Expect the best, plan for the worst, and prepare to be surprised.

Waitley’s aphorism compresses a pragmatic philosophy of optimism into three coordinated habits. “Expect the best” names a forward-looking attitude that can motivate effort and resilience; it is not passive wishing but a stance that shapes behavior. “Plan for the worst” adds sober risk-awareness—contingency planning, redundancy, and humility about uncertainty. The final clause, “prepare to be surprised,” acknowledges that reality often escapes both optimism and pessimism: even good plans fail, and unexpected opportunities appear. Together, the line advocates psychological flexibility—holding hope, caution, and adaptability at once—making it a popular maxim in leadership and self-improvement contexts.