Why Lawyers Are Trained as Pessimists — and Why That Matters

Lawyers are often described as pessimists.

The label is not entirely wrong — but it is frequently misunderstood.

Legal training does not teach us to expect the worst of people. It teaches us to anticipate the worst of circumstances.

Law as disciplined foresight

At its core, legal drafting is an exercise in disciplined foresight. Agreements are not written for moments of goodwill, alignment, or calm. They are written for moments of stress, rupture, fatigue, and fear — precisely when judgment is impaired and relationships are strained.

A well-drafted agreement does not assume cooperation. It anticipates friction.

It asks, quietly and methodically:

• What happens if communication breaks down?

• What happens if one party disengages, delays, or resists?

• What happens if good intentions erode under pressure?

This is not cynicism. It is risk management.

Drafting for breach, not for best behaviour

Lawyers are trained to assume that, at some point, something will go wrong.

Not because people are inherently untrustworthy — but because life intervenes.

Illness, financial stress, new relationships, unresolved grief, or simple exhaustion can all change behaviour. Agreements that rely on sustained goodwill tend to fail at precisely the moment they are most needed.

For that reason, careful drafting:

• anticipates breach, rather than hoping to avoid it;

• builds in process, rather than relying on personality;

• stress-tests provisions against the least cooperative version of the parties, not the best.

In other words, we draft for the worst actor, so that everyone is protected.

Why this matters most in family law

Nowhere is this approach more important than in family law.

Separation and divorce occur at times of emotional upheaval. Parents are not at their best. Children are watching. The cost of ambiguity or optimism bias is borne not by the adults, but by families navigating instability.

Clear, precise agreements:

• reduce future conflict,

• limit opportunities for power struggles,

• and create predictability when emotions run high.

They are not expressions of distrust. They are acts of care.

Pessimism as professional responsibility

Seen properly, legal “pessimism” is simply professional responsibility.

It is the discipline of asking hard questions early, so that fewer crises arise later. It is the willingness to imagine failure, so that systems are resilient when pressure is applied.

The goal is not to assume the worst of people — but to protect everyone if the worst happens.

Good lawyering is not bleak. It is quietly protective.