Tuesday morning, December 9th. Someone just asked for "clear action items" from a discussion about deep cultural problems. The request for clarity killed the conversation. You can't reduce genuine complexity to bullet points without losing everything that matters.

The Clarity Imperative

Here's what we've been taught:

Good thinking is clear thinking. If you can't explain something simply, you don't understand it. Great leaders communicate with clarity. Successful companies have clear missions. Effective people make clear decisions. Ambiguity is confusion. Nuance is weakness. If you're uncertain, you haven't thought hard enough.

The promise: Crystal-clear frameworks will guide you to correct decisions. Simple principles will navigate complex situations. Clear communication will prevent misunderstanding.

The reality: Clarity is often achieved by discarding the details that matter most. The map becomes clear by leaving out terrain. The framework becomes simple by ignoring exceptions. The principle becomes absolute by pretending context doesn't exist.

Thesis: Clarity has become a false god in thinking and communication. We've been trained to compress complex, context-dependent reality into simple, universal frameworks. The more clearly we can articulate something—the more it reduces to principles, rules, and bullet points—the more confident we become. But this clarity is often an illusion created by ignoring everything messy and important. The result is that we make confident decisions based on oversimplified models, follow clear advice that doesn't apply to our situation, and communicate in ways that feel precise but transmit almost nothing of value. Real understanding is usually messy, qualified, and uncertain. The people who actually know what they're talking about hedge, equivocate, and say "it depends." The clarity trap convinces us they're just unclear thinkers—when they're the only ones thinking clearly about complexity.

What Clarity Costs

Let's be specific about what gets lost in the pursuit of clarity:

Context Disappears

The clear version: "Exercise daily for optimal health."

The reality:

  • For some people, daily intense exercise leads to burnout and injury
  • For others, it's transformative
  • Your job, sleep schedule, existing injuries, genetics, and life circumstances all matter
  • The relationship between exercise and health is non-linear and individual
  • "Exercise" can mean wildly different things with different effects

What clarity removed: All the information you'd need to actually make a good decision for yourself.

The clear principle gives you confidence but not wisdom. You follow it religiously or dismiss it entirely, never noticing that the question "how should I exercise?" doesn't have a universal answer.

Contradictions Get Resolved Prematurely

The clear version: "Focus is essential for deep work. You must eliminate distractions."

Also the clear version: "Diverse inputs spark creativity. You must expose yourself to many ideas."

The reality: Both are true. Sometimes. The question isn't which principle is correct—it's when each one applies. But clarity doesn't allow for "sometimes." You have to pick a side. Build your identity around it. Defend it.

So you become the "focus person" or the "serendipity person" and miss the fact that effective work requires both, at different times, in different configurations.

What clarity removed: The ability to hold contradictory ideas simultaneously and apply them appropriately.

Gradients Become Categories

The clear version: "People are either intrinsically motivated or extrinsically motivated."

The reality:

  • Motivation exists on multiple dimensions simultaneously
  • It varies by domain, context, and time
  • The same person can be intrinsically motivated by art and extrinsically motivated by exercise
  • Motivation types interact—external rewards can enhance or undermine intrinsic interest depending on how they're framed
  • The concept of "motivation" itself is probably several different phenomena we've lumped together

What clarity removed: The actual complexity of human motivation, replaced with a false binary that makes you feel like you understand people when you don't.

How Clear Frameworks Mislead

The process works like this:

Step 1: Observe Complex Reality

You notice something nuanced. "Successful companies often have strong cultures, but the nature of that culture varies enormously."

Step 2: Extract a Pattern

You look for what's common. "Strong culture predicts success."

Step 3: Make It Actionable

You remove the qualifications. "Build a strong culture."

Step 4: Package It Clearly

You create a framework. "The Five Elements of Strong Culture."

Step 5: Apply It Universally

You forget the original context. You had observed 50 tech companies in a specific era. Now you're applying the framework to a small family business in a different industry and wondering why it's not working.

What happened: Each step toward clarity was a step away from truth. The clearer the framework became, the less useful it was. But it felt more useful because it was easier to remember, teach, and apply.

The Consultant Problem

This is why business consulting is simultaneously valuable and absurd. Consultants take the genuinely complex reality of your business, compress it into a clear framework, and present you with decisive recommendations.

You feel enlightened. Finally, someone who understands and can explain it clearly!

But what actually happened: They took the 10,000 variables that determine your business's success, picked the 5 that fit their framework, ignored the 9,995 that don't, and gave you clear advice based on 0.05% of reality.

Sometimes it works—because occasionally those 5 variables are the ones that matter most right now. More often it fails—because the complexity they removed was weight-bearing.

The dangerous part: The clarity makes the advice seem more reliable than messy, uncertain analysis that actually accounts for nuance.

The People Who Resist Clarity

Notice who hedges, qualifies, and says "it depends" most:

  • Doctors with 30 years of experience ("well, in most cases...")
  • Master craftspeople ("it depends on the wood, humidity, what you're making...")
  • Genuinely wise people ("I'm not sure that's quite right...")

Notice who communicates with perfect clarity:

  • Gurus selling simple systems
  • Ideologues pushing universal principles
  • People who just learned something and think they understand it
  • Anyone trying to sell you something

The pattern: Expertise makes you less certain, not more. Real knowledge reveals complexity. You become aware of all the exceptions, contextual factors, and ways things can go wrong.

But we interpret hedging as weakness. "Just give me a straight answer!" We reward people who communicate with false clarity and dismiss people who communicate with true uncertainty.

When Clarity Actually Helps

Let me be clear (ironic, I know): Clarity isn't always bad. Sometimes it's exactly what you need.

Clear Goals in Bounded Systems

When you're operating within well-defined constraints with clear success metrics, clarity helps:

  • "Get the package to this address by 5pm"
  • "Solve this specific math problem"
  • "Sand this board until it's smooth"

The system is simple enough that a clear directive loses nothing important.

Clear Communication of Clear Things

Some things genuinely are simple:

  • "The meeting is at 3pm"
  • "Press this button to start"
  • "Add salt to taste"

There's no complexity to preserve. Clarity is just efficiency.

Clear Principles as Starting Points

Simple principles can be useful if you hold them lightly:

  • "Assume good intent" (until you have reason not to)
  • "Make it work, then make it good" (but know when to flip this)
  • "Under-promise, over-deliver" (except when it causes other problems)

The principle gives you a default, not a universal truth.

The difference: You recognize that clarity is a simplification. You stay alert for when the simplification breaks down. You don't mistake the clear map for the messy territory.

Operating in the Messy Middle

So what do you do instead? How do you think and decide without the false confidence of clarity?

Embrace "It Depends"

Stop treating "it depends" as a cop-out. It's often the most accurate answer available.

When someone asks "Should I do X?" and you notice yourself reaching for a clear yes/no, pause. What does it depend on? Those dependencies are usually the most important information.

Better:

  • "It depends on whether you're optimizing for speed or thoroughness"
  • "For most people yes, but if you have [condition] then no"
  • "It worked for me because [context], yours might be different"

Think in Distributions, Not Rules

Instead of: "Successful people wake up early"

Try: "There's a weak correlation between early rising and success metrics, but the distribution is wide and the causation is unclear. Many successful people wake up early. Many wake up late. Many vary. For some individuals, early rising seems to help. For others it's irrelevant or harmful."

This feels less clear. It is less clear. It's also vastly more accurate and useful.

Hold Multiple Models Simultaneously

Don't pick the "right" framework. Hold several incompatible ones:

  • Sometimes the world is rational actors pursuing incentives
  • Sometimes it's narrative and status games
  • Sometimes it's random noise we retrofit stories to
  • Sometimes it's emergent complexity from simple rules

Different models illuminate different aspects. The question isn't which is true—it's which is useful for this specific situation.

Preserve Your Uncertainty

When you don't know, don't pretend you do. Don't reach for a clear framework to give you false confidence.

Say:

  • "I'm genuinely uncertain about this"
  • "These factors point in different directions"
  • "I can see multiple reasonable approaches"

This feels weak. It's actually strong—you're seeing reality as it is rather than forcing it into clarity it doesn't have.

Test Locally Before Universalizing

Before you turn a personal insight into a universal principle, test it:

  • Does this apply to people different from me?
  • Does this hold in different contexts?
  • What are the exceptions?
  • Where does this break down?

Usually you'll discover your "clear principle" is actually a context-dependent observation. That's fine. Context-dependent observations are incredibly valuable if you know their limits.

The Takeaway

Here's what to actually do:

  1. Recognize when you're trading accuracy for clarity. Sometimes it's worth it. Often it's not. Make the trade consciously, not automatically.

  2. Be suspicious of clear, confident communication. Especially on complex topics. Clarity often signals oversimplification, not understanding.

  3. Embrace messiness in your own thinking. "It depends" and "I'm not sure" are often the most intellectually honest positions. They're also, paradoxically, the foundation for actually learning.

  4. Look for weight-bearing complexity. When someone simplifies something, ask: What got removed? Is that the part that actually mattered?

  5. Hold your frameworks lightly. Use clear principles as defaults and heuristics, not as universal truths. Stay alert for when they stop applying.

The world is complex. Your thinking should match the territory, not simplify it into comfortable clarity. Messy, uncertain, qualified thinking is what reality requires.

The clarity trap promises that simplifying will make you more effective. The truth is that appropriate complexity—knowing when to simplify and when to preserve nuance—is what actually works.

Stay uncertain where uncertainty is honest. Stay messy where messiness is accurate. The clear path is often the wrong one.

Today's Sketch

December 09, 2025