Y’all are already proving what badass go-getters you are. And I’m so amped you’re here.

Take Helene for example. She responded to last week’s issue of Drunk Writing Advice with some absolutely killer feedback. 👇

Because Helene shared this, not only will I include at least one “finished work” example in every issue, we’re going to begin diving into some “style” lessons as of next week.

Thanks Helene!

-Kristin 🍷

🍻 In this week’s issue of Drunk Writing Advice:

✏️ Sentence School: Curiosity is a writer’s best friend.

🥃 The Writer’s Pour: Be a contrarian. It’s fun. I swear.

🎙️ Drunk Talk: Excuse me while I nap for the next week…

🤖 Robot Pals: I used AI in this very newsletter.

We’re all a bunch of nosy bastards

And that’s a good thing. 

Curiosity is a universally human trait that immediately simplifies your job as a writer. It’s a blessing because you don’t have to manufacture interest from thin air—

You simply have to tap into the nosy little voice that already exists in every reader’s head.

And there are three critical places in your writing where you should be doing this:

1. The Hook

2. The Ride

3. The Payoff

Here’s how. 👇

The Hook: Start with a tease — not a thesis

Your hook isn’t about “summing up your point quickly” or “leading with value”. That’s banal LinkedIn advice from someone who writes like a spreadsheet. 🙄

A great hook doesn’t satisfy curiosity — it provokes it. And it’s the most important part of your story because if it doesn’t work, nothing else is even getting read.

We will cover hook-writing in great detail in future issues of Drunk Writing Advice because it deserves far more attention than just a shout-out in a curiosity lesson, but for now, let me leave you with one litmus test to run your hooks through:

👉 Am I telling the reader what happened — or making them need to know what happened?

The Ride: Keep ‘em thirsty

Once you’ve hooked the reader, the only way to keep their curiosity percolating is by making them ask even more questions. 

This isn’t easy.

You need to reveal just enough to keep the audience grounded, while constantly planting new questions in their mind. Two simple ways you can introduce this into your writing are by:

1. Teasing bigger stakes — introducing an even bigger question.

2. Withholding the “why” — as we discussed last week, the human brain looks for meaning. Don’t give that up right away.

These are powerful because they signal that something important is coming. People don’t keep reading because they’re informed. They keep reading because they need closure.

The Payoff: Deliver the damn goods

Curiosity without payoff is just manipulation. And people can smell it.

Screw clickbait. 🖕

The best payoffs don’t just satisfy curiosity – they reward it.

When you’re crafting your payoff, reveal something unexpected. Flip a common belief on its head. Make the reader feel smarter, just as importantly, validated.

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

Here’s an example…

Here’s an example…

I ran out of steam

Life goes through seasons. And often, we commit to things in the future before understanding our true capacity.

Last year, when I was asked to join the thesis advisory team for the Harvard executive program I graduated from a few years ago, I immediately and enthusiastically agreed. 

What an honor! Especially since I would now be calling my own legendary advisors –Don Conover & Carmine Gallo– my colleagues. 😍

But when I agreed to take this on, I didn’t anticipate that my responsibilities would climatically converge with:

• Recovering from an insane surgery.

• Leading an alumni reunion celebrating our 25-year program history with folks traveling into Boston from all over the world.

• And -ahem- launching a new premium newsletter.

So I spent last week hobbling around campus on crutches, barely able to focus on what I needed to do in the next 10 minutes, let alone the next 10 hours.

I pretty much ignored my poor members at Stealth Mastermind. I didn’t post anything on LinkedIn. And as far as Drunk Business Advice is concerned…

👉 I published a re-run.

Here’s the thing—

We all have weeks like this, where we just run out of time, bandwidth, creative juice, whatever. 

So it’s a good idea to have some content in the bank that you can pull out, whether it’s something new you’ve put on the shelf but not yet published, or something evergreen that will seem fresh to your audience, even if you’ve run it in the past.

The most important thing is to still hit “send”.

The litmus test

The most helpful place I used AI this week was…

…crafting this very email. 😳

Y’all — I’m only three weeks into publishing this newsletter, and I’m already struggling with the (vital) constriction of introducing ONE clear writing lesson per issue in the Sentence School segment.

For example:

Issue 1: How to wrap a fact in a story so people remember it better.

Issue 2: How to find patterns and meaning when recalling personal memories.

Issue 3: How to exploit curiosity throughout a story.

Each one of those lessons can spider off into dozens of tactics. But it’s my job to uncover the ones that tie back most closely to that day’s lesson.

In today’s case, as I was crafting the lesson on curiosity, I faced a struggle—

Hook-writing and curiosity go arm-and-arm like a pair of giggling girl scouts. But hook-writing deserves its own lesson (or hundred). I needed to give you a single clear tactic you could walk away with to ensure your hooks incorporated curiosity.

So I prompted ChatGPT:

I asked for 10 suggestions, because most of what ChatGPT spits out is unusable. You must ask for a lot to get a little.

In this case, one suggestion tied back perfectly to my point about how hooks should provoke curiosity, not satisfy it.

And it landed right in this issue — word for word. 👇

One of my favorite use cases for AI is the distillation of the corruptible chaos of my brain into a single bold, clear idea.

I hope you can use it to do the same. ☺️

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!

And if you love Drunk Writing Advice, consider sharing it with a friend. 🥰