How to Tell a Funny Story with Honesty and Ease

Diving into the details and find the funny.

Telling stories from our scars, not our wounds. 

Laughter is not our medicine. Stories hold our cure. Laughter is just the honey that sweetens the bitter medicine.
— Hannah Gadsby, Nanette

When I first started telling stories on stage, I thought that what I was doing was doing stand-up comedy. I would perform on comedy nights, with other comedians, and people would laugh at what I said. But my material had a different rhythm to it. I wasn’t out there just to get a laugh every few seconds, I was sharing things from my life that I could now look back on and laugh at (and with). And the payoff for the audience — who would still laugh, repeatedly, along the way — was a complete story, that they could connect to, relate to, and feel joy from. These weren’t jokes with punch lines, they were funny stories.

One of my favorite things about storytelling as an art form is its ability to lift the tragic into the realm of funny. This happens when the storyteller is honest in their telling. They aren't making fun of what happened to them, they are living in the moment and telling us what it was like through their storyteller lens. Catherine Burns, from the Moth, has said that it is best to tell a story “from your scars, not your wounds.” This allows for time to pass, for the tragic to feel less so, and gives us a chance to reflect on our own experiences. Often this leaves us laughing and finding the funny in things that were nowhere near humorous at the time. A lot of my early stories had to do with people I had crushes on that absolutely did not like me back. Or times when I felt so horribly embarrassed, like peeing in a bush just next to where I was taking my Driver’s test, getting caught peeing by a jogger, and then failing my test within seconds. 

When we get to that moment of realization, where something that felt so awful at the time, now feels good enough to share, it’s time to tell the story.


When we’re simply being ourselves and being honest, we’re usually funniest.
— Charna Halpern

Donald Harrison is one of my favorite storytellers. The first time I saw him tell a story, it was a Moth StorySLAM and immediately got his contact info and asked him to be a part of a Tell Me A Story show. This story is from our September 2018 show, on the theme the Early Years. The quote from Charna Halpern (an improvisor, educator, and author of Truth in Comedy) definitely rings true in Donald’s story — both in the content and how he tells it. Donald is open in the way he shares his life experience, and he carefully crafts his phrasing and imagery into his own unique speaking style.


There is a thin line that separates laughter and pain, comedy and tragedy, humor and hurt.
— Erma Bombeck

Sarah Pulver is a dear friend of mine and I am so glad that she told a story at our July show. The theme was Go Away. In the beginning of her story, Sarah talks us through the various life experiences that came to mind when she thought of the theme, and how she landed on the story she told us that evening. This is one of those stories that makes you smile, and laugh, and builds to an ending that is extremely satisfying.


What truth in comedy life experiences come to mind for you? Think of the moments where you can see the humor in the situation, and you feel like you can ride that that fine line between comedy and tragedy. These are the funny stories to tell. Whatever story comes to mind first, hold on to it. Write it down or tell it to a friend.  


This article was originally posted on our blog in March of 2015. We decided to revisit, refresh and rewrite it, to keep up with our evolving philosophy on the art and craft of storytelling.


Want to hear how our clients are infusing humor into their own storytelling? Join the next Speak Up Session, a free monthly virtual gathering for entrepreneurs, leaders, and change-makers looking to communicate differently without changing who they are.