Decision-Making

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.

We often must judge others, such as when hiring, choosing who to work with, or selecting friends and partners. I find that there are two attributes most desirable in people I associate with: authenticity and intelligence. There are two simple heuristics for detecting inauthentic people and genuinely smart ones, which I’ll outline below.

Survivorship bias often gets discussed as a cautionary tale. For example, someone might point out a person’s or company’s success, and another will retort with, “But that’s just survivorship bias!” What’s rarely discussed is how to internalize survivorship bias in an actionable way. If you know that most success stories (whether in business, investing, dating, or even the actual lottery) are primarily the result of luck rather than skill, how can you use this information to your advantage?

In Daniel Kahneman’s influential book Thinking, Fast and Slow, he presents a compelling model of how our minds work: we have two distinct systems for thinking. System 1 operates automatically, quickly, with little effort and no sense of voluntary control. System 2 allocates attention to effortful mental activities, including complex computations and deliberate choice-making.

I remember when my first serious girlfriend broke up with me decades ago. Her chief complaint revolved around some recent incident, the details of which have faded from memory, but our conversation remains vivid. I pleaded with her, explaining how she was clouded by recency bias—focusing on the recent negative experience while overlooking all our positive history together.

I saw a discussion on Reddit about entrepreneurship recently that got me thinking. What’s the point of being an entrepreneur when the odds of success are incredibly low? This is especially true if you’re low on resources or clout. Beyond the Silicon Valley Narrative # The dominant narrative about entrepreneurship has become increasingly narrow: raise venture capital, grow at all costs, aim for a massive exit, and hopefully become a billionaire. It’s the script that’s celebrated in tech publications, glorified by accelerators, and drilled into the minds of computer science graduates.