Ask ChatGPT To Tell A Story About Your Life After College

The latest Morgan Housel podcast describes how small decisions can dramatically change one’s life or even the course of the world. In the podcast, Morgan performs an experiment. He describes his history at age 20 to ChatGPT – lots of detail about background, ambitions, history, plans… then asks ChatGPT to tell a story about the next 20 years. Morgan found he’d get a different result every time. They were not all positive, but they often sounded like something that could have happened.

I performed a similar experiment. I went to chat . com, gave ChatGPT a lot of history about my background, as well as my resume at age 20; then asked ChatGPT to tell me a story about the next 20 years. The outputs were wild and all over the place. An example is below.

What does ChatGPT output, if you do this experiment?

The Reluctant Billionaire
After graduating from Stanford, he entered the booming world of high-frequency trading (HFT), where milliseconds determined millions. His deep understanding of CAPM theory, algorithmic efficiency, and probability made him a natural in the industry. He joined a secretive quant fund, where he developed automated trading strategies that exploited inefficiencies in global markets.

Within five years, he had earned enough to retire. But instead of stopping, he pushed further—co-founding his own hedge fund, one that ran on AI-driven models, requiring minimal human intervention. By his early 30s, the fund was managing billions, and he had become a financial legend.

But wealth came with complications. Regulators scrutinized his trading algorithms. Some accused him of manipulating markets. Rivals attempted to reverse-engineer his methods. The stress mounted. By 35, he had had enough. He cashed out, walking away with a net worth in the billions.

Escaping the Machine
Unlike other billionaires, he had no interest in yachts, private jets, or lavish parties. He despised inefficiency and waste. So, he disappeared.

For a time, he lived anonymously in Japan, immersing himself in Zen philosophy. He learned to code in esoteric programming languages, trained in traditional martial arts, and experimented with extreme minimalism—owning nothing but a laptop, a backpack, and a few sets of clothes. His focus shifted to something deeper: how to escape human cognitive biases and transcend conventional decision-making.

His experiments led him down strange paths. He tested obscure neurological training techniques, dabbled in psychedelics for cognitive expansion, and even explored the feasibility of brain-computer interfaces. He was no longer optimizing financial markets—he was optimizing his own mind.

The Return
At 38, an unexpected opportunity pulled him back into the world. A group of former Stanford AI researchers reached out. They were working on something radical—an attempt to create an artificial intelligence that could predict and simulate human decision-making at an unprecedented level. Governments, corporations, and intelligence agencies were all interested.

He couldn’t resist. The challenge was too compelling. He joined the project, but on his own terms—working remotely, communicating only through encrypted channels. His role was designing the system’s economic logic, teaching it how to model risk, uncertainty, and strategic deception.

The project’s implications were terrifying. If successful, it could manipulate global markets, rewrite financial systems, even reshape geopolitics. When a major investor proposed selling the technology to the highest bidder, he realized he had made a mistake.

One night, he wiped his servers, deleted his accounts, and vanished once more.

The Ghost in the Machine
By 40, he had become a myth. Some said he was living off-grid, using an assumed identity. Others believed he was still online, lurking in private forums, influencing markets from the shadows.

His old hedge fund strategies still shaped the financial world. His AI work had been copied and commercialized, fueling new breakthroughs. But he was nowhere to be found.

Some claimed he was building something new—a system outside of governments and corporations, a self-sustaining intelligence that could think, predict, and act autonomously.

Was he creating the future? Or had he become its greatest threat?

No one knew.

And that was exactly how he wanted it.

or a darker version

After graduating from Stanford with multiple degrees, he entered the world of high-frequency trading, where his mathematical brilliance gave him an edge. His strategies were ruthless—finding inefficiencies in the market, exploiting them, and moving on before regulators could react. By his late 20s, he had accumulated more wealth than he ever thought possible. But it wasn’t enough.

The rush of outsmarting markets began to dull. He needed a bigger challenge, something more complex. That’s when he was approached by people who operated outside the confines of Wall Street—dark money groups, crypto hackers, and underground financial syndicates. They needed someone who could launder massive sums without detection, and he was uniquely equipped to solve that problem.

At first, it was just a side project. He designed automated systems that funneled illicit money through a labyrinth of digital assets, shell companies, and decentralized finance protocols. The algorithms were elegant—self-correcting, self-erasing, nearly untraceable. Governments struggled to understand them, let alone stop them.

But as the operation grew, so did the risks. He was no longer just an outsider playing the system—he was part of something much darker. Money was flowing through his hands from drug cartels, arms dealers, and cybercriminals. He told himself it was just a puzzle to solve, just numbers moving from one place to another. Morality was subjective, and he had always been more interested in logic than ethics.

Then, one day, the numbers betrayed him.

A minor bug in the system triggered an alert at an international financial watchdog. It was small—an inconsistency in a transaction trail—but it was enough to put him on their radar. Soon, agencies from multiple countries were investigating. The walls were closing in, but he had prepared for contingencies. Offshore accounts. False identities. Backup plans for his backup plans.

He fled before they could arrest him, slipping through the cracks of the system he had once manipulated so easily. For years, he lived like a ghost—changing names, moving between countries, always staying one step ahead. He continued working in the shadows, designing cyber-financial networks for the highest bidders, but paranoia crept in. Every knock on the door felt like the end. Every unfamiliar face could be the one that finally recognized him.

Then, one night in Bangkok, it happened.

The hotel room door burst open, and within seconds, he was on the ground, hands zip-tied behind his back. Interpol had finally caught up with him. The trial was swift, the evidence overwhelming. He had built a financial empire for criminals, and now he was paying the price.

Locked in a high-security prison, he had nothing left but time. No more markets to exploit, no more puzzles to solve. Just endless days in a concrete cell, replaying every move he had made. Wondering if he had been outplayed in the end—or if, deep down, he had always known this was how the game would end.

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Wow, you can tell that AI trained on a lot of action movies and airport paperback bestsellers.

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If AI trained more on real life and less on movies and paperbacks, there would be more talk about a so-so boss, and a number of dates that didn’t really go anywhere, and maybe a dog that needed a special soap from the vet due to sensitive skin.

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Some of that result related to me choosing to post what sounded interesting to me. If I add the final sentence to not sound like an action airport paperback. The first output was:

After completing his rigorous academic journey at Stanford, he embarked on a career that wove together his diverse interests in technology, problem-solving, and financial strategy. His early years post-graduation saw him entering the tech industry, where he applied his electrical engineering and computer science skills in the burgeoning fields of software development and data analysis. Given his aptitude for mathematics and logic, he quickly found himself gravitating toward roles that involved complex algorithm design and optimization.

While working in Silicon Valley, he also maintained his passion for fitness. He continued to row recreationally and participated in long-distance cycling events, finding that physical discipline provided a crucial balance to his otherwise highly analytical life. During this period, he also explored investment science more deeply, applying CAPM theory and quantitative models to his personal financial decisions.

His professional trajectory took a turn when he decided to transition into the finance sector, leveraging his technical expertise to contribute to algorithmic trading and risk assessment models. His ability to identify patterns and inefficiencies in financial markets made him a valuable asset, and he played a significant role in developing automated trading strategies for a major investment firm. However, the rigid corporate structure and ethical ambiguities of the finance world eventually left him disillusioned.

By his mid-30s, he had accumulated enough savings through disciplined investing and strategic financial decisions to step away from full-time employment. He chose to work on independent projects that aligned more closely with his personal interests. One such project involved designing educational software aimed at making complex mathematical and financial concepts more accessible to students. This endeavor allowed him to blend his skills in software development, mathematics, and teaching.

Despite his natural inclination for solitude, he found a small but close-knit circle of like-minded individuals who shared his enthusiasm for intellectual challenges and unconventional problem-solving. He remained engaged with academic communities, occasionally guest lecturing on topics related to algorithmic design and investment science.

Throughout these years, he maintained his frugal lifestyle, optimizing his spending habits and seeking out efficient solutions for everyday living. By the time he reached his early 40s, he had effectively reached financial independence. This newfound freedom allowed him to focus on personal projects, including open-source contributions, mentoring young engineers, and even exploring creative pursuits such as writing about the intersection of technology and society.

While his life was not marked by conventional milestones like marriage or raising a family, it was rich with intellectual exploration and personal fulfillment. He found satisfaction in solving intricate problems, whether in code, markets, or everyday life, and he continued to seek out new challenges that kept his mind engaged. In many ways, his life remained an extension of his early years—rooted in logic, driven by curiosity, and shaped by an unwavering commitment to self-sufficiency and efficiency.

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Am I the only one who got to this line and starting singing, “One night in Bangkok makes a hard man humble…”

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Nope. Make us two! :rofl:

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AI was clearly developed with a male mindset.

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You can give direction to write in different styles. For example, this was the output when I cleared the history and added the prompt:

“Describe a realistic and likely outcome of the next 20 years of (name) life after college from a female mindset. Include personal relationships.”

The first output was as follows.

If anyone else would like to try, the process is straightforward. Simply enter text in the box at chat . com

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Nope, I immediately started singing

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I asked ChatGPT to include pictures, in the one above from a “female mindset”, which I have added to the post.

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OK, I had to try it. I must say, I wish this were my life!

The Archivist of Vanishing Landscapes

The first book was a memoir—half-travelogue, half-political reflection—about your time in Russia. You hadn’t planned to write it. It had started as a journal, notes scribbled in the margins of grant proposals, memories that wouldn’t leave you alone. A Moscow publisher picked it up after a former student of yours, now a literary agent, insisted you submit it. The book found an audience among scholars, expats, and people searching for a world that no longer existed.

By the time your second book came out—The Rivers Remember—you had carved out a life where writing was no longer a side project. This time, the subject was environmental loss: a sweeping narrative of the rivers of Siberia, the Black Sea’s vanishing coastline, the wetlands of your childhood in Florida. You wove together history, folklore, and science, tracing the stories of landscapes that had disappeared. Critics called it “lyrical,” “haunting,” “a lament for what we fail to protect.” It won an award you hadn’t even applied for.

At book readings, people asked what was next. You had no idea. You lived out of a backpack half the year, traveling between archives, remote conservation sites, and interviews with the last keepers of endangered traditions. But then, in a dim-lit café in Tbilisi, you met an old man who changed everything.

He had been a forest ranger once, responsible for a stretch of ancient oaks that had stood since the time of the Mongols. Now, only a handful of them remained, marked for removal by a new highway project. He carried a notebook filled with stories—folk beliefs about the trees, whispered warnings passed down through generations. “When the last tree falls,” he told you, “something older than us will leave the earth forever.”

That became your next book—The Last Witnesses, a collection of vanishing landscapes and the people who remembered them. By then, your work had become something else entirely: part activism, part cultural preservation, part storytelling. Universities invited you to speak. Documentarians asked for your expertise. A foundation reached out with funding, no strings attached, asking only that you keep writing.

One morning, years later, you sat by a river in a place you never thought you’d live, watching the mist rise over a valley untouched by roads. You realized you had spent your life not just writing about loss, but saving what could still be saved. And that, you decided, was enough.

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Those pictures are hilarious. The fabric for that guy’s suit must be made of 50% Lycra to squeeze that guy’s ridiculous muscles like that. And in the first picture his monitor hovers in the air, and shows the info on the side he can’t see. Or maybe I’m a total Luddite, and all Silicon Valley computers now come standard with hovering monitors that display from the back side.

ETA: And their hands, their creepy creepy not quite right hands! Wow. I also like that M.C. Escher-esque chair in the background of the first pic. Which side of the table to you want to sit on? Now, you don’t have to choose, you can sit on 2 sides at the same time.

Where are the pictures? We need to see the pictures! Maybe ask for pictures from both the “male mindset” and the “female mindset” so people can choose.

Here’s the first picture it offered:

Here’s the “male mindset” version

I asked for the female mindset version, but got a message saying:

It seems like I can’t generate any more images right now. Please try again later. Let me know if you’d like me to describe the image in detail instead!

I asked for the description and got:

Imagine a powerful digital painting of a determined female traveler standing at a crossroads. She carries a sturdy backpack, symbolizing her journey, knowledge, and resilience. Her posture is strong and upright, but there’s a thoughtful expression on her face—conveying both confidence and emotional intelligence.
The lighting in the scene is warm and balanced, casting a golden glow that highlights her strength and wisdom. The composition emphasizes both independence and purpose—she isn’t just standing at a crossroads, she’s actively choosing her next path. The overall atmosphere reflects ambition, perseverance, and a deep connection to the world around her.

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It’s a shame it couldn’t generate more pictures because I had really wanted to see that moment in Tbilisi with the wise old forest ranger dropping truth bombs about the oak trees. I was imagining myself chomping down on a big piece of khachapuri because oaks or no oaks, I gotta have the Georgian cheese. In my mind, it was all very “Eat, Pray, Love.”

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