When I picked up writing again in 2014, for the first few years I shared exactly zero personal stories. I was shielding myself. But that also meant everything I wrote felt more theoretical than practical. I didn’t think I had the level of experiences required to write from a more personal place. I would doubt myself, asking who am I to share my own stories? It’s no surprise that during this time my audience failed to grow and the ideas I wrote about failed to resonate.
Without a willingness to reveal something about yourself, your stories will forever feel hollow.
Good storytelling is about creating a sense of shared humanity. That means revealing more of yourself and the struggles that make you human. It’s one of the most powerful ways to connect with people, but you have to approach it from the right angle. It’s not about attention seeking, virtue signaling, or posturing—whether hero or victim. It’s about connecting with others.
The goal isn’t to create a moat and portray yourself as some fortress devoid of a single flaw—think early Tiger Woods. Sure, people might admire you, but it’s impossible to feel connected with someone like that.
This was a tremendous benefit to Tiger early in his career. He scared the shit out of everyone else in the field because nothing about him seemed human. And while this aura might lend itself to a highly specialized, individual sport like golf, it doesn’t translate well across the rest of life. Most jobs and challenges you face require connecting with people.
You can’t lead, communicate, trust, parent, coach, teach, or learn without first connecting with the people around you. Growth is impossible if you refuse to ever let anyone in.
What I struggled with in my 20s, whether knowingly or not, was posturing. I was pulling a Tiger and masking any flaws—though I made a few dollars less than him in the process. I was adamant about presenting a perfect version of myself, in both my career and writing. And while it felt safe for me, it wasn’t relatable. People crave real stories of personal struggles and triumphs that they can relate to in their own lives. Flaws reveal your humanity.
Ego is what holds you back from sharing your own faults and personal stories. It’s what prevents you from making yourself vulnerable. It’s the thing that says, people are watching, don’t reveal any flaws. But the catch is that by revealing your own shortcomings and demonstrating self-awareness, you’re able to connect on a far deeper level. Honesty about the human condition is what resonates with people. Your stories matter.
“The call to lead well is a call to be brave and to say true things”
Abstract models and anecdotes only go so far. Most people couldn’t care less about your theories or concepts. In her book Talk Like TED, Carmine Gallo examines the most popular TED Talks and notes that those speakers spent roughly 80% of their time telling stories. That’s what people really want to hear.
Stories are the wrappers for your ideas, lessons, principles, theories, and concepts. Stories are what draw people in to actually listen to what you have to say.
In the past, I used shells of stories to guard myself and protect my ego. I didn’t want to reveal any faults. But as it turns out, the less seriously I take myself, the more helpful I can be. I’m able to illuminate feelings and stories that others can relate to and see themselves in. And that’s the power of good storytelling. You reveal fragments that people are able to identify with and latch onto. You give voice and clarity to things that people couldn’t quite put their finger on.
“Becoming a writer is about becoming conscious. When you’re conscious and writing from a place of insight and simplicity and real caring about the truth, you have the ability to throw the lights on for your reader”
Your goal in storytelling is to reveal what makes you, you. Not the carefully crafted Instagram version you’ve created. By being real, you set the depth at which your audience is able to go with you.
It’s always better to be authentic and nervous than shallow and overly rehearsed.
There’s an initial shock that comes from opening yourself up. But when you speak from your own experiences and bring out what’s inside of you, you can sustain that indefinitely.
“A moment a story works is usually a moment of vulnerability.”
Where you start to run into trouble is when you exploit “vulnerability” as a guise for attention. It’s impossible to maintain a facade of something you’re not. When attention seeking or virtue signaling dictates what you reveal, sooner or later you’ll be crushed underneath the weight of trying to keep that up.
Those who overshare fail to grasp this and end up exhausting their audience in desperate attempts for another hit of short-term gratification. There are boundaries.
At its best, vulnerability helps connect you with others. At its worst, it’s an attention-seeking behavior that those who thrive on a victim mentality lose themselves in.
It takes time to learn. If you run your own experiment—whether leading teams or writing articles—sooner or later, you’ll find that people gravitate towards what’s real. Because that’s what they can relate to. That’s what strikes the deepest chord.
Over the past couple of years, I’ve started sharing real stories—my own fears, challenges, and struggles. This shift in my approach has improved my own storytelling significantly, as measured by the number of people reached and how strongly those stories have resonated with others.
Stories are how you communicate. Not instructions. Let people interpret things for themselves. Give those around you something real to connect with.
It’s easy to feel alone in this. But remind yourself that very few of the challenges you face are unique to you. There’s someone else out there who can identify with the obstacles you’re facing. Write, speak, teach, and lead from your experiences. They matter.
“To live well is to see wisely and to see wisely is to tell stories.”