Life Lessons

The year is 2025. I’m turning 40 soon, sitting in a cramped 450-square-foot apartment with thin walls, $50,000 in credit card debt, and a credit score of 646. My financial worth: $100 in liquid assets. My net worth: deeply negative. Five years ago, I was worth over $7 million. This isn’t a story about market crashes or economic downturns. This is a story about human fallibility—specifically, mine. If you’re looking for a cautionary tale about greed, overconfidence, and the psychological pitfalls of sudden wealth, welcome. I’ve lived it all so you don’t have to.

Reflecting on the landscape of my past mistakes, I’ve noticed a consistent pattern: moments when my ego seized the controls and steered me off course. The abstract concept of “staying humble” sounds straightforward until we’re faced with real-world situations that challenge our self-image. Only when something valuable slips away do we fully grasp what humility might have preserved.

Winter has never been my preferred season. Despite growing up in a region characterized by significant cold weather, I haven’t developed any particular resilience to winter’s challenges compared to others. Yet I’ve come to recognize the value in the complete seasonal cycle and make deliberate efforts to find meaningful engagement with winter’s unique qualities, even while acknowledging my natural preference for warmer months.

Reflections on the Journey to Self-Understanding # When I look back on my life’s journey, I’ve encountered numerous learning opportunities through mistakes and missteps—some more significant than others. One pattern I’ve recognized in retrospect is how during my younger years (particularly my 20s and early 30s), I allowed my sense of self-importance to expand beyond what served me well. This reflection serves as a letter to my younger self, containing insights I wish I had embraced earlier.

Beyond the Cautionary Tale: Survivorship Bias as Strategic Insight # Survivorship bias—our tendency to focus on successful outcomes while overlooking failures—typically enters conversations as a cautionary note. We’ve all witnessed this dynamic: someone celebrates a remarkable success story, only to have another person interject with the observation that “that’s just survivorship bias,” effectively suggesting we should discount the achievement as statistical noise rather than meaningful evidence.

One of the most valuable insights we eventually encounter as we mature is that correctness alone rarely determines our impact or success. What often matters more profoundly are our relationships, timing, and how our ideas are perceived and received by others. This perspective has been developing in my thinking for some time, and I find that storytelling offers the clearest way to explore this nuanced understanding of how influence actually works.