Great founders like Sam Zell and Charlie Munger don't retire; their exit strategy is death. They work until the end because their work isn't a job, but a deep-seated passion. The ultimate sign of loving your work is that no amount of money could convince you to stop doing it.

The personality trait that drives outlier entrepreneurial success isn't mere ambition, but a "tortured" state of mind. These individuals feel a constant, painful inadequacy that compels them to achieve extraordinary things. This drive often comes at the expense of their personal well-being, family life, and mental health.

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'.

Facing the finitude of life can pivot your motivation system. Instead of chasing external rewards like money or status, which seem meaningless in the face of death, you become driven by an intrinsic desire to discover the absolute ceiling of your capabilities.

Surveys reveal that a majority of professionals (60%) would restart their careers differently. Author Daniel Pink attributes this to "boldness regrets," where the pain of not taking a chance (inaction) ultimately haunts people far more than the pain of trying something and failing. This is the root of widespread career dissatisfaction.

Founders often believe success will bring ease and happiness, but building meaningful things is a constant, hard grind. The goal shouldn't be happiness, which is fleeting, but contentment—the deep satisfaction derived from tackling important problems. The hardness itself is a privilege to be embraced.

Contrary to seeking complete satisfaction, professionals should be thankful for what they don't have. Unmet goals, knowledge gaps, and limitations are what create purpose, foster growth, and provide the forward momentum needed for a fulfilling and ambitious career.

People with a strong calling don't just work harder out of sheer will. Research indicates the primary mechanism is increased enjoyment of the work itself. This positive feeling directly translates into greater effort on relevant tasks, supporting the "love what you do" axiom.

When deciding whether to leave a stable job to start Amazon, Jeff Bezos asked which choice he would regret more at age 80. People are far more haunted by the opportunities they didn't take than the ones they took that failed. This is a powerful mental model for making bold career leaps.