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5 Proven Tips to Write Personal Stories That Stick


“If you go down to meet this guy, you may never back. He’s on another level.” 

Shortly into his career, legendary Esquire columnist Cal Fussman got the itch to interview Harry Cruz, a novelist who wrote stories on off-the-wall topics like a man who ate a car.

Despite the warnings of Cruz’s reputation as a lover of all things that impaired his ability to operate heavy machinery, Cal was all over it.

When he arrived at Cruz’s place, the novelist didn’t disappoint as Cal found him laid out stone-drunk with a bottle of rum on his belly. 

“Go down to the Gator Gulch!” Cruz announced when Cal woke him up. And after loading up on an assortment of booze at the corner liquor store — the pair sat down to talk while chasing pills with slugs of whiskey. 

“How can you write living like this?” Cal asked, in awe of the man’s ability to retain anything let alone make a living as a storyteller. “Do you keep a journal?”

“Boy,” Cruz replied in his heavy southern drawl, “the good shit sticks!”

When it comes to becoming a stronger storyteller, with the exception of maybe Stephen King, a solid rule is don’t listen to people who drink their breakfast and snort the ole’ devil’s dandruff for lunch.

Keep daily tabs on your life and the people you’re lucky enough to have in it. You don’t need to buy a fancy moleskin journal. If you have an interesting thought, write it down in a $2 notebook or on your phone. 

I may take things to an extreme by writing each day a sentence regarding the following five topics:

  • one thing I learned
  • one memory that popped into my head
  • one thing I got wrong
  • one thing I’m proud of
  • one thing about how someone helped me

But by doing so, I rarely run out of material as the habit makes my writing life easier. 

But you don’t have to take it that far. 

Pick just one of the topics above and if at any time during the day you hear or learn something that makes you go “Hmmm,” write down a spark so when you read it later, it jogs your memory.

In addition to not buying into the notion that the good shit does indeed stick, here are four other daily habits to write stories that can help you build a reputation as a memorable storyteller.

Get lost in one conversation a day

“The best storytellers I know are the best listeners I know.”

I couldn’t agree more with this thought from my friend Fred, former Global Managing Director of the design firm IDEO and author of Making Conversation.

Reading is good. 

The internet, when used properly, is good. 

But don’t underestimate the power of real-world conversations and building a reputation for being as curious as a kid.

But don’t just have run-of-the-mill conversations of asking people how they’re doing and if they have any plans for the weekend. Instead, dig a little.

  • Ask them about their childhood.
  • Ask them about their best piece of advice.
  • Ask them about their proudest accomplishment or biggest embarrassment.

Lean into the times they struggled and position yourself as the best listener in the room.

Every building or house you walk by is full of people who’ve experienced twists and turns and challenges and adventures.

Your job is to extract these stories.

Not only will this make your writing more interesting as you’ll be able to tell stories other writers can’t, but your life will also be more interesting.

It’s hard to argue with the notion that the quality of our lives is a direct reflection of the quality of our conversations.

Dissect one story a day

“Don’t just read stories, dissect them!”

I was given this piece of advice shortly into my storytelling obsession. It’s led to not only being able to write more engaging stories myself but also making a decent living as a book strategist and working with people to make their articles stronger (which can be surprisingly lucrative assuming you position yourself as a coach, strategist, or even “book doctor” and not simply an editor).

Give yourself a 30-day challenge and read or listen to one story a day on platforms like The Moth and instead of passively consuming them, actively attack them. 

How did the author start the story? 

  • Did it grab you? If yes, why? Get specific. Did they throw you immediately into the action? Did they begin with a thought-provoking statement? Did they ask you a question you couldn’t walk away from?
  • If it didn’t grab you, what could they have done differently?

How did the author keep you reading?

  • Did you move from sentence to sentence without even realizing it? Why was that? Was it because it had mini-cliffhangers sprinkled throughout? — which is just a fancy way of saying they did a good job of spreading out the tension. Or was it because they have a good tempo to their writing or because you found their story relatable?
  • If they didn’t keep your attention, where in the story did you begin to check out? Could they have done anything differently? If yes, rewrite it.

How did the author conclude their story?

  • Did they link the conclusion to the story in the introduction so you can relive their transformation and be reminded of how far they’ve come? 
  • Or did they drill into their biggest lesson learned while demonstrating how the experience changed their life?
  • If you felt so-so or even disappointed when their story came to an end, pin down where they went wrong and tinker with doing it yourself. 

How did you feel after reading the story?

  • What emotion did you feel after you turned the last page? Empowered? Contemplative? Filled with hope? Whatever the emotion, write it down and think about which parts of the story helped to stoke these feelings. 

In addition to reading articles and scanning how books begin, actively listening to talks and speeches is an underrated way to improve your written storytelling skills. 

Dissect the ones that landed well with the audience and zero in on how the speaker grabbed your attention and what they did well to hold it. 

Of equal value, dissect the ones that flopped and zero in on where they went wrong while mapping out in a stronger way to tell it.

Spin your stories sideways and flip them upside down

The beauty of stories is there are a million and three ways to tell the same one. The faster you can begin to look at stories and identify a handful of different ways to kick them off in an engaging way, the faster your stories will begin to fly. 

One thing I like to do is flip stories around and tinker with ways to kick them off to ensure I’m starting with the strongest entry point.

  • Start with the story you most want to tell right now and write your draft in chronological order to get the important steps of the stories down.
  • Then, grab your best sentence or most engaging thought towards the middle of your story and try kicking it off from there. 
  • Lastly, begin with the end in mind and show yourself standing on top of the mountain, and then backtrack to tell readers how you got there. 

When working with professional editors either here on Medium or Business Insider and Fast Company, they’d highlight a solid thought in the text or a sentence that had a decent amount of tension or human insights and recommended I try using it as my first line. 

The odds are high that the bones of your stories are already solid. 

To take them to the next level, get clear on the strong parts and build from there.

The world is getting loud. 

Taking the time to learn how to pull people into your universe is a seriously valuable quality.

Do one thing a day that makes your palms gush with sweat

I’m a big believer that one of the best ways to be a stronger storyteller is to pray for a life of problems. 

In fact, my writing career is nothing but me sharing stories of things I used to be bad at — or petrified of — and the steps I took that allowed me to be less bad or less petrified of them. 

That’s the beauty of stories — you don’t have to be an expert. 

You just have to be honest and you have to be human. 

It’s surprisingly easy to stay in your cave all day. And yes, you can make a living as a writer cruising around Twitter or YouTube and sharing the stories of others. 

But I don’t know about you, I’m kinda sick of reading about what Elon Musk eats for breakfast. 

I’d prefer to learn about you.

  • What scares you? 
  • What makes your heart tick a bit faster than normal? 
  • What challenges have you faced where you may not have aced the test but you learned something new about yourself?

Do one thing a day that makes your palms sweat a little. 

  • Maybe it’s giving a talk at your office. 
  • Sending an email to someone whom you admire. 
  • Or saying hello to a stranger on the street. 

Hell, it could even be recording yourself telling a story on your phone. 

I did that once and wrote a story about it, and believe it or not, it went viral. Today, it has over 50,000 views on Medium and another 10,000 on my website.

Easy lives make for boring reading. 

Choose what’s hard. 

Pray for a life of problems.

Make a commitment to write about it.

Most importantly, be you.

It’s who you’re going to be anyway, so what’s the point in delaying the inevitable?