Finding stories in disappointments

Author

Stephen Stanberry
November 19th, 2025

In partnership with

Hey friend! Quick question

If you had to pull a story out of a disappointment, where would you look?

Most people stare at the big stuff.
The wins.
The highlights.
The shiny moments that make you look smart online.

But that’s not where the real stories sit.
They hide in the mess.
The delays.
The letdowns.
The days you’d delete if life came with a backspace key.

Two weeks ago, when Hurricane Melissa hit Jamaica, I got reminded of this the hard way.

Everything collapsed.
Plans gone.
Homes gone.
Momentum gone.

And for a few days, I didn’t feel like writing at all.
Not because I didn’t have ideas.
Because disappointment takes up space in your chest.
It slows everything down.

But here’s the twist.
When I finally stopped resisting it, I saw the thing I’d been missing.

The disappointment was the story.

Not the destruction.
Not the chaos.
But the moment after, where you’re forced to see things clearly.

So today, I want to show you something simple.
How to take a disappointment and turn it into a story people lean into.

Let’s get started.

The Power of Disappointment

Disappointment is leverage.
It gives you an angle you don’t get from success.
It forces honesty.
It pulls emotion to the surface.
It gives your readers something to grab onto.

Most people skip past it.
Big mistake.

One honest line from a painful moment beats ten polished lines from a perfect week.
Every time.

Disappointment is not the end of the story.
It’s the part that makes the story worth telling.

How To Turn Disappointment Into Story

Here’s the simple version:

1. Name the hit.
Say what went wrong. Straight. No padding.

2. Zoom into the moment.
What did you see? What changed? What clicked?

3. Pull out the theme.
Is this about resilience? Growth? Identity? Choice?

4. Make the bridge.
Show how the lesson applies to the reader’s world.

5. Lock it in.
End with one clear takeaway. Tight and direct.

This is how you turn a low point into a high-value story.

Practice Prompts

(Non-generic. Pulled from your guide’s “Disappointment, Failure, Aha Moment” templates.)

Try one of these:

  • “The disappointment that shaped me most was ___.”

  • “I thought the plan was solid until ___ happened.”

  • “The moment that crushed me, but taught me ___, was ___.”

  • “If I’m honest, the setback I needed was ___.”

  • “I didn’t see it then, but now I understand ___.”

Pick one.
Write it.
Post it.
Tag me.

Let’s fill the feed with stories that sound real, not rehearsed.

See you tomorrow,
Stephen

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