Chasing goals for the ego—like being number one or the best—is a recipe for unhappiness. Once a goal is achieved, the ego immediately creates a new one or instills a fear of losing its position, preventing any lasting peace or satisfaction.

Many successful people maintain their drive by constantly focusing on what's missing or the next goal. While effective for achievement, this creates a permanent state of scarcity and lack, making sustained fulfillment and happiness impossible. It traps them on a 'hamster wheel of achievement'.

Chasing achievements like money or status won't fix a lack of self-worth. Success acts as a magnifying glass on your internal state. If you are insecure, more success will only make you feel more insecure. True fulfillment comes from inner work, not external validation.

If you feel unmotivated or burnt out, examine your goals. Arbitrary material targets like a specific salary or a big house are empty motivators. The moment you achieve them, you will realize nothing has fundamentally changed, leading to a cycle of dissatisfaction and a constant struggle for motivation.

The depression of someone chasing wealth is often buffered by the hope that money will solve their problems. The true psychological danger comes *after* achieving financial success, when you realize your non-money problems persist. This can lead to a profound and debilitating sense of hopelessness.

Chasing visual markers of success (cars, houses) often leads to hollow victories. True fulfillment comes from defining and pursuing the *feeling* of success, which is often found in simple, personal moments—like pancakes on a Saturday morning—rather than glamorous, external accomplishments.

A major struggle for accomplished professionals is the internal conflict between their identity as a "stone cold high achiever" and their current lack of motivation. This cognitive dissonance—knowing you should be achieving but not feeling the "juice"—is a key psychological hurdle when past success eliminates original drivers.

Achieving external markers of success, like a multi-million dollar exit, often fails to provide a sense of accomplishment. Instead, it can lead to feelings of emptiness, anxiety, and imposter syndrome because internal self-worth was tied to the struggle, not the outcome.

The lesson that 'money can't buy happiness' is often only learned through experience. Achieving material success can paradoxically lead to happiness by proving that external achievements are not the answer. This makes the pursuit itself a necessary stepping stone to discovering true fulfillment.