How To Write A Punchy Personal Story

Dickie Bush & Nicolas Cole

Ultimate Guide Table of Contents

Let me tell you a story.

Over the holiday, I was at a dinner party, and I was talking with a couple friends about how I wanted to buy my first rental property.

One of the guests, we’ll call him Jim, walks over (in his white pants and green chapeau), interjects and says, “I’ve bought over $10 million worth of rental properties over the past 10 years.” 

My eyes lit up! 

Jim had all the experience I didn’t have yet. 

He could be a terrific resource.

I tried asking a question, but he just kept going on and on about his story. How he grew up in a small town in rural Georgia. About how his dad wasn’t around much—he worked construction. About how, for many years, he wanted to be an architect, not a real estate developer.

And the whole time I was thinking, “Cool story, but… none of this is really relevant to what I’m interested in.”

Can you just tell me HOW to buy my first rental property?

Finally, I interrupted him mid-sentence.

He stared back at me for a second, paused, and then said: “That’s a great question. You know, when I was trying to buy my first rental property…” and then went into another 7-minute diatribe about how he bought his first property.

He never answered my question.

Now, was Jim’s story about real estate any good?

No, it wasn’t.

Because Jim never gave me the one thing I wanted. Sure it was entertaining, full of description, and memorable phrases, but in the end, I walked away unsatisfied.

That’s not a “good story.” That’s a waste of time.

Here’s the point (of my fictional holiday story):

When you’re telling a story, make sure it’s clear to you (and the reader)—here’s what’s in it for them!

Stories play a crucial role in your ability to build an engaged audience.

Whether you are curating stories or telling personal stories, they make it easy for the reader to both identify with you and deepen their relationship with you (especially within a specific niche). 

And If you can tell a compelling story, you can shape the world.

But diving in without a plan is a formula for failure.

Here’s a 5-step process to find viral-worthy stories in everyday moments:

And how you can deliver them with a punch.

Let’s go.

Step 1: Recall the key events that shaped your day

Most people think stories have to be some incredible adventure, like the movies.

But the truth is, you have story worthy moments every day. You've just never stopped to capture them. And that's because you've never done Homework for Life—a framework that author Matthew Dicks wrote about in his best-selling book Storyworthy

Doing Homework for Life is simple.

Every day, you take five minutes to reflect: If you had to tell a story from today about something that took place over the course of the day, what would it be? And all you have to do is write one sentence about it.

Look for:

  • Difficult times
  • Moments of growth
  • Proud and awkward experiences

Just like writing, finding stories is a skill and you need to practice it every day. That's the beauty of Homework for Life. It's simple enough to do even on your busiest days.

Two columns: date and story. 

Five minutes, one story, one sentence.

Step 2: Identify why each event left an impression on you

What are the events that you just can’t seem to get over?

If you are replaying a moment of your day constantly, there’s a reason. Don’t let those moments go. Fight the urge to ignore them and peel back the emotional onion.

  • Do they make you uncomfortable? 
  • Do they make you look vulnerable? 
  • Do they force you to confess a character flaw?

These are the seeds of fascinating stories for readers.

For example, maybe you tripped on your way into Target to pick up some last minute gifts. And the only thing to stop you from face planting into the concrete was the Salvation Army donation box that was full of change. Thankfully it broke your fall, unfortunately it didn’t prevent the coin box from exploding onto the sidewalk.  

Luckily there were no witnesses, but you can’t stop replaying your mis-step in your head a thousand times a minute.  

Stop and ask, “why?”

Which leads us to the next step.

Step 3: Identify the lesson or takeaway

The takeaway explains why your story is important. 

And the success of your story hinges on the connection between the story itself and the message you want to share. If the connection is strong, you will create a deeper emotional tie with the reader.  If the connection is weak (or irrelevant as we saw in Jim’s case), you will leave the reader feeling unsatisfied.

To do this, connect your perspective with something bigger.

  • What is the universal truth at play? What did it mean?
  • What did your experience say about you, life, or the world?
  • Is your story about frustration, injustice, loyalty, hope, misconception, etc.?

In the tripping at Target story, the reason you couldn’t stop thinking about your stumble is because you are a professional dancer. You get paid to glide gracefully. And you are definitely not the kind of person that trips over your own feet. This experience challenges a core belief of who you think you are. 

The takeaway? 

Mistakes and mishaps can happen to anyone, even professionals. 

This story can serve as a reminder to readers that it's okay to mess up. Even deeper, your story illustrates that it's important to be kind to yourself and not beat yourself up over small missteps.

Connecting your story to a universal truth makes your story interesting (and relatable).

Step 4: Build the narrative arc

Once you’ve identified your point, it’s time to shape your story into a narrative.

The story narrative is what gives the story its structure and allows the reader to follow the progression of events. A strong story keeps the reader engaged by illustrating how challenges are overcome, how conflict is resolved and how the people in the story have changed as a result.

The ABCDE storytelling framework from Anne Lamott's book, Bird by Bird, is an excellent framework that will help you construct your story.  

Here’s how it works:

  • Action: Drop the reader right into the action. No need to "set the scene." 
  • Background: Once you have the reader’s attention, tell them why it matters.
  • Development: Build the story up. Where is the story going? What’s at risk?  
  • Climax: This is the tipping point. The “aha!”  The “oh no!” The “SURPRISE!”
  • Ending: Explain what it was all for. What was the lesson?

And here’s how it looks:

  • Action: I decided to take a solo hiking trip to clear my mind.
  • Background: I had been feeling overwhelmed and stressed out.
  • Development: I hiked through beautiful, peaceful forests and enjoyed the solitude.
  • Climax: On the last day of my trip, I got lost on the trail and had to find my way back to civilization.
  • Ending: I eventually found my way back to my car and made it home safe and sound. I learned that it's important to be prepared and stay alert when hiking, but that sometimes taking risks and stepping out of your comfort zone can lead to rewarding experiences.

Now you have a narrative, but we have one final step to increase the voltage of your story.

Step 5: Connect the story to the reader

Your story isn’t really about you.

We say this all the time in Ship 30 for 30: You are not the main character of your story. The reader is.

If you want your personal story to be successful, to resonate with readers and impact them in some meaningful way, then you need to have clarity around why the personal story you are telling is interesting to the READER (not just interesting to you).

  • What’s the problem you want the reader to solve?
  • What’s the realization you want the reader to have?
  • What’s the obstacle you want to help the reader overcome?
  • What’s the takeaway you want the reader to understand by the end?

You have to know “what’s in it for the reader.”

Let’s say you are writing "The Surprising Rewards Of Changing Careers In Your 50’s."  The point of your essay is to show the reader how taking a risk and stepping outside of your comfort zone can lead to new challenges and growth. 

  • Pull your “Homework for Life” log out of your top drawer. 
  • Scan the list for a time when you experienced what you're explaining to the reader.
  • The solo hiking trip story is a perfect match.
  • Weave the story into your article and draw the connection. 


Telling a captivating story is the most powerful way to win others to your way of thinking.

And by building a habit of collecting stories, identifying lessons, shaping the narrative, and then finding an opportunity to expand what you are writing with a personal story, your writing is guaranteed to be more engaging. The stories you tell will stand out and your readers will remember them.

If you can tell a compelling story and connect it to what the reader wants, you can shape the world.

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