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No one gives a shit about your perfect moments... How to uncover your battle scars... And more!
Kristin Kenzy
September 23, 2025
If you want your readers to trust you, stop polishing and start bleeding.
(Metaphorically, please.)
Today weāre covering my favorite kind of storytelling ā mistake-driven lessons. 99% of Drunk Business Advice stories fall into this category.
So forget your trophies. Letās start comparing scars.
Thatās how real trust is built. Source: Tenor
Iāll show you mine if you show me yours.
-Kristin š·
š» In todayās issue:
āļø Sentence School: Your perfect moments suck. Lean into the screw-ups.
š„ The Writerās Pour: Uncover your battle scars and make āem sing.
š¤ Robot Pals: AI can help you find the hidden meaning in your blunders.
šļø Drunk Talk: This novel made me better at telling my own stories.
Literally all of us. Source: Giphy
Your best stories come from your worst moments
No one but your mom cares about your perfect moments.
Youāve seen this bullshit: āI built my company from nothing, scaled to seven figures in a year, and hereās why itās easier than you think.ā
Alright Chad, if you did that, youāre either tremendously lucky, or youāre leaving out the best parts of the story.
Your success should feel earned. (Read: panic attacks, terrible decisions, and crucial mistakes.) Otherwise, itās just not that interesting. And we inherently donāt trust people who boast about their successes, while hiding their mistakes.
This is why mistake-driven stories are so powerful.
But life isnāt an after-school special, so the lessons we learn from these mistakes arenāt always obvious. We donāt have an experience, immediately reflect on that experience, and learn from it.
Mistakes are messy. Learning from our mistakes is messy.
But do you know what doesnāt have to be messy? Writing about our mistakes.
Today weāre going to highlight the three most important elements of a mistake-driven story, using the Drunk Business Advice article: Chaos at the Met Gala.
Letās do this. š
1. Lure us into the chaos
When writing about your mistakes, donāt skip straight to the lesson. Readers want the oh shit moment ā thatās the exciting part of the story. The lesson only lands if itās anchored in a vivid, human blunder.
And as we learned a few weeks ago, one of the best ways to kick things off is to drop the reader into a shit-storm:
āAll youāll need to do is just show up to supervise the crew and represent management,ā my new boss told me. āThis has all been planned for months, itāll operate like clockwork.ā
Honestly?
F*ck that guy.
Because what happened next felt like Billy McFarland had been put in charge.
2. Show the pain
Mistakes are interesting because they hurt. Maybe you lost money, credibility, or half your marbles.
Donāt shy away from describing the consequences. Itās what makes the reader nod along and relate. Without showing what it cost you, the mistake feels flat.
Nobody could stand. Nobody could speak.
But they could yell ā and throw punches.
Which is exactly what happened.
I didnāt blame them. Everyone was angry and delusional, and itās surprising that it took 23 hours for a fight to break out.
But there was nothing more that could be done with the crew in this condition.
The foreman and I looked at each other, exhausted beyond belief, and heartbroken by our failure to finish the job.
If your audience isnāt cringing on your behalf, you havenāt gone deep enough.
3. Connect the scar to the lesson
This isnāt a sob story or a blooper reel ā itās proof that youāve been through some shit, and people should listen to your advice.
Draw a direct line between the misstep and the lesson you now carry forward. Thatās the moment readers go from laughing at your screw-up to trusting your perspective.
What would have happened if I had said ānoā when he doubled our scope on the fly?
He wouldāve had to figure out a different solution.
Instead, I became his solution, and all-of-sudden, I owned a problem that I was in no position to solve.
Itās one thing to have a solution to someone elseās problem ā and another thing to be a solution to someone elseās problem.
With the latter, youāre simply a scapegoat.
Remember ā learning isnāt linear. If you had asked me 10 years ago what the lesson from this story was, I would have said something like ādouble-check your logisticsā, or ādonāt trust snarly bosses with beady little eyesā.
But the deeper lesson is about knowing the difference between having the solution to a problem, and being the solution to a problem, which carries a helluva lot more weight.
So even when you think you know the lesson, dig deeper ā I bet youāll find more.
Dive into some exercises to put what youāve just learned about mistake-driven stories into practice. šļø
Exercise #1 - Short ā±ļø
Weāre going to swap some trophies for battle scars.
Grab a braggy line from something youāve written, and re-write it to reveal a bruise behind it.
Assess how much more interesting it is.
Here are some examples:
ā I graduated at the top of my class.
ā I graduated top of my class, but only because I sacrificed friendships, hobbies, and my sanity to obsess over grades no one remembers now.
ā
ā I spoke on stage at a global conference.
ā My mic cut out halfway through my keynote speech at a global conference ā so 500 people watched me shout like an unhinged street preacher until the end.
ā
ā āI was the youngest Vice President in the companyās history.ā
ā āI was promoted way too young, launched a website that got infiltrated by German porn hackers, then misled the shareholders all the way to prison.ā
Exercise #2 ā Long ā³
Write a mini mistake-driven story using the 3-part spine we discussed today:
1 - Lure us into chaos (open your story inside the moment of the mistake)
2 - Show the pain (describe the negative consequences of your mistake)
3 - Connect the scar to the lesson (if it feels obvious, try to go deeper)
Hereās an example:
Chaos:
My slides froze two minutes into a 60-minute client pitch. I stood there, sweating under fluorescent lights, clicking a dead remote like an idiot.
Pain:
The client stared in silence. My team avoided eye contact. When the tech guy finally fixed it, I was rattled, rushing, and butchered the delivery. We lost the deal.
Lesson:
At first, I was angry about the failed tech. Then I was angry at myself for not double-checking the tech. But my real failure was using a slide deck as a goddamn crutch. I should have been prepared to confidently pitch ā slides or no slides.
Exercise #3 ā Reflective š§
Look back at a mistake-driven story from your past. It could be something youāve written, or just something from your memory.
Whatās the first lesson that comes to mind from that story?
Now ask āwhy is that important?ā until you find a defining principle that would have fundamentally changed your behavior or decisions before the chaos ensued.
Hereās an example:
Mistake story: I green-lit a rushed launch without enough testing.
First lesson: Always test before shipping.
Why is that important? Because software bugs kill trust instantly.
Why is that important? Because trust is harder to earn back than to build from scratch.
Why is that important? Because the brand lives or dies on credibility.
Defining principle: Protect credibility above speed.
You just need help getting it out. Source: Giphy
Canāt find a ādeepā lesson in your mistake-driven story?
You guessed it ā AI can help with that.
If youāre having trouble surfacing guiding principles from your mistake-driven stories, here are two LLM prompts that will dig deeper into that noggin of yours, and chisel out the good stuff:
āIām going to tell you a story about a mistake I made. My surface lesson is ______. Ask me 10 questions that will help me uncover lessons that are more universal, weighty, or timeless than the surface one.ā
āHereās a personal story and the lesson I think it taught me. Reframe the story through three different lenses ā personal values, leadership, and relationships ā and ask me 15 questions that will help me uncover deeper lessons that show up under each lens.ā
Remember ā AI is better at asking you questions than it is at answering questions.
Use it to move the sludge.
Ragtimeās original book cover, and its author, E.L. Doctorow. Image source: NYT
Read good shit. Write good shit.
I recorded a podcast yesterday (Iāll letcha know when it drops), and the host had an unusual question for me:
What is your favorite novel?
I know what youāre thinking ā I must be off my plot because thatās not an unusual question at all. But it was a podcast for lawyers and business owners, so I didnāt exactly come prepared to flap about fiction.
The host assumed as much, and was planning to give me a moment to think about the answer to that question, but I quickly had one at the readyā
Ragtime by E.L. Doctorow.
It has been my favorite novel for as long as I can remember. Iāve never read anything that tops it.
Look ā this newsletter isnāt designed to teach you how to write a novel. And having never written a novel, I am outrageously unqualified to even define the kind of writing that composes a āgreatā novel.
But I do believe that reading Ragtime repeatedly, over many years, has made me a better writer for one clear reasonā
It has helped me discover connections between seemingly unrelated events in my life, and uncover meaning behind those connections.
(Youāll have to read it to understand why, but thatās not the point Iām making here.)
Drunk Business Advice simply wouldnāt be the story factory it is if I hadnāt honed this skill. And whether I consciously realized it or not, Ragtime played a role in that.
So hereās a question for youā
What novel do you believe has made you a better writer, and for what reason?
Hit reply and tell me.
If I get some good ones, Iāll share them with everyone.
Also ā go read Ragtime. Itās a masterpiece.
I donāt take my place in your inbox for granted.
Itās 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 thereās 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. š„°