AI Personalization Should Be More Than a Facebook Quiz

I notice a trend lately among people selling productivity and success type material. I define it as “We’re going to use AI to write you a personalized report or guide unique to you.”

But the execution doesn’t come out that way. In my two experiences with this so far, I’m presented with a series of questions with four or five pre-formatted answers. None of them match me exactly, so I choose the one that is least wrong. Then I get the “personalized” output, but it isn’t me at all. It’s a version of me based on the least wrong answer I had to give to the questions.

This results in forcing their framework onto me, when we have the technology to customize their framework for me but for whatever reason they don’t choose to do it this way. Then they want me to pay to get more information and “customization”, but why should I pay when the free material is wrong from the starting line?

We have the technology where I could give exact answers and the AI could customize their framework for me. I don’t understand why we’re not starting from this point. They may as well not use AI at all.

For instance, I tried one recently just to see what the output would be. One question asked where I wanted to live in five years. The least wrong answer was (not an exactly wording) “The house I currently live in, paid off and customized the way I want it.” OK, but why five years? What about seven or ten?

When it came to how much I owe on my house, I couldn’t provide the actual number for my mortgage balance. Based on the range, it decided I need to make $325,000 a year to achieve the life I want, but based on another least wrong answer, it says my self-limiting belief caps my income at $235,000 a year or within 10% of that number. I wish! Of course, it didn’t ask for my actual income. Then it generated a “customized” forward for me based on a well known author that I will not mention here. To see more, I have to pay, but if the forward and numbers we’re starting with are inaccurate they’re not getting money out of me for a “customized” book that isn’t me at all.

I ran this idea by ChatGPT. We concluded that they bolted AI onto their existing sales funnel. So rather than a truly customized product, what we got is essentially a 2011 “Which Star Wars Character Are You” Facebook quiz.

The frustrating part isn’t that the AI got me wrong. AI can only work with the information it’s given. The frustrating part is that the people building these products finally have technology capable of asking me what I actually think, understanding the answer, asking follow-up questions, and adapting their framework accordingly and they’re still giving me a multiple-choice quiz.
Don’t ask AI to write 20 pages explaining why Option C describes me. Let me tell the AI who I am.

Then we’ll see whether your framework actually fits.

My Theory On Why We Appear Stuck In 1999

I recently watched this video, which presents a theory that we’re stuck in 1999:

It says that in prior decades, they each had their own distinctive fashion, music, style, etc. But that all stopped with the 90s. If you watch a show like Emergency, you know it takes place in the 1970s. Magnum PI unmistakably takes place in the 1980s. But what about modern shows? Did it take place in 2007? 2013? 2024? There are few ways to tell. I can usually tell by the technology such as which phones the characters are using to narrow down the date range, but we’re listening to the same types of music and wearing the same clothes.

My theory isn’t a time loop. It’s the MBA and the financialization of business.

The MBA and Financialization of Business

The Master’s in Business Administration (MBA) emerged during the industrial era as businesses became larger and more complex and needed a professional class of managers. As we transitioned to a service economy, MBA programs proliferated and professional management spread throughout American institutions. I wouldn’t be surprised if cooking schools and flight schools also offered MBA programs.

As professional management became increasingly dominant in senior leadership, the way businesses thought about themselves changed. It was no longer about how do we provide value. It was about the shareholder and profit at any price. It was about EBITDA, Profit and Loss, growth, and pretty much anything other than creativity and service.

While there is nothing wrong with turning a profit, which no business can survive without, it’s how they frame the profit that causes the problem.

A Few Examples

Back in the 80s, Hollywood was effectively run by directors (they’ve always had studio executives), and the directors produced great movies. Now it is increasingly run through the same professional management mindset as other large corporations. The people making investment decisions don’t have to hate creativity; they just have to minimize risk. Rather than greenlighting the work of directors they believe can deliver, the safer bet is something that has already made money or resembles something currently making money for another studio.

Then there is private equity, which is also focused on making as much money as possible. This is where the financialization really comes in. They do Leveraged Buy Outs (LBOs) of businesses, then sell off whatever will make them money and leave what’s left of the business overloaded with the debt they used to purchase the business.

Look at Boeing. They used to be an engineering company that made exceptional and iconic American airplanes for military and civil purposes. Then in the 90s, McDonnell-Douglas bought them with their own money and started running the company off spreadsheets focused on how much value they could extract from it. While Boeing technically acquired McDonnell-Douglas, McDonnell-Douglas effectively took over Boeing’s culture. Now they can’t even design a new plane. The 737 MAX was the third update to an airframe designed in the 1960s, and with the end of its lifecycle coming up, they have nothing to replace it with. This is the difference between “we build extraordinary airplanes, and doing so profitably allows us to continue” and “we exist to maximize shareholder value, and airplanes are the mechanism by which we currently do it.”

The Heart of the Matter

This is a systems problem. Optimization narrows the solution space. Once everybody has the same spreadsheets, consultants, market research, KPIs, benchmarking, algorithms, and management education, everybody starts making approximately the same rational decisions. Nobody has to conspire to make culture homogeneous. Homogeneity emerges from everyone optimizing against similar metrics.

If ten companies independently ask, “What should we create?” they may arrive at ten different answers. If all ten ask, “What does the data show has the highest probability of delivering an acceptable return?” they are much more likely to arrive at the same answer. Each decision can be perfectly rational on its own while the aggregate result is cultural stagnation and somehow I still don’t have a flying car, can’t go to the Moon for lunch, and can’t afford a weekend in orbit.

No wonder people are starting to ask whether we’re living in The Matrix. Appropriately enough, that movie came out in 1999.

Though this is grossly oversimplified, we can summarize it as we didn’t get stuck in 1999 because people suddenly stopped being creative. We built institutions that systematically reward exploitation of proven value more reliably than creation of new value.

Perhaps the fundamental problem, then, isn’t profit at all. It’s what happens when something that should be a means becomes the end.

For the love of money is a root of all kinds of evils.

The Holy Bible: English Standard Version (1 Ti 6:10). (2025). Crossway Bibles.

Analysis of Kafka’s The Trial

I decided to finally read Franz Kafka’s book The Trial. I’ve heard of this book throughout my life. There is even an affect named after it: Kafkaesque. This is when a process makes no sense but takes on a life of its own. Having experienced this many times in my own life, I’ve developed my own business philosophy: the process exists to serve us, we do not exist to serve the process.

I won’t comment much about the book itself; I want to explore the system. The Trial is a story about a man named Joseph K. It often just describes him as K. K is about 30 years old and is Chief Financial Officer at a bank. It begins in his boarding house where people show up in the morning telling him he is under arrest. They keep him detained in his room. He talks with the guards. Then somebody shows up to interrogate him and when that is complete, they release him to go to work late.

Through the rest of the book, we get details about the system, but at no point do we learn what the charge is. K encounters people who are part of the system or confidants of it. He encounters people who are also going through trials. His uncle encourages him to get a lawyer and knows a lawyer who works through this system. He even encounters a priest who serves this system as prison chaplain.

The mysterious court system has offices in the attic of an apartment building and holds hearings in the apartments of employees. There are higher courts also, although K never makes it out of the lower court. His verdict is rendered at the end of the book but I won’t spoil it.

I can’t say I enjoyed the book or that I will read more of Kafka’s works. Kafka was a secular Jew living in Prague. He died in 1925 with The Trial unfinished. At the end of the book, they include some incomplete chapters as fragments. I read them hoping for more context, but the only interesting thing was a chapter where K refused to go to any more events related to his trial.

At a 21st Century American, while reading the book I kept wanting to scream “What is the charge?” We are never told. K never asks. That blows my mind. But having spent my life within large organizations, I’ve seen where people just endure a non-sensical system because “that’s the way things have always been” rather than question ‘Why the Hell do we do things this way?” I’ve found asking that question makes people uncomfortable. Some even get offended. That may be why Kafka never lets either the reader or Joseph K. ask the obvious question “What is this court and where does its legitimacy come from?”. That omission is so deliberate that I suspect it’s the point.

I don’t know what Kafka wanted me to get from this book, but I take it as an example of bureaucratic systems that have lives of their own and trap people within them. As an example: Years ago I tried to change my employer life insurance beneficiary after getting remarried. The office repeatedly rejected the same form for trivial reasons: a crease, an ink smudge, even an updated revision date. The purpose of the process was to change a beneficiary, yet the process itself became the object being protected. It wasn’t serving the mission anymore. The mission had become serving the paperwork.

Or consider the military. The flag officer says “I want everybody assembled at 1200.” The senior officer says “Get everybody here by 1130.” By the time the order gets to the lower NCO, you’re showing up at 0400 and sitting around for 8 hours because each layer of the chain of command builds another layer of cushion into the schedule.

Reading The Trial left me with one question that extends far beyond the novel: What systems in my own life have I stopped questioning simply because everyone around me accepts them? Every organization needs procedures. The danger begins when the procedure forgets its purpose. The process exists to serve people. People do not exist to serve the process.

The best stories are based on the Hero’s Journey frequently referenced to Joseph Campbell. There is no Hero’s Journey in The Trial. Joseph K. does not experience growth. He learns nothing. Sometimes this can be a useful way to write a book. In the book “Options” by Fake Steve Jobs (Dan Lyons), the Steve Jobs caricature doesn’t experience growth or learn anything, but that was by design. Why would a parody of such an iconic character need to learn anything? But in life, and in literature reflective of life, growth is part of the process. We all grow, however unintentionally. I used to facetiously set a single “New Year’s Resolution” every year: I resolve to keep doing everything the exact same way I did it last year. I know it was impossible to keep because through the process of growth, things would change over the course of the year.

Final thought: perhaps we should take The Trial as an example of dystopia. K. is never given a charge because he has come under the attention of a mindless system that is going to put the screws to him no matter what. What systems in our lives perform the same way?

If you’re interested in The Trial, you can buy it from my affiliate link below:

https://amzn.to/4iQAOuQ

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