Making connections through storytelling

Sep 19, 2018

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As a freelance brand storyteller, I spend my days writing stories for my business clients, but sometimes (as with this blog post) I craft stories for myself and for the “non-client” people I care deeply about. By the way, I care deeply about my clients too, but they don’t usually pay me money to write about myself.

As creatives, we need to find ways to express our personal vision, even if we don’t make money doing it. I call it the all-important “self-expression” side hustle.

I am someone who always seeks to open up new avenues for creativity, wonder, and learning. Those avenues are everywhere, of course, in music and dance and painting and photography and writing. Can a writer stand in front of an audience of strangers and tell a personal story?

I wanted to explore the answer for myself, because I believe a different skill set is involved when “performing” a story to a live audience rather than crafting it on the page. As a writer, I’m usually hunched over a keyboard, typing, scratching my head, sipping coffee, looking out the window, and typing again. Would performing a story be scarier or require a different approach?

Preparing the story

According to the rules of the live storytelling event I participated in, I’d have five minutes to tell a personal story about “Liberation” on stage (the dreaded theme night)–no notes; just me, a microphone, and an audience of strangers (actually, my wife was there, as were my friends Anna and Mary). Of course I wrote my story out on paper that morning and then typed it into a Word document. I’m a writer first and always.

Then I extrapolated the structure of the story, and put its five major “chunks” on a small notecard. I put this notecard in my pocket and walked around until 3pm, thinking about one thing: "What is my story really about and how can I connect with an audience?”

Perfecting the format

Having “incubated” all day (just as an incubator nurtures eggs and helps baby chickens hatch), I sat down at 4pm with my voice recorder iPhone app and told the full story from beginning to end. The structure was there, and the main five “chunks” were covered, but it sounded awful upon playback–halting and lifeless and lacking emotion, as if told by a nervous, distracted robot.

I felt some performance anxiety creeping in. It didn’t matter, I told myself. I wasn’t a story performer, but a writer, and I had nothing at stake if I failed as a “performer.”

And yet it mattered a lot to me, because stories are all, ultimately, about human connection. Writer, performer, videographer, actor, musician, singer, whatever. We all want to connect with others and, in that connection, transcend our own experiences to create art that others might connect with.

Performance time

In front of an appreciative audience at the storytelling event, my name was called and I walked up to the stage. I looked out at the faces looking back at me expectantly in the dark. It made me smile to see them, to inhabit this moment with those faces, as we both sought to understand what was about to happen in the here and now.

And it was that unspoken connection, that curiosity and possibility on both sides, that made the experience different and strangely intimate.

I’d had the story with me all day, and it had taken the shape it needed to take. The moments of humor and darkness were there, organized and ready to be shared. I had my beginning, my middle, and my end, so the story wanted to emerge, but I hadn’t expected to have them too, the faces looking up at me, adding this sense of human connection and mysterious longing.

Before I spoke into the microphone, I thought of nothing else but crossing that distance between us, breaking the silence in the room to find a place where we all might belong.

Making the connection

And so the story came, as if unbidden, as if emerging for the first time from the brittle egg of my mind. And they laughed and they listened, and I saw what the story did to their faces, their mouths, their eyes. I’d never experienced that before, and it was a wonderful, shared experience in a way that writing a story had never quite been.

“Only connect,” urged novelist E.M. Forster, and now I knew what he’d meant.

I thought I’d be nervous and have difficulties remembering the story, but it took on its own life and I was just there watching people’s faces become immersed in the words of the story. It wasn’t what I expected, especially the sense of calm and the urgency around connection that was in that room, filling the space.

I think I’ll be doing more of this sort of “live storytelling,” because it helps me better understand what stories do, the way they help us find and share meaning with others who are looking to find and share meaning.

We are not alone, and stories offer the promise of community. In the end, stories are all we have for each other but they’re also all we need. As freelance creative, we can never forget that the job is always to connect.

Boston-based Chuck Leddy is a freelance B2B Brand Storyteller who connects brands and customers through engaging stories. His clients include Sojourn Solutions, The Boston Globe's BG Brand Lab, MITx, abas USA, and The National Center for the Middle Market. His website is