Reconceptualizing Failure and Values

Key Insight

Starting at 'rock bottom,' such as graduating into the 2007 financial collapse, losing savings, and living on a friend's couch, can be a fortunate experience. This early exposure to significant setbacks removes the paralyzing fear of failure later in life, making it easier to take risks like starting an internet business. When there is little to lose, the perceived downside of trying new ventures diminishes, allowing for bold actions. Failure itself is a relative concept, its definition depending entirely on the metrics one chooses to apply.

The value of money as a metric for self-worth is questioned, particularly when one grows up in an environment where money is used to avoid problems rather than solve them. This insight teaches that financial gain alone does not equate to happiness and can even lead to misery. Instead, a greater value is placed on freedom and autonomy. From this perspective, the true failure lies not in being broke or experiencing conventional setbacks, but in actively choosing not to pursue one's own projects and desires, even if it means temporary hardship like sleeping on couches.

Fear of failure is often rooted in 'shitty values'—external, uncontrollable goals, such as seeking universal approval, which create anxiety because success depends on others' actions. In contrast, 'better values' are process-oriented and within one's control, like 'improving one's social life' or 'honest expression.' These values provide continuous engagement and opportunities for growth, generating sustained happiness. The example of Pablo Picasso, who remained prolific into his nineties, illustrates this: his underlying value of 'honest expression' was endless, driving constant innovation and preventing stagnation that would have resulted from finite goals like 'become famous' or 'make a buttload of money.'