Stuck on Your “Life Plan”? Zhuangzi Has a 2,300-Year-Old Antidote

9 min read

What if your anxiety isn’t about failing at life, but about insisting that it must unfold in one rigid order?

This post explores how Zhuangzi's 2,400-year-old philosophy dismantles the three anxieties quietly running your life.

Millennials were raised on a script.

Study hard.
Get into a good university.
Land a respectable job.
Climb steadily.
Buy a flat.
Marry.
Have children.
Optimise everything.
And do it in the correct order.

Miss a step—or take it out of sequence—and the anxiety kicks in.

Today I want to name three quiet but corrosive millennial pain points:

• “Rigid Life Plan” Anxiety
• The “Sequence” Trap
• Identity Fixation

And I want to show how an ancient Daoist text offers a way out. This isn’t vague mysticism. It is cognitive liberation.

The Modern Script: Three Ways We Trap Ourselves

1. “Rigid Life Plan” Anxiety

Many millennials don’t just have goals—we have architectural blueprints.

You were supposed to make manager by 30.
You were supposed to monetise your side hustle by 32.
You were supposed to be financially independent by 35.
When life deviates, like layoffs, industry shifts, caregiving responsibilities, you don’t merely feel disappointed. You feel behind. As if reality has violated a contract.

But the contract was imaginary.

Rigid Life Plan Anxiety arises from treating one projected timeline as the only “right” one.

2. The “Sequence” Trap

Even when the end goals remain possible, we obsess over order.

You must:
• Establish career before settling down.
• Achieve stability before exploring passion.
• Heal fully before dating again.
• Build savings before taking risks.

Change the order and panic ensues.

The irony? Often the total “quantity” of achievement remains the same. It's just arranged differently.

Yet the rearrangement feels catastrophic.

3. Identity Fixation

Perhaps the deepest anxiety is identity-based.

“I am a lawyer.”
“I am an academic.”
“I am the dependable one.”
“I am the high achiever.

When circumstances shift, it’s not merely a job change. It feels like ego death.

Identity Fixation locks us into a single, rigid way of being. Reinvention feels like betrayal.

But as we shall see, Zhuangzi finds this rigidity absurd.

Three in the Morning: A Story About Chestnuts (and Everything Else)

In the second chapter of the Zhuangzi, there is a story so brief it could fit in a tweet, yet so rich it has occupied scholars for centuries. It is called 'Three in the Morning' (2.23).

"A monkey trainer was handing out chestnuts. 
He told them, 'You'll get three in the morning and four at night,' and the monkeys were outraged. 
He replied, 'Fine, then — four in the morning and three at night.'

The monkeys were thrilled. 

Although the actual quantity remained identical, changing the labels and the sequence turned their fury into joy. The trainer simply pivoted according to their subjective sense of 'right' (yin shi).

In the same way, the Sage uses the world's various definitions of 'right' and 'wrong' (shifei) to maintain harmony with others, all while staying centred in the natural equilibrium of the universe, which is the Potter's Wheel of Heaven. 

This practice of living in the world's terms while remaining anchored in the absolute is called 'Walking Two Paths at Once' (liangxing)."
— Zhuangzi, 2.23

Read it once more. The trainer doesn't argue with the monkeys. He doesn't explain the mathematics. He doesn't insist on his own framing. 

He pivots and both parties win. Total chestnuts: unchanged. Harmony: restored. 
Clever? Yes. 

But Zhuangzi's point is larger than clever. The text is describing an entire orientation towards life.

The story illustrates two interlocking principles that Zhuangzi considers foundational to a well-lived life: Walking Two Paths (liangxing) and Affirming Things as They Are in Their Own Context (yinshi). 

Together, they offer something the millennial self-help industry rarely provides: not a system, but a release.

Principle One: Walking Two Paths (liangxing)

Zhuangzi describes the sage as one who “uses his own ‘this’ to harmonise with the ‘that’ of others” (2.23).

The monkey trainer had two apparent options:

• Three in the morning, four at night.
• Four in the morning, three at night.

Instead of clinging to his own judgement, he harmonised with the monkeys’ perception. 

This is walking two paths (liangxing). It is not indecision. It is transcendence of binary thinking.

Today, it looks like this: A millennial who left their law career to become a ceramicist is not failing the plan. They are walking two paths: honouring the discipline and rigour that got them into law, while affirming the new direction their life is now taking. Both can be true. Neither cancels the other.

Zhuangzi explains that the trainer can do this because he:

“stays centred within the Natural Equaliser, letting the world spin around him like a potter’s wheel (jun)” (2.23).

The Chinese word jun—the potter’s wheel—suggests equality, stability, balance. From that centre, one can rotate freely.

What does this mean for millennials?

Your rigid life plan anxiety assumes that your timeline is right and any deviation is wrong.
That is shi/fei thinking: right/wrong locked in polarity.

But Zhuangzi notes that shi (right) and fei (wrong) are complementary and inter-connected (2.16). When you stand at the centre—the Axis—you see that what appears “wrong” from one angle may be entirely workable from another.

Picture this: You planned corporate law and aim to get partnership by 35. Instead, you burn out at 30 and pivot to policy consulting.

From your old script: failure. From another perspective: adaptive reconfiguration.

Walking two paths means you don’t collapse into “I failed.” You ask: What alternative alignment is possible here?

You transcend the binary.

Principle Two: Affirming Things as They Are (yinshi)

Zhuangzi says:

“The trainer simply pivoted according to their subjective sense of ‘right’ (yinshi).

Yinshi is affirming things as they are in their own context. It is not moral relativism. It is situational intelligence.

Zhuangzi exhorts us to:

“align yourself with the natural inclination of things as they are, without letting a single personal preference cloud your response" (7.4).

Notice: the trainer did not insist on abstract logic (“Three plus four equals seven, so calm down.”). Instead, he recognised the monkeys’ psychological disposition.

He responded to what is, not to what should be.

How this plays out today: If you've bought a flat before getting married, or had a child before finishing your degree, or changed careers at 40, you have simply distributed the chestnuts differently. 

The total quantity of your life is unchanged. What changes is the arrangement — and arrangements, Zhuangzi insists, are not moral categories. They are contextual responses.

Ask yourself: is the total “seven chestnuts” still there?

Often yes.

The distress arises from attachment to order, not substance.

Zhuangzi says:

“This change of description and arrangement caused no loss, but in one case it brought anger and in another delight.” (2.23)

When facing disappointment, ask: Has the total “seven” changed? Or only the order?

An example: You didn’t get promoted. But you gained skill, visibility, and optionality. Rearrangement is not reduction.

Millennial anxiety frequently stems from rearrangement without loss.

Affirming things as they are means asking:
• Given this configuration, what is its natural usefulness?
• What does this moment allow that the previous sequence did not?

The Axis of the Way (daoshu): Psychological Freedom

Zhuangzi says:

“When ‘this’ and ‘that’, or ‘right’ and ‘wrong’—are no longer locked in a polarised struggle, you have reached the Axis of the Way (daoshu).

When you stand at this central pivot, you can respond to the infinite complexity of the world without ever being obstructed.

From this centre, you possess an inexhaustible supply of ‘rights’ and an inexhaustible supply of ‘wrongs,’ adapting to every situation as it arises.” (2.16)

This is wonderful. 

An inexhaustible supply of “rights”.

Meaning: there is rarely only one correct path.

For millennials paralysed by over-optimisation, like choosing the “best” career, partner, city, the Axis of the Way offers relief.

You do not need the single perfect move. You need responsiveness.

Walking Two Paths also offers liberation from the cognitive exhaustion of treating every decision as a binary verdict. 

Should I stay in this job or leave? Should I move cities or stay close to family? 

When you stand at the axle of the wheel, the question shifts from "which is right?" to "what does this situation actually call for?"

That is a far more interesting and tractable question.

Identity Fixation vs. The Dragon and the Snake

Zhuangzi describes the person who lives by yinshi as:

“At times a dragon, at others a snake, which means constantly transforming alongside the seasons of life, refusing to be pinned down to a single, rigid way of being." (chapter 20).

The authors of Zhuangzi is not celebrating inconsistency. They are celebrating responsiveness. There is a crucial difference. 

The dragon-snake does not change randomly. It transforms alongside the seasons — in response to what each moment actually demands. 

The monkey trainer doesn't give the monkeys random quantities. He gives them what the situation calls for, based on genuine knowledge of both the chestnuts and the monkeys.

This demolishes Identity Fixation.

You are not “a consultant”.
You are not “the responsible sibling”.
You are not “the creative one”.

You are transformation.

Yet Zhuangzi adds that such a person remains:
“one and unchanging” by resting in the middle of Heaven the Potter’s Wheel (2.23).

Outwardly adaptive. Inwardly centred.

The modern self is fragile because it confuses role with essence.

Zhuangzi’'s self is stable precisely because it refuses to be pinned down.

The natural inclination of things as they are, for the millennials in this piece, might be: that the job market has changed irreversibly, that the housing ladder is structurally broken, that linear careers are a twentieth-century artefact, that relationships no longer follow Victorian scripts, that your values at 35 will differ substantially from your values at 22.

These are not failures. These are the seasons. Yinshi asks you to affirm them, and respond accordingly.

When feeling trapped by a role, recall:

“At times a dragon, at others a snake…” (chapter 20).

Try low-stakes identity experiments:

• Teach one workshop outside your field.
• Volunteer in a completely different domain.
• Write anonymously in a new voice.

Transformation is not betrayal. It is alignment with seasons.

Ancient Wisdom, Applied

Five ways to practise Zhuangzi's principles before your next existential crisis.

1.  Audit your binaries

WALKING TWO PATHS · LIANGXING

The next time you face a major decision, like job, relationship, place of residence, write down the binary you're unconsciously using (stay vs. leave; committed vs. directionless; succeed vs. fail). 

Then ask: what is the third position, the axle of the potter's wheel, that allows both to be partially true? 

Liangxing is not about choosing between two paths. It's about finding the standpoint from which both can be seen clearly, without either destroying you. 

Practise noticing when you've collapsed a complex situation into a binary, and resist the collapse.

2.  Ask 'what does this situation actually need?' — not 'what does the plan say?'

YINSHI · CONTEXTUAL RIGHTNESS

Yinshi requires you to 'align yourself with the natural inclination of things as they are, without letting a single personal preference cloud your response' (7.4). 

Before your next big decision, try setting aside what you planned to do at this stage of life. Instead, examine what is actually true right now, like your circumstances, your energy, your relationships, the realistic options available to you. 

The monkey trainer's success came from his knowledge of the monkeys and the chestnuts as they actually were, not as he wished they'd be. Your life deserves the same clear-eyed attention.

3.  Practise the pivot — without losing yourself

THE AXIS OF THE WAY · DAOSHU

The Axis of the Way (daoshu) is described as a hub that 'can respond to the infinite complexity of the world without ever being obstructed' (2.16). 

This is a skill, not an insight, and like all skills, it is developed through small, low-stakes rehearsals. 

Start deliberately pivoting in minor situations: let someone else choose the restaurant; present the same idea to two different audiences in completely different ways; change your morning routine for a week. 

The point is not disruption for its own sake, but building the internal stability that allows external flexibility: learning to stay centred while the wheel spins.

4.  Give yourself permission to transform publicly

DRAGON AND SNAKE · TRANSFORMATION

Zhuangzi's image of the person who is 'at times a dragon, at others a snake, constantly transforming alongside the seasons of life' (Chapter 20) is a direct antidote to Identity Fixation. 

Much of identity anxiety is actually audience anxiety: we fear what people will say if we change. The practical move is to stop announcing your identity as a fixed product and start narrating your evolution as an ongoing process. 

Tell the people who matter: 'I've changed my thinking on this.' Do it before you feel ready. The dragon who waits until everyone approves of its transformation never leaves the snake stage.

5.  Replace 'am I on track?' with 'is this actually working?'

EVERYDAY USEFULNESS · NATURAL FUNCTION

Zhuangzi instructs us to assign the definition of 'right' to 'the natural, everyday usefulness of things as they already exist' (2.28). 

This is a profound reframe for the Sequence Trap. Instead of measuring your life against an abstract timeline, measure it against something immediate and real: is this arrangement of your life actually useful to you right now? Is it producing satisfaction, growth, connection, meaning? 

If the chestnuts work better distributed differently, distribute them differently. The total remains unchanged. Only the sequence shifts — and sequences are not morality.

Final Thoughts 

The monkey trainer doesn't win because he is smarter than the monkeys. He wins because he is not imprisoned by his own sense of how chestnuts ought to be distributed. 

He can hold his own judgement lightly, stay rooted at the axle, and give the situation what it actually needs.

That's not weakness. That's the most demanding kind of wisdom there is. 

And it's been sitting in a Daoist text for two and a half millennia, waiting for a generation anxious enough to finally need it.