“Value” has become the holy gospel of business content.

I mean, it makes sense. Why would someone give you their attention if you’re not teaching them something helpful? And why would they come back for more if they didn’t feel like they received “value” the first time?

If this was truly the case, Drunk Business Advice would have been out of business after a handful of issues. 

But hey, people love it. And writing it has attracted more opportunities than any other initiative I’ve ever tried.

Why?

Because my readers trust me. And what other reason do any of us have for putting our ideas and our stories into the world than to build trust — at scale?

“Value” transfers knowledge.

“Vulnerability” transfers trust.

Focus on the trust first.

-Kristin 🍷

🍻 In today’s issue:

✏️ Sentence School: Make you reader see themselves in your story.

🥃 The Writer’s Pour: “I was wrong” is so f*cking powerful.

🤖 Robot Pals: Don’t stare at a blank page. Let AI help.

🎙️ Drunk Talk: Yep. I had a crazy stalker this weekend. 🤦

It’s all about balance. Source: Giphy

Vulnerability earns more trust than value

Being vulnerable in your writing doesn’t mean trauma-dumping, or confessing your deepest shame to strangers. It’s simply the willingness to show imperfection — on purpose.

When you lead with vulnerability, you humanize your expertise, turn lessons into earned wisdom, and most importantly—

You make the reader see themselves in your story.

This sort of empathy is far more powerful on your reader’s brain than any semblance of logic. Scientifically.

When you reveal something personal, your reader’s brain releases oxytocin — the same chemical that nurtures intimacy. Vulnerability chemically bonds your reader to you.

Meanwhile, value without vulnerability triggers zero emotion. It’s just information. And information is both cheap, and forgettable.

So how can you be (tactically) vulnerable in your writing?

I’ve always said that writing for an audience is a far better exercise than journaling because it forces you to find –ahem– “value” in your vulnerable moments.

“But Kristin. You’ve been shitting on ‘value’ since I opened this email.”

Ok. Fair point. But the true genius is in combining the two things. And I don’t mean “What getting engaged taught me about B2B sales”. 🤮

(That’s not vulnerability. That’s performative garbage.)

Here are two ways you can deploy tactical vulnerability in your writing:

👉 Anchor the story to a belief. Vulnerability is most powerful when it reinforces a conviction your reader can adopt or challenge. Your story should reveal why you think the way you do. Otherwise it will feel disjointed, like a random confession. Your vulnerability shouldn’t hijack your message.

👉 Show imperfection in progress. This is one of the best ways to uncover vulnerability. Give your audience a peek behind the curtain on what you’re still learning. Even better — ask them to share their own advice. The best relationships are those where both partners learn and teach.

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

Exercise #1 - Short

Write a few sentences about a time you completely misjudged something in your work, and why you made that misjudgment.

BUT — No moral grandstanding. Don’t defend yourself. Just be honest.

Kick it off with this single sentence: “I was wrong.”

Then, if you’re brave, post it on LinkedIn. 😬

Here’s an example:

I was wrong. 

I thought launching Drunk Business Advice as a podcast was a solid strategic choice because conversations about business f*ck-ups felt more authentic than writing about them. 

But I had no audience, no distribution, and no clue how to generate traction in a broadcast medium. It was a dumb plan.

Exercise #2 – Long

Write a personal essay about a moment when fear or embarrassment pushed you to form one of your core professional beliefs.

Here’s an example from Drunk Business Advice:

I puked with Olympians — Issue from March 6, 2025

Exercise #3 – Reflective 🧠

Go through the last five pieces of writing you’ve published (LinkedIn posts are fine for this exercise, or grab longer form writing if you have it).

Ask yourself these questions:

-Am I sharing expertise, or sharing an experience?

-What core belief of mine does this content tie back to?

-Is this performative? Or would I actually tell this story to a friend?

-How could I have shown more vulnerability?

Riiiiiiiight. Source: Giphy

AI can help you find the feeling — and the meaning behind it

AI can’t feel.

(Or at least I hope not.)

But AI can help you feel.

One of the biggest challenges we all face is “blank page syndrome” (i.e. — trying to decide what the hell to write about). This compounds when you begin adding restrictions like “It’s gotta show vulnerability while still being valuable and oh god what the hell I’m never going to think of anything I might as well give up where’s the whiskey it’s time to drink my pain away.”

Yep. Been there.

Here’s an AI prompt that can pull you out of that pit of despair:

I want to write a personal story that builds trust with my audience.

Ask me 20 questions that will help me uncover moments of imperfection, failure, or doubt that ultimately shaped my core beliefs about my work.

Focus on stories that show transformation, not trauma.

Or, if you have a core belief you’d like to dive into, use this prompt to help you uncover the best story:

I’m going to give you one of my core professional beliefs.

Ask me 10 questions to trace where that belief came from — specific memories, moments of conflict, or mistakes that solidified it.

Your goal: help me find the emotional story behind my logical stance.

It’s actually pretty terrifying. Source: Giphy

This is why I use a pen name

Kristin Kenzy isn’t my real name. It’s my pen name.

And events this weekend have proven why adopting a pen name was a damn good idea.

Since I began publishing Drunk Business Advice, I’ve had a few, well, “stalkers”. No true threats to my safety — just weirdos who have demonstrated what my Secret Service husband calls “undue interest”.

The MO among these interactions has been consistent — obsessive emailing / messaging, and irritation when I don’t reply.

And so far, the only action I’ve needed to take is removing them from my email list, and then blocking them on any platform they’ve used to contact me. And then just moving on with my life. No biggie.

But on Sunday, I had a really strange one…

I was chilling on the couch, cheekily bantering with folks on LinkedIn about the demonic nerds-candy-corn-hybrid I had come across while ordering my groceries for the week, when I came across a comment from a 3rd+ profile which had literally nothing to do with that topic—

“You’re not listed in the Harvard Alumni Directory. All alumni are listed in it. Why can’t I find you?”

Then my notifications started popping off. This guy was commenting some version of that statement on heaps of my old posts — some going back years.

And every comment was getting more and more aggressive, accusing me of faking my Harvard Alumni status because he couldn’t find “Kristin Kenzy” in the directory.

Of course he couldn’t. Thank f*cking god. I’m in the directory under my legal name, not my pen name.

I took a look at the profile, and it was brand new. A generic name. A company that Google has no record of. No followers. And the only activity records were the abusive comments he was leaving on all my posts.

So I reported the profile for harassment, and blocked it.

But here’s what really freaks me out about this — the general public doesn’t have access to the Harvard Alumni database. To access it, I have to login through my “Harvard Key” — a special authentication system.

So… it’s quite possible that this stalker is, in fact, part of the close-knit Harvard community. A place where (up until now) I haven’t felt the need to set the kind of boundaries I do with my “public” profile.

Honestly, that breaks my heart a little.

Today we talked about the importance of being vulnerable in your writing. And I stand by that.

But it’s also important to protect yourself from creeps. Share vulnerable stories — not vulnerable information that opens you up to harassment and stalking. 

Use a pen name. Don’t allude to the specifics of where you live, or places you visit frequently. Unapologetically block people who give you a bad feeling.

Stay safe out there, friends. ♥️

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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