You have chosen the wrong path if it’s not fun. And you are probably not taking enough risk if it’s not hard and rocky sometimes.

Benioff’s remark links two entrepreneurial “signals” to a life and career well chosen: enjoyment and difficulty. If the work contains no fun, it may indicate misalignment with one’s talents, values, or intrinsic motivation—an early warning that the path is unsustainable. Conversely, if the path never feels “hard and rocky,” it may mean the person is avoiding meaningful risk, challenge, or innovation, settling for safe incrementalism. The quote frames struggle not as failure but as evidence of ambition and growth, while insisting that challenge alone is not enough; the pursuit should also be energizing. Together, fun and friction become a compass for purposeful, high-impact work.