Understanding, Not Judging: Hemingway’s Quiet Rule for Writers

March 12, 2026

Someone once said something like,

"As a writer, you should not judge, you should understand." (It's been attributed to Ernest Hemingway, but there's no definitive source for this quote.")

At first glance, this sounds simple, but it's one of the deepest lessons a writer can learn. Judgment is easy - It's quick, absolute, and leaves no room for complexity. Understanding, though, takes effort. It requires curiosity, patience, and a willingness to step into your characters' lives without condemning or excusing them.

When we write with judgment, we don't leave any space for readers to engage. A "good" character stays good, a "bad" character stays bad, and there's nothing left to discover. But when we write with understanding, we unlock something far more powerful: empathy. We invite the reader to see a character's humanity, even in the people they might otherwise despise.

Judgment vs. Understanding in Action

Here's what it looks like on the page:

Judging Version

Mark was selfish. He never cared about anyone but himself, and when his sister begged for help, he refused without hesitation.

Flat, definitive. The writer does all the thinking for the reader.

Understanding Version

Mark stared at the stack of unpaid bills on his table, the weight of them pressing harder than his sister's voice on the phone. He wanted to help - God, he did, but after a year of scraping by, he'd learned that every "yes" left him hungrier, colder.

"I'm sorry," he said, quieter than he meant to. He hung up before she could hear the crack in his voice.

We don't have to agree with Mark, but now we see him. His decision isn't a flat act of selfishness anymore - it's human, complicated, and tinged with desperation. By writing with understanding, you let readers wrestle with their own conclusions.

A Second Example: The "Villain" Who Isn't

Consider Victor Hugo's Les Misérables. Inspector Javert is the antagonist, a man obsessed with justice who hunts Jean Valjean relentlessly. If Hugo had judged Javert, he might have written him as nothing more than a cruel enforcer of the law. Instead, he understands Javert.

Javert is not evil; he's a man whose entire identity is built on an unshakable belief in order and duty. When Valjean shows him mercy; Javert's worldview collapses. He cannot reconcile kindness with the rigid world he's built for himself, and in the end, that conflict destroys him. Hugo doesn't excuse him, but he doesn't reduce him either. He lets us see Javert's fatal flaw, and in doing so, we almost pity him.

This is what Hemingway was talking about: stop judging. Start understanding.

Why is this important in writing?

When you write with judgment, you hand the reader a finished answer. When you write with understanding, you hand them a question. And questions stick. Readers keep thinking about characters who surprise them, who contain contradictions, who feel like real people.

Hemingway's advice is less about morality and more about craft. Understanding isn't agreement; It's exploration. It's looking at a thief and asking what hunger drove them, or at a hero and asking what fear nearly stopped them. Every character is a door, and judgment slams it shut. Understanding pushes it wide open.

If you want proof this works, look at some of the most enduring characters in literature and film: Javert, Severus Snape, Walter White. None of them is purely likable, yet all of them are unforgettable because their writers understood them rather than judged them.

How can you practice and develop understanding in writing?

So the next time you sit down to write, take Hemingway's advice. When you're tempted to slap a label on a character - selfish, cruel, noble, good - stop. Ask instead: Why are they like this? What's the hidden fear? The old wound? The one decision that shaped everything else?

The difference between judgment and understanding is the difference between a caricature and a character. The open quote's wisdom isn't just about writing; it's about creating work that lives beyond the page. As writers, we don't need to defend or condemn. We just need to see.

Because when you understand your characters, your readers will too.

Try these writing prompts to develop your understanding of your characters

The Sympathy Rewrite

Take a judgmental sentence about a character (e.g., "Tom was lazy and useless.") and rewrite it from a place of understanding. What happened in Tom's past that might explain his behavior?

The Hidden Wound Exercise

Pick a "villain" in your story. Write a one-paragraph backstory about the moment that made them who they are, then see how it changes the way you write their next scene.

Flip the Perspective

Rewrite a scene from the antagonist's point of view. Don't make them "right," but let them feel right. Understanding begins where condemnation ends.

The "Why" Chain

For any major decision a character makes, ask "Why?" five times. The first answer is surface-level; the The fifth is often where the truth and humanity live.

Further practice

The next 5 weeks, I will post a new writing prompt with instructions and examples for you to use to develop writing with understanding:

• Week 1: The Sympathy Rewrite - Turning Labels into Lives

• Week 2: The Hidden Wound Exercise - Writing What Hurts

• Week 3: The Reversal Test - Break the Expected

• Week 4: The Mirror Scene - Show Who They Really Are

• Week 5: The One Secret Rule - Build Your Character's Core