A storytelling framework to normalize startup failure
Most human beings like a good story. Stories shape how we understand the world. Whether it’s Grimm’s fairy tales, La Fontaine’s fables, or Greek myths, we’ve all grown up listening to tales that helped us make sense of life. As adults, the stories just change form—now they show up in audiobooks, team retrospectives, or startup pitch decks.
But storytelling isn’t just for entertainment. It can be a powerful tool for transformation. Especially in fast-growing organizations where failure is inevitable—but rarely spoken about.
As Jordan Peterson once said, “People live inside the stories they tell about themselves. And they use those stories to interpret everything around them.”
The question is—what happens if the stories we tell ourselves about failure are flawed?
Why Startups Need a Better Way to Talk About Failure
In startup environments, failure is often either:
Dismissed as irrelevant (“fail fast” and move on), or
Internalized as shame (“we got it wrong—we must be incompetent”).
Neither approach helps a team develop a healthy, sustainable culture. What we need instead is a structured, emotionally intelligent way to look at failure—without blame or spin.
That’s why I created the Failure Storytelling Framework. I developed it during a four-week sprint while working on a book manuscript—pulling together ideas from narrative therapy, self-coaching, and my experience in transformation work.
the narrative therapy lens
I have had very good experiences using narrative therapy, both personally and in organizational settings. Its principles are deceptively simple and deeply powerful.
Three ideas in particular can be applied to startup failure culture:
Externalizing the problem – You are not the failure. The issue is not you. It’s something outside of you.
Re-authoring the story – You can choose how to interpret what happened.
Reviewing unique outcomes – Moments where you deviated from the expected story and discovered something useful.
When startups build reflection into their rhythm—and do it in a way that honors the emotional and operational realities of failure—they make room for growth. Actual, grounded, culturally embedded growth.
The Failure Storytelling Framework (for Startups)
Use this when the launch flops, when you spent your valuable marketing dollars on the wrong customer persona, when investors pull back. Ask yourself these questions, write down your answers. Take your time to reflect on them.
1. The stories we tell ourselves. What happened—at first glance? What really happened? Who contributed? Who were the observers?
2. Which myth are we living in? Are we reacting based on the myth “there’s no time to fail”? Or the myth “failure means incompetence”?
3. Reframing If we step outside that myth, what do we see? Was it over-investment? Misapplied strength? A missing pause for validation?
4. Moving forward What do we do differently next time? What lesson do we integrate? What’s the new story we tell—individually and as a team?
Let’s bring this to life with one example.
Photo by Rodion Kutsaiev on Unsplash
Glossier: A Case Study in Failure Storytelling
The American company Glossier began as Into the Gloss, a beauty blog with a cult following. It evolved into a direct-to-consumer brand that raised millions and defined the aesthetic of a generation. But in 2022, the leadership laid off its entire tech team. They had over-invested in retail and tech infrastructure—before product-market fit was stable. They tried to pivot into a “tech platform” without enough evidence that customers needed one.
So—what happens when we run this moment through the failure storytelling framework?
Step 1: The stories we tell ourselves
At first glance: We scaled too fast. The market didn’t want what we built.
What actually occurred: We believed in the myth “There’s no time to fail.”
We tried to force product-market fit rather than listening to what was emerging.
Who contributed: The founder and leadership team. The VCs backing them.
Who observed: Employees executing the plan. Customers confused by the sudden shifts.
Step 2: The myth at play
Two dominant startup myths surface here:
“There’s no time to fail.”
So we scale before validating. Build before listening.“Failure = incompetence.”
So we polish, over-perform, and hide the cracks until they can’t be hidden anymore.
Sometimes, teams disguise this as boldness:
“We go big. We don’t take prisoners.”
Which really means: We don’t make time to reflect.
Step 3: Reframing
This wasn’t a disaster. It was an overextension of ambition.
We were aligned, driven, and committed. But we skipped the reflective pause.
Next time, we balance execution with intentional slowness—especially when building something outside our core.
This is what a healthy failure culture looks like: no finger-pointing, no denial. Just honest reflection and a new story.
Step 4: Moving forward
If Glossier had used this framework internally:
They might have piloted at 15–20% scale.
Teams could have openly voiced doubts before major spend.
A new cultural script could have emerged:
“We learn out loud. We name missteps early. We don’t equate failure with shame.”
And the heroine story becomes:
“She was ambitious. She took a risk. She owned what didn’t work—and kept going.”
That’s a story a team can rally behind.
Why We Need to Normalize Failure in Startups
Startups aren’t failing because they’re bad. They’re failing because they’re building.
If we do not make space to process what goes wrong—culturally, not just operationally—we miss the chance to learn. Or worse: we repeat the same pattern in more expensive ways.
This framework helps teams:
Move from shame to analysis.
Externalize the failure, not internalize it.
Normalize honest, reflective dialogue.
Because you are not the failure. The problem is the problem. And the story? You get to rewrite it.