like people.

    Pretty useful when there’re 135,000 of them reading =)

    In his epic Writing Handbook, Julian Shapiro explains what makes an idea compelling. You need to make someone feel seen. To go "Yes! That's exactly how I feel!"

    It's the little thoughts as you go about your day that help you make a big point.

    Here’s one from the gym:

    And on the way back up from the gym (sucks):

    Pay attention to what gets your attention, then articulate in a way that helps other people.


    Mistakes are my favourite because they show a degree of vulnerability and humility that’s like branding cocaine. Plus, it forces you to reflect, so you act better in the present (but I mainly enjoy the cocaine).

    People are sick of the social media highlight reel, and they don't enjoy being told what to do.

    When you take your ego out of the equation and share from errors, you go from guru to guide. You show you're human. You're out there ballsing up like the rest of us, just trying to get a little better each day.

    Trust me, that’s a good place to be.

    3. FEARS

    Everyone is worried about something, but not many speak about it. Honesty about your fears is a great way to build authenticity.

    Two questions for ya.

    What did you used to worry about that you now know was misplaced (and why)?

    What are you worrying about right now that you know you shouldn’t be?

    If you can make your reader fear less and act more, the goodwill it builds is insane.

    4. WINS

    Ah, wins.

    The story people share the most, yet get the most wrong. There’s a fine line between a humble brag and looking like a tit. Let me help you walk it.

    If you share a win without a lesson, you are a tit.

    If you share a win with a lesson, you are not.

    And so ends the lesson =)

    Wins are great if you do 'em right. Talk about the struggles. Share yours and your client's results. Proof is persuasion gold-dust, and people love to feel inspired.


    If your brand is a puzzle, experiences are the difference between a masterpiece and a crayon drawing.

    Think about:

    • The worst time of your life
    • The best time of your life
    • Crazy shit that happened
    • Most impactful lessons
    • Most impactful people

    Remember, the stories are about you - but the lessons are for your reader.

    Putting in the reps

    I know not everyone who reads this email will take me up on the story-a-day rule. I hope you will. Storytelling is a skill you build like any other.

    With consistency.

    But it's worth every effort because on a long enough timeframe, the writer who earns the most trust wins.

    But what if you don't have an interesting story?


    Create one.

    The greatest stories happen in real time. So set a big goal and document the journey.

    Become someone worth paying attention to, and people will.

    When you share stories, you won't wake up tomorrow with double the followers. Hell, growth might not change much at all. But not everything that counts can be counted. Every story you share alters the way your audience sees you.

    Followers become fans.

    Those fans have aligned interests, shared beliefs, and a similar mission.

    They trust you. They want you to win because if you succeed, they believe they can too. Some people will feel like they know you despite never meeting.

    And that, my friend, is an incredible position to be in as a creator.

    Storytelling is a superpower.

    Don’t neglect your best asset.


    Kieran Drew

    About Kieran

    Ex dentist, current writer, future Onlyfans star · Sharing what I learn about writing well, thinking clearly, and building an online business