8 Ways to Be a Better Storyteller

Trish DiFranco tells a story on stage with laughing people watching

The first story I ever told was in 2010 at a divey lounge bar, in front of fifteen people, half of which were family members. It was neat n’ tidy with a beginning, middle, end and it was the most fantastic story I could drum up. The one I could count on being a crowd-pleaser – my prized story of going from a starry-eyed Conan O’Brien fanatic to an official Conan O’Brien intern. I remember thinking, “everyone loves that ginger beanstalk so surely everyone will love my story, right?!”


In hearing and performing stories for eight years now, I’ve learned a whole lot. Especially with company like Deena Nyer Mendlowitz of This Improvised Life, Dana Norris of Story Club and Dionne Atchison who slays any gig she gets. In watching and performing with these Cleveland-based queens of storytelling, they’ve taught me that the best stories are the brave ones. That sometimes the most trivial stories get the biggest reception. And that just because there’s a celebrity in your story, doesn’t make that ish good.

A woman tells a story on stage in Cleveland

1) Don’t try to please your audience.

You’ll never win over your crush by pretending to be something you’re not. It’s inauthentic and eventually they’re going to find out that you actually haven’t seen The Big Lebowski and no, it’s not real, it’s Sun-In. If you want an audience to connect with you, be authentic and tell a story that matters to you. If it matters to you, it will matter to them.

Don’t try to tell a story like anyone else. Put you on stage. And share the things that might not be easy to share. – Deena Nyer Mendlowitz

2) Embrace the sh*t out of your sh*t.

Everyone struggs to func on some level and that’s the stuff that connects people in a real way. So don’t try to force your story into a perfect package with a Disney® life lesson at the end. We’re onto you, sista-friend.

The best stories are usually about hardship, difficulty, frustration. People want to know the truth, they want to know how other people handle the chaos of life, and they respond well to honesty, even brutal honesty. – Dana Norris

3) Tell your own story.

No one wants to hear about your loudmouthed coworker Janice or your idiot ex-boyfriend who lit his pants on fire at prom. Yes, it might be a hilarious story but it’s not your story to tell. Speak your truth and nothing but your truth. And let Janice tell her own damn story. And you know she will. (Dammit Janice.)

4) Ain’t no climax without the foreplay.

How’s this for a story? “Once upon a time there were three little pigs. Some stuff happened and then a wolf just ate them all. ISN’T THAT CRAZY?” This is what happens when you don’t build up your story. Because without investment, there’s not much payoff. Storytelling audiences are kind and supportive and want to take the journey to the summit with you – let them!  

When the trend first started, I didn’t want to listen to stories but then it became really comforting. It transports me to a different place and time – I find that’s so needed. – Dionne Atchison

5) Don’t just read the room, create it.

Getting vulnerable in front of strangers can make your brain and body go gonzo. So when you get up to the mic, take a deep breath before you begin. When you’re tuned-in to the energy of the room, you’ll tell a better story because you’re actually entering the experience together.

6) God is in the details.

My friend, storyteller and improviser, Kimberly Pride, once told the most beautiful and precise story about shopping at CVS, about how and why it brought her so much joy. It wasn’t dramatic or pivotal or life-changing, in fact, it was microscopic – studded with small moments like contemplating items in the travel aisle and anticipating coupons in her receipt. It was delightful the way she brought that very specific experience to life for everyone. I still think about that story every time I stroll through CVS.  

My favorite stories are ones that reveal previously unspoken truths, so I’m always pushing myself to dig deeper, unpack more, find out why I felt that way, why that person said that, why I’m still thinking about it, and what it all means in terms of our society and our culture and what we value. – Dana Norris

7) Memorization is not key.

Personally, I like to read my story enough times to where I can deliver off-book but that doesn’t always happen because, ya know, life. When I do deliver without notes, I like to imagine I’m sitting around a campfire with friends, where it’s easy, light, and the punches come naturally. When you’re writing, it’s easy to get wrapped up in the preciousness of words, but I find my stories always hit better if I make an outline of the guard rails, practice hitting those guard rails and then just focus on telling a great story.

8) Lastly, you don’t have to be the next Sedaris.

In fact, often stories from noobs or stories that haven’t been over-processed can be some of the best. Those stories force you in the now, and conjure up actual human feelings – the ones that make you choke on your own throat parts. Those moments are heavyweight. Those moments are take-home. That doesn’t mean you should blow into the gig with a blank slate, but if you’re curious about telling a story and you’re nervous because you never have, there’s no better time like the present!

A woman smiles as she tells a story on stage at the Happy Dog in Cleveland

Have a story to tell? Here’s where to go in Cleveland.

Story Club

This Improvised Life

Storytelling Workshop @ Mass Hysteria Comedy Fest

Great storytelling podcasts:

This American Life

The Moth

Snap Judgment


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