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Jacob O'Brien

@jacobobrien

I write children's stories for adults and some other things. www.jacobobrien.ca https://medium.com/@jacob.obrien985

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16.06.2025
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Latest posts by Jacob O'Brien @jacobobrien

Ironically, no group comes across as being more desperate for money than rich people.

19.02.2026 18:42 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0
Preview
Norm Macdonald’s Moth Joke and the Cost of Optimizing Everything How one of the best jokes ever told reveals the hidden value of inefficiency.

Wrote a piece on #Medium about Norm's moth joke and why #AIcontent fails to connect with audiences.

medium.com/@jacob.obrie...

#comedy #creativity #AI #creativewriting #Mediumwriters

15.01.2026 18:38 πŸ‘ 2 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0
Preview
I Thought Small Talk Was a Waste of Time. Then I Bought Some Almonds. How a short conversation changed my perspective on weak social connections.

I forgot to mention I'm posting articles on Medium now for some reason. This is my first one.

medium.com/@jacob.obrie...

08.01.2026 22:54 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

2028 is going to be a great year for me. i know it's only 2026, but i'm pretty sure the next two years are going to be total crap. i am looking forward to 2028.

03.01.2026 22:30 πŸ‘ 1 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

Was happy to wake up this morning to see it is J. R. R. Tolkien's birthday today.
Then was immediately sad to learn that he's dead. He's been dead for a while.
Yet he still lives on in a way. I guess that's one of the benefits of being a writer. You get to keep living after you die.

03.01.2026 13:49 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

I read it this year, too, but did not enjoy it. Then again, I've always been too simple-minded to appreciate Bradbury.

Also, I disagree with those who say it is relevant today. Because if someone burned all the books today, there are still e-books. You can't burn those. They are on the internet.

01.01.2026 00:02 πŸ‘ 2 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

here are the things i learned in 2025:

-old ppl love Sprite

that is all

31.12.2025 23:43 πŸ‘ 1 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

This whole thread is just the best! Everyone's so funny! 🀣🀣🀣 Even the r-word guy who wasn't trying to be.

29.12.2025 13:29 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

Thank you!!

03.12.2025 00:48 πŸ‘ 1 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0
Preview
The Free Genie A former genie questions whether true freedom is attainable when he is forced to take on adult responsibilities.

Oh, also, this story technically isn't a WIP as of a few days ago. Here's the link if anyone wants to read the whole thing. I'm really proud of it. :)
www.jacobobrien.ca/post/the-fre...

01.12.2025 13:27 πŸ‘ 3 πŸ” 2 πŸ’¬ 1 πŸ“Œ 0
But being carefree, Gene realized, was not the same as being park-bench free. If he was being honest with himself, once he had acclimated to his new income, he wasn’t even sure he felt any freer at 45K a month than he had at 5K.
Because with his higher income came new, unexpected rules to follow. These weren’t the same kinds of rules that McGrady and Mindy had made him followβ€”and while nobody in particular was forcing him to follow these new rules, he felt compelled to follow them nonetheless. For example, he frequently interacted with other businessmen and felt an illogical need to prove he belonged among them by wearing the trendiest brands, schmoozing the right people, and constantly buying new phones. And he now had a public image to maintain. That was a new thing he could say he didn’t care for at all. It was all so horridly restricting.
One night, as Gene was contemplating his lack of freedom, he had an epiphany. β€œI must not be making enough money,” he told himself. β€œPerhaps if I were to make a million dollars. . .” He thought about how frequently his masters had wished for this sum of money. Perhaps they somehow knew this was the exact amount it took to achieve true freedom.
β€œYes,” he declared. β€œI must become a millionaire. Only then will I be free.”

But being carefree, Gene realized, was not the same as being park-bench free. If he was being honest with himself, once he had acclimated to his new income, he wasn’t even sure he felt any freer at 45K a month than he had at 5K. Because with his higher income came new, unexpected rules to follow. These weren’t the same kinds of rules that McGrady and Mindy had made him followβ€”and while nobody in particular was forcing him to follow these new rules, he felt compelled to follow them nonetheless. For example, he frequently interacted with other businessmen and felt an illogical need to prove he belonged among them by wearing the trendiest brands, schmoozing the right people, and constantly buying new phones. And he now had a public image to maintain. That was a new thing he could say he didn’t care for at all. It was all so horridly restricting. One night, as Gene was contemplating his lack of freedom, he had an epiphany. β€œI must not be making enough money,” he told himself. β€œPerhaps if I were to make a million dollars. . .” He thought about how frequently his masters had wished for this sum of money. Perhaps they somehow knew this was the exact amount it took to achieve true freedom. β€œYes,” he declared. β€œI must become a millionaire. Only then will I be free.”

In this snippet from "The Free Genie," Gene is nearing the point where he will realize that generating wealth does not equate to attaining freedom.
#WIPSnips #WritingCommunity #WriteSky #WritingPrompts

01.12.2025 13:23 πŸ‘ 22 πŸ” 3 πŸ’¬ 1 πŸ“Œ 0
Preview
The Free Genie A former genie questions whether true freedom is attainable when he is forced to take on adult responsibilities.

I think this is the best thing I've written in my life so far.
#writesky #writingcommunity #shortstories
www.jacobobrien.ca/post/the-fre...

29.11.2025 16:26 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

I don't have any #WIPSnips to share today, but I wanted to give thanks and express my appreciation for the organizer of this community and everyone who takes part.
And I'm Canadian, so I'm not even doing this because it's Thanksgiving--I'm just a really good person. πŸ˜‰

27.11.2025 15:08 πŸ‘ 15 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

ive said it before and ill say it again: more men need to read romance novels

26.11.2025 21:05 πŸ‘ 25 πŸ” 3 πŸ’¬ 0 πŸ“Œ 1

From where I sit, the first-person POV is definitely going to help people connect. I'm glad you didn't give up. 😸

26.11.2025 13:40 πŸ‘ 1 πŸ” 0 πŸ’¬ 1 πŸ“Œ 0

Thank you!

26.11.2025 13:34 πŸ‘ 1 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0
I stay up into the morning drinking extra-strong coffee and searching the internet for things like β€˜how to trick a good woman into marrying you.’ But all the advice assumes that you’ve already met a woman who likes you and have been dating her for a while. I can’t find any advice on how to get a complete stranger to marry a good-natured, dog-mouthed buffoon in a matter of months in order to win a hundred-thousand-dollar bet and avoid having your legs broken by a man who was simultaneously born and bred in China and Texas. It’s like no one else has ever been in my exact situation.

I scour the web all morning, but the only thing I learn is that the internet knows nothing about real, genuine love. Almost like it’s a cold, soulless system made up of a bunch of servers that couldn’t give a shit either way whether people are happy or not.

I stay up into the morning drinking extra-strong coffee and searching the internet for things like β€˜how to trick a good woman into marrying you.’ But all the advice assumes that you’ve already met a woman who likes you and have been dating her for a while. I can’t find any advice on how to get a complete stranger to marry a good-natured, dog-mouthed buffoon in a matter of months in order to win a hundred-thousand-dollar bet and avoid having your legs broken by a man who was simultaneously born and bred in China and Texas. It’s like no one else has ever been in my exact situation. I scour the web all morning, but the only thing I learn is that the internet knows nothing about real, genuine love. Almost like it’s a cold, soulless system made up of a bunch of servers that couldn’t give a shit either way whether people are happy or not.

In this #WIPSnips from "Dubble or Nothing," Ace realizes that his usual method for solving his problems--doing research on the internet--won't work for the problem he's currently facing.
#WritingCommunity #WriteSky #WritingPrompts

25.11.2025 13:05 πŸ‘ 27 πŸ” 2 πŸ’¬ 2 πŸ“Œ 0

Your snippets are always so good!

25.11.2025 12:54 πŸ‘ 3 πŸ” 0 πŸ’¬ 1 πŸ“Œ 0

You cannot be the richest man in the world and NOT be evil. You can't get there without being just the most awful piece of shit.

24.11.2025 16:00 πŸ‘ 288 πŸ” 19 πŸ’¬ 2 πŸ“Œ 2
Do you know what the odds are of losing a hand of Five Card Draw with a jack-high straight flush? It’s gotta be, like, 150,000-to-1 or something stupid.
I’ve never felt lucky. I’ve always suspected God created the universe just so he could fuck with me. But this bad beat takes it to a whole new level. Never have I been given such indisputable proof that the universe hates Ace Dubble.

Do you know what the odds are of losing a hand of Five Card Draw with a jack-high straight flush? It’s gotta be, like, 150,000-to-1 or something stupid. I’ve never felt lucky. I’ve always suspected God created the universe just so he could fuck with me. But this bad beat takes it to a whole new level. Never have I been given such indisputable proof that the universe hates Ace Dubble.

I went beyond global to the entire universe (twice). From my upcoming debut novel, "Dubble or Nothing."
#WIPSnips #WriteSky #WritingCommunity #WritingPrompts

23.11.2025 15:53 πŸ‘ 16 πŸ” 1 πŸ’¬ 0 πŸ“Œ 0

I love thinking (and reading) about this kind of stuff. Great snippet!

23.11.2025 15:43 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

I thought the same thing. 😊

23.11.2025 15:41 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

I haven’t lost my faith in humanity, I never had any to begin with.

23.11.2025 14:35 πŸ‘ 88 πŸ” 31 πŸ’¬ 3 πŸ“Œ 0

For every carefree, "Don't stress, things always work themselves out!" person there is at least one extremely anxious, detail-oriented, forward-thinking loved one or coworker who has spent years behind the scenes making sure things work out

22.11.2025 17:13 πŸ‘ 378 πŸ” 59 πŸ’¬ 14 πŸ“Œ 7

This is so powerful and raw. It made me feel.

22.11.2025 15:22 πŸ‘ 3 πŸ” 0 πŸ’¬ 1 πŸ“Œ 0

Sweet. I'm not sure what the impact will be on my amazon recs, but I'm definitely going to check it out. πŸ™‚

21.11.2025 17:30 πŸ‘ 1 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

Ooooh, looks so good! Can I have a slice? I'll have one of the rose ones, please. 😊

20.11.2025 14:18 πŸ‘ 1 πŸ” 0 πŸ’¬ 1 πŸ“Œ 0

So, I've never read erotica before, but I'm really curious about this. What's book one called, and is it available anywhere where I can check it out?

20.11.2025 13:23 πŸ‘ 2 πŸ” 0 πŸ’¬ 1 πŸ“Œ 0
Post image

Since being freed from his lamp, Gene the genie has been learning that being free isn't all it's cracked up to be.
#WIPSnips
#WriteSky
#WritingCommunity

20.11.2025 13:19 πŸ‘ 21 πŸ” 2 πŸ’¬ 0 πŸ“Œ 0

What a premise!

20.11.2025 13:15 πŸ‘ 1 πŸ” 0 πŸ’¬ 1 πŸ“Œ 0