How to tell a better story

Need to know

People tell stories all the time: at parties, at dinner with family or friends, at work, in job interviews, on blind dates. Storytelling is pretty much everywhere. But somehow the skill of storytelling can feel mysterious. We all know someone who seems so comfortable and engaging when they recount a funny experience to coworkers or share a moving episode during a wedding toast. What’s their secret?

While some people do have an easier time speaking to a group, there isn’t a ‘storytelling gene’. I’ve been participating in storytelling events for more than a decade and have coached hundreds of storytellers, many of them totally new to the idea of sharing a story in front of a crowd. And I can tell you for sure that the ability to tell good personal stories isn’t something you’re just born with. It’s something that anyone can learn, practise and enjoy.

The first time I told a story onstage was sort of an accident. I was at an open mic show with a friend, and she wanted me to put my name in the hat along with her as a form of moral support. I looked at the crowd – 250 people! – and did the math, and I figured there was almost no chance I’d get called onstage to tell a story, so I agreed. As luck would have it, I got called up to the stage first.

I told a (pretty awkward) story about a love triangle. And it was terrifying, yes, but it was also exhilarating. After I sat down, my heart was still pounding, and I got to listen to nine other people tell true stories about their lives. It seemed to make the whole crowd feel so close. Stories created a kind of alchemy in the room, giving us all a way to know each other, whether we were telling or listening.

Since then, I’ve heard stories about so many different experiences, from so many different lives: artistic victories, childhood fears, travel adventures, tiny moments of true love, epics about career change. Why do I love doing this work so much – telling my own stories, and listening to others? I think it’s this: we connect to each other by sharing our lives, and having a frame (such as a story) makes that sharing easier. Stories let us reach out to other people and say: Me too! I’ve had things happen to me too. You’re not alone, and neither am I.

Not all stories are personal stories. I happen to love stories of every kind, whether it’s sharing work gossip, writing a novel, or giving your best friend a synopsis of your favourite TV show’s season finale. But in this Guide, I’ll be talking about the practice of planning and sharing, out loud with others, a story about your own experience that is true as remembered by you. People often tell these stories on the fly, but it can be useful to prepare and practise a story with a particular intention or situation in mind. So, in this Guide, we’ll explore some powerful ways to level up your storytelling game. And we’re going to focus on verbal storytelling, but I think you’ll find a lot of this guidance will be relevant to written stories, too.

Why tell a personal story?

Personal stories are useful for more than just dinner party chitchat. A teacher might have a personal story about their own attempts at learning to read, ready to share with an anxious kindergartner. A researcher looking for funding might share the story of an important discovery with an interested acquaintance, just in case that person is seeking a cause to support. If you’re nervous about meeting people – say, your new partner’s parents – having a couple of stories in your back pocket, ones you feel great about, can be a game-changer if conversation starts to flag.

A personal story has a special something: it doesn’t just entertain or inform your listener (though it can do both), it also lets them get to know you better. Personal stories make great persuasive tools, too. When it’s a first-person account of events, a story has more credibility – we, the listeners, can trust that it happened this way, because you were there.

So personal stories can have an impact. A story might illustrate a concept that is tough to understand, move people to take action, or change someone’s mind about an issue. Personal stories told with intention and purpose have value in classrooms, presentations at work, fundraising pitches, negotiations and more.

Of course, we often tell stories about ourselves simply to make a connection with others. You might want to show your listener that you’ve been through something similar to what they’ve experienced; show them your vulnerability; or get them to understand where you’re coming from.

There are many ways to tell a great story

In my doctoral research on narrative and storytelling, I came across the helpful concept of situated stories. It’s the idea that any time you tell a story, you’re choosing it, changing or shaping it specifically for the people you’re talking to, the context you’re in, and your purpose in telling it. The story of a wild night from your teen years that you share with your boss at the office Christmas party is likely to be quite different from how you’ll share it with your friends. Usually this ‘editing’ is an unconscious process, but you can make it intentional in order to make your stories work well for the audience you’ve got.

There’s no such thing as ‘the right way’ to tell stories, but there is a right way for this time, this goal and this audience – and a right way for you. My goal for my storytelling students and clients is for them to find that very personal ‘right way’. So if you want to feel better telling a personal story out loud to an audience – and it could be an audience of one – keep reading. I’ll help you tell a story that connects with your listeners, feels true to you, and serves your goals. We’ll talk about ways to share a story with confidence, and how to make sure your audience is hearing what you mean to say.

Let’s dig in.

What to do

The process of telling a personal story can be broken down into a few main activities: choosing it, shaping it, sharing it, and reflecting on it. Let’s look at each of these, along with some quick exercises. If you already have a story in mind that you’re hoping to tell, great! Feel free to skip the first two steps below, though reading them might inspire you to think of other stories that you’d like to share.

Choose a story to tell

Every time you tell a story spontaneously, you’re making choices about which events or details from your experience are the funniest, or the most relevant to a conversation, or will help demonstrate your bravery, empathy or something else. But to make this process more intentional, you can just ask yourself a few questions:

1. Who is my audience? This could be narrow (a first date) or broad (people I meet as part of my job).
2. What do I want my story to do for the listener? Inspire them? Show them a new side of me? Convince them to join my project? Feel reassured that they aren’t the only ones who feel a certain way?
3. How do I want to feel when I tell this story?

These questions might already lead you to a story choice. Let’s look at a few ways this could work:

• Let’s say you’re a coach, you’re talking to your new team, and you want them to trust that you know what you’re doing. You might choose a story about a problem that you managed to solve, or a team you were on that faced the same challenges your players will.
• You’re a teacher getting ready to welcome your new students at the start of the school year, and you want everyone to feel energised and optimistic. You might choose a story about a time during your own childhood when you were nervous about starting something new, asked for help, and ended up having a great experience.
• Here’s one from my own life. I was once asked to give the keynote address at the Rare Books and Manuscripts Section conference. I wanted the attendees, who were librarians, to trust me and buy into some of my ideas about storytelling and libraries, even though I’m not a librarian. So, to open my talk, I told them about a time in high school when I tried to woo my crush with a set of rare books. It made them giggle, but it also showed them that I share their passions.

If you’re feeling stuck or blank and no stories spring to mind, don’t worry. We hear so many shocking or astonishing stories in the media, it’s easy to think: Well, nothing that’s happened to me is interesting enough to be worth telling a story about. In fact, the number-one thing I hear from students is: ‘I don’t have any stories.’

But an experience does not have to be extraordinary to make for a good story. I’ve heard a story about a crime heist that, honestly, had me yawning, and a story about ordering a sandwich that blew me away, because I really felt like I knew the storyteller by the end. It’s not just what happened: it’s how you let us into the experience.

So with that in mind, let’s do a little brainstorming to assist you in choosing a story.

Try a brainstorming exercise

A really simple writing exercise can help you ‘map’ your memories and identify possible stories. I sometimes call this a heart map or a life web. The ideas that emerge don’t have to be as targeted as the examples in the preceding section. The aim here is to really let your mind wander, and then choose some story ideas that might work for your specific purposes. Don’t worry too much whether they’re ‘good’ story ideas just yet.

Here are the steps:

1. On a blank sheet of paper (or on your computer), write down four to five things that MATTER to you, with some space under each one. It could be a person, place, group, art form, sports team – anything, as long as it matters to you right now. These are things you love, things you prioritise, or things you think about a lot.

I do this periodically, and my four or five things change all the time! At the time of writing, for example, mine are my brother; my health; the city of Portland, Maine; poetry; and US politics.

2. Under each Thing That Matters, try thinking of a couple of MOMENTS or HABITS that feel memorable and connected to that thing. It might be the first time you discovered the instrument you play; a time when you got lost in the place; etc. You don’t have to write the whole story – just a phrase to remind you.

My example is for my brother – I note down a few, including the time we got in a fender bender when we were teenagers; the first time he trusted me to babysit my niece (and I couldn’t get her to sleep!); and the habit we have now of calling each other when one of us is on a long drive. You might not think of a moment or habit for everything, and that’s OK. This is just to get you started.

3. Now for the alchemy – the step that can turn a memory into a story. This involves a key feature of meaningful stories. The storyteller and comedian Ophira Eisenberg put it really well during a performance I attended: ‘A story is when things change. If you started out awesome, things were awesome, and they ended up awesome – that’s not really a story, is it?’ So, for each memory that you feel like exploring, ask yourself this question to help you decide if it’s just a memory, or if there’s a story that lives in that memory: how did things CHANGE for me because of this?

Continuing with my ‘brother’ example, I think each of the moments I named actually did change things for me. Here’s how I might think of them:

• The car accident was luckily pretty minor, but it changed things for me because it was the first time it felt like we were in something together, and we were kind of partners in crime after that.
• Babysitting my niece was, similarly, a moment when I felt like he was treating me as a grownup whose help he needed, and not as an annoying younger sister. (I’m seeing a pattern… Maybe those first two belong in a story together.)
• And, finally, the way we call each other has changed over the years – and when I moved away from his city, it paradoxically made us closer, because we kept in touch with more intention.

Any of those stories might be a great way to share about the growth of our relationship. And I’ve got some funny details and memories associated with all of them that I could delve into as I develop my story.

I like this exercise because it starts with ‘what matters to me’, not ‘what’s most interesting or tragic or noteworthy about me’. (We are not only worth listening to because of those parts of our identity.) And it lets you sort through your memories to see which ones were transformative in some way – because, again, change makes a story really compelling.

Once you’ve identified some story ideas, you can go back to the questions you answered before – who are you going to speak to, and what do you want your story to do? See if any of your story ideas could be useful for your purposes.

Shape your story

It might seem strange to think about ‘shaping’ a story when we tell stories off the cuff all the time. It may never have occurred to you that you can get intentional about how your story will go, before you tell it in public. You don’t have to plan and practise every story in advance, of course. But making some choices about what you want to say, and trying it a couple of times out loud before you tell it ‘for real’ to your intended audience, can help you feel confident that you’re telling the best possible version of your story.

So, if you do want to shape your story: once you’ve got an idea, what details do you choose? How do you give your story a satisfying ending? How long should it be? Here are some ideas and a powerful exercise to help you feel really confident in what you’re sharing. But remember, who you’re talking to and why you’re telling the story will really help you shape it appropriately.

Give some context: sometimes, what a story really needs is the right information at the beginning. Before you get into the action of your story, consider letting the listener know more about who you were at the time it happened, or anything else they’d need to understand. For example, if you’re telling a story about being the star in the school play, it could help to reveal that you were a loud kid, or painfully shy, or obsessed with musical theatre. That way, when things happen in the story, we’ll be right there with you – we’ll already understand why the events are terrifying, or wonderful, or a relief.

Also consider your audience. Do they already know you well, or are you new to them? This will help you decide what kind of context you need to give as well.

Convey the stakes: this is a classic element of stories that storytellers of all kinds recognise as a priority. What did you have to win or lose in the situation you’re describing? If you tell us ‘it was important’ but you don’t tell us why, we’ll have trouble connecting with your point of view. So make sure to share not just what happened, but what you were feeling, expecting, hoping for, or afraid of in those moments.

Note: your story doesn’t have to be ‘objectively’ high stakes to be interesting! If you show what was important, listeners can still get invested in a relatively small goal or fear. My friend in middle school once had to find her retainer in the dumpster behind school. It was her fourth retainer. A matter of life and death? No. But high stakes for her. There was no way she was going home to tell her parents she’d lost her fourth retainer.

Choose a theme: here’s another place to think about your audience and aim. Once you have a story you feel good about, you might keep it exactly as you like it, in your back pocket, to tell when it’s relevant. But bear in mind that a single story can be told in many different ways, depending on what you want that story to do. Once you decide the point of the story, you can choose the details or ideas that really matter for this particular telling. My friend and storytelling colleague Catherine McCarthy likes to talk about theme as a ‘magnet’: once you have it, the details that matter will stick to it, and the others can fall away.

This also means that you don’t always have to think of a brand-new story for every new purpose. You can rework a story you already know, to fit a new context.

Here’s an example: in college, I worked at a scientific publishing company, and we did old-fashioned editing on the manuscripts, with little bits of paper and wax to cover up typos. (It was the late 20th century!) There was one book I worked on where I made a big mistake, and had to either hide it, or try to fix it.

If I told this story with the theme of ‘unexpected kindness’, I could emphasise the moment my boss discovered my error – and didn’t fire me. If I told it with the theme of ‘compassion for my younger self’, I’d emphasise how much I messed up, and then reflect on it now with some sympathy. Or if I were sharing it with high-school students in a jobs programme, I might emphasise the anxiety I felt at my first ‘big job’ and how, afterwards, I saw that relationships at the job were more important than perfect performance.

Consider the details: don’t worry about recreating your experience with photographic precision. After all, a story should sound pretty conversational, and we don’t usually describe absolutely everything in a story.

Instead, reflect on what was important to you at the time. That way, the details you share will give us a sense of who you were in the story. I tend to describe people’s haircuts, for example, because I hated my hair when I was a kid, so I always noticed everyone’s hair.

Also, think ahead about what the audience might already know, and what they might need explained. Fellow faculty members at your school, for example, don’t need you to describe your principal; they already know her. But if you’re sharing a story about her at a dinner party, your listeners might need a thumbnail sketch.

Finally, you don’t owe anyone all the details of your story. If you want to skip bits that feel too personal or painful, that’s in your control.

Don’t force a happy ending: many of us feel tempted to ‘smooth out’ our experience, to just go for a happy ending or a neat conclusion. But life doesn’t always work like that, and you shouldn’t have to pretend that it does. You don’t need an ending to the experience, just a last line for your story. You can even say what you hope will happen moving forward.

Try the ‘Story Spine’: finally, here’s one of my absolute favourite tools: it’s a fun and easy story-structure framework.

The Story Spine was created by Kenn Adams, an improviser. Pixar screenwriters actually use this framework to write their movies. And it’s super simple on purpose. Try filling out the sentences to see how your story should begin, continue and end. Then add in the details.

• Once upon a time…
• Every day… [Here’s where you can give us some context.]
• But, one day… [What happens to set your story in motion?]
• Because of that… [Make sure all the action leads from the previous action!]
• Because of that…
• Because of that…
• Until finally… [This is the ‘climax’ of the story, when things come to a head.]
• And ever since then… [As a result of this story, what’s changed?]

Share your story

When you’ve got a story and you’ve shaped it to your liking, next up is getting ready to tell it out loud.

Practising: if you do decide to practise, should you write it down or say it out loud first? This is totally personal for you as a storyteller. Some people like to write out their whole story before saying a word, while others like to note bullet points and improvise from them.

I usually fall in the ‘improvise’ camp. Memorising a written story might be tempting, since you’ll know exactly what to say – but it can also keep you from feeling totally natural when you’re sharing your story. So, if you want to feel more conversational and present when you tell your story, I recommend that you avoid fully scripting it.

In fact, try telling your story out loud as soon as you can. Telling your story can show you important things about what you might want to include or keep out. Choose a trusted listener or two to be your ‘guinea pigs’ here – and be sure to let them know that you’re practising a story, so they don’t interrupt with their own stories!

If I’m nervous about remembering everything, I do sometimes like to record myself talking as I’m sharing with trusted listeners (or by myself), and transcribe that recording. That way I have my story written out, but it ‘sounds’ like me.

Delivery: there’s no right way to share a story. There’s your way. For me, the key thing is to be relaxed. But there are a few general tips that work for storytelling in front of a group:

• You don’t have to make eye contact the whole time. People usually don’t do that in conversation, so you don’t need to do it in storytelling.
• Use your hands as you normally would in conversation. Next time you’re with friends, notice what you do. Do you paint the picture with your hands? Or keep ’em in your pockets?
• To find places where you might improve your delivery, you can try out your story with your trusted listeners and ask them: was I too loud/soft/fast/slow? Did I do anything that distracted you from my story?
• Likes and ums: I actually don’t ask my students to get rid of these. Thinking about it too much can, in fact, make you more stressed as you share your story. And a few of them can make a story feel more conversational. Often, once you’ve practised your story a bit, those likes and ums just go away.

Reflect on your story

Reflecting on your story after you’ve told it can reveal new possible meanings and angles. I used to tell that story about babysitting my niece at parties, as a funny story about my own ditziness. But once I reflected on the change captured by the story, I realised it has more significance than I originally thought, and it’s also an example of my evolving relationship with my brother. So I’m planning on sharing that story with my niece one day soon, now that she’s a teenager, as a way to start a conversation about her relationship with her own brother.

Another reason to reflect: you might feel that your story didn’t have the intended effect on your audience. If they reacted in an unexpected way, or your story didn’t do what you wanted it to, this is also a chance to ask yourself what you might want to change or adjust. Here, again, a trusted listener can be helpful. You don’t have to figure it all out on your own. Do you need to add more details? Fewer? Did you assume that the audience would understand the basics of goat farming, but in fact they need a little more context?

Stories change and grow over time: not just what the story means to you, but how you tell it. You’ll get better the more you do it, and the same story can take on new significance with new audiences. Try exploring a story you’ve worked on already, for a different context. What new details would you need to add in order to share it with, say, your team at work? What if you found a different theme for your story?

Links & books

My weekly newsletter, The Story Letter, is all about telling better stories. I share strategies, recommendations and new ideas about storytelling, as well as stories of my own. And my podcast of the same name is coming this winter. This first season, we’re going deeper into many of the ideas outlined in this Guide: both how to find stories we want to tell, and how to shape them once we’ve got them.

The Moth podcast and The Moth Radio Hour (which airs on hundreds of radio stations in the US) are great places to hear good stories being told, and to get inspired to tell your own. The Moth also has live events in cities worldwide, both curated shows and open-mic competitions. You can find out more about those events here.

The book Long Story Short (2015) by Margot Leitman is a wonderful, funny, quick guide to telling short personal stories. Leitman is a great storyteller herself, and she offers concrete tips for shaping your story and feeling more confident in telling it.

Mary Karr’s beautiful book The Art of Memoir (2015) is focused on memoir-writing, but I’ve found her philosophy and strategies useful for any kind of first-person narrative.