My Hawaiian Jailbreak and the 30 Day Savage Reset (I WROTE THIS IN JAIL)

I'm free now biotch

Guess who’s back back again the sun soaked outlaw, Day, freshly imported from paradise straight into a cockroach infested, Samoan overrun, fat fuck everywhere, concrete and regret Hawaiian jail cell. Hypothetically, of course. If you could see me right now, you'd be laughing your fucking ass off. Seriously, I’m painting the most tragically beautiful portrait a golden haired deity whose luscious locks practically drink sunlight for sport, whose annoyingly symmetrical face that should be getting licked by models in Saint Tropez instead of plastered on a mugshot. In here, I stick out like a MAGA hat at a gay pride parade in Seattle. Only brighter, prettier, and much, much more punchable.

I'm hunched over on a piss stained concrete floor scribbling this masterpiece with a pencil so short it looks like it got chewed on by orphans, on paper borrowed from my new friend Tiki, whose credentials include tooth loss and the complete inability to form coherent sentences. My writing hand cramps worse than a grandma with stage 4 arthritis giving a vigorous handjob and let me pause dramatically here to mournfully scream in my head I MISS MY BEAUTIFUL FUCKING MACBOOK.

I SPENT FIVE FUCKING DAYS IN JAIL AND NOW IM COPYING THIS DOWN FROM THIS PISS STAINED AND COCKROACH GUTS PAPER.

Now, the fact that I got arrested probably surprises exactly nobody. You roll the dice every single time you step out the door with a face like mine, and a personality finely tuned to make prolonged, unsettling eye contact. When you make a pact to yourself that you won’t take disrespect and adopt the views I instilled in my mind, life gets more beautifully fun but infinitely more dangerous. When you combine the shamelessness of a sociopath with the mouth of a writer, trouble isn't just inevitable it practically books a reservation months in advance.

But before I dive into the sordid details of precisely why I’m currently incarcerated, let me bitch for a moment about the existential horror of spending a night in Hawaiian jail. Whoever says Hawaii is paradise clearly hasn't spent even five minutes in this place. The architecture screams, "we built this while wearing loin cloths " the cells are packed tighter than termites in an antique dresser, and every surface feels like it's permanently coated in the sweat and sins of a thousand regretful humans.

And the cockroaches holy mother of all that’s unholy. Last night, as I tried desperately to pretend this wasn't reality, one particularly ambitious cockroach staged an expedition across my lips and chest,I bet I swallowed ten last night, I woke up feeling full, violated, humiliated, and inexplicably curious whether this qualifies as an interspecies hookup.

I'm also especially furious because I had to surrender my meticulously pressed, sky blue striped Ralph Lauren shirt an item of clothing more elegant than 90 percent of the population of this shithole to a smiling Samoan guard who handed me back a ratty ass jumpsuit that smells suspiciously like disappointment and processed cheese.

Throughout the whole degrading experience, from mugshot to strip search to being marched to my luxurious concrete accommodations, I cracked jokes like a desperate court jester dancing on the edge of sanity. Now, waking up sober in this literal dumpster fire, I feel less like a beautiful outlaw and more like a genuine dumbass who walked willingly into the world's ugliest circus.

Does Day feel Fear? Sure, I should probably feel more of that. Instead, I’m strangely amused, watching my carefully curated bravado fight a losing battle with common sense. Because here’s a little secret not all of you know I USED TO WORK IN A FUCKING JAIL. That’s right, baby girl former insider now turned reluctant guest. If a single soul discovers this dirty little tidbit, I’ll instantly become inmate enemy number one, staring down a category 5 shitstorm with no lifeboat in sight.

But they never will find out, because despite my stunning incompetence at avoiding trouble, I'm spectacularly talented at bullshitting my way through chaos.

Okay, welly welly well, enough philosophizing. I suppose I should recount the tale of how my ass got arrested while it's still painfully fresh in my mind…

It’s Friday night, and my balls are humming with the kind of restless electricity you only get when you know you’re about to do something that’ll either make your life a legend or a cautionary tale they whisper to dumb tourists at Waikiki. Staying home in my villa yeah yeah, the one with sheets softer than most men’s character was never an option. You don’t pay for ocean views and Italian marble so you can sit around nursing your anxiety like some sad, beige accountant. No, you go out and remind the city who the real fucking animal is.

So I tell my girl to throw on the sexiest black dress she owns. She smiles at me, this feral, unhinged grin that says she’s either going to fuck me or get me arrested before sunrise either way, I’m hard. I pull on my Ralph Lauren button down, half unbuttoned to show God’s craftsmanship and my general disregard for public decency. Linen pants so white you could snort coke off ‘em, shoes that would get me stared at in half the bars on this island and maybe not let in for being too white, and that’s just the look. That’s before the scent, sweat, and that salty tang of “I might ruin your night, and you’ll still thank me.”

Honolulu at night is a hallucination in 4K. The air smells like sunscreen and crotch, the neon signs flicker like strippers winking from purgatory, and the street is clogged with vacationers who look like they just realized they can’t afford to leave. It is a human zoo and I feel like the zookeeper tonight. I watch men old, young, half dead wander the boulevard looking for something that won’t wake up next to them in the morning. You can feel the tension, this ambient sex and rage in the air. The kind of night where every woman is prettier, every man is more desperate, and every cop is two drunks away from giving up on law and order altogether.

We get to this Tiki bar one of those places where the drinks are overpriced and the only thing stickier than the floor is the bartender’s heavy hands. There’s a pool table, warped from decades of spilled beer and failed marriages, and a jukebox that only plays songs you’d hear during an awkward handjob in 1987. I grab my girl by the hips, pull her close, make a show of “teaching” her how to line up a shot at the pool table while everyone else in the bar tries to pretend they’re not jealous. She’s laughing, pressing her ass against me, and I’m thinking, “I hope nobody here has a working camera.”

And then the door opens, and the entire tone shifts. In walks the kind of trio that could clear a dive bar just by existing. A lesbian couple and their slave. First, there’s Butch a slab of lesbian gristle with a crew cut and shoulders like she’s been training for the female prison Olympics. Her face is a warning label, her arms could bench press a Vespa, and she’s scanning the bar for fresh meat or an excuse for manslaughter. Next to her is Leslie, the femme tiny, hot, and clearly the only one in this triangle who’s ever known the touch of a real man. She’s got this way of looking at you like she’s mentally cataloguing all the ways she could hurt you and then fuck your dad for the trauma. Behind them lumbers Tom the “friend.” He’s six foot four, built like a bouncer who failed the background check, and has the moist, hopeful look of a man who’s never gotten past third base with anyone who wasn’t holding a taser.

Now, I know I have a problem staring, but this is like watching a car crash orchestrated by horny demons. I’m locked in. Can’t stop. I’m trying to figure out which one of them is the real threat, which one is the bottom, and what Tom had to trade to get into this clown car of sexual frustration.

We keep playing pool, but Leslie keeps glancing over. Eventually she slinks up, voice dripping honey and napalm: “Hey, white boy, mind if I play the winner?” Her voice is a dare. I lean in, “Darling, you can watch all you want, but I play to win” She laughs, and it’s the kind of laugh that could get you both excommunicated. My girl nudges me and points out how Butch is now full on staring, jaw clenching, fists balling. I’m loving every second.

“Why don’t you and your friend take on me and my girl?” I say. Leslie shrugs, probably thinking about what it’d be like to leave Butch for a night. Naughty Leslie playing Jealous games I see. My girl is grinning, loving the chaos. And Butch is losing her mind, lips curled in a snarl, eyes screaming violence.

She stomps over, gets in my face, her breath hot and aggressive. Screaming “WHY ARE YOU HITTING ON MY GIRLFRIEND?” I just smile, cool as hell, vodka soda in hand, and say, “Sweetheart, she came up to me I think you should get a better handle on your bitch, I can’t help it” Leslie laughs. Butch looks like she’s going to rip my throat out and eat it raw. All the signs were there that something was going to happen but she looked funny staring up at me so angry and I had that fearless drunk wanting something to happen.

That’s when SHE PUNCHES ME RIGHT IN THE FUCKING NOSE. I get mad when my nose gets hurt. “OOOH BABY KISS ME AGAIN THAT FELT GOOD ”I say laughing. I start slapping my own face, yelling, “KISS ME AGAIN” I know I look nuts yelling this and slapping my face way harder than I should, but this is the best I could think of because I don’t believe in hitting women. I have a rager of a headache right now as I’m writing this. Everyone is staring. Leslie’s aroused, my girl’s mortified, Tom’s confused, and Butch is now screaming incoherently, I laugh, blow her a kiss, and say, “You punch like a vegan” (girl punches don’t hurt)

That’s Tom’s cue. He comes flying up to me, tries to be the hero, and gets so close I can taste every mistake he’s ever made. He’s got the breath of a dying alcoholic and the jawline of a man whose dad paid for all his abortions. “Back off, and leave them alone” he says, voice quivering. I smirk, “Touch me and I’ll break your fingers and shove them up your ass so you can finally feel what it’s like to be wanted.”

The room is melting down. Bouncers are moving. People are filming. For one perfect second, I feel truly alive bleeding, laughing, ready to ruin my future for the story. Then two Samoan bouncers built like refrigerators on steroids barrel in, and grab us like feral dogs, I hear one last “Fuck you!” from Butch.

And for legal reasons this is where we enter blackout zone and I don’t remember anything.

And that, kids, is how you go from villa to jail cell in under 4 hours. God bless America.

I am now half drunk and entering the Jail from a way I never have before.

Booking Welcome to the Zoo

Let me walk you through the kind of humiliation that only comes with being processed into the state’s favorite fuckhole where you go from demi god to government property in under fifteen minutes and nobody even pretends to care if you’re wearing designer underwear. First, the strip search. The most action I’ve gotten all weekend, and not even a happy ending to show for it. They herd you into a concrete room colder than a Minnesota Winter, tell you to drop your pants, and suddenly the word “bend over” takes on a whole new meaning for you. I’m standing there, bare assed, trying not to shiver because there’s nothing more emasculating than goosebumps during a cavity search. The guard let’s call him Officer COCO, because he had the bedside manner of a pissed off coconut that got cracked open looks me up and down like he’s seen better bodies in the morgue. “Any contraband?” he asks. “Just my hopes and dreams, officer,” I deadpan. He doesn’t laugh, but I do. If you can’t make yourself laugh while you’re naked in front of four Samoans and a camera, you’re already dead.

Shoelaces gone, belt confiscated, dignity missing in action. I’m handed a set of state issued clothing, a orange jumpsuit with all the comfort of sandpaper and the aroma of fifty years of processed meat. I’ve worn cum stained motel sheets that felt classier than this. They take your personal effects and dump them in a bin that looks like it last saw sunlight in the Reagan era. My beautiful wallet, my phone, even my pinky ring gone, locked away, while I’m left standing in a polyester onesie feeling like a toddler at the world’s most dangerous daycare.

Then comes the medical screening, which is a joke even by hospital standards. A nurse who looks like she’s one prescription away from a meltdown asks if I have any “suicidal ideation.” I tell her, “Only when I see people posting inspirational quotes on Instagram.” She writes something on her clipboard, probably ‘smartass double the sedatives.’ She asks if I’m on drugs. I look at her dead in the eye and say, “Only the purest dopamine and delusion.” She rolls her eyes. No one here appreciates honesty.

Then you’re marched yes, marched, like the world’s prettiest POW down a hallway that smells like bleach, mildew, and generational trauma. Every surface is either sticky or suspiciously slick, and I’m sandwiched between two Samoan tanks whose arms are thicker than my girls trust. We pass the holding cell a glass box full of men who look like extras from a Faces of Meth documentary. I catch my reflection and think, “You, sir, are too fucking pretty to be here.” I wink at myself. A meth head sees it and winks back. I hate drugs.

Then it’s photo time mugshot hour. “Face forward, don’t smile,” the bored technician tells me, like smiling would be the real crime. I try to channel my best Dorian Gray meets David Goggins, a combination of mythic beauty and dead eyed lunacy. I want this photo to haunt someone’s dreams. Click. “Next.”

Fingerprints each finger inked and rolled like they’re prepping me for the world’s most unwanted Tinder profile. I make a joke about my hands being too manicured for jail. Officer Sulu says, “You won’t need them much where you’re going.” Good one, Sulu.

Then it’s off to classification where they decide which box to throw you in based on your answers to questions nobody’s qualified to ask. “Any gang affiliation?” “Yeah. Writer’s Guild. We’re ruthless.” “Are you a flight risk?” “Only if the window’s open and an Indian is farting garlic on me.” “Any allergies?” “Authority and latex.” This guy doesn’t laugh at all. Tough crowd.

Now you wait. Jail is 90% waiting, 10% regretting, and 100% wondering which bodily fluid you’re currently sitting in. You sit on a bench so hard it could double as an execution device, surrounded by a crew of misfits that would terrify Stephen Kings nightmares. There’s Tiki, the toothless meth goblin shaped like a potato bag who’s convinced he’s a reincarnated king; Big Joe, who’s in for assaulting a guy over a parking spot; and some tweaker in the corner muttering about shadow people and eating his own scabs. The smell in here is so thick you could chew it. It’s a cocktail of BO, fear, and the faint scent of Taco Bell diarrhea.

I crack jokes because that’s all you have left. I ask the room if anyone’s here for being too good looking. Tiki grins and says, “You must be stupid, white boy.” I wink. “Arrested for defending beauty. Too G-Look for the streets.” Joe laughs. The tweaker doesn’t even look up. They ask what I did. I say, “Stared at the wrong lesbian, got punched by a girl, and made a straight man jealous. Basically, the American dream.” Big Joe gives me a fist bump. Tiki tells me not to drop the soap. I tell him I never wash my girl loves my natural scent. I get my phone call and tell my girl to post a note on my precious substack and tell you all I love you and to bail me out asap, should be monday or tuesday and this will be a nice meditative retreat for the weekend.

Eventually, I’m led into a cell my new home, my concrete chateau, my cockroach B&B. It’s hotter than Lucifers asshole, and the air is heavy with the moans and shrieks of men rediscovering that rock bottom is, in fact, a basement. I don’t even get a fucking bunk there are two other monsters in here with me and I am the last to join. I nestle up on the floor. The pillow is a rolled up towel that smells like every man who’s cried into it since 1993. I curl up in my jumpsuit, listening to the symphony of psychosis echoing through the night.

The toilet is stainless steel, bolted to the floor, with stains that look like modern art and a seat so cold it could castrate you on contact. There’s a drain in the middle of the room that occasionally gurgles out the secrets of past occupants. The walls are decorated in scrawl gang tags, phone numbers, phone numbers for lawyers, and the occasional philosophical gem like “Trust No Bitch” and “Life Sucks, Then You Marry One.” Deep.

I try to sleep, but the noise is relentless. Someone’s yelling about the government stealing his organs. Someone else is laughing at nothing. Roaches the size of iphones scuttle across the floor, bold as hell, as if daring you to flinch. One runs over my leg. I flinch. He wins.

I drift off to a fitful, nightmare plagued sleep, dreaming I’m back in my villa with my girl, except the sheets are made of paper towels and the ocean’s been replaced by the sound of a thousand men snoring and farting in chorus.

At some point in the night, I wake to a commotion two guys are fighting over a packet of ramen. I close my eyes and wish for sleep or, failing that, a decent cup of coffee. Neither comes.

By sunrise, I am a changed man filthier, funnier, and somehow even cockier than before. I rise from my slab, stretch like a panther, and announce to the cell, “Gentlemen, I survived. Who’s ready for day two in the zoo?”

Nobody laughs. But I do.

Because in this place, if you can’t laugh, you’re already dead.

Jail hacks, survival secrets, and existential revelations, straight from the concrete mouth of hell itself. You want to know how a beautiful bastard like me doesn’t just survive in here, but turns purgatory into performance art? You want the gospel of not losing your mind when you’re too alive, too pretty, too mythic for cages built by men with hairlines receding faster than their dignity?

Welly well your humble narrator will show you how Day handles the apocalypse one pencil nub, one cockroach, one near homicidal mood swing at a time.

The first night, I decide that if I can’t run the place, I’ll haunt it. You’ve got two choices when you’re thrown in the shit. you can break, or you can get weird enough that the universe gets nervous and backs away. So I claim my throne a piss-stained patch of concrete beneath a fluorescent bulb that flickers like God’s eyelid twitching from all the prayers He’s ignoring tonight. My roommate Tiki (zero teeth, ten felonies, a face only a mother could abort) hands me a sheet of legal pad so dirty it’s probably a biohazard. For a stale Pop Tart, I buy his pencil, short enough to make every stroke feel like I’m carving my sins into the Book of Life.

I start writing my novel, because there’s nothing else left to do but immortalize the madness, make art out of the rot. My first sentence “If you wake up in jail and you’re still good looking, the Devil hates you just a little more.”
The other inmates start circling like hyenas with diabetes. One guy wants in on the action he'll trade his mystery meat sandwich if I make him a legendary character. I look him dead in his lazy eye and promise, “In my story, you fuck your way out of jail using only charm and a toothbrush.” He grins, toothless. Pop Tarts for chapters, ramen for sex scenes, and a future in which I ghostwrite his suicide note if he gets denied parole. We’ve got a system. Jail is just prison with more haggling.

Jail Hacks Step one: be so insane, nobody tries you. If you’re too handsome, don’t make eye contact for too long unless you want a new boyfriend or a shiv in your liver or your eye I’ve seen both Step two: never eat the bologna. It’s not a metaphor. It’s a death wish for your asshole. Step three: give everyone a nickname before they give you one. Trust me, it’s a power move. Step four: laugh. Loud, unhinged, and too often. It terrifies the actual psychos and attracts the best stories. Step five: always sit with your back against the wall, your feet ready, your fists relaxed but not too relaxed.
Jail is a chess game, only the pieces are illiterate and horny.

I sleep with one eye open, one hand over my crotch, and a rolled up jumpsuit as a pillow. Cockroaches crawl over me, but I whisper Bible verses to them and hope for reincarnation as something with a trust fund. In the darkness, men moan, cry, curse. Someone’s laughing about a murder; someone else is weeping over a woman who already forgot his name. The toilet gurgles, the air is humid and ancient, and the whole place feels like a stomach that’s about to vomit. Don’t be piss shy you don’t have a choice in a cell with this many people and get used to holding your shit in because they will want to kill you if you think of going to the toilet while they are still in there.
At 3 a.m., a fight breaks out over a Pop Tart. I keep writing. I can see in the dark I have superpowers.

The truth hits if you want to keep your sanity in here, you have to treat every second like it’s stand up comedy for a hostile, half asleep crowd. I start telling stories some true, most invented about how I was arrested for being “too fucking beautiful for freedom.”
I get laughs. They ask for more. I give them what they want, and in return, they leave me the hell alone. Legend is currency. Insanity is armor.

But it’s in the silent hours, when nobody’s asking for a joke, that the real epiphanies hit. Why do I always end up here? Why does chaos have my number on speed dial? Why do I run headfirst into every storm like a dog chasing lightning?
Because I’m too alive for any cage. That’s the curse. When you burn too bright, you blind the guards, you scare the herd, you end up chained just to see if you’ll break.
But I don’t break. I mutate. I get smarter, crazier, funnier. Every time the world tries to corner me, I pull out a pen and start taking notes for my comeback.
When they take everything from you freedom, style, even your shoelaces all you’ve got left is your mind and your balls. You better use both. This is the moment where most men wilt, but I get this feral grin. With nothing to lose, you can plan anything. Revenge, reinvention, the next viral post that’ll make the free world gasp. Every man should be this naked, at least once. Nothing to hide, nothing to lose, just a brain full of blueprints and a pair of brass ones to make it real.

I stare at the concrete ceiling and imagine what I’ll do when I’m out how I’ll write the next chapter, how I’ll live like I can’t be killed, how I’ll make every sorry bastard who ever doubted me eat their words, raw, no salt.
When you’re too alive for a cage, the only way out is to become the storm they tried to lock away.

I’m gonna tell you something most men will never understand, no matter how many sunsets they Instagram or how many “Seize the Day” coffee mugs they own I am more free, right here in this cinderblock zoo, than ninety nine percent of the sad faced, screen glued zombies shuffling around in the outside world, pretending their routines are freedom just because they haven’t been fingerprinted. I am sitting in a cell that smells like a hooker’s armpit after a hurricane, writing this with a pencil so short it feels like I’m carving into stone with a chewed off tooth, and still still my mind is so free it’s making the rats nervous.

You could chain my hands, lock my ankles, strip me down, toss me into a room with nothing but cockroaches and existential dread, and I’d still find a way to make a joke and a plan and a piece of art. Most men are in a bigger prison than this and don’t even know it the prison of fake comfort, meaningless meetings, mortgages, traffic, inboxes full of “per my last email,” porn and junk food and hope that tomorrow will be different if they just keep shrinking themselves down for one more year.

Not me. Not ever. My freedom isn’t a place it’s a refusal. My freedom is that no man, no badge, no concrete, no fucking Samoan linebacker in corrections gear can reach into my skull and cage the part of me that laughs when the door slams. I can lose my shirt, my money, my MacBook, my villa, my Friday night, my pride, even my future but I will never lose the sickness, the holy madness, the wild little corner of my mind that won’t bow to anybody.

I swear, I love freedom more right now broken nosed, dirty, hungry than I ever did on the outside. Only in here do you realize how beautiful it is to be able to just walk where you want, eat what you want, touch who you want, even just to breathe air that doesn’t taste like mop water and failure. Freedom is a beauty so sharp it draws blood. That’s why I’ll live twice as hard when I’m out. That’s why I’ll remember every sunrise on the outside is a gift most men waste on autopilot. I will take every risk and laugh in the face of fear while I live this life.

So lock me up. Make your threats. Strip away every little comfort. You can put my body in a box, but you can’t touch the outlaw in my head. And when I’m out, I’ll kiss freedom like a lover I thought I’d lost, and I’ll live with the memory of this place branded into me the reminder that freedom isn’t a right, it’s a savage, holy privilege you have to fight for every day you’re alive.

The only thing that can ever truly cage you is forgetting how much you love your freedom.

And that, boys, is why I’ll never be tamed.

Even in this moment I am grateful to God.

And that, my friends, is the beginning of my hard reset the reason you’ll never forget my name, and why, when I’m out, the world’s going to pay the fuck attention.

I wrote much more in Jail pages of confession, confession, and lunacy that will leak out here in time, raw and unedited, like blood from a fresh split lip. But this is where this post ends and the next chapter, the actual reset, begins.
Because I am free now.
And the thing you learn in a cage whether it’s four walls and a locked door, or just the soft, numbing prison of your own comfort is that freedom isn’t a place, it’s a fucking decision. I wrote this plan on the piss wet floor of OCCC, with my knees aching, my head pounding, on a scrap of filthy legal pad paper traded from a toothless philosopher named Tiki. My pen was a chewed on pencil so sad it belonged in a hospice. And yet, this right here is where real life starts where there’s nothing but you, your pain, and your will to crawl out of it.

If you want to become immune not just numb, but truly immune to fear, boredom, mediocrity, the soft death of “fine,” this is where you start.
This isn’t some gentle “detox” you can put on your Instagram story and forget by Tuesday.
This isn’t a motivational circle jerk where everyone claps and nobody changes.
This is a fucking exorcism for your soul. Paid only, because freedom isn’t for freeloaders and comfort is the real enemy.

DO THIS WITH ME STARTING TODAY I WILL BE.

I am new now, whether the world likes it or not. You can be too. If you bounce back, you bounce back harder. You become a man people can’t ignore.

The Day 30-Day Reset (Jail Edition):
You want out of your cage? You want to actually change? Here’s the only blueprint you’ll ever need each day is a war, and if you don’t want it bad enough, don’t even start.