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Each Obstacle Harder Than the Last: Why the Cinderella Structure Works in Magic

Advanced Scripting & Character Written by Felix Lenhard

The Cinderella story has survived for more than two thousand years. There is a Greco-Egyptian version from the first century B.C.E. Every culture on earth has some version of it. And the reason it endures is not the fairy godmother or the glass slipper or the prince. The reason it endures is the structure.

Every time Cinderella gets close to what she wants, a new obstacle appears. And every obstacle is harder than the one before it.

Pete McCabe lays this out in Scripting Magic’s chapter on drama with such clarity that I had to set the book down and stare at the wall of my hotel room in Salzburg. Because I realized, sitting there, that every multi-phase routine I had been performing violated this principle. Every single one.

The Flat Structure Problem

Here is how my three-phase mentalism routine used to work. In the first phase, I would correctly identify a card the spectator was thinking of. In the second phase, I would correctly identify a word the spectator had selected from a book. In the third phase, I would correctly identify a personal detail about the spectator — their birthday, their hometown, something specific.

Each phase was a success. Each phase was impressive. And each phase was roughly the same level of difficulty. The card was no harder or easier to identify than the word, which was no harder or easier than the personal detail. The structure was flat. Three effects of equal weight, lined up in sequence like items on a shopping list.

The audience reacted well enough. They applauded after each phase. But I noticed something that bothered me: the reactions did not build. The reaction to the third phase was roughly the same as the reaction to the first phase. There was no crescendo. No momentum. No sense that we were building toward something extraordinary.

The performance was a plateau, not a mountain.

What Cinderella Teaches

McCabe’s retelling of the Cinderella story is a masterclass in escalating stakes. Look at the structure:

Cinderella wants to go to the ball. Obstacle: her sisters destroy her dress. This is bad, but it is a solvable problem. The fairy godmother provides a solution.

Cinderella is at the ball, dancing with the Prince. Obstacle: the magic expires at midnight. This is worse — it is a time-limited problem with no apparent solution. She must flee.

The Prince sends the Duke with the slipper. Obstacle: the stepmother locks Cinderella in her room. This is worse still — she is physically prevented from reaching the solution.

Cinderella escapes and the slipper is brought to her. Obstacle: the slipper shatters. This is the worst — the solution itself has been destroyed. There is no way forward.

Each obstacle is harder than the last. Each one raises the stakes. And the final obstacle seems genuinely insurmountable. The audience — or the child hearing the story for the first time — genuinely believes, in that moment, that all is lost.

And then, of course, there is a final triumph. Cinderella pulls out the matching slipper. The obstacle was not insurmountable after all. But the audience did not know that until the resolution.

This escalating structure is what creates emotional momentum. The audience’s investment deepens with each obstacle because each obstacle raises the question: how can this possibly be resolved? And the deeper the investment, the more powerful the final resolution.

Redesigning My Routine

After reading McCabe’s analysis, I went back to my three-phase mentalism routine and redesigned it using the Cinderella structure. The process required me to think about each phase not as an independent effect but as a chapter in a story with escalating difficulty.

Phase one: I attempt to identify a card the spectator is thinking of. This is the simplest form of mind reading — a thought, a card, a binary result. The stakes are clear and contained. I identify the card correctly. The audience is impressed but not overwhelmed. This is the ball invitation — the first step, the proof of concept.

Phase two: I attempt something harder. Instead of a simple card, I try to perceive a memory — something personal and specific that the spectator has not told me. The difficulty has increased. Cards are abstract, neutral, impersonal. Memories are specific, emotional, private. The spectator is visibly more guarded, more uncertain. I work harder — I concentrate longer, I ask the spectator to hold the memory clearly. And I begin to struggle. My first impression is vague, possibly wrong. I refine. I narrow. The audience watches someone attempting something more difficult than what they just saw, and the uncertainty is palpable.

Then I get it right. The memory is confirmed. The reaction is stronger than phase one because the audience saw the difficulty. They saw the struggle. They felt the increased stakes. This is the midnight clock — a harder obstacle overcome.

Phase three: I attempt something that should be impossible. I ask the spectator to think of something they have never told anyone. Something completely private. Something that no research, no prior information, no educated guess could possibly access.

This is the shattered slipper. The audience does not believe I can do this. The spectator does not believe I can do this. I am not entirely sure the audience believes I am even going to try.

I take my time. I close my eyes. I describe receiving fragments — disconnected images, sensations, half-formed ideas. Some of what I describe is wrong, or seems wrong. The audience sees genuine difficulty. The tension builds.

And then I name it. The specific, private, never-shared piece of information. The room erupts.

The reaction to phase three, under this escalating structure, is dramatically, measurably stronger than the reaction under the old flat structure. Not because the effect is different. The effect is essentially the same. But the journey to the effect is different. The audience has traveled through increasing difficulty, increasing uncertainty, increasing emotional investment. By the time the final revelation arrives, they are emotionally primed for maximum impact.

The Escalation Toolkit

After redesigning my own routine, I developed a framework for creating escalation in any multi-phase effect. The framework consists of five escalation dimensions, and you do not need to use all five in every routine. But using at least two or three creates the escalating structure that drives emotional momentum.

The first dimension is difficulty. Each phase should appear harder than the last. The simplest form of this is to move from impersonal to personal — a card, then a word, then a memory, then a secret. The deeper you go into the spectator’s inner world, the harder the task appears.

The second dimension is conditions. Each phase can add a condition that makes the task more challenging. In the first phase, I hold the spectator’s hand. In the second, I stand across the room. In the third, the spectator writes their thought down and seals it in an envelope held by someone else. Each condition creates a new obstacle.

The third dimension is stakes. What happens if I fail? In the first phase, failure is mildly embarrassing. In the second, failure is more significant because the audience now expects success. In the third, failure would be devastating because the buildup has raised expectations to their peak. The escalating stakes create escalating tension.

The fourth dimension is audience involvement. In the first phase, one spectator participates. In the second, a small group is involved. In the third, the entire audience has a stake in the outcome. As the circle of involvement widens, the emotional investment of the room deepens.

The fifth dimension is time. The first phase is quick — thirty seconds. The second takes longer — a full minute of concentration and struggle. The third stretches even longer — two minutes of building tension. The elongation of time signals increasing difficulty and gives the audience more space to invest emotionally.

The Failed Attempt as an Escalation Tool

One of the most powerful tools in the Cinderella structure is the failed attempt. In the story, each failure is not a dead end — it is a pivot point that raises the stakes for the next attempt.

I have incorporated deliberate failed attempts into my routines, and they are among the most effective dramatic tools I use. When I fail to identify something correctly — when I pull the wrong card, when my first impression is wrong — the audience’s investment does not decrease. It increases. Because now they know this is not guaranteed. Now they know I can fail. And that knowledge makes the eventual success more meaningful.

The key is scripting the failure so that it feels genuine without undermining the audience’s confidence in the overall performance. The failure must be partial, not total. I get close but not quite right. I identify the right category but the wrong specific. I sense the right emotion but not the right memory. These partial failures tell the audience: this is real, this is hard, and the outcome is genuinely uncertain.

The Shattered Slipper Moment

Every great multi-phase routine needs what I call a shattered slipper moment — a point, ideally near the end, where the audience genuinely believes that success is impossible. Where the obstacles have accumulated to the point that resolution seems unreachable.

In the Cinderella story, this is the moment when the glass slipper breaks. The one physical object that could prove Cinderella’s identity is destroyed. There is no path forward. The audience (or the child) experiences a genuine sinking feeling — it was all for nothing.

In my mentalism routine, I create this moment in the third phase by appearing to run into a wall. After fragments and partial impressions, I stop. I look at the spectator. I say, with quiet honesty, “I am not sure I can get this one.” The room goes still. The audience believes me because they have seen the difficulty building across three phases. They have seen partial failures. They know this is not guaranteed.

And then, after that moment of apparent defeat, I say, “Wait. Something is forming.” And I describe, with increasing specificity, the private thought the spectator has been holding.

The contrast between the apparent defeat and the final triumph is what creates the emotional peak. Without the defeat, the triumph is merely impressive. With the defeat, the triumph is cathartic. The audience has experienced the emotional arc of a story — hope, difficulty, increasing difficulty, apparent impossibility, and finally, resolution.

This is the Cinderella structure. Each obstacle harder than the last. The final obstacle apparently insurmountable. And a resolution that arrives precisely when all hope seems lost.

Why Flat Routines Fail

I can now watch other performers and immediately identify when their routines are flat. The effects are good. The methods are clean. The performer is skilled. But every phase hits the same emotional register. There is no escalation. The audience reaction to the third effect is the same as the reaction to the first, because the third effect asks nothing more of them emotionally than the first did.

These performers are presenting three effects. They are not telling a story.

The difference between three effects and a story is the structure. A story has rising action. It has escalating conflict. It has a climax that arrives at the point of maximum tension. Three effects lined up sequentially have none of this. They are a list.

I perform at corporate events across Austria — in Vienna, in Graz, in Salzburg, in Linz — and the audiences at these events are sophisticated, often skeptical, and accustomed to high-quality entertainment. They are not easily impressed by a list of effects. But they are consistently moved by a story. Even when the story is as simple as: someone attempts something difficult, faces increasing obstacles, appears to fail, and ultimately succeeds.

That is not just the structure of Cinderella. It is the structure of every compelling human narrative. And it is available to every performer who is willing to design their routines with escalation rather than repetition.

The Redesign Process

If you have a multi-phase routine that currently has a flat structure, here is the process I used to redesign mine.

First, identify the current difficulty level of each phase. Is each phase roughly the same? Most likely, yes.

Second, reorder or redesign the phases so that each one is genuinely harder than the last. Start with the simplest, most accessible demonstration of your ability. End with the most complex, most personal, most seemingly impossible demonstration.

Third, add at least one moment of apparent difficulty or partial failure. Not in the last phase — that would undermine the climax. In the middle phase. Let the audience see you struggle, and then let the final phase begin with the knowledge that success is not guaranteed.

Fourth, create your shattered slipper moment. A point in the final phase where everything seems lost. Where the audience genuinely believes you might not succeed. Then deliver the resolution.

The investment of time in this redesign was minimal — a few hours of scripting and a few weeks of rehearsal in hotel rooms. The return on that investment has been the biggest single improvement in audience reaction I have ever achieved.

Each obstacle harder than the last. That is the Cinderella principle. It has worked for two thousand years. It works in magic. It works in keynotes. It works in every story anyone has ever cared about.

Because we do not remember the triumphs that come easily. We remember the ones that seemed impossible.

FL
Written by

Felix Lenhard

Felix Lenhard is a strategy and innovation consultant turned card magician and co-founder of Vulpine Creations. He writes about what happens when you apply systematic thinking to learning a craft from scratch.