Three Tips for Becoming a Better Storyteller

Great stories happen to those who can tell them. ― Ira Glass

Great storytelling can transform a seemingly mundane event, like emailing a professor, into a suspenseful, nail-biting thriller. I remember about a year ago, telling my friend about a series of frantic emails I wrote as I tried to submit a final essay, (which normally isn’t a chaotic process). I was severely sleep deprived, on the verge of tears. The midnight deadline was getting closer, and writing on the phonology of Gulmancema was as difficult as ever. I believe there was also a librarian who starred as the villain, since I was getting kicked out of the library as I tried to turn in my paper.

My friend was on the edge of his seat as I told that story; and we joked afterwards that I had somehow made email exciting again. I’m bad at a lot of things (like regularly posting on Wednesdays), but storytelling isn’t one of them. But that has come with a lot of practice. Storytelling is a craft that takes time and effort to improve. When I was younger, I mostly told stories so long, none of my family members ever waited to hear the end of them. Now I just tell stories to people/strangers/acquaintances too polite to walk away. Problem solved.

In all seriousness though, my storytelling has become a lot better over the years, and I’m glad for it. Though storytelling, I’ve strengthened friendships, connected with people very different than me, improved my public speaking skills, and shared life lessons with others facing similar struggles. My stories are also a reflection of who I am and what I most value. All of which seems to fall in line with this Wall Street Journal article, which argues that good storytellers are generally more happy in life and love. While I’m skeptical of any piece of writing that includes the phrase “Since the dawn of language” (all the linguists scoff), I really liked Dr. Winter’s piece of advice at the end:

Dr. Winter suggests the three Rs: Reflect on the events. Refine what they meant to you. Read. “Learn from the masters,” she says.

(emphasis added)

I thought this was fantastic because any good storyteller lives by the three Rs. Hence, I was disappointed WSJ did not go into more depth on why the three Rs are so effective. Luckily for you and me, I have this handy blog to talk all about it.

1. Reflect

I think a very common misconception is that storytellers make it all up on the spot. When I tell a story, usually it’s an anecdote that I’ve spent time thinking about. I’ve carefully considered why a moment was meaningful and memorable. Reflection is critical to good storytelling because whenever we tell a story, there’s an implied understanding that this story is worth telling. By the end, your listener expects to know why you told that story at all. Some storytellers make the purpose clear from the get go while others build up to the takeaway. Either way is fine, but reflection on events is necessary in both.

Memorable moments are surprisingly easy to miss. I’m sure you’ve heard people lament how fast time flies or heard parents complain how quickly their cute babies became angsty teenagers. While it seems like the present is always running away from us, I think the reality is we are blind to our own forgetfulness and obliviousness. Reflection forces us to stop and take note. To take stock and evaluate. Storytellers make reflection a regular practice. Without it, we might not even realize we have a story to tell in the first place. Reflection probably looks different for each person. For me, I’ve been journaling on and off for the last 10 years. However, sometimes journaling doesn’t help me focus when my mind is buzzing with too many thoughts. When that happens, I find it easier to pair reflection with a physical activity like taking a walk or driving. Experiment with what works best for you. My only advice is not to try to do so when you’re already in bed, or you might end up sleeping through your reflection time.

A story might take a few minutes to tell, but every great story is preceded by a long time of reflection.

2. Refine

Get ready for the fun part. (Then again, I also find peculiar etymologies a delight, so take “fun” with a grain of salt.) Dr. Winter says “to refine what [an event] meant to you.” I’m going to modify that slightly since that’s too close to reflection. Instead, refine what were the key aspects of the event. Think about what were the most important details you would like to highlight. Stories in their simplest form are only a sequence of events. When I’m asked to tell a story, the first thing I do is condense the event into a few bullet points. Then, I consider how to connect the dotsWhich narrative and character arcs will best lead to the next dot? What kind of delivery (e.g. intonation, hand/facial gestures, etc.) will best highlight these points? I think about my audience: Is there additional information they’ll need to understand the story? How can I help them relate to the story? Remember to keep it simple. Everything between the dots should connect the dots. So if I’m telling that story about emailing my professor, for more reasons than one, you’ll be annoyed if I go on a long tangent about the Mexican murals decorating that section of the library (I took a class on them, so I really could go on for a while). Finally, when you connect all the dots, you should have the image of a unicorn. Okay what I mean is, when you finish a story, the main aspects (“dots”) should connect in such a way that the reader is left with a new picture or takeaway. The picture you create is directly tied to my discussion under “Reflect”; the image reveals why the story was worth telling in the first place. It’s a “the whole is greater than the sum of its parts” kind of moment.

In school, teachers often explain this same concept using Freytag’s Pyramid (i.e. exposition, rising action, climax, falling action, denouement). That’s a good way of visualizing stories. However, I find that narratives can have more than one point of rising and falling action, which is why I’d rather think of stories as a game of connect the dots, or a series of events carefully tied together with an overarching purpose. Good stories also function more like waves. With emotions running high, they leave us guessing, not knowing if a bigger wave is coming next. J.K. Rowling does an amazing job of this with the character Severus Snape. If you read the Harry Potter books as they came out, you probably second guessed his character a million times.

Reflection and sequence (“connecting the dots”) work interchangeably. I think Ira Glass does a great job in this video explaining how the two are the basic building blocks of stories.

3. Read

Like most things in life, there’s always someone better than you. The same is true for storytelling. The good news is that there are lots of great storytellers to learn from. While I think Dr. Winter was only referring to books here, I would extend this to also mean reading the world in general, from the tv shows and movies we watch to even news coverage. Stories are everywhere, and storytellers are always thinking critically about the stories they consume.


As with other art forms, storytelling takes practice. At some point, you’ll inevitably be faced with a blank stare and finish a story with the sad words “I guess you just had to be there.” Hopefully, that won’t be the last story you tell. While I am skeptical of the study mentioned in the WSJ article, at the same time, it makes sense. Storytelling makes you appreciate life more. I tell stories not only to pass the time, but also to reflect and acknowledge the wonders and sorrows that surround me. 

Unfortunately for me, my one redeeming quality–storytelling–won’t help me attract a mate anytime soon since the WSJ article also states that “The men didn’t care whether the women were good storytellers, the research showed.” Fine then. If they don’t care for my stories, out of spite, I think I WILL go on that tangent about the Mexican murals and the symbolism behind each brushstroke. 

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