Create Compelling Content Using the 5 Commandments of Storytelling

Kyle’s Note: It’s no secret that I’m obsessed with frameworks and systems that make storytelling easier and more natural. A few weeks ago I met a kindred spirit named Jarie Bolander who offered to introduce us to The Story Grid framework and give us some examples of it in action.

I remember the first time I browsed a Sky Mall catalog on a flight from San Francisco to Denver. I was just a kid; around eighteen I think. From that point onwards, I was hooked.

I’m not really sure what the attraction was. Sure, the gadgets were cool and who doesn’t need a garden gnome that could potentially travel the world? Sadly, much to my dismay, Sky Mall no longer puts catalogs on flights. However, their legacy lives on, online, where you can by the latest suction bowls or traveling makeup kit but unfortunately, no garden gnomes.

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You may be asking yourself, what does Sky Mall have to do with creating compelling content? Well, as it turns out, a whole lot.

Everyone Loves a Good Story

Humans have been telling stories for thousands of years. The reason we love stories so much is because they capture the human condition. They are the easiest way for us to relate to others. It’s stories that teaches us about the world so that we can avoid the tiger, gather honey, and even navigate using the stars. Without story, our lives would be less rich and a lot more scary. It’s stories that allows us to make sense of the world and communicate memes (wisdom) from generation to generation. Without well-crafted and meaningful stories, the wisdom of ages will go the way of cassette tapes, CDs, and 8-track tapes. These examples are not random and here is why:

The stories that those brands and technologies told did not compel customers to keep them around. In fact, there is only one story that has bucked the digital music gold rush – That story is vinyl.

The story of vinyl is a perfect case study in the 5 commandments and the love and devotion audiophiles have for the “richness and depth” of vinyl. Playing records is an experience and vinyl gives audiophiles a unique and compelling experience. It’s the story of how you found the record, your turnable, the artwork, etc. We’ll take a look at how vinyl does that a little later.  

For those of us who need to write compelling content, we can take advantage of this baked-in love of story to get our messages heard even if we are up against all the odds, convenience, and better sound of digital (in my opinion). The way we can at least have a shot at it is if, and only if, we follow the 5 commandments of story and spin a tale that people will believe. We need to make it personal and compelling by allowing the reader to use their imagination.

Our imagination both follows stories and puts ourselves in the shoes of the protagonist — their problems, ideas and goals become ours. This is why you start screaming at the television when your favorite character is about to make a bad decision. Now, this may seem a bit woo woo but the truth is, the best ads, web copy, literature, TV shows, movies, speeches, and sales pitches suck us in because they all weave a compelling story that we just can’t resist. A great story allows us to image what it might be like to hear the original pressing of Stairway to Heaven. From birth, we are a sucker for a good story. Compelling content must stir up these primordial feelings and allow the reader to image a world that solves their problems and transports them to a better way of life.

The Story Grid’s 5 Commandments of Story

Shawn Coyne wrote an excellent book on how stories work called The Story Grid. His book details several aspects of story ranging from beats, scenes, and genre. All these ideas are applicable to content but one in particular directly applies to writing compelling content — the 5 commandments of storytelling.

The 5 commandments of story need to be present at every level of story to ensure that the story you are telling works. Why is this so important for content? Well, applying these commandments ensures that your content is telling a compelling story about your idea, brand, product, or whatever. This ability to tell a better story than your competitor is a huge advantage that makes you look like the hero to your potential customer – and who doesn’t want to be a hero?

A brief synopsis of The 5 commandments of Story (page 157 of The Story Grid) is presented below (check out Shawn’s book for more details. It’s well worth it).

  1. Inciting Incident: This is the big event that kicks off the story. There are two kinds:
    • Casual: The protagonist makes an active choice.
    • Coincidence: Something unexpected or random or accidental happens.
  2. Progressive Complication: The escalating degrees of conflict(s) that face the protagonist. This ups the stakes and makes things exciting. It also moves the story forwards, never backwards.
    • Active: The protagonist takes action themselves. They make an active choice to do something.
    • Revelatory Turning Point: The protagonist realizes something internally based on external circumstances or figures something out.
  3. Crisis: This is the point where the protagonist must make a decision. They have to do something. This is always a question. There are two types.
    • Best Bad Choice: Given a set of two things, both of which have downsides, the protagonist must pick one.
    • Irreconcilable Goods: The protagonist has to pick between two equally good things, which then precludes choosing the other good thing.
  4. Climax: The protagonist acts on the choice they made in the crisis. It’s the actions that matter the most — not what they say they will do. It’s the ultimate “show me the money” moment.
  5. Resolution: This is an important part of the story because it tells the reader what happens when the protagonist took the action in the climax. It’s the payoff of the story that fulfills the reader.

All great stories, from Pride and Prejudice to the Old Man and the Sea, follow these commandments because great authors realized that compelling stories need the 5 commandments in order to work.

Let me be clear on one thing. This is not a formula but a framework in which to view your content so that your content will be more likely to hit the mark. Remember that all the content you generate needs to create value to the reader and hopefully by doing that, have the reader become a customer by choosing your offering.

Photo by Johannes Plenio on Unsplash

Applying the 5 Commandments to Content

Content, such as sales copy, blog posts, ads, etc. are special stories where you want your reader to not only get sucked in, but also take some sort of action. Usually, that action is to buy something or at least give you their email address.

All content, no matter what it is, should adhere to the 5 commandments of story.

Since content is a special case of the 5 commandments, I came up with an adaptation that will help you remember how to apply them. In the below adaptation, the customer is the protagonist and the offering is the hero or you as the solver of the customers’ problem.

  1. Customer has problem that your offering might be able to solve (Inciting Incident).
  2. Unclear solutions. Lots of options. Customer is confused (Progressive Complication).
  3. Can your content fix the customers problem? The customer needs to choose between your offering and another one (An Irreconcilable Goods Crisis).
  4. The content needs to convince the customer to put aside disbelieve and take action (Climax).
  5. The customer needs a clear path to accept the hero’s help or wisdom (Resolution).

As you can see, the 5 Commandments of Story fit nicely into the goals of compelling content. The customer is looking at your content to see if you can help them solve a pressing problem. If you can deliver on the 5 commandments, your content should give them the solutions they need.

Sky Mall does this brilliantly for all of their products — even the ones you don’t need. I fondly recall taking their catalog out of the seat pocket in front of me to go on a journey of discovery. Frankly, most of the stuff I did not need but it was fun and entertaining to get sucked into the story of the garden gnome, the vintage seat from Wrigley Field, the Zap a Bug or my personal favorite, the personal submarine. Oh the tales I could tell if I just had that $15,000 personal submarine to explore the uncharted ocean looking for pirate treasure.

One thing that’s important to realize is that although your content must have all the commandments, they don’t all have to be on the page. It’s enough to have the reader assume certain things or imply certain benefits or feelings. All this will become clear when we look at some examples below.

Photo by Yaroslav Blokhin on Unsplash

Be Unique Like Nobody Else

With most frameworks, it’s how you apply them that makes the difference. There is a lot of noise out there in the world and it’s important to realize that your content is competing with the rest of the Internet for attention. This provides both frustrations and unique opportunities to create great stories about your offering. These narratives are the ones that get noticed and some of my favorites are:

Vinyl Records

Digital is better than Vinyl. There I said it. The “depth and richness” is not “real” but the experience makes it real. That’s why it’s the perfect story to start off with. For my audiophile friends, let’s just agree to disagree. Now onto the analysis:

  1. Customer Problem (Inciting Incident): All these MP3s and CDs sound horrible.
  2. Unclear Solutions (Progressive Complications): Hard to get records. No one makes them anymore. I want my records back.
  3. Can Your Offering Solve My Problem? (Crisis): Should I go cruise the used record stores?
  4. Convince me by showing me (Climax): Records are richer, artists are making them, and the experience is a lot better.
  5. Ways to take action (Resolution): I’m going to buy a record player and tweet at my favorite artists to press some vinyl.

Okay. Okay. I admit it’s not as clean and clear cut as you might think but sometimes, this stuff is not cut and dry. Don’t dismay since I bet that if you were going to write content to get people to buy your used records, you would have to spin a narrative that grabs their imagination and pulls at nostalgia.

The Hustle

The Hustle is my all time favorite email newsletter. It’s the perfect mix of topical news, wit, wisdom, and compelling storytelling. If you’re someone who writes for a living (or enjoys witty content), then sign up for it and help me get some awesome socks!

All the content that The Hustle puts out adheres to the 5 commandments because they know that a well crafted story will keep their readers coming back for more. As an example, let’s take a look at a recent story in their newsletter to show you what I mean.


This story about robots picking produce is a great example of what I’m talking about. Let’s apply the 5 Commandments so you can see what I mean:

  1. Customer Problem (Inciting Incident): Robots are taking over the world!
  2. Unclear Solutions (Progressive Complications): No one wants to pick fruit. It’s hard for robots to get right.
  3. Can Your Offering Solve My Problem? (Crisis): Should I worry about our robot overlords?
  4. Convince me by showing me (Climax): Lots of efforts afoot. Nothing is a good as people.
  5. Ways to take action (Resolution): And at least for now, these bots aren’t replacing jobs.

If you were someone who cared about farm workers or cheap produce, then this story has all the makings to suck you in. If you do click on the “Bot’s got the touch” link, which is the desired result, you’ll see how this benefits The Hustle. Go ahead do it now. I’ll wait ….


If there is one brand that is aligned to a certain lifestyle it’s Chubbies. All of their videos, ads, and content directly relate back to their mission:

We exist to bring you the best weekend clothing that has ever been conceived.

That’s both a simple and straightforward story of why they exist. Their content also delivers that message every single day, especially their videos which are a masters class in targeted storytelling. Take a look at my favorite below. Pay particular attention to the story Chubbies is telling about the weekend and the images they use. Why don’t you see how the 5 commandments apply? Feel free to put your answers in the comments.

Dollar Shave Club

Shaving is something that most men have to do daily. Traditional razors are expensive and most men, me included, are not so great about remembering to change their blades — not any more.

Dollar shave club does an outstanding job on telling their story that Gillette, the 1,000 pound gorilla of shaving, copied their concept. Their blog is even better and tells wonderful stories about the Dollar Shave Club lifestyle. Yes, that is actually a thing.

Warby Parker

Thankfully, I don’t have to wear glasses but if I did, this would be the first place I would shop. Everything Warby Parker does is on message and tells great stories. It starts out strong with their history:

Warby Parker was founded with a rebellious spirit and a lofty objective: to offer designer eyewear at a revolutionary price, while leading the way for socially conscious businesses.

Just that first paragraph hits almost all of the commandments because as consumers, we know how much of a pain in the butt it is to buy glasses as well as how expensive glasses are.


Pillow Talk is the perfect name for a blog that’s all about getting a better night’s rest. Casper’s simple style coupled with it’s great narratives about the people who bought their mattress, such as actor Michael Rapaport, prove that the power of story is what compels us to take action.



It’s no surprise that companies that create compelling content get noticed. It’s in our DNA to be driven to act on stories that resonate with us. Stories change our hearts and minds. It’s the way humankind has passed on wisdom, overthrown tyranny, and sold you that vinyl is better than digital.

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The next time you need to write a piece of content, give the 5 commandments a whirl. Not only will you get people to notice your content, you might even inspire them to buy a cute garden gnome.

About the Author

Jarie is an engineering by training and an entrepreneur by nature. He has published four books — The Entrepreneur Ethos, Frustration Free Technical Management, #ENDURANCE tweet — A Little Nudge to Keep You Going, and Business Basics for Entrepreneurs.

You can read his thoughts on management and entrepreneurship via his blog, or follow him on Twitter @TheDailyMBA. He’s also a Story Grid Certified Editor that recently launched a podcast that discusses Story Grid principles, like the 5 commandments, so that you can become a better storyteller and editor.