I don’t think stories have to be funny.
I also don’t really have any evidence that funny stories perform any better than serious stories.
But you’re here because you enjoy Drunk Business Advice, which has a humor-forward voice. I personally lean into this because it feels natural to me.
And many of you have asked me how to “write funny”.
Here’s the thing…
I’m not a joke writer.
In fact, I don’t really know how I became funny. I was an annoyingly serious kid — the polar opposite of a class clown. Then I woke up one day, and all of a sudden, I’m a LinkedIn shitposter.
(The only thing that’s clear about this situation is that I probably need some therapy.)
But that’s not helpful to y’all.
So I asked ChatGPT “Why is Drunk Business Advice funny?”.
Here’s what it told me:
It’s brutally honest
It turns disasters into comedy
It has a “WTF just happened” vibe
It punches up, not down
It’s self-deprecating and relatable
The consistent theme throughout these five “humor” elements is that they all feel authentic to me.
That’s the thing about humor — people sniff insincerity a mile away. And it f*cking stinks.
-Kristin 🍷
🍻 In today’s issue:
✏️ Sentence School: Why you shouldn’t try to be funny.
🥃 The Writer’s Pour: Tricks for finding and deploying irony in your stories.
🤖 Robot Pals: If your understanding of irony is equivalent to Alanis Morisette, then please, for the love of god, use these two prompts.
🎙️ Drunk Talk: I’m about to do something really smart or really stupid.
The laughter will come. I swear. Source: Giphy
Forget humor — lean into irony
Could you imagine John Mulaney delivering a Chris Rock bit? Or Bill Burr replacing Will Ferrell in (literally) any of his roles?
It would be horrifying.
That’s because humor is directly tied to authenticity. This is why I clam up every time someone says “teach me to write funny like you”.
I want you to write… like YOU. And if that’s funny, fantastic.
Authentic humor can’t be faked.
But I do believe it can be found — by letting irony do the heavy lifting.
Irony occurs when there’s a gap between expectation and reality. And that gap can be hilarious.
👉 Maybe you started a business to gain financial freedom, only to find yourself trapped in a 24/7 grind.
👉 Or maybe the skill you once dismissed as useless ended up being the foundation of your greatest success.
👉 Or maybe… just maybe… you began your life as a super serious no-nonsense go-getter, and you ended up a shitposting clown. 🤫
Recognizing these moments of irony in your own journey can make your storytelling sharper, more memorable, and yes — funny.
There are two steps to this:
1. Look for the situational or dramatic irony of the story.
This happens when life takes an unexpected turn. When you worked hard to avoid a particular fate, only to land squarely in it. Or a belief you once held strongly is later disproven by your own experience.
Another way of thinking of it is when your past self would be really surprised by what your current self is doing.
Look for moments when you were blissfully unaware of what was coming.
For example (from this issue of DBA):
I accepted a job at Rockefeller Center to escape the stress of running my own business. I thought this corporate gig would provide stability and let me focus on my expertise. Instead, I landed in a toxic, political hellscape, and had more stress than ever before.
2. Once you’ve uncovered these moments, deploy some verbal irony.
This is where you turn the observation into a lol.
Verbal irony happens when what you say contradicts what’s actually true — often in a self-aware or exaggerated way. The goal isn’t to be sarcastic for the sake of it. It’s to point out the absurdity of a situation by pretending not to notice it.
You’re not “telling jokes” — you’re reframing reality in a way that exposes its weirdness.
To use the Rockefeller Center example:
“I traded the chaos of self-employment for the peaceful, grounded environment of corporate America — said no one who’s ever worked in corporate America.”
Here are some other examples:
“I started freelancing for flexibility. Now I just work 12 flexible hours a day.”
“My dream was to ‘be my own boss.’ Turns out my boss is kind of an asshole.”
“Nothing screams ‘financial freedom’ like refreshing QuickBooks at 2am.”
“My client said, ‘We love your creative vision — just make sure it looks exactly like last year’s campaign.’”
“We called it a ‘team retreat.’ But we just worked somewhere with worse Wi-Fi.”
“I went to bed early to be productive. Then laid awake for three hours thinking about productivity.”
“I told myself I’d start saying no. Then immediately said yes to writing this sentence.”
These aren’t jokes. The humor in these lines don’t come from setup >> punchline.
It comes from contrast >> recognition.
You’re holding up two truths that shouldn’t coexist… but somehow totally do.
So when you spot irony, force yourself to say the thing that everyone else is thinking, but no one wants to admit out loud.
That’s where the humor lies — not because it’s “funny haha,” but because it’s “true oh god”.
Dive into some exercises to put what you’ve just learned about irony into practice. 👇️
Exercise #1 - Short ⏱
Think about some times when life or work didn’t go to plan. Then deploy some verbal irony using this setup:
“The plan was to _____. The reality was _____.”
I recommend repeating this 3-5 times.
Here’s are some examples:
The plan was to get organized. The reality was spending $300 on Notion templates I never used.
The plan was to work less. The reality was I just started working weird hours in different pants.
The plan was to hire help. The reality was spending more time teaching them than it would’ve taken to do it myself.
Exercise #2 – Long ⏳
Write a 200-300 word story about how your past self and your current self wouldn’t recognize each other.
Here are some prompts to help you find the story:
-What’s something you used to measure success by — title, money, followers — that now feels meaningless (or hilarious)?
-What habit or trait you once mocked in others have you now fully adopted?
-Recall a version of yourself who was absolutely certain about something. When did life prove them wrong?
Here’s an example:
I used to be a f*cking lunatic.
I was a figure skater, and thought I was limitless. That same mindset pushed me toward insane goals, and motivated me to work my ass off.
That’s a good thing, right? Well, not really. It also left me exhausted, anxious, and convinced that grit could fix anything.
These days, I find the “old me” to be insufferable.
I’ve got titanium screws in my pelvis, and a very healthy respect for limits. I no longer worship the “hustle.” I build systems that serve my energy instead of draining it. I say no a lot. I prioritize my relationships.
Back then, success meant prestige — Harvard credentials, high-profile clients, shiny headlines. Now, success looks like joy, freedom, and only working with people I’d actually want to drink with.
If past me walked in the room, she’d probably accuse me of going soft. I’d hand her a beer, pat the seat next to me, and say, “Relax, kid. You don’t have to work so damn hard to earn your worth.”
Exercise #3 – Reflective 🧠
What belief, mantra, or motto have you completely outgrown?
We often label ourselves by our beliefs. And when those beliefs change, we just change the labels.
But what would happen if you labeled yourself by your TRANSFORMATION between beliefs? How much more interesting would that be?
Canada’s best export. Source: Giphy
Not good at irony?
Irony is a tricky motherf*cker.
Even Alanis’s famous song about irony doesn't correctly identify irony in most of her examples (but whatevs, I’ll love her ‘till the day I die).
So if you need a little assistance with finding irony in your stories, you’re in good company.
Here’s an AI prompt to help:
I’m going to tell you a story from my life. Your job is to help me identify where the irony lives. Ask me questions specific to the story I tell you that will help identify:
-What did I expect to happen in this situation?
-What actually happened instead?
-Why was that outcome surprising, disappointing, or absurd?
-What belief, assumption, or “rule” of mine did this experience completely destroy?
-How would my past self have reacted to this moment — and how does my current self see it differently?
-What’s the hidden contradiction that makes this story interesting or funny?
After I’ve answered the questions, use those answers to generate 5 different statements that capture the central irony — a clean “expectation vs. reality” contrast.
After you’ve got a clear grasp of the irony of the story, AI can also help you deploy some verbal irony (helpful for humor if that’s your jam).
Try this prompt:
I’m going to give you a personal story with a statement that contains a clear irony or contradiction. I want you to help me express it using verbal irony — a sentence or two that sounds like something I would actually say.
Here’s how I want you to approach it:
-Identify the core irony (what I thought would happen vs. what actually happened).
-Write 3 alternate versions of a closing line that exposes that irony using humor or understatement.
-Keep the tone self-aware and conversational — it should feel authentic, not like a “joke.”
-Avoid setups and punchlines. Instead, use contrast or reversal to make the humor land.
-Make sure it sounds like something a normal person could mutter under their breath and get a knowing laugh.
You oughta know that I’m thinking about doing something crazy... Source: Giphy
I’m thinking about sending a newsletter… daily 😳
I’ve got some new programs cookin’.
And y’all will be the first to know when I’m ready to announce them (plus you’ll get freebies and discounts galore, because you’re my favorite people ♥️).
But as it pertains to writing, I’m considering a major decision—
Publishing a daily newsletter.
I know. This sounds like a batshit crazy undertaking, especially without hiring writers, which I’m absolutely not doing (all my content is 100% USDA Certified Kristin).
But hear me out.
The format of the daily newsletter I’m considering is basically a pimped-out LinkedIn post — NOT long-form editorial like the weekly Drunk Business Advice, or a multi-segmented tactical newsletter like this one.
It would be a brief, personal note. A daily reflection. An ironic observation. A radical thought.
I’ve got notebooks filled with shit I want to write about, but most of it doesn’t fit the format of Drunk Business Advice.
Plus, there’s another (far more practical) reason why I want to start sending more emails…
Newsletters are now my business. This is how I earn a living. And showing up in my audience’s inbox once on Sundays is like opening a grocery store and only selling almond milk.
Sure… almond milk sales look great. But there’s so much untapped potential.
Stay tuned. 😉
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. 🥰