The history of storytelling isn’t one of simply entertaining the masses but of also advising, instructing, challenging the status quo. Therese Fowler, Z

“To hell with facts! We need stories!” Ken Kesey, “One Flew Over the Cuckoo’s Nest”

“This is our story to tell. You’d think for all the reading I do, I would have thought about this before, but I haven’t. I’ve never once thought about the interpretative, the storytelling aspect of life, of my life. I always felt like I was in a story, yes, but not like I was the author of it, or like I had any say in its telling whatsoever.” Jandy Nelson, The Sky Is Everywhere

Storytelling is an invaluable skill.

As I’ve been talking to people about TheRightMargin, listening to our CEO Shivani’s pitch practice, and listening to speakers at local design events such as Products That Count, Cascade SF, and XX+UX in SF, I’m reminded over and over that just talking about something vs. telling a story about something are miles apart in memorability, empowerment and compelling power.

For example, instead of telling a friend what TheRightMargin does (e.g. “It’s a goal oriented writing tool…”), I’ve realized telling a story about how TheRightMargin will help writers finish their writing projects (e.g. “You’re sitting down to revisit an old story and can’t get yourself to make progres…”) is much more memorable and retellable.

A key meeting I had last year that further impressed upon me the power of storytelling was when I met with Jessica Mastors, story consultant and creative strategist. We were talking about how she had gotten interested in teaching people how to craft their stories, and I was blown away by her presence, self-awareness and conviction as she told me her story. The following are the highlights of what Jessica said about the importance and power of storytelling in sharing your message and empowering the audience to respond.


“You hike your own hike.”

A few years ago, I decided to hike the Appalachian Trail. And most people I’ve told that to have responded in the same way: “Wow, I could never do that.” But I always tell them the same thing; you could! You just don’t want to, and that’s ok. The Appalachian Trail: sure, it’s the same 2,186 miles for everyone, and yes it’s the same elevation change, and each hiker has to do the same stuff to keep going. But it is a wildly different challenge for everybody and it doesn’t make sense to to compare your experience or your approach to anyone else’s. Everyone has his or her own thing going on and that’s really respected.’

“When you can tell your stories in a way that communicates your top one, two or three values, then that’s powerful.”

We’re bored by all the marketing campaigns that target all our deficiency needs, when what people want to be is empowered. We’re at this time in our evolution as a society where we’re hungry for people and things and organizations and causes that embody values.

Story is a way to express your values without having to explicitly say ‘this is what I care about’. So when I’m told “Tell me about yourself…” this is what I say. “Well I have 3 buckets, nature, education and story. Which one do you want to hear about?”

And they say “Well, tell me about education.”

And so I say, “Well let me tell you a story. When I was in school…” and I bring them on this journey that helps them see that what I’m really questing for relevance. I’m looking for relevance and truth in education and that I think we’re doing a disservice to our young people by continuing to teach them skills that are no longer relevant, that are relics of our industrial era.

“Know that a personal story is compelling to the listener if it taps into their own quest.”

The hero of my story about hiking the Appalachian Trail is the audience. Each person is engaged in their own quest, so when I talk about these things we all share, I’m tapping into the audience’s personal quests. Everyone you talk to is trying to locate themselves in your story. So you are not the hero. The listener is the hero of your story.


“The source of your authority comes from your experiences.”

That’s literally how we learn. It is not through books, it’s not through people lecturing us, it’s through experience.

So the story I want to hear, when I want to hear who you are and what you value, is something you’ve been through, something you’ve experienced firsthand and how it affected the way you perceive the world. And you can be totally candid if you haven’t been focused on your values recently. For example, you can say, “You know, I had an experience when I was young that made me really care about human rights. And then in my desire to build my career and become successful I got away from that. But I feel like it’s missing in my life and I really want to get back into it.”

“Story is the way to get around that logical critic and touch that emotional gut.”

I think a lot of us get really distracted by the desire to paint this big picture of the world, and the numbers help us do that, and all these experiences help us do that. But what people really can connect with, and want to know, is how one experience affected you, how you affected the life of one young person. So you paint a large picture of what’s happening… and then support that with the story of just one of the people in that broader picture.

“Your goal, when you have the opportunity to tell your story, is to have the other person cut you off and say ‘I know what you’re talking about! I had a similar experience, let me tell you the story.’”

Your goal is to get them to participate in the conversation with you, to create dialogue. Counterintuitively, if we meet and you spend most of the time talking to me, and I’m listening, and you walk away, and I walk away–who do you think walks away remembering the other person more? Because you shared an authentic part of yourself with me and I received it and made you feel good, you remember me much more than I remember you, even though you were the one telling the story.

“Remember, the ultimate goal of sharing a story is to strike a chord in the the emotional belly of the other person.”

Needless to say, I was inspired. I spoke with Jessica over a year ago, yet all the above still stayed with me ; which I think is a testament to the power of her storytelling. (If you’re interested in finding out more, her website is, and I found out she’s hosting an event in Oakland on April 7,  Storytelling for Impact, too.) So whether you’re writing or expressing yourself in another way, remember to tap into this power!

Do you have examples of powerful storytelling? Or do you believe in the power of storytelling as well? Let us know!