RIP JR. WON’T VAN WINKLE

Not long ago, on a silent Tuesday in a small upstate New York town, nestled between a vape shop and a closed-down RadioShack, a man named Rip Van Winkle Jr. lived.

Unlike his namesake ancestor, who slept through the American Revolution (or at least dodged HOA dues for twenty years), Rip Jr. had a singular problem.

He could not sleep.

Not wouldn’t. Not shouldn’t. Couldn’t.

“I can’t sleep,” Rip muttered again at 3:17 am. The blue glow of his laptop reflected the twenty-two tabs open on his browser: “5 Foods That Cure Insomnia,” “Are You Secretly a Dolphin?” and “Melatonin Overdose – Myth or Miracle?” to name the first three.

He lived alone in a modest house surrounded by pine trees, conspiracy theorists, and a Starbucks with a drive-thru line longer than a CVS receipt. Rip worked as a freelance “Remote Productivity Consultant,” which meant he told people to close Slack sometimes and drank cold brew until his stomach trembled.

In truth, Rip wanted very little from life. A good nap. Maybe a goldfish. But mostly the nap.

And so, on that fated Tuesday, driven half-mad by another night of Twitter-induced insomnia, Rip decided to hike into the Catskill Mountains in search of silence, disconnection, and perhaps a legally questionable edible.

That’s when he found them.

They were men, probably. Or very lifelike animatronics. Dressed in powdered wigs and 18th-century waistcoats, these spectral fellows were gathered around a glowing punchbowl and playing what appeared to be vintage Wii Bowling.

“Are you... colonists?” Rip asked.

“We are the Founding Fathers of the United States of America,” said one with a suspicious Bluetooth earpiece. “And also... sleep influencers.”

“You’re what?”

“Sleep Influencers,” repeated a man who looked like George Washington and smelled like lavender. “We’ve come to warn you: sleep is dying. Sleep has become performative. Monetized. Measured in REM and posted on Fitbits.”

Rip blinked. “Did you just say 'performative'?”

Washington nodded solemnly. “They track their dreams. Post about them. Sell dream-based NFTs. We tried to intervene before. But the curse was already spreading.”

“What curse?”

“The Curse of the Eternal Wake,” Ben Franklin whispered dramatically, emerging from a beanbag chair.

Rip was offered tea brewed from a plant called caffeina insomnica and told it would give him “clarity.” After sipping it, his heart played Double-Dutch, and a voice echoed in his brain: “Awaken and never sleep again.”

Rip ran.

He didn’t stop running until he arrived home. But the tea had already done its work. He cleaned his entire house in 34 minutes.

He reorganized his cloud storage.

He started a podcast about the ethics of yogurt.

He joined six Discord servers and wrote a 200-tweet thread about the Federal Reserve---still, he did not sleep. A month passed. Then three. Then twelve. Rip tried everything: weighted blankets, sleep ASMR, chamomile bath bombs, a hypnotist named Gary, who smelled like onion dip, and even a sleep coach who charged $800 an hour to tell Rip to “just breathe.”

He installed blackout curtains that made his bedroom resemble a sensory deprivation tank and even wore a full-body adult swaddle suit that made him look like a burrito with abandonment issues.

He counted sheep. Then alpacas. Then existential dread. Nothing worked.

Meanwhile, the town below changed. People began spotting Rip as he sprinted across parking lots at 3 a.m., and talked about Alexander Hamilton’s microdosing habits.

Parents warned their children, “Don’t stay up too late or the Awake Man will get you!” Rip became folklore. Memes. A Joe Rogan guest.

The mayor tried to capitalize on his popularity by launching an annual “No-Sleep Festival,” complete with caffeine shots, silent discos, and a “Who Can Stay Awake the Longest?” competition.

Rip wandered into one by accident, muttered something about “Jefferson’s sleep journal,” and was carried off by a crowd of techno-hippies who thought he was channelling the Founders through his chakras.

One day, bleary-eyed and clutching a large mug labelled “Still Not Sleepy,” Rip wandered into the local library, where a historian named Dr. Lenora Quibble gave a talk on “The Evolution of American Rest.”

“Is it possible,” she mused, “that Rip Van Winkle was not a sleeper of decades, but a Waker?

A man caught in the surge of productivity obsession, lost in the tides of time without a moment’s rest?”

Unlike his forefather of yesteryear, “I KNEW IT!” Rip screamed. The crowd gasped. He stood atop a folding chair. “I am Rip Van Winkle the Younger! I haven’t slept since the Obama administration! I watched four presidential debates in one sitting! I remember when TikTok was just clock-based content!”

The lights flickered. Someone screamed. Dr. Quibble fainted. Rip fled once more, this time into the woods. Rip constructed a shelter from Kindle Fires and sleep masks in the wild. He meditated.

He screamed at owls. He recited lullabies backward. He started a religion called “Napsterism” based on sacred silence and discontinued MP3 players.

He tried to forget the Founding Fathers.

But he couldn’t. They haunted him, whispering constitutional amendments in his dreams that never came. He created a shrine of noise-cancelling headphones and diffusers. He wrote a 700-page e-book called The Declaration of Unconsciousness, but could not remember what it said. Then, one night, something shifted.

A raccoon brought him a package: inside was an eye mask and a single note: “Only the truly sleepless shall find sleep. Let go. Stop trying.” Rip sat down. Closed his eyes. And then...Nothing. Not darkness. Not sleeping. Just... waking.

Rip Van Winkle never slept again. But he did find peace in accepting wakefulness.

He roamed the earth like an insomniac monk, gently whispering, “You’re more than your

hustle” into the ears of stressed-out interns and Silicon Valley executives.

He gave TED Talks in dreamless states, where CEOs cried and finally went offline.

He was nominated for a Nobel Prize in Circadian Psychology but was disqualified for

winking at a judge too many times.

He became a myth. Meme. TikTok trend.

And in a Wi-Fi-free corner of the Catskills, his hut still stands.

In time, Rip began to wonder—had his ancestor truly “missed” anything by sleeping through the Revolution, or had he simply dodged twenty years of awkward conversations and overdue taxes?

And had Rip himself, wide awake through every streaming update, app redesign, viral dance challenge, and election cycle, not also missed something? His inbox was clean, his Fitbit maxed out, and he had thirty-seven drafted medium essays about the decline of civility—but no idea what season it was.

One slept too much. The other, not at all. Yet somehow, both Rips blinked at a world they no longer recognized.

It dawned on Rip Jr. that maybe missing the world wasn’t about how long you were gone, but how little you noticed while you were here.

He had once believed that staying informed, productive, and ever-ready was noble—heroic, even. But now he wasn’t sure if heroism had anything to do with reading 400 news articles a day or knowing how many steps John Adams allegedly walked in a powdered wig.

He chuckled at himself.

“All this effort,” he muttered, “and the squirrels still don’t care who I am.”

And maybe that was the point. Maybe everyone was just squirrels with smartphones—desperately trying to matter, to stay alert, to go viral before the forest took them back.

So, did it matter?

Did it matter if you complained? If you resisted the change? If you refused the nap out of stubborn pride, or begged the stars for rest and none came?

Rip didn’t know.

He only knew that some nights, under a cold moon and a warm blanket of forest sounds, he tried no more. Not to sleep. Not to stay awake. Just… to be.

And that, finally, was enough.

Somewhere, deep in the Catskills, his hut still stands. A structure made of silence and discarded smartwatches.

A sign above it reads: “Welcome, fellow 'Tireds.” You are not alone.”

And if you listen closely, through the wind and the Wi-Fi static, you might still hear the echo:

“I can’t sleep.”