How To Tell A Story: The Beginner's Guide To Live Storytelling
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How To Tell A Story: The Beginner’s Guide To Live Storytelling

by | Oct 13, 2018

After interviewing an award-winning radio producer (This American Life‘s Seth Lind), seasoned television writers (Bojack Horseman‘s Shauna McGarry and The State‘s Kevin Allison), a competitive storytelling champion (The Moth‘s David Crabb), multiple podcast hosts (RISK!‘s Kevin Allison and Michelle Walson), and a best-selling author (Margot Leitman), Washington Post contributor and two-time Moth champion, Melanie Hamlett has narrowed down the key actions newcomers should take to most efficiently learn the art of storytelling.

The Best Storytelling Resource You Can Buy:

“Margot Leitman’s book, Long Story Short, was recommended by everyone interviewed as the best for total newcomers”

The Highest Impact Learning Method You Can Pursue:

All of the experts agreed. “Nothing will give you as much mileage for your efforts as simply telling a story to people”

See this section of the guide for tips for how to get started telling stories to people even if just the idea of talking to more than one person scares you!


Every single one of us is a storyteller, from cavewomen and men gathering around a fire back in the day to family members catching up around a stuffed bird on Thanksgiving. But to become the kind of storyteller who leaves a lasting impression for baring their soul in front of a live audience, you have to be willing to do only one thing. No, really! Just one thing. Get. On. Stage. Now. Reading, talking, and taking classes about storytelling helps, but the experts all agree that nothing compares to literally just doing it. Sorry, but there’s just no way around it. Having an audience is the most critical part of your learning process.

Whose “Expert” Advice Is This Anyways?

I’ve spent weeks getting practical storytelling advice from some of the best storytellers in the country, all of whom which are also authors, TV writers, TV producers and editors, stand-up comedians, and teachers. I also posed questions about this up-and-coming artform to storytelling forums on Facebook, each with thousands of members, in both the Los Angeles and New York City communities, as well as a storytelling fan group for the Risk podcast. Plus, I myself know a thing or two, having thrown myself into the NYC storytelling scene in 2008, just as it was having its debutant ball moment, and then into the Los Angeles storytelling community the last four years, just as it was starting to catch fire. The main people interviewed either started at the same time I did or are a few years before, meaning they were largely responsible for this art form blowing up in America in the last decade.

Margot Leitman not only wrote arguably the most comprehensive book about storytelling on the market (as well as a memoir based on her stage stories), she also taught some of the very first storytelling classes offered in New York City and, later, Los Angeles. She was my teacher ten years ago, actually, as well as most of my peers’. Almost everyone I interviewed mentioned Margot as one of the main people who either inspired or taught them to pursue this mysterious art form. It’s only in the last five years people have stopped assuming I tell stories in a library to a circle of Kindergartners when they hear the word storyteller and that’s largely due to Margot Leitman.

David Crabb is one of The Moth’s golden boys as well as a regular host of their Mainstage Shows on the road. Like most of us, he moved from New York City to LA recently, where he now teaches storytelling at Occidental College (Obama’s old stomping ground) and also coaches private lessons all over the country. He’s also the author of Bad Kid, which was based on stories he’s been telling over the years and later a one-man show of the same name. He too was mentioned by almost everyone I spoke with.

Kevin Allison was a star of MTV’s The Slate before starting the hugely successful podcast and live show, Risk! He admittedly knew diddly squat about storytelling when he first started out, but after seeing Margot Leitman perform at a show in New York, he threw himself into creating Risk!, which now has millions of fans, tours the country, just published a new book, and regularly features celebrities like Dan Savage, Sara Silverman, and Marc Maron.

Shauna McGarry is a successful TV writer currently staffed on Bojack Horseman and Netflix’s new show, Tuca and Bertie, after years writing on other popular shows. She also co-produced and hosted Radio Picture Show in Los Angeles for years and had a hit one-woman show at the world-renowned Upright Citizens Brigade Theater (where Leitman and several of us got our start).

Seth Lind is the director of operations at This American Life, where he’s been working since 2006. He also created and hosted the live storytelling show, Told, in NYC from 2008-2012, which almost everyone interviewed graced the stages of. He’s been performing improv at the UCB, where we first met, for over a decade and is currently the co-creator of the popular sci-fi podcast Mission to Zyxx.

Michelle Walson is the co-producer of Risk!, along with Kevin Allison, as well as a story editor and coach for successful authors. Her and Kevin run workshops and coach storytellers on the side, both new and established ones. She edited my last book proposal and is a genius.

Jeff Simmermon is a This American Life and Moth storyteller who’s been teaching it for years in New York City. Braver than most, he threw himself into the stand-up scene after storytelling and has now mastered a combination of the two, which is rare. He pushes himself more than any artist I know and, as a result, has excellent advice based on wisdom and experience.

A handful of other storytellers offered advice for this guide, all of whom which run storytelling shows in NYC or LA, teach, host podcasts, and/or edit. These include Tracy Rowland, Jonathan Bradley Welch, Sandi Marx, Alex Stein, Christina Igaraividez, Nimisha Ladva, Marlene Nichols, Tracey Miller Segarra, Emerson Dameron, Prarthana Joshi, Elizabeth Collins, Mimi Hayes, Erin Miller, Stuart Jacobson, others.

Everyone I spoke to, from gurus like Margot to newbies just now getting their feet wet, all had the same piece of advice to someone brand new to the craft—get on stage, no matter how amazing or terrible you are, as soon as humanly possible.

Who is storytelling for anyways?

Usually, the people most drawn to the storytelling stage are the ones who do it naturally in their everyday lives. That doesn’t, necessarily, mean they’re the jazz-hands type extroverts. In fact, a lot of us used to be painfully shy before finding our voice through storytelling. When I finally landed in the storytelling community in NYC, I came out on stage like a woman jumping out of a paper birthday cake. “I’m HERE!” Others, like Shauna McGrary, aren’t the attention-hog, drama queen types that I am. She’s more soft-spoken and calm like several I know, which is a super power. This less intrusive style makes her razor-sharp jokes and Yoda-level insights hit people way harder than my in-your-face approach. But really, we’re just being who we are in real life, which is exactly who you should be on stage. In fact, the only people who fail miserably at storytelling are the ones trying to be anyone but themselves. Several storytellers spoke extensively of how there’s nothing more off-putting to an audience than someone pretending to not care about something we know they care about or the opposite. Storytelling is about truth. That’s all the audience wants from you and they can see right through your armor. Unlike other art forms, the whole point is to NOT be performing.

Despite being so different personality-wise, though, what storytellers have in common is their attitude in general. Jeff Simmermon says we tend to be adventurous, delusional, and a little bit crazy. David Crabb thinks we’re all a bunch of masochists on top of that. “So much of storytelling is about revisiting profound pain and bad times,” Crabb said. “Normal people really don’t like to do that!” I agree with him. We are masochists. But there is a payoff. Emerson Dameron said his personal goal as a storyteller is to take experiences that were painful to him and use them to make others laugh. “It’s like turning sh*t into gold.” I do that myself, but I like to think of it as a way of tricking people into feeling less ashamed about the stupid things they’ve done. Which then makes them feel less lonely in the world. Which then makes me feel less alone. As Simmermon pointed out to me, human beings are so desperate to connect, they’ll talk to a volleyball on a desert island. And then we’ll cry over a movie about a man talking to a volleyball. That’s how desperately we want to connect.

You might be here, like other storytellers, to inspire others. This may not even be the goal, but it’s often the end result. For instance, a couple months after I told a story at The Moth about helping this teenage bully on an Outward Bound backpacking course, a girl came up to me after a show and said she was leaving the next day for Florida to be an OB instructor in the swamps. “Your story made me realize I hated my life and my career and wanted to change kids’ lives like you did.” I still wonder about that girl. I didn’t have the heart to tell her even I wasn’t crazy enough to work at the branch she was headed to.

There are a few unicorns out there who are making a living off of storytelling, usually by repackaging it to corporations. It’s also been making its way into professions that already exist, like marketing and even law. Michael Ahn is a public defender who says he’s been using storytelling techniques in his trials and it’s really paying off. But for the most part, people who purpose storytelling aren’t in it for the money or the career boost. “Storytelling is the only form of art that pays even less than standup,” Simmemon said. It takes a certain kind of person who’s willing to bare their soul and risk so much rejection in exchange for little to no financial gain. So, if money and fame is your end game here, maybe try something else.

For a lot of people, storytelling is a form of personal activism. Christine Igaraividez says she feels morally obligated to keep telling stories because Latinas constantly tell her how much her voice means to them. In fact, most of the marginalized people I know have similar experiences. Even I do it. Every single story I tell has a feminist subtext hidden in the jokes. I used to protest. Now I use stories as my means of fighting against misogyny. A funny story can teach people things they wouldn’t dare hear someone try to lecture them about. No matter what your motive for being here, if you’re a masochist at heart with a sick sense of humor who’s desperately trying to connect with humanity, then you’re in the right place.

The Best Ways To Get Started

Most of the people I interviewed suggested that newcomers take classes, read books, watch live shows, and just sit down and write, but they also believed that nothing will give you as much mileage for your efforts as simply telling a story TO people. Not just to get comfortable doing so, but because their reactions to your story will teach you how to fix it.

Storytelling shows, open mics, and classes are the best and most obvious places to go, but this isn’t always an option for people in more rural areas. Kevin and Margot suggested putting together a group of friends, almost like a book club, and meet every week to share and workshop stories. Whatever it takes to get another human being, and therefore accountability, feedback, and strict deadlines, involved in your process. Michelle Walson agreed that there just isn’t a replacement for first-hand experience.” Margot stressed that it doesn’t even matter what venue it is, just do it. “Even if that stage is your living room with friends.” She also said variety shows are great alternative to open mics, which aren’t always as welcoming. Jeff Simmermon thinks newcomers should challenge themselves to “turn every no into a yes… just get on a stage.” He said even stand-up stages and poetry slams aren’t off limits. “You can’t just wait around to get booked on a storytelling show because they’re so infrequent and you have to hustle to get good enough to be invited.” So he suggests doing what he did and get up on stand-up stages to work out funny parts of your longer stories. Of course, you should always respect the event and fellow artists, but don’t worry about it too much. “Just get up and tell a 2 ½ minute story—nobody else is going to be funny either.”

Jonathan Bradly Welch challenges newcomers to go and start your own show, especially if you live in smaller towns. Look beyond theaters, which can involve more pressure to sell tickets. Instead try bars, coffee shops, and bookstores, as they’re usually pretty open to hosting any event that will bring in more customers. At the very least, look for or create your own Facebook group for storytellers. That way you can collaborate and make something happen. Kevin Allison said another great way to get comfortable telling stories, but without the added pressure of seeing your audiences’ faces, is to start your own podcast. “I understand why people don’t want to start a podcast or YouTube channel because the world is so inundated with them already,” Allison said, “but it’s a great way to create deadlines for yourself and just put your work out there.”

I took two back-to-back storytelling classes myself from Margot Leitman in the beginning. While they gave me the confidence and tools to work on my stories, what taught me more than all of them combined was standing in line outside The Moth, usually in the rain, for an hour and a half every week, just for a chance to get on that stage (they draw 10 names from a hat of 30-50). Obviously, stage time is the most valuable experience, but only slightly more than having to show up every week with a new five-minute story. Not knowing if you’re going to get picked to go up at The Moth is actually great for newcomers, because it forces you to spend hours creating, practicing, and editing stories for the stage. Even if you don’t use them there, you’ll have a pocket full of solid stories you can show up with once you do start getting booked on shows.

But Knowledge Never Hurt Anyone

Getting on stage as much as possible is key, but it’s also okay if you’re a little gun shy in the very beginning. Most of us find out pretty quickly that storytelling is a lot harder than you think. We aren’t just telling stories like we would to friends. No, we have to figure out a way to tell a compelling, relatable, interesting story to a room full of strangers who don’t know us or give a crap about our life. That’s a pretty taller order. And if you’re shy or a perfectionist, you probably want to learn at least something about it before you go out there, guns blazing. I myself just got on a stage in front of 250 people at The Moth before knowing anything about storytelling. It was fine. But it could have been ten times better if I’d even taken five minutes to read an article online about how on earth you write a story.

That’s why classes are great alternatives to stage-time. They not only teach critical lessons about the whole process, from brainstorming to execution, and force you to start telling stories in front of your classmates, they also connect you with people on your own level. Many of them will become close friends or at the very least, provide ongoing moral support and encouragement, especially when you’re too hard on yourself. Christina Igaraividez said she wouldn’t have gotten on a stage after her class had it not been for these new story pals. Stuart Jacobson said don’t let a lack of classes in your area stop you. Instead, seek out people who are doing this work, form a group on your own, and workshop your stories in front of each other. There’s something about the level playing field that takes a lot of the fear out of practicing in front of others.

Not all classes are going to be as good as Margot Leitman’s and that’s fine as long as you’re coming away from them feeling inspired instead of defeated. A seasoned teller in LA said to make sure you ask around and do your research, especially in places like LA, where the scene has blown up and the market is saturated. He said there are some people teaching classes, in LA at least, who have no idea what they’re doing. “They should concentrate, instead, on upping their own storytelling game instead of ripping apart new storytellers to feel better about themselves.” He feared that these particular teachers can actually be quite harmful to newcomers, who are more sensitive and need encouragement. Don’t assume the classes around you are the only ones either. Look outside your immediate community and even online. Almost all the coaches I spoke with do classes or coaching sessions via the internet. Local colleges, like the one David Crabb teaches at, offer storytelling now as well. And check accredited theaters in bigger cites. The UCB in New York and LA is the best. iOWest and The Nerdist have shows in NYC. Even join bigger FB storytelling groups outside your city if you must. You can learn a lot from reading years’ worth of posts. With so much on the internet, there’s no excuse not find classes or a community. Writing Pad offers online classes with some of the most successful writers in Los Angeles.

Don’t limit yourself to official “storytelling” classes either. Susan Shapiro teaches personal essay classes and has helped several storytellers, like 19-time Moth winner, Adam Wade, write put them on the page. Right before I started my storytelling classes, I took a personal essay writing class with Julie Klausner, star and creator of Hulu’s Difficult People. She was the person who finally convinced me, after years of doing improv in New York, that I was actually funny and that my stories were unique. “You have to write a book,” she demanded in our first class. “I’ve never heard of anyone with your kind of life experiences.” I’d never realized until her feedback that living in your truck for five years is kinda weird and might be interesting to talk about. So don’t worry about the perfect class. Just find someone who helps you mine your gold and find your voice. Seth Lind, of This American Life, thinks improv classes are great for storytellers. That’s where he and I met actually. While I eventually quit improv, it’s what I attribute my stage confidence to. You never worry about forgetting your story if you’ve taken an improv class.

In addition to classes, every single person I asked, both vets and newbies, suggested you watch as many storytellers as possible. Because you will learn just as much from the worst as you will the best. What to do and what not to do. The Moth, which is now is cities all over America, is a great place to start because they actually judge each story, which helps you understand what audiences like and why.

Books and articles are another great way to teach yourself about storytelling. Margot Leitman’s book, Long Story Short, was recommended by everyone as the best for total newcomers. Another favorite was Storyworthy by Matthew Dicks, which many felt was more for intermediates. Jeff Simmermon wrote this great article up. The Artist Way was suggested by several, myself included, in terms of giving you concrete ways to tap into your creative freedom and let go of your worst critic—you. David Crabb and I both agree that Anne Lamott’s Bird By Bird is great for understanding any kind of personal stories. Memoirs are also a great place to start if you’re totally new at this. Dry by Augustine Burroughs is what planted the seed for me to give up my adventurous life as a white-water raft guide and backpacking for the concrete jungle of NYC. I’d never read anyone who laughed at their tragedies the way I did. Susan Shapiro wrote a great book that helps you generate ideas for stories to write, which you can later take to the stage. And then there’s David Sedaris. I’ve never met a storyteller who didn’t have almost an unhealthy obsession with the brilliance of that man. Spalding Grey is another favorite. Memoirs by some of our favorite storytellers include Kimberly Auerbach, Jonathan Aimes, Carrie Fischer’s memoir, Mike Birbiglia’s Sleepwalk with Me (the play, book, or movie), Chris Gethard, Chelsea Handler, Dave Hill, David Car.

Podcasts are a great way to learn about stories while driving, cooking, or whatever. Kevin Allison has to listen to hundreds of stories as a producer of RISK!. He says he literally stops and says “WOW” sometimes while doing his errands in NYC. He suggests that newcomers notice those WOW moments themselves and ask yourself what about that story is getting such a big reaction. Let those moments teach you what to strive for. In other words, don’t just read about the craft itself, devour actual stories. This American Life and The Moth Podcast are probably the most well-known storytelling podcasts. To get a story on either of these shows, though, is like making it to the showcase showdown on The Price Is Right. Every storyteller I know desperately wants to get a story on TAL. I’ve only had one pitch accepted in my 12 years, but then it got tabled when the chaos of Trumps’ inauguration and Muslim ban took center stage. Despite winning the Moth multiple times, none of my stories have made it onto their podcast either. They’re too R-rated for public radio. More importantly, though, I cuss. One of the producers of The Moth pulled me aside one night and said, “I’d love to get one of your stories on the radio, but good God, woman, you’ve GOT to stop throwing f-bombs.” I still haven’t learned how to do that but take note. If you want to get on public radio, you can’t talk like a 13-year old boy.

But that’s where RISK! comes in. I’ve told nine stories on the RISK! Stage, have seven stories on their podcast, including an hour-long one featuring just my (which is over an honor), and I have a story in their new book. As much as I’d love to be on TAL or The Moth podcast, my stories and my style fit in best on an edgier platform like Risk. So, don’t get discouraged if you submit to shows and get rejected. And really know the show you’re pitching to and their voice. Try everything when you start out of course but put your energy towards the shows that reflect your style most. The reason Kevin started Risk, actually, was because he knew misfits like us needed a home. The Moth and TAL are sometimes a little too curated or feel-good for some folks, so Kevin created a platform for stories that no radio in their right mind would dare to air.

One final suggestion to get started in storytelling is to read scripts. Shauna McGarry became a storyteller at the same time she started getting staffed as a writer on TV shows. While being her dream job, she also found that writing for a show left her feeling uninspired at times because you have to detach from your own voice and style in order to mimic that of the show’s creator. But what it did do was teach her how to look at herself as a character on a sitcom. To detach and be more objective, like a writer staffed on the show about her own life. In doing so, she was able to explore who she was, how others perceived her, and what motivated her behaviors in a way that people like myself have to hire editors to help us see. The basic principles and rules are the same across the board for all types of storytelling, so never underestimate how much you can learn from other mediums. I personally learned more about story structure, eight years into my career, from Tom Vaughn’s screenwriting classes in LA and a TV pilot writing workshop. Shauna’s most recent one-woman show in Los Angeles was a huge hit, and all she did was sit down to write it just like a pilot.

Get to work

Enough talk, it’s time to get to work. But where do you start?

Everyone usually has at least one story they’re dying to tell. That’s usually the one you should start with. But make sure it’s because you love this story and not because you think it’s a good story. Passion is critical to the success of a story. If you don’t care about your story, nobody else will.

But what about people who aren’t ready to tell their best story yet or want to start somewhere else? Well, that’s where brainstorming comes in. Susan Shapiro suggests starting with your most humiliating secret. Shame is one of the most relatable human emotions out there. David Crabb always gets his students to think of inciting incidents instead of big events. Your wedding day may be the most important day of your life, but possibly the most boring story you could tell. But sleeping with a guy in the parking lot of your sister’s wedding reception because you felt abandoned by her? That’s weird, relatable, and a much better story (and probably the next one I’ll pitch Risk). Kevin says he’ll usually ask students to look at their life as if they’re a therapist or a detective. Don’t just list interesting events, poke and prod and uncover every dirty little stone. That’s where the gold is. Another storyteller told me they write the words “best,” “worst,” and “first” at the top of a page, then make a list of events: kiss, school dance, job, etc. These are the diamonds in your memory’s rough.

Kevin says that Risk gets inundated with story submissions, so he has to make a lot of hard choices. Sadly, he gets a ton of stories about people being molested, abused or raped, so he only goes with ones that really stand out to him. In our interview, he actually mentioned my hour-long episode about my abusive ex to explain his point. “The magic is in the details and point of view,” he explained. “What struck me about your story was the humor you peppered throughout. And the insane details of it all—the characters of both you and your ex, and the empathy you had for both.” I didn’t just tell a story of dating a violent man. That’s depressing and too upsetting. Instead, I told a story of falling in love with a “free spirit” who lived on trains for ten years… that I later caught eating dog food, brushing his teeth with dirt, and faking his own death. The details not only flesh out the character, but they also gave an otherwise tragic story some much-needed humor to make it more digestible for the audience (and fun to tell instead of traumatizing for me). If your story is just sad or just funny or just crazy, it won’t work. For a tragic story, you need to work in humor to give the audience a break. If it’s sad, the same goes. If it’s funny, you need serious moments, or it will seem like you’re hiding. In other words, you’re asking a room full of strangers to go to very dark places with you. The least you can do for them is give them a much-needed break here and there. Not with stupid jokes but funny, relatable details.

Because stories are about you more than anything else, don’t shy away from stories with a seemingly boring premise. Emotions drive stories, not plot. One of the most riveting stories I’ve ever heard was about a woman getting her boss a cup of coffee. I’m pretty sure she won The Moth that night because it wasn’t about the coffee. It was about her irrational fear of getting fired and how that perfectionism consistently made her life unnecessarily dramatic. Shauna is another example. “I’m not the most adventurous person,” she said, “so I blow out the smaller moments and use observational humor.” She and I have been on shows and together it’s like yin and yang. She can make the most mundane experiences heartbreaking, hilarious, and riveting. I, on the other hand, have the opposite problem. Living in a clown house in Chile and hooking up with one of them is not a normal experience most can relate to. In fact, the job of storytellers like me, who’ve done pretty insane things, is to explain why so the audience doesn’t think “This chick is NUTS.” Our challenge, instead, is to make crazy situations that nobody can relate to somehow relatable. For instance, the only way I could tell a story about dating a fellow raft guide while living in my truck in Wyoming was to make it about housing. I focused on me not wanting to break up with the guy because he had a house (with lights and running water!) so I essentially was using him for his utilities. Every New Yorker in that room knew what it’s like to stay in a bad relationship because you don’t want to have to look for a new apartment. They were all shaking their heads yesssss. That’s how a hippy raft guide hooked them in. Whether your story is action-packed or about small moments, figure out what is relatable to the human experience and let that be your driving force.

Crafting the story

In every part of the storytelling process, being personal is one of the most important things to must do. Michelle Walson says that and being specific are hands down the most critical part of storytelling. Jonathan Bradly Welsh said, “If being an awful person with poor decision-making skills is your thing, own it.” Self-awareness and honesty are crucial parts of the writing process. If you try to skate over something or pretend like you were a great boyfriend when the audience can see your actions and tone paint a different picture, they will hate you for it. But if you can help people see the driving force behind your terrible decisions, why this was a pattern or a break in a pattern, and how it changed you, they will forgive you for the shittiest of behavior. As Walson put it, “Stories are about change. Audiences want to go on a journey with you.” But the journey itself isn’t nearly as important as who’s taking us on it. The wow that Kevin listens for is never about the plot. It’s about the storyteller and their ability to change throughout a story.

The other critical part of crafting a story is figuring out why on earth a room full of strangers who aren’t the least bit emotionally invested in you or your life should care. You can be the most likable character on stage, but if your story doesn’t have a point, even humor can’t save it. The audience will think you’re a lazy narcissist for making them sit through it. Seth Lind says this comes up a lot at This American Life. “The audience has to care,” he said. “Part of our job is helping the storyteller figure out why this thing matters so much to them.” If passing a test is important in the story, we need to know why. Otherwise, the audience will think, “It’s just a test. What’s the big deal?” Because it was never about the test anyways. It’s about the stakes driving your reactions to the test. Without emotional stakes, you have a flat story that’s confusing and unrelatable. This is especially true with confessional stories. “Just admitting something isn’t impressive,” Seth said. “So you need to not only own up to but explain how and why you came to make such a terrible decision. Not in terms of exposition, but emotion.” Again, forget plot. It’s useless. Emotions are what drive all your actions and reactions.

Now that we’ve got the most important stuff out of the way, what about the logistics? I bet you want a magic formula, don’t you? A cookbook that gives you specific instructions? You’re in luck! The best one I’ve come across so far, that’s a quick read but incredibly thorough is Jeff Simmermon’s How to Find Your Story’s ‘North Star’. It breaks it down into charts and simple ideas. For those who are more math-minded and often formulaic in their approach to things, this breakdown will help.

Most stories, whether they be movies or plays, follow the three-act structure. Within this structure are five parts to the story:

  1. You
  2. Need
  3. Go
  4. Get
  5. Return

In other words, you start off with the background so we care who this hero is and understand their situation. The “inciting incident” is the need, both external and internal motivations. In other words, what on earth do you want and why do you have to have it so bad? The internal motivations (the emotional stakes or ego) are what Simmermon calls your North Star. Let that be your guide for the whole story. Go is the adventure you’re embarking on and everything that happens, especially everything that stands in your way. The Get is actually getting the thing you wanted or, rather something else you didn’t realize you wanted before the adventure started. And the Return is you going back to your world as a changed person as a result of this little jaunt. If you haven’t changed, scrap this story. It’s worthless.

Another fun visual to help, also thanks to Jeff Simmermon, is the “so that” chart. The South Park creators suggested this too. It’s commonly used in the film and TV biz.

Want… that….so that… so that… so that…. So that….

Seems way too simple right? Well, it is. But it helps you know your motivations for every single scene in your story. Without knowing WHY you’re doing what you’re doing, the audience won’t care about WHAT you’re doing.

An example would be making the cheerleading squad… so that. I’m popular… so that… guys will like me… so that… I have somewhere to go on the weekends… so that… I don’t have to be at home to take care of my drunk mom… so that…

This was a depressing example. Sorry! But you get the point. Motivation or why is the driving force of your story. Without it, it’s just plot, emotionally empty, and you will feel the audience getting bored.

Tips for The Non-Mathy Types

We’re all different though and I have yet to meet a storyteller who has the same process for crafting stage stories. I personally can’t do outlines. They make me nuts. Scripts are the only time I’ll use them and even then I do so with the utmost contempt for the process. If you’re like a lot of artists, you might thrive more in the “contained chaos” approach. Just like my packing process for a trip, I have to literally throw everything on the floor and make a huge mess before I can pack it into a carry-on suitcase. So here is my process, which is similar to those who hate math and outlines. First, I brainstorm some ideas and choose the story I’m most passionate about. Next, I’ll write sentences or phrases to summarize what happened in consecutive order (almost always consecutive… that’s how life is!). Then I’ll stand up, set a timer, and just tell the story. The first go at it is usually stupid long. At least 15 minutes, if not 25. For a ten-minute story on Risk, that’s a lot of cutting. But for a five-minute story at The Moth, we’re talking about a massacre. But, as any writer already knows, writing is about rewriting and cutting. Once I figure out what huge chunks to cut, I then start the tedious practice of shaving the fat.

Kill Them Darlings

Editing is the most painful, but critical, part of creating any story. It’s what makes or breaks a story to be honest. Michelle will always ask storytellers point blank why they are telling this story, what points are they trying to get across, and then helps them highlight everything that supports those themes. “Often what’s important to them isn’t coming across because it’s buried under extraneous details and logistics,” she said. Yes, we just said before that the magic is in the details, but not too many details. This, she said, is why telling your stories, even casually, to friends, co-workers, the cab drivers, are so important. Pay attention to their response. What questions they ask, what makes them light up with curiosity or excitement, and where they get confused. Once you do that, you can start to cut your story down making intuitive edits. “Once you’ve got it down to ten minutes, see if you can get to seven. Then to five.” If you don’t miss what you left out, keep it out. Tracey Rowland said she used to give way too much backstory because it was just soooo important to her… though not necessarily to the story. I still struggle with this. Then our friend and TAL storyteller, David Dickerson, told her to ditch the first whole page of every story “because nobody cares.” It sounds harsh, but it’s true. I end up ditching the beginning of every single story I write, for the stage or magazines. Consider the first two minutes of every story to be a warm-up song that doesn’t need to be on the album itself.

A lot of storytellers I spoke with, both new and veteran, record themselves at least once before making the final edits. You won’t believe how much you’ll cringe. Because you are now hearing it as the audience would and boy oh boy do we think they’re stupid. Storytellers and writers are often so afraid they’ll be misunderstood or judged harshly that they’ll overexplain everything (or not enough). Don’t. Given people credit. It doesn’t take five sentences to explain a character was angry. Saying he ripped out all the grass around him during a picnic is not only more clever and visual, but it’s also a more efficient use of time. If nothing I’ve said so far has convinced you how important it is to cut your stories down as much as humanly possible, here’s something else to keep in mind—nothing will get you blacklisted from shows sooner than consistently disrespecting the host and your fellow tellers by going way over on time. All of the tellers who’ve run live shows said their biggest pet peeve was when people didn’t pay attention to the light that signals it’s time to wrap things up. Shauna stressed that it’s not only disrespectful, but it’s also selfish. “No one is ever as interesting as they think they are,” she said. “And the best stories are almost always the shortest versions.” She, Margot, and a dozen others said the same thing—come prepared by practicing your story, so you don’t ramble.

The Execution

When we say practice your story, we don’t mean memorize it. And for God’s sake, don’t read it or even bring notes. Nothing will create a wall and remind the audience you aren’t their friend than to pull out a piece of paper. Respect the craft and the intimacy that comes along with it. Some people do write out their stories and memorize every line, but every teacher I spoke with suggests the bullet point approach instead. Not only because you don’t sound like a robot reading a speech, but it’s also safer for you. There’s nothing more painful than watching a great storyteller stop mid-story and ruin the flow, if not the story itself, because they couldn’t remember what happened next. This is your story! You know what happened. But if you memorize lines you’ve so perfectly crafted, you are less likely to recover if you hit a bump and get derailed. Besides, people came to hear you tell stories to them like you’re a friend with a secret, not someone reading their new memoir from Barnes and Noble.

People don’t want actors though either. Yes, be in the moment, but don’t act out the story. You’re not performing your story, you’re literally just telling it. I’m pretty animated myself, but that’s how I am in real life. People constantly tell me “that thing you do with your arms” is hilarious. I had no idea what they were talking about until I saw a video of me at The Moth. I guess I flail around like a muppet when I talk. It runs in the family, so that makes sense. I’ve seen videos of me actually kicking my legs in the air like a dancer and thrusting my hips like a pervert. You really do learn a lot about yourself from watching tapes of your shows! The point is, if that’s what you do naturally, don’t change a thing. You’re just you doing you. Nothing will make you more awkward and disingenuous to an audience than forcing new behaviors or putting a straitjacket on natural ones. That doesn’t mean you can’t use crazy voices or accents when using dialogue for other characters. Especially if that’s what you do in real life. Just make sure you’re not overdoing it or offending people in the process, which is a common and cringe-worthy mistake newcomers make. Especially if you’re white and imitating a person of color. If you can’t do it respectfully, don’t do it at all.

Kevin is a huge fan of using dialogue and voices to give life and layers to a story as well as sensory memory while telling it. Basically, tell your story as cinematically as possible. The smells, noises, textures, sights. The look of devastation on your mom’s face over something you said at breakfast. Anything you can do to take the audience back there. He’ll even have students to use tone, volume, and pauses to convey the emotional honesty of a story. The thing is, though, a lot of us are terrified of silence, especially in the beginning, and will go for a laugh when we’re nervous. In doing so, though, we skate over heavy moments to get to a cheap laugh. This not only doesn’t do your story justice, but it’s also really unfair to the audience. As storytellers, we are the ones driving this bus, and the audience has graciously entrusted their emotions in our hands. If we’re careless and just speed past a moment they really need time to take in, feel and process, then you’re robbing them of that chance to connect with you, themselves, and even the collective whole. You may even be triggering some by carelessly taking them into traumatizing stories without thinking of their well-being. Kevin said the majority of stories that bomb on the Risk stages are because someone was too afraid to be emotionally honest while telling their story, which either confuses or frustrates an audience he believes will go anywhere with you. There’s nothing quite like a storytelling audience.

The audience

It may sound like we’re giving audiences way too much power here, but they are the ones you’re doing this for aren’t they? If not, they should be. One of the biggest mistakes people make is to tell stories just to “get them off their chest.” Or for applause. Of course, what artists don’t like their ego stroked with validation and praise here and there? But to be good at storytelling, you have to abandon your needs entirely and put the audience first. Yes, it’s cathartic and yes, it’s fun. But human connection is the heart and soul of storytelling, not to mention life in general. What you realize after doing this for a while is that they, like you, also want to be heard. So, if you’re not thinking of who will be hearing this story when you write and perform it, you’re missing the point. Here are a few other things to consider when telling you stories:

Unlike you, the audience doesn’t have a microphone and spotlight. So, instead, you have to be plugged in and actively listen to them. Not just the laughs but the silence. Acknowledge that silence sometimes to show you’re listening. Sometimes there will be low rumblings, which means you may need to explain yourself or backtrack. The worst thing you can do is gaslight them by pretending their reactions don’t exist. On some love, the audience helps write the story. Some of my best lines, and even my most profound epiphanies have come from me stopping to acknowledge and address a surprising reaction from the audience. Seth and I agree that this is where improv classes are hugely beneficial. One of the most important rules of improv is to “yes, and” people. By acknowledging their unexpected delight or disappointment of even a pipe banging out of control behind the curtains, you’re acknowledging that this is a conversation between you and them instead of an egomaniacal tirade of a total narcissist. More importantly, these unplanned moments often create the element of surprise, which Seth says is the best way to win over an audience. They always think they know what’s going to happen next and finding a way to “ring that bell” as Simmermon calls it, is the difference between winning The Moth and coming in second.

This doesn’t, of course, mean that you tell your stories in a codependent way. Far from it. But you always keep impact in mind. Shauna and I spoke about how much we’ve both evolved as storytellers and how we tell new and even old stories totally different now. Both of us used to do a lot of self-deprecation to get laughs, partly because it’s how we really felt about ourselves and party because it comes across as self-aware. But as we have both matured and learned to like ourselves more, we’ve stopped doing it as much because it’s a defense mechanism. “It’s one thing to cut yourself down in front of your friends in real life. Everyone does that, usually without even realizing it,” she said. “But this is a story you’ve actually crafted, meaning we get to choose what we say about ourselves.” As a woman with a mic, she has influence. It started to really bother her seeing younger women in the audience listening to her criticizing her own weight or her clothes. It’s not only mean, it normalizes self-hatred and women really don’t need anyone else telling them it’s okay to hate their looks or feel slut-shamed. I used to call myself a slut to remind people of the messages our culture inundates sexually active women with, but I often took it too far and probably ended up reinforcing the very rape culture I claimed to be fighting against. Now I walk the line more carefully and try to be a self-aware, fallible, but confident role model.

The other critical thing to consider when thinking about your audience is who this story is about. This has been discussed to death in FB forums, as it is a big issue with sometimes devastation consequences. David Crabb’s biggest piece of advice for new storytellers is to make sure you’re careful when telling a story that can’t be erased. You have a lot more liberty when telling a live audience about your dad’s porno collection or your mom’s affair with the neighbor. But if you go on a podcast or any forum that you don’t have ownership of with that same story, you can do irreparable harm to not only them but yourself. He suggested the book The Art of Memoir by Mary Karr to help storytellers decide what to share and what to keep private. It’s totally acceptable to change names and defining characteristics of real people to protect their anonymity. But there are a handful of people you cannot protect, mainly your spouse, family, and maybe bosses. On the one hand, storytelling can be a Valentine to the people you love “almost like you’re a tribute artist,” Crabb said. A poor lapse in judgment, though, can ruin relationships permanently. “Your family members are people you’re going to have in your life forever,” he said. “So, to protect not only them, but yourself ultimately, it’s best to tell a story about them in a way that’s both honest, but that they can sign off on.” He learned the hard way from his memoir, which destroyed his relationship with his father, despite the book portraying him as an extremely likable character. So do not take this responsibility lightly. Either don’t tell the story at all or don’t tell it yet. Both Kevin and David advise their students to run a touchy story by a therapist first. Or write it just for yourself. Because once you put it out there, you can’t take it back. And if you really hate someone, don’t tell a story about them. The wound is too fresh and you’ll look like a jerk for trash-talking them. “The audience collectively cringes at emotional dump truck stories,” Crabb said. “Not only does it make them feel emotionally unsafe, it frustrates them because they can’t rush the stage, give you a hug, and make sure you’re okay the way they would literally any human being they saw break down in front of them.” So when in doubt, hold off on telling a story you’re not over yet or aren’t sure how to tell in a fair way.

Now Some Biz Talk

There are a few more tips and fare warnings storytelling teachers, producers, hosts, and fellow creatives thought you should know before you venture out to stages. First of all, don’t ask to be on shows you haven’t attended yet. It makes you look lazy and entitled and is just bad karma. If you can’t go to storytelling shows you’re not actually in, don’t expect your storytelling friends to come to yours. Once you do get booked, do not be late. It’s not only rude, but it also causes the host stress, making you less likely to get booked again. Make sure you come prepared but don’t over-rehearse. Sandi Marx said it best, “Tell your story like it’s friends. Not Carnegie Hall.” Never assume gay characters in your stories are out. One storyteller that I spoke to still can’t believe she outed him to everyone. And don’t give feedback to other storytellers, even if you value it yourself, unless they ask. Especially if you’re a man. Women don’t like being story-splained things they may know more about than you. Try not to say “um” too much or start every single story with “sooooo…” Another pet peeve is starting a story with “picture it….” or “the day was dark…” This isn’t a book chapter. Just talk to the audience. And the same goes for the end. Don’t force a moral lesson at the end. Yes, every story has to have a point, but if you’re good, you will have woven it throughout the story. I’ve seen so many good stories ruined by an unnecessary explanation of how the teller changed. It usually looks like “and that’s when I realized” or even worse, “So the moral of the story is…” Again, your audience is two steps ahead of you at all times. On that note, know when your story ends. Alex Stein said, “I’m amazed that people don’t recognize when their story has ended and instead keep going and going, piling on one ending after another, until the audience is just exhausted and no longer cares.” Or similarly, ending too soon or not sticking your ending. I ruined the only serious story I’ve ever told at The Moth because I ended my story like a sloppy gymnast instead of sticking it. Even if you limp across that finish line, act as if you meant to end it like that.

Tips For Pitching

Performing is that classic catch-22. Once you get on shows, it’s easy to get on shows! But how do you… get on shows? Well, it helps to have a Moth win or some credit to your name. Or a connection, which is where a community is key. A lot of people from your class or feedback groups will start their own shows eventually. If they’ve seen you tell before, they won’t care if you don’t have credits. Once I told some killer stories at a few shows, other guests on those shows would then invite me on their shows. It’s a lot of networking, but not in a gross way. But when all else fails, you can always send the producer a pitch. Here’s the best format I know of, which the talented Andie Christie of the Liar Show in New York told us about:

Pitching in 8 sentences or less: Start with a sentence or two about where you are and what’s happening, then a sentence or two about the problem/conflict. Then a sentence or two about what’s at stake because of it, and finally, a sentence or two about the outcome.

Why Storytelling

I have yet to find a community of people or audiences as welcoming as those in the storytelling world. Stand-up is notoriously competitive, and the audiences can be almost combative at times. But the people who share and listen to stories tend to have a genuine desire to connect with people through their own vulnerability instead of hiding behind jokes. The only downside to this is that it’s easy to get complacent in the storytelling world. “To become a better artist, you need to be both nurtured and pushed,” Simmermon said. So he’s been grinding his storytelling ax in the stand-up world, which few storytellers have the guts to do. It’s shockingly hostile when you come from the storytelling world. But it will teach you how to handle hecklers, think on your toes, engage with the audience more, and learn how to tell your story even when you can’t remember it. By learning how to stay focused when you get thrown by a heckler, you become not only better but less afraid of failing. In other words, failing is an essential part of learning any craft and storytelling is no different. So don’t be afraid to show up at open mics and fail. It will teach you more than your successes.

Whether you get out there in classrooms, living rooms with friends, open mics, bookstores, or even create your own show, the point is to just get up in front of people and DO IT. As Simmermon says, cookbooks are fun to read and make you feel good, but you’ve got to actually cook. That’s the whole point. To cook.”

The Best Storytelling Resource You Can Buy:

“Margot Leitman’s book, Long Story Short, was recommended by everyone interviewed as the best for total newcomers”

The Highest Impact Learning Method You Can Pursue:

All of the experts agreed. “Nothing will give you as much mileage for your efforts as simply telling a story to people”

See this section of the guide for tips for how to get started telling stories to people even if just the idea of talking to more than one person scares you!