Betting the Impossible: 

The Perfect Plan That Wasn't:

I was given the opportunity not to be a doctor.

My parents didn’t have that choice. Growing up in India, they had two options: become a physician or become an engineer. They made sure my sister and I grew up differently. We were given the greatest privilege anyone can have: the freedom to choose what we wanted to do. Of course, even they were disappointed when I told them I wanted to become a professional gambler.

It was 2008, and I was in sixth grade. Wall Street had just caused the worst recession since the Great Depression. I watched the news and listened to the adults talk, but none of it made sense. How could a select few individuals have caused such widespread devastation? How could they have gambled so recklessly with the livelihoods of everyday people? And, above all, how could they have been so greedy?

These were supposed to be the smartest people in the world, and yet it seemed a middle schooler could find the fault in their logic. They had placed blind faith in models built on incorrect assumptions. What I couldn’t understand was why no one had stopped to ask how the models worked – or if they were even correct?

It was then, as a sixth grader, that I realized a simple truth about the world: people are terrified of looking foolish. If a ‘smart’ person tells you something, you’re expected to accept it as fact. Few dare to ask why, because most would rather be accepted and wrong than risk being right and ostracized. By concealing the flaws in their models under layers of math and financial wizardry, Wall Street had convinced themselves and the world that 2+2 = 5. After all, who was anyone to question the greatest minds in the world?

Apparently, me. I wrote my middle school research paper on collateralized debt obligations and the collapse of the global financial system. Don’t be fooled, though–it was terrible. I only passed because the teacher didn’t understand a word of it. However, that experience taught me what made me different: I wasn’t afraid to look foolish. I was willing to challenge the so-called “geniuses” and question the ideas everyone else took for granted.

My parents might have been disappointed that I wanted to join the largest casino in the world, but I knew then that I belonged on Wall Street. No other profession could leverage my skill set to have such a profound impact on the world.

The next decade of my life was carefully structured to prepare me for a career as a trader at an investment bank. I honed my math and science skills at a science and engineering high school and later attended an undergraduate business school. But I was wrong about what mattered most. My greatest asset wasn’t the technical skills I developed – it was the interactions and experiences I shared with the people I met along the way.

Meeting Miles obviously changed the trajectory of my life, but it was the others in the learning center who helped forge my mindset and beliefs. I had a front-row seat to how some of the smartest people in the country handled stress, faced adversity, and reacted to being wrong. These were highly analytical individuals, yet even in the face of overwhelming data they struggled to accept when they were incorrect. To them, it was more likely that the rules of mathematics had been violated than their hypothesis was flawed. Their identities were so deeply tied to their intelligence that admitting they were wrong felt like a shattering of their self-image.

These interactions shaped my view of people and the world, giving me a unique lens for processing information. I became convinced many widespread assumptions were flawed, but people were too afraid to challenge them. The thing about assumptions is they can hold true for 99.9% of scenarios yet still be false if .01% of the time something unexpected happens. The most striking examples during my college years were when interest rates and the price of oil went negative. For decades, business schools had drilled into students that zero was the lower bound – until suddenly, it wasn’t. Anyone who dared to question this beforehand would have been mocked, but they would have also been right.

People often rely on simplified paradigms to make sense of a chaotic and unpredictable world. Issues arise when they forget the limitations of these frameworks and begin building models on top of them. Over time, this cycle spirals out of control, and the original assumptions–along with their known limitations–are forgotten entirely. The result is a web of systems so intricate no single individual can decipher them, even though they are based upon flawed and incomplete foundations.

The complexity of the real world is unavoidable; the problem lies in our hubris. It is both naïve and arrogant to think we can model every outcome of a situation. There are simply too many variables and too many unknowns. Imagining a world different from today is challenging enough; accounting for every possible outcome within that world is impossible.

I wasn’t immune to this arrogance. A decade earlier, I had meticulously designed my life around becoming a top trader at an investment firm. I had unknowingly built a career plan on a foundation that couldn’t account for all the variables. I believed my skill set would create a mutually beneficial relationship with the institution, enabling me to influence real change. But, as with any model, my plan had its flaws. The real world is far more nuanced than a simulation, and I hadn’t accounted for the unpredictable forces–the people and environment–that would shape my experience. One such factor forced me to rethink everything. My childhood dream had come true, but was it turning into a nightmare?

Don't miss Part 3 - coming next Sunday!