Learning From Failure: How the Try-Fail Cycle Works

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You have a goal. You make a plan. You give it your best effort.

And it doesn’t work.

So you make some adjustments and try again. This time you make progress, but your success introduces a whole new set of problems.

Sound familiar?

We tend to imagine success as a straight line between where we are and where we want to be. But real life rarely works that way.

In storytelling, there’s a name for this pattern: the try-fail cycle.

Writers use try-fail cycles to create compelling stories in which characters face repeated obstacles, experience setbacks, and develop the abilities needed to overcome their challenges.

And the same pattern appears throughout our lives.

But failure doesn’t automatically lead to growth. What matters is how we interpret our setbacks, what we learn from them, and what we do next.

In this episode of the Full Mental Bracket Podcast, Brent and Camille Diggs explore how to learn from failure, develop perseverance, and recognize the try-fail cycles unfolding in our own lives.

From Inigo Montoya’s relentless pursuit of the six-fingered man in The Princess Bride to the psychology of motivation and the unexpected benefits of shared struggles, they examine why progress rarely happens on the first attempt—and how the difficulties we encounter can prepare us for what comes next.

Brent and Camille explore how the try-fail cycle helps us understand failure, perseverance, and personal growth.

🧠 What the try-fail cycle is: How writers use repeated attempts, partial successes, and unexpected complications to develop compelling stories.
🧠 Why progress rarely happens in a straight line: Understanding the difference between a partial success and an attempt that makes matters worse.
🧠 How to learn from failure: Why setbacks can provide information that helps us adapt, develop new abilities, and approach problems differently.
🧠 The psychology of perseverance: What research into dopamine and motivation suggests about our responses to disappointing outcomes.
🧠 Why shared struggles can strengthen relationships: How working through difficult experiences together can create lasting connections and memories.
🧠 How interpretation affects our response: Why the story we tell ourselves about a setback can influence whether we become discouraged or continue making progress.

Brent and Camille explore how the try-fail cycle helps us understand failure, perseverance, and personal growth.

⏳ 00:00 – What Is the Try-Fail Cycle?
⏳ 05:40 – Why Progress Includes Setbacks
⏳ 07:21 – Inigo Montoya: A Lesson in Perseverance
⏳ 11:27 – How Failure Fuels Growth, Resilience, and Self-Development
⏳ 13:27 – Dopamine, Disappointment, and Motivation
⏳ 16:56 – Learning to Adapt and Keep Going
⏳ 18:21 – How Shared Struggles Strengthen Relationships
⏳ 21:26 – Changing How We Interpret Setbacks

Full Transcript

The try-fail cycle is a storytelling technique in which a protagonist makes repeated attempts to overcome a problem or accomplish a goal.

Some attempts bring the character closer to success. Others fail completely or create unexpected complications.

Each attempt changes the situation, requiring the character to reconsider their approach and try again.

The concept is discussed by writers including Brandon Sanderson and Dan Wells on the Writing Excuses podcast, where Brent first encountered it while studying storytelling.

The basic idea is simple.

Every story presents a problem that the protagonist must solve. Each attempt raises a question: Will this choice bring the character closer to the goal?

If the answer is always yes, the story becomes predictable.

If the character fails repeatedly without making any progress, the story becomes frustrating.

But when successes and failures create new complications, the story becomes more interesting.

Writers often describe these outcomes using two simple phrases.

Yes, But: Success Creates Another Problem

The protagonist accomplishes something, but the success introduces a new complication.

Maybe they reach their destination, but discover that the person they’re looking for has already left.

Maybe they solve one problem, but the solution creates another.

Progress has been made, but the larger challenge remains.

No, And: Failure Makes Things Worse

The protagonist attempts something and fails.

And now the situation is worse than before.

Maybe their attempt to escape gets them captured.

Maybe a plan fails and costs them resources they needed for the next attempt.

Now the protagonist has fewer options and a more difficult problem to solve.

These patterns create the tension and complications that make stories engaging.

But they also describe something familiar about everyday life.

We make plans based on what we know. Then reality introduces circumstances we didn’t anticipate.

Sometimes we make progress. Sometimes we make things worse.

And sometimes the solution requires learning something we didn’t know when we started.

One of the best examples comes from The Princess Bride.

Inigo Montoya has spent twenty years searching for Count Rugen, the six-fingered man who killed his father.

He’s devoted much of his life to becoming a skilled swordsman, preparing for the confrontation he hopes will finally bring his quest to an end.

When he eventually finds Rugen, you’d think the story would reward all that preparation with a quick victory.

Not quite.

Inigo defeats Rugen’s guards, but the Count escapes and locks himself behind a door.

Inigo gets through the door, but Rugen throws a knife into his stomach.

Inigo manages to get back into the fight, but he’s stabbed again.

Every success introduces another problem. Every failure makes the situation more difficult.

By the time Inigo finally defeats his enemy, the audience has watched him overcome a series of increasingly difficult obstacles.

The victory feels earned.

Brent and Camille break down the scene to show how multiple try-fail cycles can unfold within a single confrontation.

And they point out that Inigo’s struggles began long before that final fight.

Twenty years of preparation, searching, setbacks, and failed attempts have brought him to this moment.

The scene works because his success has a history.

In our own lives, we often want the final victory without all the complications that precede it.

But the abilities we need to succeed may be developed through those earlier attempts.

Failure is disappointing.

We invest time, energy, and resources into an effort because we expect—or at least hope—that it will produce a worthwhile result.

When it doesn’t, frustration is a natural response.

But an unsuccessful attempt can also provide useful information.

Maybe we misunderstood the problem.

Maybe our approach wasn’t effective.

Maybe we need another skill, a different strategy, or help from someone with more experience.

The failure doesn’t automatically teach us anything. We still have to examine what happened and decide what to do differently.

That’s one reason the try-fail cycle is such a useful way to think about personal growth.

Instead of treating every unsuccessful attempt as a verdict on our abilities, we can recognize it as one part of an ongoing process.

Sometimes the next attempt will succeed.

Sometimes it will reveal another complication.

And sometimes we’ll discover that the original goal or approach needs to change.

Learning from failure means using what happened to make a better decision about what comes next.

Why do some disappointments encourage us to try harder while others make us want to quit?

Camille introduces an interesting piece of research involving dopamine, a neurotransmitter associated with motivation, reward, and learning.

We often think of dopamine in connection with getting something we want.

But researchers have also investigated how dopamine systems respond when an expected reward doesn’t appear.

A study involving rats identified dopamine signals associated with adjusting behavior after disappointing outcomes.

The findings suggest that certain neural responses may help support continued attempts when a reward is unexpectedly absent.

The research doesn’t mean that failure automatically makes people more motivated or resilient. But it offers an interesting look at how the brain processes disappointment and prepares for future attempts.

Brent and Camille connect this discussion to their own differences in perseverance.

Camille describes how, once she’s committed to a task, she wants to keep going until she finishes it.

Brent admits that he’s sometimes more easily discouraged.

But understanding the try-fail cycle has helped him approach those moments differently.

Instead of seeing each obstacle as another reason to quit, he can recognize that developing the ability to solve difficult problems often requires repeated effort.

The challenge is learning to work through disappointment without allowing it to determine the entire direction of our efforts.

We often describe perseverance as refusing to give up.

And determination matters.

But continuing to repeat the same unsuccessful approach isn’t necessarily progress.

Sometimes perseverance requires changing the plan.

You may need to develop a new skill, reconsider your assumptions, or recognize that the problem is different from what you originally believed.

That’s part of what makes the try-fail cycle valuable.

It encourages us to look beyond the immediate outcome of an attempt.

What changed?

What did we learn?

Are we closer to the goal, or have we discovered that our approach needs to change?

These questions help us separate the process of learning from the frustration of not succeeding immediately.

They also challenge the expectation of instant success.

We live in a culture where the finished achievement is often far more visible than the effort required to produce it.

We see the successful business, the accomplished musician, or the finished project.

We rarely see the countless mistakes, revisions, and disappointing attempts that came before.

And that can distort our expectations about how progress works.

The try-fail cycle reminds us that developing capabilities takes time.

Sometimes the person who eventually succeeds is someone who couldn’t have accomplished the goal when the journey began.

The attempts along the way helped make that success possible.

Not every try-fail cycle is something we face alone.

Sometimes the most memorable parts of our lives come from the challenges we’ve experienced with other people.

Brent and Camille discuss how shared struggles can contribute to stronger relationships.

They recall a family adventure involving inner tubes and a river that seemed like a perfectly reasonable idea at the time.

Unfortunately, the trip involved shallow water, unexpected obstacles, and considerably more walking than anyone anticipated.

What was supposed to be a relaxing float became an exhausting adventure.

And years later, it’s still a story the family remembers.

Not every difficult experience creates a happy memory, of course.

But working through challenges together can give people opportunities to develop trust, cooperation, and a stronger sense of connection.

Sometimes we discover what our relationships are capable of handling when circumstances don’t go according to plan.

And sometimes those experiences become part of the shared history that connects us.

The try-fail cycle can be something we experience together, learning from one another as we work toward a common goal.

One of the most useful lessons from the try-fail cycle involves how we interpret our setbacks.

Imagine facing a difficult challenge that seems beyond your current abilities.

You could look at the situation and think:

I’m in over my head.

That may be true.

But you could also recognize:

I’m learning to swim.

That might be true, too.

Both interpretations acknowledge the difficulty. But they place the experience in a different context.

One emphasizes how overwhelmed you feel.

The other recognizes that you’re developing an ability you didn’t previously possess.

The way we interpret a situation can influence our emotions, expectations, and decisions.

When we treat every setback as evidence that life is working against us, discouragement can make the next attempt feel even more difficult.

When we recognize that learning often involves unsuccessful attempts, we may be better prepared to examine what happened and decide how to continue.

Of course, not every struggle is a useful learning experience. Some situations are genuinely harmful, and some call for changing direction, getting help, or stopping altogether.

But when we’re pursuing something worthwhile, the try-fail cycle gives us another way to understand the difficulties we encounter.

An unsuccessful attempt doesn’t have to be the end of the story. It can become information that helps shape what happens next.

As Brent and Camille conclude the conversation, they leave listeners with several questions about their own try-fail cycles.

1. Are you expecting success too quickly? Have you allowed enough time to develop the abilities and experience your goal requires?
2. What might your current struggles be teaching you? Are there problems, assumptions, or approaches you need to reconsider?
3. How are you interpreting your setbacks? Are you treating them as permanent failures, or examining what you can learn from the experience?
4. Are you learning from your attempts? What could you change before trying again?
5. How might your experiences benefit someone else? What lessons from your own struggles could help another person facing a similar challenge?

We don’t get to choose every difficulty that enters our lives.

And we can’t guarantee that every attempt will lead to success.

But when we’re working toward something meaningful, we can examine the results, learn what we can, and decide how to respond.

The try-fail cycle reminds us that progress often involves setbacks, adjustments, and unexpected complications.

What matters is what we learn along the way—and how those lessons shape what comes next.

🎬 The Princess Bride — Inigo Montoya’s final confrontation illustrates how multiple successes and failures can build toward a satisfying resolution.

🎬 The Lord of the Rings — A humorous discussion of how quickly the story might have ended if the heroes could have simply flown the Ring to Mount Doom.

🎬 How It Should Have Ended — Animated movie parodies that demonstrate what happens when familiar stories are resolved without their usual complications.

• Writing Excuses podcast — Why Should My Characters Fail Spectacularly? -A discussion of the try-fail cycle and how writers use Yes, But and No, And to develop compelling stories.
• How It Should Have Ended
• Failing Forward: Unlocking the Power of Dopamine for Success — Marwa Azab, Ph.D.– An exploration of research into dopamine, motivation, and how the brain responds when expected rewards don’t appear.

• EP005 — Facing Life’s Obstacles → Learn how to develop a healthier relationship with adversity, discomfort, and the fear of failure.
• EP006 — Your Character Arc → Explore how our responses to adversity shape our abilities, identity, and the kind of person we become.
• EP015 — The Princess Bride & Growth Mindset → Discover what The Princess Bride teaches us about developing our abilities and embracing opportunities for growth.
• EP004 — Find Your Tribe → Explore why relationships and supportive communities matter when facing life’s challenges.
• Explore the Complete Hero’s Journey Series →

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Your first attempt might not work.

Neither might your second.

But what you learn from those attempts may help you become capable of something you couldn’t accomplish before.