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Time charter

# 'Write Drunk, Edit Sober': How to Use AI Without Losing Your Voice


by 

[Jonathan Raymond](https://time.com/author/jonathan-raymond/)

Sep 23, 2025 10:30 AM UTC

![Illustration by Charter · Photo by Nitat Termmee, Getty](https://static.time.com/v3/assets/bltea6093859af6183b/blt7d0aa984b7048da7/6998c9ecd32e93064fcd759b/charter-ai-voice.jpg?branch=production&width=3840&quality=75&auto=webp&crop=3:2)

Illustration by Charter · Photo by Nitat Termmee, Getty

Illustration by Charter · Photo by Nitat Termmee, Getty

by 

[Jonathan Raymond](https://time.com/author/jonathan-raymond/)

Sep 23, 2025 10:30 AM UTC

“Write drunk, edit sober.”

That quote, falsely attributed to Ernest Hemingway, is famous for good reason. Not because being drunk helps (it doesn’t), but because the most important constraint you have to remove to create great writing is the worry about your reader. You’re just trying to get from zero to one, to move the idea from the inside to the outside.

When I wrote [_Good Authority_](https://bookshop.org/a/664/9781940858777), the first draft I handed my editor was some 70,000 words. The first edit I got back had kept about 15,000 of them, meaning that around 20% was useful—but getting the other 80% out of me was essential to finding the good stuff. I took a breath and got back to work.


This is the first half of what makes using AI to write as a leader so tricky.

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You’re busy. You’ve got pressure from above, confusion below, and no time to sit and figure out how to say what needs to be said. So you reach for AI to help.

And it does. Clean. Sharp. Well-worded. But it skipped the most important part: you.

AI works by predicting what _sounds_ right, based on patterns in the writing it’s already seen. But it hasn’t seen what you’ve seen. It doesn’t know what’s at stake for your team. It doesn’t remember what you promised last quarter. It can’t feel the tension in the room—or the silence in Slack.

That’s why the “write drunk” part matters. AI can’t tap into the lived experience, the emotional undercurrents, the nuance. It doesn’t carry the weight of what’s unsaid.

It doesn’t know this is the fifth shift in strategy this year.

It doesn’t know your team is still nursing the bruises from the last reorg.


It doesn't know your top performers are eyeing the exits. It doesn't remember that in the last all-hands, you dodged a question because you didn't have a good answer.

And it certainly doesn't carry the emotional load your team needs you to carry. Your job isn't just to inform—it's to inform from context, to hold space, to say what needs to be said in a way that's grounded instead of destabilizing.

So no matter how well it writes, if you let AI do the whole job, your message might come across as clean but hollow and your people will feel that. 

You might think, “Just tell the AI all that context upfront” as part of your prompt. But here's the thing: you don't know what context matters until you start wrestling with the words yourself. The act of writing is the act of thinking—and half of what you need to say only becomes clear once you start saying it.

Used well, AI can help. It can sharpen your thinking, challenge your assumptions, and help you say things more clearly. It just can’t go first.


**Step 1: Just say it.**

Start by saying what you think and feel.

Not for the comms team. Not for the press. Not even for your team yet.

Write it. Speak it into your phone. Talk it out with a friend. Don’t worry about formatting. Don’t backspace. Don’t clean it up.

Some prompts to help:

* Why do I feel I have to say something?
* What’s bothering me about this situation?
* Why does this matter—to the business and to the team?
* What would I want to know if I were hearing this for the first time?
* Where am I uncertain—and how can I share that without pretending I’m not?

One of the biggest traps in leadership communication is forgetting that _you’ve had time_ with this. You’ve been chewing it over. They haven’t. So when you drop a memo in your team members’ lap, it can land like a surprise grenade.

Letting yourself speak or write it out first helps drain out the extra emotion, clarify what you mean, and make sure you’re saying something real, not just something safe.


**Step 2: Use AI to think, now that you’ve felt.**

Once you’ve got something true on the page, _then_ it’s time to bring in AI.

You’re using AI the way a great editor works: to challenge, clarify, and clean up what’s already there.

Here are a few ways:

**Use AI as a thought partner.**Ask:

* What’s unclear or contradictory here?
* If someone had no context, what might confuse them?
* Rewrite this paragraph to clarify the intention, but keep the tone.

**Use AI to check for emotional blind spots.**Ask:

* What might a skeptical team member think?
* Does this sound defensive or overly corporate?
* What feelings might this stir up?

You can also ask it to generate a few versions: one more direct, one more empathetic, one more context-rich. Pick the one that feels truest.

**Use AI to rebuild missing context**Ask:

* Have I explained why this is happening now?
* Can you help connect this to what I said last quarter?
* Does this acknowledge the team’s likely concerns?


This is where AI shines—not in creating emotion, but in helping you remember to include it. Not in writing for you, but reflecting what you missed.

**Step 3: Don’t let it flatten you.**

Sometimes AI makes your message worse. It polishes the soul right out of it.

Say:

* You cut the part where I admitted I got it wrong—put that back.
* This is too polished. I’d rather it feel raw but honest.

You wouldn’t let a copy editor rewrite your voice. Don’t let AI do it either. 

The pressure to get it “right” is real. But your team doesn’t need a perfect memo. They need _you_. Someone they can trust. Someone who sees what they’re up against. Someone who isn’t afraid to show a little doubt or vulnerability when the road ahead isn’t clear.

AI can help. It can boost clarity, build momentum, and reflect your ideas back to you. But it can’t tell you what matters. It can’t give your words meaning. That’s your job.

_Jonathan Raymond is the author of_ [_Good Authority_](https://bookshop.org/a/664/9781940858777) _and the founder and CEO at_ [_Ren_](https://tryren.com/)_, an AI manager copilot that helps leaders and teams build trust, accountability, and clarity. He has spent more than a decade coaching executives and managers, with a focus on how organizations can grow without losing their humanity._ 


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