Jason Dookeran
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shortdropstt.bsky.social
Jason Dookeran
@shortdropstt.bsky.social
Travel and Tech freelance writer, hobbyist game developer, and a fan of treating people like people.
https://beacons.ai/jdookeran
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Hello new followers! I'm Jason.
Professionally, I'm a writer, working on travel writing, tech writing, content for law firms and AI/ML writing.
For fun, I collect board games, play TTRPGs, OPTCG, and program.
I'm a Indie gamedev with a few projects on hold.
Thanks for following!
I love when a project starts with, “We don’t really have documentation… we have some notes somewhere.”

It’s like being handed a treasure map drawn by someone who was actively being chased by wolves.
November 13, 2025 at 1:24 PM
Checklists don’t make good memories.
The best stories I’ve brought home came from slowing down, not speeding through.
My new piece: Slow Travel for People Who Hate Lists
jdookeran.medium.com/slow-travel-...
I wrote this for people who believe in slow travel and sustainable tourism more than lists.
Slow Travel For People Who Hate Lists
“Here’s Ten Things You Should Do In <Insert Place Here>”
jdookeran.medium.com
September 4, 2025 at 1:55 PM
Founders don’t usually lack ideas. They struggle with how those ideas come across. I help refine that #voice so the best thinking gets heard. I’m opening space to work with one or two #founders this month. Reach out if that’s you.
August 18, 2025 at 4:00 PM
www.patreon.com/posts/no-one...

Here's some fun writing, if you're into noir fiction. And yes, the entire thing so far is free.
#writing #fiction #caribbeanwriter #noirfiction
No One Dies in Tobago Chapter XV | JD Writes
Get more from JD Writes on Patreon
www.patreon.com
August 18, 2025 at 12:04 PM
Founder content math: every hour writing is an hour not spent on product, customers, or fixing fires. You know it builds credibility, but time always loses. Push it to nights/weekends & it never happens. #startups #founderlife #contentmarketing #buildinpublic thechain.substack.com/p/the-founde...
The Founder's Bandwidth Bottleneck
You just can't do everything
thechain.substack.com
August 13, 2025 at 4:48 PM
"Emancipate yourself from mental slavery, none but ourselves can free our minds."
Happy Emancipation Day.
#history #culture
August 1, 2025 at 11:40 AM
A metal man holding up a tree in Recoleta, Buenos Aires. The cool part?the guy is welded out of scrap metal parts. And he actually has the weight of the tree on his shoulders! #photography #buenosaires #travel #dailyinspiration
July 30, 2025 at 11:24 AM
Clear water, smooth stones, and the kind of quiet that feels earned. Can you guess where this is?

#Trinidad #DailyInspiration #Photography #ForestScenes #RiverMood #Travel #TravelPhotography
June 18, 2025 at 1:25 PM
Quiet palms along the Ortoire River mouth by the Atlantic. Manzanilla named for manchineel’s ‘small apples’. Be careful though. The Manchineel will kill you. #dailyinspiration #travelphotography #CaribbeanVibes
June 10, 2025 at 3:40 PM
Bacolet, Tobago. Shade, sea, and not much else. Which is exactly the point.

#Tobago #Bacolet #DailyInspiration #Photography #CoastalCalm #travel #travelphotography #beachphoto
June 4, 2025 at 3:08 PM
Shark Hole, Barbados. No sharks, just a carved-out cove with calm water and coral cliffs. Easy to miss, but so worth the detour!

#Barbados #SharkHole #DailyInspiration #Photography #HiddenSpots
June 3, 2025 at 11:45 AM
A driveway near Parlatuvier, Tobago. Just morning light, moss on concrete, and no reason to rush anywhere.

#Tobago #DailyInspiration #Photography #IslandScenes #CaribbeanMood #travelwriter #travel
June 2, 2025 at 10:44 AM
El Misti over Arequipa. It hasn’t erupted in centuries, but it’s still active. Looks calm now.

#Arequipa #DailyInspiration #Misti #Peru #PhotographyNotes
June 1, 2025 at 11:32 AM
Midday at Huaca Pucllana. You take a short walk and end up face to face with a pyramid in the middle of Lima. No fanfare, just bricks and time.

#Lima #HuacaPucllana #DailyInspiration #CityLayers #PhotographyNotes #travel #travelphotography #photography
May 30, 2025 at 10:09 AM
Huacachina, Peru. A palm-lined oasis in the middle of the sand. Everyone’s here for the dunes, but this quiet moment was the better view.

#Huacachina #Peru #DailyInspiration #Photography #DesertOasis #TravelNotes #TravelWriter #TravelBlogger
May 29, 2025 at 2:31 PM
Home is where you make it. In less than two months, I'll be making somewhere else home. But then I'll miss shots like these.
#trinidadandtobago #trinidad #carnival #costume #dailyinspiration
May 28, 2025 at 2:19 PM
A quiet fountain in Cusco, Peru. Stopped because I saw alpacas. Even the stone ones have presence.

#Cusco #AlpacasAreMajestic #DailyInspiration #StreetScenes #TravelNotes #Travel #Photography
May 26, 2025 at 1:21 PM
Somewhere before Salkantay Pass. The air felt thin, the sky felt heavy, and I stopped pretending the mountain owed me anything.

#Salkantay #Peru #DailyInspiration #MountainPhotography #TrekkingNotes #Travel #SeeTheWorld
May 24, 2025 at 10:11 PM
Lima stays grey more often than not. But in Comandante Espinar, early enough in the day, there’s a kind of calm that makes the color stand out. You just have to look for it.

#Lima #DailyInspiration #ComandanteEspinar #UrbanPhotography #CityDetails
May 23, 2025 at 2:00 PM
Dead fan, sticky heat, one napkin he cannot ignore. Room 203 keeps whispering. Chapter III of No One Dies in Tobago just dropped on Patreon.
www.patreon.com/JDWritesTT
#Mystery #CrimeFiction #Caribbean #Noir #IndieAuthor #Reading
May 23, 2025 at 10:47 AM
Maracas Lookout, Trinidad. That stretch before the descent, where the sea pulls your attention and the trees frame the edge just right.

#Trinidad #DailyInspiration #Photography #MaracasLookout #IslandViews #CoastalFrame #Travel #TravelPhotography
May 23, 2025 at 10:42 AM
Passed the old Usine Ste. Madeleine stack today and felt the whole sugar story press in, factories gone quiet, ghosts still loud. Full reel on how King Sugar reshaped our islands and us. Read on if you’re ready to hear the echoes.
shortdropstt.net
#Caribbean #Sugar #History #HistoryWednesdays
May 22, 2025 at 11:35 AM
Valencia River, Trinidad. A quiet bend in the trail, filtered light, everything green and gold. You don’t plan these shots — you just catch them.

#Trinidad #ValenciaRiver #DailyInspiration #Photography #NatureScenes #HikingViews
May 22, 2025 at 10:28 AM
A crumpled napkin. A number that won’t let Sten forget.
Chapter III of No One Dies in Tobago just dropped on Patreon, come see why 203 changes everything.
www.patreon.com/JDWritesTT

#Mystery #CrimeFiction #Caribbean #Tobago #Noir #IndieAuthor
May 22, 2025 at 10:08 AM
That’s not a storm, just a sky with too many ideas. Shot this off the coast of St. Lucia.

#StLucia #DailyInspiration #Photography #CaribbeanCoast #TravelNotes #Travel #Water #TravelPhotography
May 21, 2025 at 11:09 AM