Metaphors aren’t there to make your writing cute. They’re there to do job.

The best ones collapse complexity into something so simple your reader feels it in their gut (or, in today’s case… their bathroom).

This week, we’re getting real about shitty metaphors, botched deadlines, and how to make both you –and your AI– a helluva lot sharper.

-Kristin 🍷

🍻 In today’s issue:

✏️ Sentence School: Metaphors should do a job — sometimes a dirty one.

🥃 The Writer’s Pour: Practice clarifying complicated concepts with… toilets.

🎙️ Drunk Talk: I really screwed myself this week.

🤖 Robot Pals: AI is shitty at this, but here’s how you can make it less shitty.

You’re doing metaphors wrong

I was an architect wrangler in another life. No shit.

My job used to be all about reigning in architects who valued form over function. I had to convince them that creating a space which truly supported the business that lived inside it was more important than some prestigious design award.

It was much harder than it should have been. 🙄

When I first started out, I would dive deep into the operational details, explaining why their proposed designs were –ahem– sub-optimal (read: shitty).

This would often elicit pushback from them, using logic that made sense in their minds as designers, but was utterly absurd to an operator.

So after many conversations that went nowhere, and left everyone frustrated, I began using a metaphor that everyone could understand — bathrooms.

I would say:

Without fail, that metaphor always got everyone on the same page.

Everyone can feel the pain of a squat-waddle. Because, as the popular potty-training book proclaims — everyone poops.

Metaphors should do a job

Sure, metaphors can be fun. They can be clever. They can add color to your writing.

But like we discussed with naked numbers last week, they have a much more important job to do—

👉 To simplify and contextualize complex ideas.

My bathroom metaphor worked because it collapsed pages of operational detail into one clear, visceral image. It painted a quick mental picture that communicated everything.

That’s the secret — the best metaphors aren’t decorative. They’re shortcuts. They compress complexity into something the reader already understands.

Drunk Writing Advice reader Maxim Cramer is a master of metaphor. She’s a computer scientist who helps non-tech founders build tech products. Which is f*cking complicated because tech people and non-tech people speak different languages — literally.

So instead of describing the complex nuances between different coding languages, and why they’re technically compatible, but not ideal, for different use cases, she puts it like this:

(Subscribe to Maxim’s newsletter here, it’s badass.)

If you’re not using metaphors to concisely create context, you’re doing it wrong.

Use them like workhorses — not fancy goldfish.

Dive into some exercises to put what you’ve just learned about contextual metaphors into practice. 👇️

Here are some examples:

Here’s an example:

I got screwed. Then I screwed myself. 🤦

On Saturday night, I promised my husband that I would have my work wrapped-up in time to go on a dinner date. And everything was on track for me to keep that promise.

(Embarrassingly, we haven’t been out to dinner for two months.) 😔

I finished writing that week’s issue of Drunk Business Advice around 6pm, and just needed to get it designed and scheduled for Sunday morning. 

So I gave him the 1-hour warning — “Hop in the shower babe! I’ll be ready to hit the town in an hour!”

I copied the article into beehiiv (my ESP), and immediately encountered an issue. None of the images were loading.

I figured it was a temporary bug, and reloaded the site. Nope.

I logged out and logged back in. Nope.

I cleared my cache. Nope.

I restarted my computer. Nope.

Finally, I opened a panicked support ticket with beehiiv. I couldn’t send out an entire issue of Drunk Business Advice with NO images.

And even worse — I couldn’t start my date night until I got the newsletter scheduled. My husband looked at me with droopy, sad, toddler-told-no eyes as I broke the news to him.

I returned to my desk, and kept refreshing my email, waiting for a response to my Saturday-night support ticket. In between refreshes, I continued to try to load my images into beehiiv until…

Success! The bug was still live, but my relentless poking had inadvertently found a workaround.

I used the workaround to upload all the images, and get the email scheduled. Woohoo! I danced into the bedroom with the good news, and we set out on our date night.

The next morning, as I awoke bleary-eyed from the many Manhattans I had enjoyed the evening before, I opted not to check my email — and instead enjoy the morning reading a good old-fashioned book.

Around noon, I figured I’d check to see if that morning’s issue of Drunk Business Advice had elicited any responses— and was shocked to see the email was missing.

Welp. In my mad rush to get the email out, I had accidentally scheduled it for 8PM instead of 8AM.

F*ck.

I was ready to blame it all on a platform bug. But it was my own damn oversight that screwed me in the end.

AI tends to suck at metaphors

Your friendly neighborhood LLM wasn’t trained on writing metaphors that simplify and contextualize complex ideas.

It sees the word “metaphor” and instantly clouds your idea with flowery words that make it more complicated.

Here’s what it did when I asked it to write an example metaphor for Exercise #2 above:

Um. WTF?

The metaphor is more confusing than the jargon.

But here was my mistake— I told AI to write a metaphor. But if you want to get a good metaphor out of AI, the last thing you want to do is tell it to write a metaphor.

Instead, try this prompt:

And while they still need some work, these are a helluva lot better than asking AI to write a metaphor:

I don’t take my place in your inbox for granted.

It’s an honor to be welcomed into your world, and I know I have to work to continue to earn it, week after week. So if you have feedback, or if there’s a topic you want me to cover, just hit reply and tell me!

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