When we talk about strategy, we are easily pulled into one central question:
“How do I win?”
So we think in terms of greater investment, faster tempo, more sophisticated tactics.
As if pushing a little harder, holding on a little longer, would eventually buy us victory.
But The Art of War · Chapter on Momentum (Shi) reminds us of something far more brutal—and far more mature:
What truly decides victory is often not how much force you exert,
but whether you are standing in the direction where winning naturally happens.
In this chapter, Sun Tzu is not talking about how to struggle harder.
He is talking about how to arrange conditions so that events naturally move in your favor.
He calls this concept — Momentum (勢, Shi).
What Is “Momentum” (勢)?
Momentum is not brute force released in the heat of the moment.
Nor is it an emotional, all-in gamble.
It is the arrangement you have already completed before you act:
- Whether the structure is on your side
- Whether the rhythm is under your control
- Whether conditions favor you
- Whether the opponent has been guided into terrain you designed
When all of this is in place,
victory no longer needs to be forced.
It no longer depends on willpower or heroic effort.
It rolls forward like a round stone from a high mountain—
not because you pushed harder,
but because it was already positioned to roll.
From Strategic Positioning to Momentum
From “Not Losing” to “Winning”
If you look back at the previous chapter, Chapter IV: Strategic Positioning, one idea is repeated again and again:
A true master is not someone who wins every time,
but someone who does not lose.
That chapter deals with static safety—
how to place yourself beyond defeat,
how not to collapse, not to be dragged down.
Momentum is the next step.
It asks:
Once you are no longer losing,
how do you make advantage start to move?
In other words:
Strategic Positioning lets you stand firm.
Momentum teaches you how to move forward.
This transition—
from stability to motion—
is exactly where many people get stuck
in careers, startups, investing, and negotiations.
They keep applying effort,
when what is required is redesign.
Original Text: The Art of War · Chapter V: Momentum
(Original Chinese text preserved)
Sun Tzu said: Managing a large force is the same as managing a small one: it is a matter of organization.
Fighting a large army is the same as fighting a small one: it is a matter of formations and signals.
That the whole army can engage the enemy without being defeated—this is due to the interplay of orthodox and unorthodox forces.
Striking the enemy is like throwing a whetstone against an egg—this is a matter of solidity and emptiness.In all warfare, the orthodox engages; the unorthodox wins.
Thus those skilled in surprise are endless as Heaven and Earth, inexhaustible as rivers and seas.
They end and begin again, like the sun and moon; they die and are reborn, like the four seasons.
There are no more than five musical notes, yet their combinations are inexhaustible.
There are no more than five colors, yet their combinations are inexhaustible.
There are no more than five flavors, yet their combinations are inexhaustible.
In battle, there are no more than the orthodox and the unorthodox, yet their transformations are inexhaustible.
The interplay of orthodox and unorthodox is like an endless cycle—who can exhaust it?The onrush of rushing water that can move boulders—this is momentum.
The strike of a falcon that shatters its prey—this is timing.
Thus, a skilled commander creates dangerous momentum and strikes in short bursts.
Momentum is like a drawn crossbow; timing, like the release of the trigger.Amid chaos, order is not lost.
Amid confusion, defeat is impossible.
Disorder arises from order; cowardice from courage; weakness from strength.
Order and disorder are matters of organization.
Courage and cowardice are matters of momentum.
Strength and weakness are matters of formation.Thus, those skilled at moving the enemy present forms the enemy must respond to;
offer bait the enemy must take;
draw them with advantage, and wait with strength.Therefore, those skilled in warfare seek victory from momentum, not from individuals.
They select people to fit momentum.
Those who rely on momentum move others as one rolls logs or stones—
logs and stones remain still on flat ground, but move when placed on steep terrain;
square ones stop, round ones roll.
Thus, the momentum of a skilled commander is like rolling a round stone down a steep mountain.
The Core Thesis of the Momentum Chapter
If the entire chapter were to be summarized in one sentence:
Do not rely on people to endure—let momentum carry them forward.
Not improvisation, but premeditated design.
Broken down, the core ideas are:
- Engage with the orthodox; win with the unorthodox
- Avoid strength; strike weakness through solidity and emptiness
- Align accumulated momentum with precise timing
- Embed victory into systems and terrain, not personal heroics
Let’s unpack these one by one.
1. Orthodox and Unorthodox: Engage with the Standard, Win with the Unexpected
Key Passage
“In all warfare, the orthodox engages; the unorthodox wins.”
Orthodox and unorthodox are not opposites.
They are a sequence, not a polarity.
Many misunderstand “unorthodox” as opportunism or gambling.
But in Sun Tzu’s framework, the unorthodox always rests upon the orthodox.
Orthodox means: standard, predictable, repeatable, sustainable foundations
- Processes
- SOPs
- Reliable delivery
- Trust
Unorthodox means: innovation, asymmetry, breaking the opponent’s prediction model
- Strategic surprise
- Design ingenuity
- Narrative shifts
Great strategy is not constant surprise.
It is preparing to rewrite the game when the opponent thinks you are following the script.
In Work and Business
Product
- Orthodox: stable, reliable, consistent experience
- Unorthodox: one or two features that make you irreplaceable
Marketing
- Orthodox: dependable channels
- Unorthodox: narrative hooks, cultural moments, event-driven spikes
Organization
- Orthodox: cadence, systems, metrics
- Unorthodox: cross-team strikes and narrative reversals at critical moments
Action Checklist｜Dual-Track Strategy
- Each quarter, fully stabilize the orthodox base: reliability, delivery, metrics.
- Reserve 10–20% flexible resources for high-leverage experiments.
- Design “inflection days” where unorthodox force is concentrated (launches, summits).
- Convert successful surprises into the next round of orthodoxy.
One-line takeaway:
Stabilize the terrain with the orthodox—reshape it with the unorthodox.
2. Solid and Empty: Don’t Test Their Strength with Your Weakness
Key Passage
“Striking the enemy is like throwing a whetstone against an egg.”
The stone is not powerful because it is strong—
but because it hits the right place.
Solid: the opponent’s strengths, core forces, heavily defended ground.
Empty: neglected gaps, blind spots, unprotected weaknesses.
Strategy is not proving how strong you are,
but ensuring your force lands where the enemy is most fragile.
Practical Tools
- Solid-Empty Mapping: four quadrants—strong, weak, under-defended, over-defended.
- Reverse Recon: observe where competitors under-invest (stale features, weak support).
- Red-Blue Teaming: penetration drills to expose breach points.
Individual and Team Moves
- Product: solve pain points others avoid—small but painful, niche yet high value.
- Sales: bypass fortified procurement gates; enter via peripheral use cases.
- Career: avoid overcrowded arenas; build proof assets in niche scenarios.
One-line takeaway:
Use your stone to find their egg.
3. Momentum and Timing: Store Like a Drawn Bow, Strike Like a Trigger
Key Passage
“The onrush of water… is momentum.
The strike of the falcon… is timing.”
Momentum: accumulated potential—brand, data, networks, cash flow, IP.
Timing: decisive release—window selection, compression, all-in execution.
Masters seem to act rarely,
but every action releases compressed energy.
Five Ways to Build Momentum
- Narrative momentum: a coherent roadmap (Why → What → When).
- Evidence momentum: testimonials, dashboards, case libraries.
- Resource momentum: key partnerships and anchor clients.
- Data momentum: datasets convertible into advantage.
- Cash momentum: runway and opportunity funds.
Three Rules of Timing
- Short: minimize force windows (e.g., two-week cross-team sprint).
- Precise: choose the right moment.
- Decisive: commit fully—resources, story, channels aligned.
One-line takeaway:
Build thick momentum; release it fast and clean.
4. Structure and Naming: The Bigger It Gets, the Less You Can Rely on Feelings
Key Passage
“Managing many is the same as managing few—it is a matter of division and designation.”
When complexity grows,
“watching more closely” becomes a sign of failure.
Sun Tzu advocates replacing emotion with structure.
Manager’s Notes
- Task decomposition templates (inputs, outputs, standards, acceptance).
- Consistent naming conventions.
- RACI matrices to eliminate shared irresponsibility.
One-line takeaway:
Clear divisions turn armies into squads.
5. Order Within Chaos: Remaining Unbeatable Amid Disorder
Key Passage
“Amid chaos, order is not lost.”
True mastery is not neat appearances,
but control within turbulence.
Sun Tzu warns of a paradox:
extreme order breeds chaos; extreme strength breeds weakness.
Practices
- Incident response playbooks.
- OODA loops to compress decision cycles.
- Red-team drills.
- Rotations and redundancy to avoid hero dependencies.
One-line takeaway:
Guard the core of invincibility beneath surface chaos.
6. Move Them with Advantage, Wait with Strength
Key Passage
“Entice with advantage; wait with solidity.”
- Shape perception through information and narrative.
- Offer bait to draw opponents into your terrain.
- Wait fully prepared—supply, compliance, cash, backups.
Negotiation fails not because the other side is smart,
but because you weren’t ready when they entered.
One-line takeaway:
Pull with incentives; absorb change with preparation.
7. Rely on Momentum, Not Heroes: Write Victory into Systems
Key Passage
“Seek victory from momentum, not individuals.”
Do not bind outcomes to heroics.
Embed correct behavior into systems, incentives, and defaults.
Momentum makes the right choice the easiest choice.
Momentum Design Checklist
- Defaults that favor desired behavior.
- Incentives aligned with long-term value.
- Compounding assets: data, content, communities.
- Constraints that prevent waste.
- Fixed rhythms that create predictable force fields.
One-line takeaway:
Make victory structural, not accidental.
Conclusion: From Invincibility to Effortless Success
You don’t need to overpower every encounter.
You need environments and systems that act on your behalf.
When momentum is built, timing is set, the orthodox is stable, and the unorthodox arrives on cue—
victory is not created.
It happens naturally.
The goal is not to force a win.
The goal is to make winning the natural outcome of your momentum.
Exploring the meeting point of technology and the inner world is often a solitary journey—but a meaningful one.
If this article has brought you a moment of clarity or inspiration, you’re welcome to buy me a cup of coffee and support me in continuing this kind of thoughtful, in-depth writing.
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