When Rules Replace Judgment

The Hidden Cost of a Society That Trusts Rules More Than People

“It behooves us to remember that men can never escape being governed… They can prevent the need of government from without only by showing that they possess the power of government from within.”

— Theodore Roosevelt, 1907

If you’d rather listen or watch than read, here is the recording of this piece. Feel free to choose whatever resonates most with you.

When I worked at McDonald’s in the United States, I noticed something that bothered me.

In large public companies, lawyers are everywhere. Every sentence you write, every statement you consider making, has to be reviewed.

I understood why. But I also felt handcuffed. Leadership requires judgment, yet the system increasingly rewarded compliance.

Over time, I began to notice the same pattern across many institutions.

I kept returning to the same underlying question:

Why do structures designed to guide us so often end up replacing judgment?

People are no longer asking “What’s the right thing to do?” but “What am I allowed to do?”

The irony is striking. The more rules we create to guarantee good behavior, the less we cultivate the very thing that actually produces it: human judgment.

It shows up inside companies, institutions, and everyday decisions.

That small shift points to a much larger problem. Well-intentioned systems begin to produce behavior that feels constrained rather than responsible, cautious rather than wise.

I remember sitting in meetings where the room was full of capable people, yet no one would move forward without first asking what the policy allowed.

The instinct wasn’t to exercise discretion. It was to check the rulebook.

That small hesitation might seem harmless. But multiplied across thousands of decisions, it slowly changes how institutions behave.

Along the way I encountered thinkers who helped articulate what I was seeing.

In the early 2000s, I met Dov Seidman, whose work focuses on why how we act often matters more than what we do. He later developed this idea in his book How: Why How We Do Anything Means Everything. Among many insights, he makes a simple but unsettling case: rules have limits. They can narrow our thinking and clip our wings.

Dov’s work, and my close relationship with him, have profoundly shaped how I navigate the world.

Around that same time, I met Philip K. Howard, whose book Life Without Lawyers approached the same problem from a different angle. Coming from a practicing lawyer, his argument was especially striking. We have written too many rules and, in doing so, have allowed them to overwhelm the judgement they were meant to support.

What results is not the kind of rightness or justice we imagine.

I don’t believe you can dictate people into goodness. I wish we could. It would certainly be convenient.

But that isn’t how human behavior works.

The Limits of Rules

When things feel uncertain, our instinct is to reach for rules. But human behavior is not shaped by rules. It is inspired by values.

Healthy societies understand this intuitively. They focus less on prescribing behavior and more on nurturing cultures that want to do the right thing. They give people room to arrive there in their own way rather than binding them to an instruction manual most people will ignore anyway.

History offers a useful contrast.

Some of the most powerful moral frameworks ever created were remarkably spare: the Ten Commandments, the United States Constitution. Few words. Broad principles. Yet they shaped centuries of human behavior; not by scripting every action, but by pointing toward shared values.

Law should work in much the same way. At its best, it provides moral frameworks, not moral programming.

Dov has long argued that rules are external by design. They are written by others often in response to past failures, and they treat human behavior as something to be constrained rather than cultivated.

Because they rely on proxies, rules are always both over- and under-inclusive. They set boundaries and floors, but they also create unintended ceilings.

Rules are not moral.

They are procedural.

Today we increasingly see brilliant lawyers whose expertise lies in navigating rules and ensuring technical compliance, even when fairness is lost.

Dov recently gave a powerful commencement address at the University of Miami Law School calling on future lawyers to join what he calls a “Moral Renaissance of Should.” As Justice Potter Stewart once put it, ethics is knowing the difference between what we have a right to do and what is right to do.

Over time, the proliferation of rules becomes a hidden tax on the system itself.

Few people can remember them all. Productivity slows as judgment is replaced by rule-checking. Responsibility erodes as people begin to assume that if something truly mattered, there would be a rule for it.

Every decision slows.

Every initiative requires permission.

Every action becomes a compliance exercise.

Philip often points out that we have created a sprawling bureaucracy with billions of lines of regulatory code.

What began as guardrails slowly becomes a straightjacket.

And here lies the paradox:

The more we try to legislate virtue, the less space we leave for people to practice it.

Character does not come from a checklist.

It grows in families, traditions, communities, and through the slow practice of judgment.

When the rule of law works well, it supports agency.

It should function as a trellis, not a cage.

The Price of Agency

When judgment is replaced by rules, agency becomes risky.

Because agency has a price. To act is to enter a jungle of legal, reputational, and professional risk. Many people still know exactly what the right thing to do is. They simply no longer feel safe doing it.

Can I do this?

Can I say this?

What happens if I do?

Will someone be furious?

Will I be attacked?

Will I be sued?

If I don’t do anything, I can’t do anything wrong.

Trial and error is replaced by stagnation.

Progress requires people to act. It grows out of taking small risks, making mistakes, learning, and adjusting.

When fear takes hold, people get stuck. They end up broadcasting opinions on social media or retreating into inaction. Neither builds much of anything.

One of the most dangerous confusions in modern life is the belief that legality equals morality. For me, just because something is legal does not mean it is right.

Legality is only a floor. A healthy society operates far above it.

Modern-day governments often aim to function more through process than purpose.

Leadership vs. Lawyership

One of the most useful distinctions I’ve encountered comes from Philip Howard, who draws a line between leadership and what he calls “lawyership.”

Following the law does not automatically make you a great leader.

Lawyers are trained to define what is permissible.

Leaders must decide what is right.

In my own imagination, and in my romantic sense of America at its best, we are a nation of builders and entrepreneurs. We invent things. We take risks. We create.

Yet over time legalism has been elevated inside many of our institutions. Congress itself is filled with lawyers trained to think adversarially and defensively.

Leadership requires navigating ambiguity. Taking responsibility. Forging consensus where none exists.

Lawyership defines boundaries, minimizes risk, and determines what cannot be done.

Leadership requires freedom to act.

When Complexity Outpaces Judgment

Our systems today face a simple problem: complexity has begun to outpace judgment.

As systems grow more complicated, exercising discernment becomes harder. Faced with uncertainty, our instinct is to write another rule.

But this often makes the problem worse.

Rules add complexity.

Complexity invites more rules.

What begins as guidance slowly turns into bureaucracy.

When Trust Breaks Down

What worries me most is that this mindset is no longer confined to corporations or government. It is becoming cultural.

People move through the world armored, suspicious, and defensive.

Is this person dangerous?

Are they on the other side?

That is not a healthy posture from which to approach life.

At the center of this cultural climate crisis is a breakdown of trust between people and the institutions meant to serve them.

And when trust declines, rules multiply.

We cannot build a just society by holding up a document and saying, “Sign here.”

Trust grows from judgment, character, and shared norms.

Low trust slows everything down.

In a world running on speed, that becomes a massive tax on the system.

Dov often reminds us that trust is a powerful performance-enhancing force.

Reclaiming the Freedom to Act

Freedom is not just the absence of oppression.

It is the presence of trust.

Trust requires courage, initiative, and judgment.

It requires leaders willing to stand up for what is right.

If the future is to be reclaimed, agency must be reclaimed with it.

Action cannot wait for perfect certainty.

As Philip Howard has argued, what we have built today is in many ways profoundly un-American. It reflects an Anglo-style legalism rather than the spirit of self-governance the founders rebelled to create.

I want to be clear that this is not an argument against rules.

I believe in rules.

I simply believe in fewer of them, and better ones.

The focus should be on the big rules that matter.

Think about a family. You don’t write a constitution for family life. You don’t dictate every behavior down to the minute.

You establish a few core principles:

Be kind.

Help out.

Take responsibility.

Work hard.

Stay connected.

Honor one another.

Those values shape behavior far more effectively than hundreds of rules ever could.

That feels like a balance worth reclaiming:

Fewer rules.

Stronger norms.

Deeper trust.

In the end, the strength of a free society depends less on the rules that govern it than on the judgment of the people who live within it.

Your Turn

Where in your own life have rules begun to replace judgment, and where might regaining self-trust change how you act?

For those interested in exploring these ideas further, I recommend the work of Dov Seidman, Philip Howard, Jennifer Pahlka, and Francis Fukuyama, all of whom have written thoughtfully about how complexity and bureaucracy can weaken the ability of institutions to act.

The ideas in this essay later took musical form in a song I wrote about a simple tension: the more we try to govern behavior through rules, the more we risk losing the judgment that makes good behavior possible.