Think of a compliment you still remember.

I’m not talking about the passing comment of "great job." At your level, you get plenty of those, and most are gone before you've reached the elevator. I mean the one that really stuck, maybe from years ago, maybe from someone whose opinion you didn't realize mattered that much to you.

If it’s still with you, I'd wager it wasn't the compliment itself you kept, but what they compared you to.

I've been on both ends of this. On one hand, I’ve given people feedback like "that was excellent, genuinely strong work," where I meant every word and I’m sure it was nice to hear, but it was also somewhat forgettable.

At the same time, I've been handed a single comparison, once, that I still turn over long after the details have faded.

A coworker once told me I'd handled a tense meeting like a fire marshal, not a firefighter. I was more interested in finding what was actually fueling the problem than in rushing to spray water on a fire we hadn't even located yet. I still reach for that image before hard conversations, because it named something about how I work that I'd never quite been able to put into words myself.

Neither piece of feedback was empty.

The praise I gave was genuine and the comparison I got was just as sincere. One just slipped away almost as soon as it was said, while the other has stayed with me for years.

The only real difference was that one was anchored to a comparison and the other wasn't.

None of this is confined to praise, or to the spoken word. It works the same way on the page as it does out loud. You can build an airtight case in a memo and watch it get skimmed and shelved, or deliver one flawlessly in a meeting and feel it slide off the room. Spoken or written, what makes your words hold is usually what you set them beside.

We use comparisons all the time without thinking much about them. Hot versus cold, taller than expected, wider than a bus. I think they're so embedded in how we talk that we often stop noticing them, which is exactly why most of us never get deliberately good at using them.

That's the part worth getting deliberate about.

The test of a comparison isn't whether it's accurate. Plenty of accurate comparisons land with a thud. The real test is whether it survives a busy mind: remembered, repeated, and put to use long after you've left the room.

Consider the difference between these two sentences.

  • The sun is huge compared to the Earth.

  • Did you know you could fit a million Earths inside the sun?

The first is accurate, but about as memorable as a grocery list. The second is the same fact and a completely different experience of it.

For me, it invokes awe, creates a vivid image, establishes clear scale, and hands you something you want to tell someone else before you've even finished processing it.

That's the difference between a fact and an idea that travels.

The right comparison doesn't just clarify your point. It does the work of convincing, connecting, and spreading it at the same time.

You already know this on some level.

Comparisons, and their close cousin, metaphor, are among the oldest and most studied tools in human communication.

Aristotle argued that mastery of metaphor is the mark of genius, not because of style, but because a good metaphor reveals an intuitive grasp of likeness in things that seem unlike. In his view it's a cognitive skill: a way of making the unfamiliar intelligible by anchoring it to what an audience already understands.

  • The Federalist Papers leaned on analogy and historical comparison throughout to make abstract arguments about constitutional design land with readers who had no existing framework for what a republic of this scale might look like.

  • Churchill popularized "an iron curtain has descended across the Continent" in 1946. The phrase itself wasn't new, but his Fulton speech lodged it in public consciousness as the defining image for postwar Europe's division. We still reach for it today, which is what a truly well-chosen comparison does. It outlives the moment that created it.

It's a learnable skill, and most people at your level already use it instinctively. The only real question is whether you're using it deliberately.

The Framework: Three Moves for Choosing the Right Comparison

You've almost certainly done all three of these on instinct.

The point is being able to run them on purpose, in the moment that matters, when instinct alone won't reliably show up.

Gif by wolfentertainment on Giphy

Let’s get it…

1. Anchor to Something the Reader Already Knows and Feels.

The comparison that works isn't the cleverest one. It's the one that connects to something already alive in your reader's experience.

Not similar in content; similar in scale, ratio, relationship, or feeling.

The question I start with is this: what does this person already understand that's structurally similar to what I'm trying to explain?

Picture a budget request that isn't breaking through, until someone reframes it as less than the organization spends on printer paper. It works because everyone already has an intuitive sense of what printer paper costs: mundane, unremarkable, something you barely notice.

Setting the ask beside it creates an instant sense of proportion that three slides of numbers never could.

"The difference in processing speed is approximately 40%" gives the reader a number to hold. "The difference in processing speed is roughly the gap between walking and driving" gives them a body memory to attach it to. The second one sticks because the brain already has a folder for it.

Payoff: The reader doesn't just understand the point. They feel the scale of it.

2. Choose the Comparison That Travels.

The most useful comparison isn't the one that makes your point clear to the person in front of you. It's the one they'll use the next time they explain your idea to someone else.

Most of us optimize for clarity in the moment, but the more useful optimization is whether someone repeats it two days later without their notes.

A comparison that travels has three things going for it. It's vivid enough to picture without effort, simple enough to repeat without notes, and it produces a small moment of awe or recognition — that "I never thought of it that way" response that makes people want to share it before they've even decided to.

The million-Earths comparison has all three. So does the iron curtain. So does "less than printer paper."

When you're building one, run your candidates through those three.

If it's vivid but complicated, trim it. If it's simple but flat, you haven't found the right anchor yet. If it produces awe but takes three sentences to set up, it won't survive the retelling.

"The complexity of this system is somewhat like navigating a large urban transit network at peak hours while managing incoming communication streams" is technically a comparison. Nobody is repeating that at dinner. "Running this system without the upgrade is like driving a highway in first gear." That one travels.

Payoff: Your idea keeps moving after you leave the room.

3. Match the Comparison to What You Want Them to Feel, Not Just Understand.

Every comparison activates a feeling alongside a concept, and this is the move most people never make deliberately.

"Wider than a bus" activates size, but also a specific kind of personal, slightly surprising scale. "Less than printer paper" activates proportion, and a quiet sense of "that's smaller than I assumed." The million-Earths comparison activates awe. None of that is accidental. That's how the mechanism works.

So before I settle on one, I ask what this person needs to feel in order to act, not just understand. Understanding alone rarely changes behavior.

Understanding combined with the right feeling does.

  • Urgency wants a comparison with a closing window.

  • Proportion wants something so mundane it reframes the scale, which is why "less than printer paper" works.

  • Awe wants something vast or ancient or almost unimaginable.

  • Simplicity wants something everyone has already done with their own hands.

The wrong move is reaching for whatever comparison comes first, which is almost always the most obvious and least effective one. The right move is generating two or three candidates, asking what each one activates, and choosing the one that produces the right feeling alongside the right understanding.

Payoff: People don't just leave knowing more. They leave feeling differently about it, and that's what actually changes what they do next.

The right comparison doesn't just explain the idea. It makes the idea impossible to forget.

LEVEL UP
AI Prompt: The Comparison Sharpener

Copy and paste this into your favorite LLM:

I need to explain the following idea to [describe your audience — a leadership team, a skeptical stakeholder, a general audience]: [describe the concept, fact, or argument you need to land].

Help me generate five comparison options that would make this land more vividly. For each one, tell me:

  1. what it anchors to in the reader's existing experience,

  2. whether it would travel if someone repeated it to a colleague, and

  3. what feeling it activates alongside the understanding.

Then recommend the strongest option and explain why.

POLL

CURATED ROUNDUP
What to Review This Week

  • Read: Made to Stick by Chip and Dan Heath.

  • Watch: Metaphorically Speaking by James Geary (TED Talk). Nine minutes on why metaphor is a way of thinking before it's a way with words and why the right comparison reshapes how we understand an idea, not just how we phrase it.

In Case You Missed It!

It Comes Down to This

The sun is huge compared to the Earth is a factual statement.

You could also say you could fit a million Earths inside it.

One of those sentences ends a thought. The other starts a conversation.

Every idea you need to move through a room has a million-Earths version waiting to be found. The work is learning to look for it.

Thanks for reading. Be easy!

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