James Clear and I have an uncanny amount of shit in common.

James was a baseball player who took a bat to the face, ended up in a coma, and worked in small, consistent iterations to return to the ballfield — thus creating a framework that launched his career.

I was a figure skater whose competitive chapter ended with a broken hip, but my skating fundamentals of “preparation, execution, review” built me into the person I am today.

James wrote Atomic Habits to help people build better personal systems — one small habit at a time.

I write Drunk Writing Advice to help people build better storytelling systems… usually with a glass of wine. 🍷

So yeah — the man speaks my language.

And today, you’re gonna learn to speak that language, too.

-Kristin 🍷

🍻 In today’s issue:

✏️ Sentence School: If it ain’t a habit, you ain’t gonna do it.

🥃 The Writer’s Pour: I’m shining the spotlight on you, and asking for a commitment.

🤖 Robot Pals: Holy shit. Every LLM in one place?

🎙️ Drunk Talk: I’m thinking about breaking up with the software I built my entire business on. And I’m kinda shitting myself.

I have faith in you. Source: Giphy

Build a writing habit that actually sticks

Even though Atomic Habits isn’t technically about writing, it’s the single best framework I’ve found for actually doing the damn thing.

You can’t expect to build your writing muscles without building a writing habit.

So today, I’m sharing one tactic from James, and one tactic from me, on how to create writing a habit that feeds your goals.

Tactic from James: Design your system, dammit.

Most people think they need “discipline” to write every day. You don’t need discipline — you need a damn system.

Here’s how James recommends you design a system to build better habits:

  1. Make it obvious

  2. Make it attractive

  3. Make it easy

  4. Make it satisfying

Let’s break that down:

1. Make it obvious

Plant the “cue to write” in a place where you can’t ignore it.

Leave Google Docs open on your desktop. Set a reminder in your calendar. Tape a sticky note to your Playstation that says “WRITE FIRST, YOU DEGENERATE”. 

(Just kidding… be kind to yourself. 😉)

2. Make it attractive

This is my favorite tip from James: Bundle writing with something you already love.

Coffee. Music. Whiskey. Petting your cat. Whatever.

I love to bundle writing with a lo-fi playlist and a glass of wine. It gets me excited to sit down at the keyboard and pour out my stories.

James calls this temptation bundling — pairing a new habit with a favorite one. When the brain starts associating “writing time” with “dopamine time,” you’ll crave it.

3. Make it easy

First, remove all friction from your starting process — because the harder it is to start, the less likely you’ll do it.

For instance, use one file for all your drafts instead of a labyrinth of folders you have to poke through until you find what you’re working on. 

Second, lower the damn bar. Instead of saying “I’ll write one 2,000-word essay per week”, commit to writing one 2-sentence LinkedIn post per day. Work up to the big outcomes.

By the time I started publishing Drunk Business Advice, I had already been creating content for The Hustle and my ghostwriting clients for 2 years. I didn’t just decide one day to write a long-form weekly newsletter. It took time for me to build up a strong-enough writing habit to commit to that.

4. Make it satisfying

Reward the act, not the outcome. 👏

Don’t wait for the day your post “goes viral”, or your newsletter hits 10k subscribers to celebrate your achievement. Instead, celebrate the tiny wins — your daily streak, your 30 minutes of focus, your butt in the damn chair.

Draw the bath. Pour the drink. Dance in the kitchen. Whatever your “guilty” pleasure is, reward yourself with it every time you make incremental progress on your goal.

Tactic from Kristin: Go public or go home.

The biggest accelerator for building a writing habit isn’t private willpower — it’s public accountability.

When no one’s expecting your words, it’s easy to bail. 

“I’ll write tomorrow.” 

“I’m too tired.” 

“The muse is drunk and unavailable.”

(It’s me. I’m the muse. And I’m sometimes drunk and unavailable.)

But when you’ve promised your readers — or even just your LinkedIn followers — that you’ll show up on schedule, something magical happens…

You. Stop. Flaking.

Because suddenly, skipping isn’t just breaking a personal habit — it’s breaking a public promise.

That’s why I recommend you commit to a publishing cadence — something you announce publicly. Even if it’s tiny, like “I post on LinkedIn every Wednesday”, or “I send my newsletter every other Sunday”.

The frequency doesn’t matter as much as committing to (and sticking with) a cadence.

“But Kristin… I’m writing a book. This doesn’t apply to me.”

Let’s chat in a year and see how much progress you’ve made without committing to sharing thoughts from it on a regular cadence with your audience.

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

Exercise #1 - Short

Build your temptation bundle. 

List three things you already enjoy (your favorite tea, a particular playlist, a soothing candle, whatever). 

Then pick one that you’ll only allow yourself to have while writing. Commit to it for an entire week. Don’t cheat. Only allow yourself to have it when you sit down to write.

Want to level-up? Add more than one thing.

Exercise #2 – Long

Before you commit to your publishing cadence, you need to be honest with  yourself about two things:

1. Your time.

2. Your capacity.

So grab a notepad and answer these questions:

-What does a realistic writing session look like for me right now? (Be honest — 15 minutes counts.)

-How many of those sessions can I fit into a typical week without risking skipping sessions, or giving up?

-What’s one platform or format where I could publish something regularly — even if it’s short?

-What cadence feels ambitious but sustainable for the next 90 days?

-What would make me actually excited to show up for that cadence — not dread it?

Then make the commitment, announce it on your platform of choice, and send me a link to it. You badass. 👊

Exercise #3 – Reflective 🧠

Perform a friction audit.

Write down every reason you’ve skipped writing in the last month — real or imagined.

Next to each one, note one small way to remove that friction. You’ll see how many are self-inflicted.

I can’t f*cking keep up. Source: Giphy

Do you have LLM whiplash?

Look y’all — ChatGPT is my go-to LLM. It was the first to the playing field, so we’ve built a pretty damn deep-seeded relationship. It’s the AI that, frankly, knows me the best.

But if (like me) you have LLM whiplash, and never know which model is “best” for your particular use case, I’m going to clue you in on a tool that I’ve been using for the last 10 months or so…

It’s called Lex

I am not affiliated with Lex in any way — there’s just one feature that I think can be super helpful (especially if you haven’t “chosen” an LLM to commit to yet as your writer’s assistant):

It’s got every damn model inside of it. 👇

So you can play with all the different LLM models by paying for one subscription ($15-$25 monthly + usage above a certain threshold).

They do free trials, so check it out and lemme know what you think!

I don’t know what to do. Source: Giphy

I have a really f*cking hard decision to make

You are receiving this email courtesy of Beehiiv — my “ESP” (email service provider).

Beehiiv was founded a few years ago by Tyler Denk, after he led the product team over at Morning Brew — one of the biggest newsletters in the world. He set out to build a platform that was truly designed for newsletters.

The timing couldn’t have been better.

In August of 2023, I was wrapping up my time at The Hustle (Morning Brew’s biggest competitor), and launching a newsletter program for a private equity-backed EdTech company. 

Beehiiv was the perfect ESP for that project, so I dove in, learned it, and loved it.

Not long after that, I launched Drunk Business Advice on Beehiiv. And for the first year, it was pretty much peas and carrots. 

As a young software company, it wasn’t without its issues. A bug here or there… missing a feature or two that would be nice to have… but generally, it served my needs extremely well.

I built multiple newsletter programs on it for myself, and my clients. I recommended it to literally everyone who wanted to start a newsletter (even you guys, as recently as a few months ago). And when they opened up a crowd raise, I even invested.

But y’all — the last six months have been chaos. 🤦

In that time, I’ve experienced three separate catastrophic failures — not just little bugs that I could report and work around. Literally shit that drove my business to a halt, and/or damaged my reputation.

Amazingly, as I was pondering that Beehiiv may no longer be a reliable enough platform for me to build my business on, I received a random email from their VP of Sales, J.T. Levin, asking to meet with me at a conference we were both attending last week.

Score! I could bring up these issues with a real person in leadership, instead of the frustrating back-and-forth with a faceless customer service team.

But lord, J.T. WAS NOT prepared. He didn’t even realize that I was a current customer of Beehiiv when we sat down face-to-face.

And when I began to detail the Beehiiv’s reliability issues, he said, “You should really be talking to Tyler,” (you know — the founder). “He’s here.”

Great! F*cking tee it up, bro.

We agreed that he would email me with a precise time and location to meet with him and Tyler after the following round of panels I was attending at the conference that day.

Long story short, I’m still waiting on that email. 🤦

What would you do?

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. 🥰

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