How to tell better stories | Matthew Dicks (Storyworthy)

Executive Summary
Matthew Dicks joins Lenny Rachitsky to explain storytelling through opposing moments, natural delivery, stakes and surprise. This selected coverage omits the opening student-anxiety anecdote and later personal-interest inventory. His advice about attention and story structure is presented as a teaching method, not a universal psychological rule. Untimed topics are editorial, not video chapters.
Key Takeaways
Start a true story with its ending
Dicks says that a lived story about yourself, a company or a product starts with knowing the moment worth communicating. That ending helps determine what must appear earlier. He distinguishes this method from his fiction writing, where the ending may emerge through discovery.
Set the beginning against the ending
He describes a story's beginning and end as opposing states. A change in belief, confidence or desire gives the audience a meaningful journey. A chronological list of events without a change may be a report rather than the kind of story he recommends.
Use the dinner test
A keynote or pitch should sound like a slightly more shaped version of a story you would tell at dinner. Dicks rejects theatrical openings that do not resemble ordinary speech. Keep the structure while removing filler and unnatural performance habits.
Make the stakes clear
Stakes are what the audience wants, worries about or wonders about. Dicks argues that a title or a seated audience does not automatically give a speaker attention. Give listeners a reason to care about the next sentence rather than assuming they already do.
Put an elephant near the opening
His elephant is an early concern or question that tells the audience what kind of story it is entering. It need not reveal the entire story. It should create an immediate reason to wonder what will happen, not simply add noise or a sensational fact.
Give the audience a backpack
Describe the plan before carrying it out so listeners can share the narrator's hopes and recognize when the plan goes wrong. Dicks calls this a backpack. Without that context, a setback may look like just another event rather than a meaningful obstacle.
Prepare a surprise that makes sense afterward
Dicks separates stakes from surprise. He recommends planting enough information for a turn to feel understandable once revealed while avoiding an obvious setup. His breadcrumbs and slowing down at a critical moment are storytelling tools, not permission to invent facts in a true account.
The Conversation Breakdown
Start a true story with its ending
⏱ Untimed topicDicks says that a lived story about yourself, a company or a product starts with knowing the moment worth communicating. That ending helps determine what must appear earlier. He distinguishes this method from his fiction writing, where the ending may emerge through discovery.
Set the beginning against the ending
⏱ Untimed topicHe describes a story's beginning and end as opposing states. A change in belief, confidence or desire gives the audience a meaningful journey. A chronological list of events without a change may be a report rather than the kind of story he recommends.
Use the dinner test
⏱ Untimed topicA keynote or pitch should sound like a slightly more shaped version of a story you would tell at dinner. Dicks rejects theatrical openings that do not resemble ordinary speech. Keep the structure while removing filler and unnatural performance habits.
Make the stakes clear
⏱ Untimed topicStakes are what the audience wants, worries about or wonders about. Dicks argues that a title or a seated audience does not automatically give a speaker attention. Give listeners a reason to care about the next sentence rather than assuming they already do.
Put an elephant near the opening
⏱ Untimed topicHis elephant is an early concern or question that tells the audience what kind of story it is entering. It need not reveal the entire story. It should create an immediate reason to wonder what will happen, not simply add noise or a sensational fact.
Give the audience a backpack
⏱ Untimed topicDescribe the plan before carrying it out so listeners can share the narrator's hopes and recognize when the plan goes wrong. Dicks calls this a backpack. Without that context, a setback may look like just another event rather than a meaningful obstacle.
Prepare a surprise that makes sense afterward
⏱ Untimed topicDicks separates stakes from surprise. He recommends planting enough information for a turn to feel understandable once revealed while avoiding an obvious setup. His breadcrumbs and slowing down at a critical moment are storytelling tools, not permission to invent facts in a true account.
Core Frameworks & Ideas
Opposing-moments structure
For a lived story, find the ending and choose a beginning that shows the prior state.
Dinner test
Tell a shaped version of a natural dinner story rather than putting on an artificial performance.
Elephant and backpack
Open with a reason to wonder, then share the plan so setbacks have meaning.
Actionable Next Steps
- ✓Write the ending and the opposing starting state in one sentence each.
- ✓Read a draft aloud and remove phrasing you would never use at dinner.
- ✓Name the concern that should make the listener want the next sentence.
- ✓Explain the plan before its setback, and check that every fact stays true.
Notable Quotes
“Essentially, a story is about these two moments in time, a beginning and an end, and they're operating in opposition to each other.”
“If your audience isn't wondering what you're about to say, they're no longer listening to you.”
“So the dinner test is pretty important in that regard.”
The One Thing to Remember
Find the meaningful change, then give the audience a reason to care about how it happens.