How to Tell an Authentic and Impactful Leadership Story About Yourself
My personal leadership story about walking to The End of the World:
I remember one New Year’s Eve when the future looked impossibly bright. My wife and I had traveled to Italy with my two brothers and their partners. At midnight, we sat atop our AirBnB and toasted each other with champagne as we watched the fireworks exploding in every direction.
Oh, should I mention the year: it was January 1, 2020.
At the time, I was running a very successful storytelling training business. 2019 had been my best year. I had traveled all over the world, flying to New York, San Francisco, Paris, Bangkok… to deliver my seminars to big name corporate clients. Everything I did was in person. My future looked as bright as those fireworks. I was planning growth, expansion… my first million was on the horizon!
To make a long story short… well, you know what happened next….
Luckily, I was able to escape the worst health effects of the initial COVID wave. Almost no one I knew or loved was affected. However, economically, the lockdowns brought my business to a stand-still. Travel was out of the question; workshop cancellations were pouring in. Suddenly, everyone and their uncle were shilling content online, and I didn’t want to do that.
I decided that the best thing I could do was wait.
The pandemic lockdowns emptied city streets… and tanked my business in the process.
Flash forward a year, and my business was tanking… fast. My year over year revenue had gone down 75%, and I was starting to panic.
What was I going to do? Should I have followed the trends and started selling online workshops and courses, like everyone else? This direction “made sense”, but it didn’t feel right… But should I trust my feelings? Or, was there some other, more creative option?
It was a big choice, and I didn’t know which alternative I should pick.
I remember where I was when the reality of all this hit me. I was in Europe. My wife and I had traveled to Portugal to walk the Portuguese segment of the famous Camino de Santiago. Starting from Porto, a city in Northern Portugal, we would walk north for 150 miles until we reached the famed cathedral town called Santiago de Compostela. Then, we would hang a left turn and head for the Atlantic coast, where there was a town called Finisterre that looked west towards the sunset.
Finisterre… or, in English, “The End of the World.”
Given what was happening in my professional life, The End of the World seemed like exactly where I was heading.
The lighthouse at Finisterre… aka The End of the World
For fifteen days, we walked towards The End of the World. We walked through sun and rain, along beaches and through forests, through towns, villages and cities.
The whole time, I kept asking myself the same question, over and over again:
What am I taking with me to The End of the World? And once I get there, what do I want to leave behind?
Finally, at long last, I spotted the famed lighthouse on the horizon. We had arrived late in the afternoon. The shadows were long, and the light was golden. I felt a swelling of emotion in my chest.
Step by step, as I approached, I realized that what I needed to leave behind was an old idea of myself. My old self was over, and something new—something creative!—was waiting in its stead.
But what did that mean? What’s the business model? Will I be a success?
I felt overwhelmed by confusion and fear.
Then, as the sun dropped into the Atlantic, I heard an inner voice say: trust yourself.
In that moment, I realized that my journey to the End of the World wasn’t an End. It was the beginning.
We sat there as twilight crept in above the crashing waves. And then we turned and walked away from the End of the World.
That’s me watching the sun set at the End of the World
Learn The Building Blocks of an Authentic Story About Yourself
So what makes a good story? How do we take the details of our life and transform them into an authentic representation of who we are?
How can we present those stories in short, succinct ways that are designed to create impact?
Let me suggest three key ideas, and then you can go back to my story to see how I used them.
Those three key storytelling ideas are:
Choice
Perspective
Emotionality
Let’s look at each of these one by one.
To Tell a Good Story About Yourself, Focus on a Difficult Choice
Sure, some of us might tell stories about what we did last weekend, or what happened at our child’s soccer game. Those stories might be interesting to our friends or our family… but it’s unlikely that anyone would consider these “good stories”.
Why not? There’s a famous line about storytelling: a story is a person in a place with a problem.
A story is a person in a place with a problem.
Why is this the case? Because “problems” are a code word for “drama”. And drama is what makes a story interesting.
If you are going to engage us—as listeners or readers—you have to find the drama that will make the story worth our time. Otherwise, I’m just going to flip on Netflix or YouTube or TikTok, and I can find my drama there instead.
The challenge for many of us is that we would rather tell our story about what happened at our child’s soccer game than share a story about a real problem we’ve had—especially if we are telling that story to colleagues or strangers. This is the hump of “vulnerability” that we all need to get over if we are going to become better leadership storytellers. We need to find some drama in our story if we want others to find it interesting.
Otherwise, the story becomes what I call a “fish” story. Well, you think you caught a big fish? Last year, I caught a fish that was ten times that size…!
That may be true, and there may have been some drama for you when you were reeling in your white whale. But you’re going to need to convey that drama to me if I’m going to find your story interesting.
To solve this problem, see if you can find a situation in your life where you faced a difficult “choice”. Choice is another code word for drama.
At their root, all good stories are about choices. A choice could be about whether to follow love or responsibility. Whether to marry the right person or the wrong one. Whether to play it safe or to put a big bet on one spin of the roulette wheel.
Here’s an example from TED speaker Mark Bezos. In this short story, he talks about a choice he faced—and how it led him to learn an unexpected lesson.
Mark could have easily told us a “fish” story about all the good that he did as a volunteer fire fighter. By making the story about a difficult choice— overcoming his self-centeredness—he presented himself as much more human… and therefore, much more relatable.
His story went from being about him to being more about us. Therefore, it was much easier to trust him when he reached for the inspirational message at the end of the narrative.
What’s a difficult choice you’ve faced? That’s where you should start if you want to tell a good story about yourself.
2. To Tell a Good Story About Yourself, Focus on a Shift in Perspective
Perspective and tone are everything in storytelling. As audiences, we’re not just listening to the “facts”. We’re also listening to how you depict the facts. And we’re also paying attention to why you are telling the story.
These three categories can be summarized in three words:
text
subtext
context
Great leadership storytellers know that every message has a text, a subtext and a context. Let’s go through each of these one by one.
Text is the easiest idea to understand. The text of the story is what is literally being said. In a written story, like this blog post, the text is the words on your screen. In a verbal story, like the one that Mark Bezos delivered above, the text are the words that are coming out of his mouth.
If you go to watch a movie in the theater, the “text” of the movie is everything you are seeing on the screen: the actors’ faces, the set decorations, the lighting, the background music… All of that is considered part of the text.
So what’s the subtext? Subtext is what we mean when we say “reading between the lines”. The “subtext” reminds us that there is always more going on beneath the surface level of the story.
Let’s look at a few practical examples of subtext. Here’s a famous one—a six-word story that is purportedly written by Ernest Hemingway:
For sale: baby shoes, never worn
The text of the story is obvious: it’s six words, with a couple punctuation points. Taken alone, those six words don’t mean much. Who cares that baby shoes are for sale? What is this, a Craigslist ad?
But the meaning of the story is carried through the subtext. Reading “between the lines”, we can let our imagination run wild. Who is selling baby shoes? Why have they been never worn? What happened to the baby? What happened to the parents, or the grandparents, or the neighbors, or the friends? How did they feel? How do we feel?
See why subtext is so important?
Let’s look at another, more visual example. Here’s a photograph from the Barbie movie:
What do we see in the “text” of this image? A couple of good looking blond people, dressed entirely in pink, with a pair of neon rollerblades.
But what do we see in the subtext? Can we see the longing in Ken’s eyes? What does Barbie’s expression tell us about what she is thinking and/or feeling? What do the neon rollerblades represent?
Questions like these engage us, the audience, in the “story behind the story”. That is the literal definition of engagement.
Compare that with this photograph. Probably, you find it much less interesting:
Barbie and Ken: all text, no subtext.
Let’s get to our third and final category: context.
Context is about background information. For example, even though I don’t know you, I can make a pretty guess that you’ve heard of the Barbie movie, because I know that it was wildly popular last year. You probably know what it was, even if you haven’t seen it. So when I reference it above, there’s probably something in you that has felt a flicker of recognition.
I’m using that “flicker” intentionally, hopefully as a way of creating more engagement for your learning. So that’s one important role that context plays in storytelling. If I had chosen a wildly different example, like a movie filmed in a language you don’t speak, then that would have been “without" context”. That would have probably made it more confusing for you.
(Of course, if you haven’t heard of the Barbie movie, you’re probably wildly confused right now. Sorry. Go watch it.)
So context is about what’s happening in the background of the “story”. It’s the additional information that the audience uses to make sense of both the text and the subtext. But context goes one step further.
Context is not just about what’s happening inside the story. Context is also about why the story is being told at all.
For example, as you’re reading or skimming this blog post, you’re probably asking yourself questions like: who is this guy? What is his goal?
Maybe you’re a skeptic, and you’re expecting that I’m building up to selling you some course at the end. (I’m not.)
Maybe you’re a student, and you’ve never heard of these concepts, so you’re taking notes furiously.
Maybe you’re a bot, and you are scraping all this information so you can use it in the next version of ChatGPT.
All that plays into the context also.
This story isn’t just words on a page. The relationship between text, subtext and context inside of your own head is the meaning of the story.
So let’s come full circle now to what I called perspective. What you can hopefully see is that a storyteller has a much different job than someone who is just reporting the facts. Storytellers think about the text, the subtext, the context… the meaning.
Telling a good leadership story is all about how you put these pieces together.
Storytelling, at its core, is about a perspective shift. Rather than relaying just a bunch of details about ewhat happened last weekend, a storyteller steps back and asks questions like:
what is the point of this story?
which parts are most interesting to the audience?
which parts are least interesting to the audience?
what needs to be said in the text?
what can be implied through the subtext?
what further context does the audience need?
Each of these questions are rabbit holes, in that they can go deep. The “point” of asking these questions is that they will inevitably lead to more interesting and more creative stories. They will shift our perspective of our job, as storytellers, by guiding us to create enaging emotional experiences for our audiences.
How we do that is where leadership storytelling moves from science to art. You need this artistic quality to tell a good story about yourself.
As an example, let’s watch the beginning of this famous TED talk by the author Brene Brown.
Pay attention to the initial 90 seconds, when Brene tells the story about her conversation with the event planner. Ask yourself:
what’s the text?
what’s the subtext?
what’s the context?
And then think about why Brene is telling this story. That’s how you’ll develop the perspective that will lead to telling good stories about yourself.
3. To Tell a Good Story About Yourself, Focus on Creating Emotionality.
A little storytelling secret: structure is not nearly as important as you think.
(Sorry, I spilled a sacred cow :P)
No, it’s true! Because, the truth is, the people listening to your audience aren’t critics. They don’t want to evaluate your story for structural mistakes—at least, most of them don’t.
What do they want? To be entertained, to be engaged, to learn something. More specifically, they want to feel something.
Our job as storytellers is not just to convey information. Our job as storytellers is to make people feel.
Perhaps it goes without saying, but to make someone else feel something, you need to feel that thing also.
Ultimately, storytelling is about creating an emotional connection. It’s about two people sitting face to face—or fingers to eyes,—and sharing a moment together. As storytellers, our job is to create that moment from within ourselves and transmit it in some way to another human being.
That might sound New Age-y, but it’s actually the literal truth. An emotional experience is a chemical reaction, and your job as a storyteller is to be the catalyst.
That’s why vulnerability is such an essential part of telling a good leadership story about yourself. Vulnerabilty catalyzes the emotional chemical reaction. You share something so the other person feels something.
If you don’t share, there’s no feeling. If you don’t share, it’s just facts.
So when you’re setting out to share an authentic story, the place to start is by asking yourself some frank questions:
why am I sharing this story?
what message am I trying to get across?
how do I want them to feel?
how does this story make me feel?
how aligned are what I want them to feel, and what I feel?
The old phrase is true: in the end, people won’t remember what you said, they’ll remember how you made them feel. So our job, as storytellers, is to reach inside of ourselves to find the emotionality that will connect.
That’s the storyteller’s job description in a nutshell.
As an example, I’m going to share one more TED talk from the master rock climber, Alex Honnold. Alex’s story is gripping. As you’re watching this video, ask yourself: what is he making me feel? Where is that feeling coming from?
Can you imagine what it would be like to be up on that cliff?
Can you feel the bridge that connects you to him?
So what next?
At the beginning of this blog post, I set out to tell you a story about storytelling. As I did, I hope you realized that I’m only scratching the surface.
There’s no magic formula to tell a good leadership story about yourself. Instead, there are questions, ideas, emotions and, most importantly, curiosity that will encourage you along this creative journey.
If you’re interested to learn more about personal story, here are a few resources that I recommend:
Books about Storytelling:
Want a Personal Leadership Storytelling Coach and Guide?
Are you needing to tell your personal story as part of a speech or talk? I can help you find the right story and deliver it in an authentic way.
You can reach out here:
Happy storytelling!
