When I bumped into a friend at my favorite local coffee shop a few weeks ago, I was excited. I hadn’t seen this friend all summer long.

What’s been new in his world, I wondered? What has he been solving, moving toward, creating? How are his kids? Yet what unfolded between us was humdrum, socially-polite, and altogether boring.

It went like this:

Me: “Hey man!”
Him: “What’s up Dave, long time no see.”
Me: “I know, seriously. So how was the rest of your summer?”
Him: “Good! Busy. Really busy. How about you? Busy too?”

My response was a stutter and stammer of comfortable crutch phrases:

Things are good. I’m well. Been teaching, writing, you know. Enjoying summer. The usual…

The moment of excitement that I felt on the edge of a personal exchange with a friend I hadn’t seen in a while — when anything and everything is possible and just waiting to be spoken — vanished in an instant.

After I sat back down to sip my cappuccino, I was left wondering why the flat-lined exchange wasn’t just disappointing, but frustrating, too.

So, Mr. Writer, I silently said, Is that what you call storytelling nowadays? You’re “well”? Things are “good”? Is that what you call an interesting exchange? Seriously?

When a few hours passed, I recognized why the conversation left me wanting for more — and why my frustration with myself was triggered.

It was because I didn’t have a story to tell.

I don’t mean that I was wishing to have an exciting tale of international intrigue to share. It’s not that I regretted not having some new, passionate romance to brag about, or a major work accomplishment to share.

When I say I didn’t have a story to tell, I mean that I wasn’t sure what the narrative of my life had been over recent months.

That felt terrible. Because not having a “story” is just another way that I couldn’t “make sense of it all.”

While the word “story” may make you think of Tolkien-style adventure books with epic quests and built-up climaxes of action, a story is really just choosing to place a narrative of understanding around events and details of our lives.

Even in our ordinary, everyday conversational exchanges with friends, we tell stories.

We tell stories about the long and tiring work week. You’re job searching? That’s a story. How’s that guy you’ve been dating? Your response is a story. You say you’ve been loving the cooler autumn weather and relishing the outdoors after the particularly hot, humid summer? That’s a story too.

The definition of a story is broad but, ultimately, all of our stories are chosen.

We choose our stories.

And, most importantly, the stories we tell become the stories that we live.

The stories we think and those we share become the fabric of our everyday lives.

Stories shape feelings of purpose, or lack of fulfillment. Stories give us hope and strength, or worry and fear. Our stories are how we define the otherwise random assortment of facts, events, faces, moments and details that make up our lives. Our stories are how we choose to make sense of them all.

Good, bad or indifferent, how we interpret the unfolding of our lives is always our choice.

The result is what we call a story.

When I saw my friend that day, I had fallen out of touch with “the story I was living.”

I wasn’t sure what story I had been living – but I didn’t realize it until that coffee shop exchange.

Unable to offer a narrative around the last few months of my life, I was left stuttering and stammering through colloquialisms and socially-expected responses. I was boring. What I offered was empty. It felt like white noise.

If you think I’m being hard on myself, you’re right:

Because everyday conversations are precious opportunities to live the stories that we want to be telling.

I believe that the ordinary, routine chats that we have with people everyday are really special chances for us to witness our own Selves — through the words and rhythms that we express, when prompted — and, as a result, to witness if the stories we tell on instinct are in alignment to the what stories we want to be living.

You know how so many people act uncomfortable, awkward, even imposed-upon by everyday conversations? It’s like our most human, natural moments have become riddled with doubt, fear and anger. It feels like a miracle to have the opportunity for a short, simple, honest interchange with someone new.

Is it that we’ve become less intrapersonal because of our comfort using impersonal technology to communicate?

Or is it that we don’t know how to respond in any other way than closed-off, awkward, boring, safe, story-less?

Is it both?

Maybe that’s why so many routine conversations in the day-to-day feel lacking. Maybe that’s why so many exchanges — even between acquaintances and friends — feel absolutely empty of connection. Maybe that’s why dialogue seems to leave more of a bitter taste of sorrow, shame or sadness in its wake, than joy.

What would happen if we each took a bit more time to sculpt our own understanding of the arc of our recent lives, even the mundane weeks or fast-moving months?

What if we dared ourselves to have more of a story to share?

Conversations are Chances to Cultivate Our Stories

When I lived in Hawaii for 5 weeks in 2012, my travel buddy Jacob Sokol, life coach for life coaches, wanted us to make a pact: no boring conversations with people, he implored. The introvert in me reluctantly agreed.

As travelers in a new place, we found ourselves forced into either “making friends the old fashioned way,” by talking to strangers, or falling apart in our own boredom of being stuck together.

So we did.

At our hostel. At dive bars. In line at the noodle shop. On the sidewalk. And in this magical little vortex of a place where we seemed to make fast acquaintances with single young women who actually gave us the time of day. Miraculous!

It turns out that, when you communicate bravely — pledging to volunteer vulnerability, or pressing yourself to ask a semi-interesting question — connecting with people is easy. Really easy.

The reluctant introvert in me found it was far less awkward to swear away crutch phrases like “busy” among other passive, boring, expected ones.

Instead, the writer in me fell in love with the wordy-little-challenge of prompting a unique exchange with a stranger.

It felt more comfortable than doing the socially-expected-yet-infinitely-weirder dance of modern conversations with others:

“How are you? Nice weather isn’t it? What’s that over there, a pigeon? Pigeons are something, aren’t they? Okay, bye!”

Thinking back to my coffee shop exchange with my friend, it seemed as though I was due to recommit to the pledge I had made to Jacob years ago.

To not be boring. To be braver. To embrace the story in the moment. And to share it more willingly — if only because what we choose to share becomes the story of our lives.

Maybe this time, you and I can make the pledge to one another.

Let’s Be Braver in the Stories We Share

From those weeks in Hawaii and throughout solo travels where my words were the only way to feel less alone in the world, I’ve learned that conversations are unique opportunities. They’re the ways we actually bond on an emotional, resonant, real level with other human beings.

And when we share stories — even in conversations at coffee shops — our lives become better. They become more meaningful. Not only do our conversations benefit from becoming less awkward, humdrum and mundane — the stories we bravely share reinforce the meaning, responsibility and choice we have over our lives.

We worry less. We experience more. We tell stories bravely, and start to live more bravely, too.

So let’s pledge to stop being boring with our conversations.

Let’s escape the doldrums of socially polite interchanges, and expected dialogue, and wasted opportunities to connect with one another on a meaningful level.

Let’s share our stories with reckless abandon.

How do you do it?

First, examine the stories you’re living. Make the time to reflect. A simple way is to journal it through.

Second, challenge yourself to love conversations again. Consider them opportunities, not just “something to endure.”

Next, bear the responsibility for non-boring and well-storied exchanges by asking better questions — questions that elicit a natural, effortless story in response.


  • “What was the story you were living this summer?”
  • “What have you been striving towards since we saw each other last?”
  • “What’s been lighting you up lately?”
  • “What are you looking forward to the most in the next 3 months?”

Even if you do default into polite habits and expected cues of conversation like “What’s new?” and “How have you been?” keep going. Try asking again, but from a slightly different angle.

After you prompt someone into a story, it’s your turn to practice what you preach. That’s the final step.

Be braver in the stories that you share.

Because we all need you to be living your story, bravely. We need you to live your life boldly and with great, ambitious love. Dare to live for more than “busy.” Challenge yourself to find more meaning than “the usual, same ol’.” Expand your intentional life beyond the story that your best friend expects to hear. Open the door to an entirely new story, instead.

So, what is the story that you’ve been living lately?

Here are a few practice exercises that you can write, or recite, when you find yourself in your next cafe catch-up conversation:n

  1. What 3 words would you pick that best describe your life lately?
  2. What is the theme you’re exploring?
  3. Where has your journey been taking you?
  4. How has the journey beneath your feet been feeling?
  5. What are you creating nowadays?
  6. What are you striding towards?
  7. Did your summer mimic winter hibernation? Is your autumn begging for spring-like growth?
  8. Are you itching for newness? Pushing yourself to escape routines? Are you rewriting old habits to become healthier regimens?

Play with your words. Be brave. Be bold. Experiment. Risk being seen. Elicit a moment of intrigue — a follow-up question. Don’t dodge connection. Don’t default into your conversational crutches.

Your story is yours to tell.