Personal storytelling both informs and improves everything you create.

Nobody has your lived experience. Your memories, your moments, and your daily observations as you move through the world represent a powerful source of stories, whether they serve as metaphors, as doorways into a larger theme you want to discuss with your audience, or as end-to-end stories — standalone pieces that inspire reflection and action in others.

Telling more personal, powerful stories is a great way to resonate deeper with others and earn trust and love — and represents THE way we can become irreplaceable in the age of AI.

This menu guides you to explore turning memories into meaning, transforming experiences into anecdotes, and understanding the role of specific stories in the ways we convey the universal.

 
 
 

design by:

Tyler Littwin

We collaborated with artist and illustrator Tyler Littwin, best known for his design, art direction, and illustration for software companies like HubSpot, local bands and singer-songwriters, and soccer clubs throughout the US. Explore his work at blakeink.com.

Tyler’s take:

"Telling our story and using our imagination: two of the most important ways we process and define the world around us. Never too young (or too feline) to create something new and unique to you. Think big and start small. There's beauty in every scribble, every word, every scratch."

 
 

🎓Masterclass

 

 

🎓 guest chef Ann Handley on using personal story

Ann is the author of the WSJ bestseller, Everybody Writes, as well as Content Rules. She’s also a Partner and the Chief Content Officer at MarketingProfs and a globally touring keynote speaker. Her newsletter reaches over 50k readers each edition. Ann visited the Kitchen for a members-only chat and Q&A.

 

 

❤️ How to Tell YOUR Story (Better Bios)

A roundtable discussion and short presentation from Jay.


👨🏻‍🍳 Video Tutorials

 

 

personal storytelling prompts

  • “This happened…” (Describe a memory or moment in brief. It’s something true you experienced.)

    e.g. The other day, I asked a waiter at my local pizza place how their dough could taste so much better than everyone else in town. He told me no two starters make the same dough. The variables it’s exposed to plus the time it takes to ferment means their dough could taste different than competitors. That was their secret.

    “Which made me realize…” (What popped to mind as a result? What comparison back to your audience’s topics or desires?)

    e.g. Which made me realize that WE are the starters in our work. Everything you’ve experienced and all the time it’s taken you to become who you are means YOU are the starter in your work.

    “Which means…” (What do they do with that info? Address the topic you know they care about, which you teach, to reveal the hidden lesson here.)

    e.g. Which means that, even with the same or fewer resources as others, and even with access to similar “toppings and cheese” (tools and content) as everyone in our space, each of us can create original work. The trick is to start with our own personal experiences, memories, and moments and use that as material in our work. Because no two starters make the same dough.

  • Imagine you’re asked to tell your story. “How’d you get here? What’s your story?” Instead of answering that directly, write about ONE moment that sums up your whole deal. Don’t describe your LinkedIn bio. Lift something from those experiences that allows us to understand you emotionally. THEN, tell the rest of your bio quickly, through that same framing.

    So for instance, Jay likes to describe a moment working for Google, in ad sales, when he realized: “I don’t want to make people like stuff. I want to make stuff people like.” That short anecdote is then used to tell the rest of his career story, pressed through the lens of constantly pursuing that idea personally — “and so now, today, I help others pursue that same idea.”

  • Tell the story of when you first encountered a concept, or most recently encountered it. (Consider how your thinking has evolved on the subject, and what caused that change … then consider writing that as a story too.)

  • Write about an observation using this template: action > observation > insight/question (“Yesterday I was [X], when I noticed [Y], which made me realize/wonder [Z].”)

  • What frustrates you in your space that others just seem to accept? Share one moment you encountered that frustration, and try to land on an insight as to why it bugs you — and what should replace it.

  • What are the memories and ideas that keep coming up in conversation with those closest to you — or in your own head? Describe it in vivid detail, and extract a lesson you can learn or use it as a metaphor the audience can relate to (or simply use the memory to help others understand you — “I’m like THIS, for instance, when I was 12…”)

  • Tell the story of a childhood memory, something pure or naive and good. (“I remember…” // “and because we were young, we would…”) Then, jump to today. How has that been lost as we aged? What can we do to reclaim it?

  • What everyday, mundane, routine things do you experience or execute differently, in a quirky, personal way? What can that teach us about your topic in your next piece? (YOU see the world that way. Help us do the same.)

  • What’s the WORST advice you’ve ever received directly and personally (i.e. NOT secondhand by consuming content)? Conversely, what’s the BEST advice you’ve ever received that you applied? Take us into either of those moments, described in detail. Where were you? What were you going through? What do you remember feeling? Place us there. How did your world change after that moment? How can we apply what you learned in our lives too?

  • Think of something you do or experience often, sitting on either extreme of your interests. You LOVE doing it or you HATE doing it. Then, turn that into an allegory — a story with hidden meaning you reveal:

    DESCRIPTION >> MOMENT: “I was doing X, when THIS happened...” (e.g. I was skydiving, when I arrived at the moment when you’re supposed to open your arms and legs.)

    REALIZATION APPLIED TO THAT SAME THING: “And I realized in that moment...” (e.g. I realized that the key to a successful, enjoyable experience skydiving isn’t the moment you leap from the plane as many assume. It’s the moment you open your arms and legs. That’s because… X, Y, Z.)

    APPLY REALIZATION TO THE THING YOUR AUDIENCE CARES ABOUT: “And that helped see, in our lives/work… X, Y, Z.” (e.g. That helped me see, in our work culture, we think risk-takers are great at making the leap, when really, they’re great at being open to what happens once they do.)

    SO WHAT NOW? “So if we want to X, then we should Y.” (e.g. So if we want to do bolder work, we have to ask: Then what? It’s not enough to launch the thing or get the initial buy-in. We have to understand that this initial leap takes us on a journey that doesn’t resemble what came before. We have to be open to constant change, not just one moment of leaping.)

    END WITH A MEMORABLE PHRASE (e.g. It’s not about making the leap. It’s about embracing what happens once we do.)

 

 

📂 Additional Resources

 

 

✅ Personal Storytelling Examples

Rather than simply use as inspiration (though that too), consider how you might use the underlying structure or general story beats of these examples in your own work. Do you have something similar in your life? Create it!