The primary error founders make is confusing external achievements (revenue, exit) with internal fulfillment. Financial success should be viewed as a tool that enables a life aligned with your personal values, rather than being the source of fulfillment itself.
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.
When founders define success by external metrics like net worth or exit size, the target constantly shifts upward upon achievement. A $1 million goal becomes $10 million, and a single exit becomes a need for multiple. This creates a perpetual cycle of striving without ever feeling successful.
The common advice to 'find your purpose' can be counterproductive. It boxes you into a static self-identity, creating friction and existential crises whenever you grow or your interests change. A more flexible approach is to focus on a set of core values that guide you, rather than a single, reductive 'purpose'.